United States v. Amirnazmi

PRECEDENTIAL

UNITED STATES COURT OF APPEALS
FOR THE THIRD CIRCUIT
___________

No. 10-1198
___________

UNITED STATES OF AMERICA

v.

ALI AMIRNAZMI,
Appellant
_______________________

On Appeal from the United States District Court
for the Eastern District of Pennsylvania
D.C. Criminal No. 2-08-cr-00429-001
(Honorable Cynthia M. Rufe)
______________

Argued January 11, 2011

Before: SCIRICA, BARRY and VANASKIE, Circuit Judges.

(Filed: May 13, 2011)
ELIZABETH K. AINSLIE, ESQUIRE (ARGUED)
VINCENT A. LaMONACA, ESQUIRE
Schnader Harrison Segal & Lewis
1600 Market Street, Suite 3600
Philadelphia, Pennsylvania 19103
Attorneys for Appellant

BERNADETTE A. McKEON, ESQUIRE (ARGUED)
STEPHEN A. MILLER, ESQUIRE
Office of United States Attorney
615 Chestnut Street, Suite 1250
Philadelphia, Pennsylvania 19106
Attorney for Appellee
_________________

OPINION OF THE COURT
_________________

SCIRICA, Circuit Judge.

In pursuit of his stated goal of transforming the Islamic
Republic of Iran into a global chemical powerhouse, Ali
Amirnazmi, a chemical engineer, marketed a dynamic
software program to Iranian actors and entered into
agreements with various Iranian entities in which he pledged
to provide technology to facilitate the construction of multiple
chemical plants. Following a jury trial, Amirnazmi was
convicted on ten charges—four counts stemming from
violations of the International Emergency Economic Powers
Act (IEEPA), three counts of making false statements, and
three counts of bank fraud. Amirnazmi moved both for a

2
judgment of acquittal and for a new trial. The District Court
denied both motions and sentenced him to a four-year prison
term. We will affirm.

I.

Amirnazmi, a dual citizen of the United States and
Iran, founded a company called TranTech Consultants, Inc.,
in 1981. Billed as a business geared toward providing “an
innovative approach to strategic decision making for the
Chemical Process Industries,” TranTech marketed its primary
product—a computer software program called ChemPlan—as
an “exclusive, fully integrated, worldwide database” designed
to allow chemical companies to assess product viability and
cost based on a number of variables. ChemPlan had two
principal functions. As a database that illuminated how
chemical reactions could be disaggregated into their
component parts, it included both public information and
proprietary data derived from Amirnazmi’s expert analysis of
the various processes. 1 And as a dynamic planning tool,
ChemPlan enabled end users to determine individualized
production costs and the feasibility of embarking on
prospective projects by allowing them to change the input

1
ChemPlan’s licensing agreement alerted software
purchasers to the proprietary nature of the database,
indicating it contained “valuable TRADE SECRET and
confidential, unpublished information developed or acquired
by TranTech at great expense, including data, data structure,
data processing algorithms, innovations and concepts.”

3
variables in order to generate “what if” scenarios accounting
for market fluctuations. These features made ChemPlan
attractive to major manufacturers such as the Dow Chemical
Company, LyondellBasell Industries, and Rohm and Haas
Company.

Aiming to facilitate Iran’s transformation into “an
independent chemical powerhouse,” 2 and seeking to spur “a
flow of Iranian[ ] [scientists] back to Iran” where he would
ultimately join them to impart his expertise, 3 Amirnazmi
began, in the mid-1990s, to explore business partnerships
with Iranian entities. First, he initiated efforts to sell
ChemPlan to the state-owned National Petrochemical
Company of Iran (NPC). In August 1997, TranTech and NPC
executed a Software/Data License Agreement whereby NPC
agreed to purchase a subscription to ChemPlan for $64,000.
Amirnazmi directed NPC to wire payment to a European
bank account, and he traveled to Iran to demonstrate the
product’s functionality to NPC officials. In 1998, NPC
purchased a software update for $18,000. In 2000, NPC
enlisted Amirnazmi’s assistance in its quest to obtain an off-
the-shelf software package called BoxScore, a suite of
programs manufactured in the United States and consequently
unavailable to Iranian entities affected by U.S. trade

2
Letter from Ali Amirnazmi to Mrs. F. Parvaresh, Manager,
National Petrochemical Company of Iran (April 30, 1998).
3
Email from Amirnazmi to Mr. Robert G. Williamson,
Attorney at Law (undated).

4
sanctions. Amirnazmi procured the software, sent it to an
intermediary in Germany, and charged NPC $667.85 for his
efforts.

Amirnazmi met in person with NPC personnel at a
2000 international petrochemical conference held in Iran.
Thereafter, he sent NPC’s Director of Planning and
Development a letter in which he encouraged NPC to renew
its ChemPlan subscription and proposed three options—
including the formation of a joint venture—for tailoring
ChemPlan to NPC’s unique needs. Amirnazmi attended the
same conference in 2001 and again attempted to solicit NPC
interest in a customized ChemPlan package by sending an
NPC contact several renewed proposals along with
subscription order forms.

In 2002, Amirnazmi endeavored to engage an Iranian
company to handle its advertising and promotional efforts. In
connection with this deal, Amirnazmi attempted to transfer
$250 to an Iranian bank account. The U.S. bank declined to
complete the transaction, and the Treasury Department’s
Office of Foreign Assets Control (OFAC) requested from
Amirnazmi a detailed explanation for this attempted transfer.
Amirnazmi responded that he had not known such a
transaction was prohibited by the sanctions then in place
against Iran. 4

4
OFAC, the arm of the U.S. Treasury Department
responsible for administering the regulations implementing
the embargo against Iran, had previously flagged

5
 After indicating he was willing to conduct business
with Iran, Amirnazmi was granted a private audience with
Iranian President Mahmoud Ahmadinejad at an event in New
York City in September 2006. At this meeting and in
subsequent correspondence, Amirnazmi expressed his desire
to transfer ChemPlan’s technical and economic knowledge to
Iran and sought President Ahmadinejad’s assistance in
helping him return to Iran so that he might serve the country
in his “field of expertise.” 5 In a January 2007 letter,
Amirnazmi beseeched President Ahmadinejad to arrange an
in-person meeting in Tehran so that he might unveil his
“plan” to help Iran, and he decried the United States’ “cruel
and tyran[nical]” treatment of the Iranian people. 6

Having brought himself to President Ahmadinejad’s
attention, Amirnazmi’s efforts to improve Iran’s chemical

Amirnazmi’s attempt to wire the registration fee for the 2000
petrochemical conference to an Iranian bank. After
Amirnazmi’s local bank informed him it could not forward
funds to a bank owned or controlled by Iranian authorities,
the conference organizers waived Amirnazmi’s attendance
fee.
5
Letter from Amirnazmi to Mahmoud Ahmadinejad,
President of the Islamic Republic of Iran (Nov. 7, 2006).
6
Fax from Amirnazmi to Ahmadinejad (Jan. 24, 2007) (as
read from the witness stand by Special Agent Eugene Robert
Lanzillo, Jr.).

6
capacities began to show results. In December 2007,
Amirnazmi (on behalf of TranTech) signed a Memorandum
of Understanding with the Institute for Business Analysis and
Consultancy (IBACO), an Iranian company, regarding the
provision of technology for a proposed polyvinyl butyral
chemical plant to be constructed in Iran. In May 2008,
Amirnazmi entered into a separate confidentiality agreement
with IBACO in which he agreed to have TranTech provide
software licensing, equipment and chemicals in connection
with the construction of a glacial acrylic acid and super
absorbent polymer plant in Iran.

Amirnazmi and NPC rekindled their working
partnership in 2008, entering into a new licensing agreement
for the ChemPlan software. During the negotiations leading
up to this agreement, Amirnazmi represented that the 1997
ChemPlan licensing agreement was “still valid.” 7 And in June
2008, Amirnazmi entered into a Memorandum of
Understanding with the Nokhbegan Institute of Technology
Development (NITD), an Iranian company, to create a joint
venture to provide software, database and technology transfer
services to clients in the chemical process industry. Under the
agreement, Amirnazmi pledged to have TranTech transfer the
ChemPlan system to a newly-formed company in Iran in
which TranTech would have been the majority shareholder.

The Memorandum of Understanding with NITD
expired by its own terms after two months. The 2008

7
Fax from Amirnazmi to Mr. Gorbanpour, NPC official (Feb.
26, 2008).

7
licensing agreement with NPC, which was signed by the
counterparties and which fixed the subscription fee at
$270,000, was to become effective upon installation of
ChemPlan on NPC hardware. Amirnazmi twice met with
IBACO officials in 2008 to negotiate the terms of a formal
contract covering the polyvinyl butyral plant, but the resulting
Technology Transfer and Construction Agreement was never
signed by the parties. And the IBACO confidentiality
agreement concerning the super absorbent polymer plant
contemplated further elucidation within the framework of a
formal contract drafted upon “finalizing negotiation[s] with
investors.”

Amirnazmi drew the attention of U.S. Customs and
Border Protection by traveling to Iran in 2007 and twice more
in 2008. Customs agents interviewed Amirnazmi upon his
return to the United States in both April and June of 2008.
Upon questioning, he claimed both trips were to visit his
elderly mother and that the latter trip also permitted him to
attend a petroleum conference. Although Amirnazmi
repeatedly disavowed any commercial purpose for his travels,
the presence of ostensibly business-related possessions cast
doubt on the credibility of his responses. In April he claimed
the sundry business cards and documents found in his
briefcase were personal effects he had not made use of on his
trip. In June 2008, confronted by Customs officials with
computer files and hard copy documents detailing plans to
build chemical plants in Iran, he declined to offer an
explanation.

8
 On June 4, 2008, the day after his second encounter
with Customs officials, Amirnazmi contacted the OFAC
compliance hotline to inquire in general about U.S.
restrictions on commercial activity with Iran. Without either
delving into the specifics of how ChemPlan operated or
mentioning his prior business dealings with Iranian
companies, he asked whether making public documents
available on a website would fall within the informational-
materials exemption to IEEPA and whether exporting an
unidentified “good” would theoretically require dispensation
in the form of a license issued by OFAC.

Two days after this telephone conversation,
Amirnazmi was questioned by agents from the Internal
Revenue Service and the Federal Bureau of Investigation. He
acknowledged meeting President Ahmadinejad but denied
having conducted business on either of his 2008 trips to Iran,
and he claimed his only two financial transactions with Iran
had been the disallowed wire transfers much earlier in the
decade. The agents subsequently obtained a search warrant
for Amirnazmi’s business. Despite Amirnazmi’s protestations
that none of the documents named in the warrant were located
on the premises, the authorities seized numerous physical
documents and the hard drive from his computer, which also
contained pertinent documents. Upon further interrogation,
Amirnazmi conceded he had business relations with NPC
both in 1997 and in the more recent past, and he
acknowledged having met with Iranian state officials during
his trips abroad.

II.

9
 On July 24, 2008, the government filed a ten-count
indictment against Amirnazmi in the Eastern District of
Pennsylvania charging him with (1) one count of conspiracy
to violate IEEPA, in violation of 18 U.S.C. § 371; (2) four
substantive counts of violating IEEPA, in violation of 50
U.S.C. § 1705, and of aiding and abetting the same, in
violation of 18 U.S.C. § 2; (3) one count of conspiracy to act
as an illegal agent of a foreign government, in violation of the
Foreign Agents Registration Act (FARA) and in violation of
18 U.S.C. § 371; (4) one substantive count of acting as an
illegal agent of a foreign government, in violation of 18
U.S.C. § 951, and of aiding and abetting the same, in
violation of 18 U.S.C. § 2; and (5) three counts of making
false statements to government officials, in violation of 18
U.S.C. § 1001. On October 2, the government filed a
superseding indictment, charging Amirnazmi with three
additional counts of bank fraud, in violation of 18 U.S.C. §
1344, and supplementing the original indictment with further
factual allegations.

Prior to trial, Amirnazmi filed a motion to dismiss in
which he alleged (1) IEEPA regulations are the product of an
unconstitutional delegation of legislative authority to the
Executive; and (2) portions of the superseding indictment
referencing conduct that occurred more than five years prior
to the indictment should be barred by the statute of
limitations. The court denied the motion, concluding IEEPA
does not violate the nondelegation doctrine and that
Amirnazmi’s actions prior to 2003 were part of a continuing
course of conduct that extended into the limitations period
and contributed to the charged conspiracy. See United States

10
v. Amirnazmi, No. 08-CR-0429-01, 2009 U.S. Dist. LEXIS
624 (E.D. Pa. Jan. 5, 2009). 8

The jury convicted Amirnazmi on all but one of the
IEEPA counts and on all of the false statement and bank fraud
counts. 9 Amirnazmi was acquitted of the FARA violations
charged in Counts Six and Seven. Amirnazmi moved for a
judgment of acquittal under Fed. R. Crim. P. 29 on the IEEPA
counts, the false statement counts and one of the bank fraud
counts. He reiterated his argument that IEEPA

8
Also prior to trial, the government moved to admit audio
recordings and transcripts of certain conversations in which
Amirnazmi had participated while in pretrial custody.
Amirnazmi moved to suppress, arguing the government had
used trial subpoenas to conduct further investigation after the
indictment had been returned in violation of Fed. R. Crim. P.
17(c). The court determined the subpoenas properly directed
the custodian of records to appear with the documents on
dates that corresponded with scheduled proceedings in the
case and consequently allowed the government to admit the
evidence.
9
Amirnazmi was found not guilty on Count Three of the
superseding indictment, which charged him with violating
IEEPA by entering into an agreement with the Research
Institute of Petroleum Industry, a division of Iran’s Ministry
of Petroleum, in which he agreed to conduct negotiations with
a Danish chemical company for the purpose of establishing a
joint venture in Iran.

11
unconstitutionally delegates to the Executive authority to
criminalize commercial conduct, and he added an argument
that the accompanying OFAC regulations under which he was
convicted are unconstitutionally vague. He also argued the
evidence was insufficient to prove his conduct did not fall
within IEEPA’s informational-materials exemption and that
the government failed to prove IEEPA required him to obtain
a license to engage in his activities. The court denied
Amirnazmi’s motion in its entirety. It rested on its previous
ruling concerning the nondelegation doctrine, concluded that
the IEEPA regulations are not unconstitutionally vague, and
determined the government had produced sufficient evidence
to sustain each conviction. See United States v. Amirnazmi,
No. 08-CR-0429-01, 2009 U.S. Dist. LEXIS 74833 (E.D. Pa.
Aug. 21, 2009).

Amirnazmi also moved for a new trial under Fed. R.
Crim. P. 33. Amirnazmi reiterated his claims that the prison
tapes were improperly obtained and should not have been
admitted and that evidence of his conduct prior to 2003
should have been barred by the statute of limitations. The
court denied this motion, resting on its previous ruling with
respect to the tapes and concluding Amirnazmi’s pre-2003
actions fell within the scope of his conspiracy “to bring his
technical wherewithal, especially the ChemPlan system, back
to Iran for the benefit of that country.” See United States v.
Amirnazmi, 648 F. Supp. 2d 718, 723 (E.D. Pa. 2009).

12
 As noted, the District Court sentenced Amirnazmi to a
48-month term of imprisonment followed by five years’
supervised release. Amirnazmi timely appealed. 10

III.

On appeal, Amirnazmi principally challenges the
constitutionality of IEEPA and the accompanying OFAC
regulations. We will first address the constitutionality of the
statute itself, which Amirnazmi challenges on two fronts.
First, he argues that Congress—when delegating the authority
to create criminal offenses—must articulate the standards by
which executive conduct will be governed with greater
precision than is required in the context of delegations of civil
authority. IEEPA, Amirnazmi contends, lacks the requisite
specificity. Second, he claims Congress’s failure to comply
with its statutory responsibility to oversee the implementation
of the Iranian sanctions regime left the Executive’s discretion
wholly unchecked. Because IEEPA reserves for Congress the
final word in determining trade policy during peacetime
emergencies, Amirnazmi alleges, Congress’s abdication of its
oversight role rendered the delegation unconstitutional. 11

10
The District Court had jurisdiction under 18 U.S.C. § 3231.
We have jurisdiction under 28 U.S.C. § 1291.
11
We review challenges to the constitutionality of a statute de
novo. United States v. Fullmer, 584 F.3d 132, 151 (3d Cir.
2009).

13
 A.

As the source of statutory authority for the Executive’s
exercise of emergency economic powers in response to
peacetime crises, IEEPA traces its provenance to § 5(b) of the
Trading with the Enemy Act of 1917, Pub. L. No. 65-91, § 5,
40 Stat. 411, 415 (1917), as amended, 12 U.S.C. § 95a
(TWEA). Dames & Moore v. Regan, 453 U.S. 654, 671
(1981). TWEA endowed the President with sweeping powers
to regulate international trade in times of war or “national
emergency,” but it lacked a countervailing mechanism to
divest the President of such authority once the emergency had
ebbed. Because Presidents had displayed a tendency to allow
“emergency” declarations to linger “even after the
circumstances or tensions that had led to the declaration could
no longer be said to pose a threat of emergency proportion to
the Nation,” some expressed concern that TWEA effectively
served as a “one-way ratchet to enhance greatly the
President’s discretionary authority over foreign policy.”
Regan v. Wald, 468 U.S. 222, 245 (1984) (Blackmun, J.,
dissenting).

In an effort to address TWEA’s evolution into a
“flexible instrument of foreign policy in nonemergency
situations,” id. at 246, Congress amended § 5(b) in 1977,
restricting the Executive’s ability to act under that statute
strictly to times of war, Pub. L. No. 95-223, Tit. I, § 101, 91
Stat. 1625, 1625 (1977) (striking “or during any other period
of national emergency declared by the President” from the
text of § 5(b)). Contemporaneously, Congress enacted the
International Emergency Economic Powers Act to serve as

14
the locus of executive economic authority during national-
emergency situations. See id. at Tit. II, 91 Stat. at 1626
(codified at 50 U.S.C. § 1701 et seq.). Although the powers
conferred in IEEPA closely mirror those granted in its
progenitor, IEEPA removed certain tools from the President’s
peacetime kit. 12 And, significantly for our purposes, IEEPA
subjected the President’s authority to a host of procedural
limitations designed to ensure Congress would retain its
essential legislative superiority in the formulation of sanctions
regimes erected under the Act’s delegation of emergency
power. 13

The predicate for an exercise of executive authority
under IEEPA is the declaration of a national emergency under
the National Emergencies Act (NEA). See 50 U.S.C. §§ 1621,
1701(b). Under IEEPA, the emergency must stem from an
“unusual and extraordinary threat, which has its source in
whole or substantial part outside the United States, to the
national security, foreign policy, or economy of the United
States.” Id. § 1701(a). After declaring such an emergency, the

12
Unlike TWEA, IEEPA does not authorize the Executive to
take title to foreign assets, to regulate purely domestic
transactions, to regulate gold or bullion, or to seize records.
See Regan, 468 U.S. at 228 n.8.
13
As explained at greater length in Section III.C.2 infra,
Congress’s reservation of a stricter oversight role in IEEPA is
relevant to Amirnazmi’s separation-of-powers argument.

15
President may, through “regulations . . . instructions, licenses,
or otherwise,”

(A) investigate, regulate, or prohibit —

(i) any transactions in foreign exchange,

(ii) transfers of credit or payments
between, by, through, or to any banking
institution, to the extent that such
transfers or payments involve any
interest of any foreign country or a
national thereof,

(iii) the importing or exporting of
currency or securities,

by any person, or with respect to any property,
subject to the jurisdiction of the United States;

(B) investigate, block during the pendency of an
investigation, regulate, direct and compel,
nullify, void, prevent or prohibit, any
acquisition, holding, withholding, use, transfer,
withdrawal, transportation, importation or
exportation of, or dealing in, or exercising any
right, power, or privilege with respect to, or
transactions involving, any property in which
any foreign country or a national thereof has
any interest by any person, or with respect to
any property, subject to the jurisdiction of the
United States . . . .

16
Id. § 1702(a)(1).

In tandem, IEEPA and NEA subject the President’s
exercise of emergency economic powers to an assortment of
procedural requirements. The President must consult with
Congress before exercising any of his powers under IEEPA
“in every possible instance,” and he “shall consult regularly
with the Congress so long as such authorities are exercised.”
Id. § 1703(a); see also id. § 1703(c) (stipulating that the
President must report to Congress “[a]t least once during each
succeeding six-month period after” the initial exercise of any
authority granted by the IEEPA). Whenever the President acts
pursuant to IEEPA, he must provide Congress with a report
detailing:

(1) the circumstances which necessitate such
exercise of authority;

(2) why the President believes those
circumstances constitute an unusual and
extraordinary threat, which has its source in
whole or substantial part outside the United
States, to the national security, foreign policy,
or economy of the United States;

(3) the authorities to be exercised and the
actions to be taken in the exercise of those
authorities to deal with those circumstances;

(4) why the President believes such actions are
necessary to deal with those circumstances; and

17
 (5) any foreign countries with respect to which
such actions are to be taken and why such
actions are to be taken with respect to those
countries.

Id. § 1703(b). After each six-month interval, Congress “shall
meet to consider a vote on a joint resolution to determine
whether that emergency shall be terminated.” Id. § 1622(b);
id. § 1706(b) (providing for the cessation of presidential
authority under IEEPA upon congressional termination of an
emergency declared under NEA).

Substantively, the regulations contain several
exemptions and constraints. That is, regulations promulgated
under IEEPA may not impinge upon transactions incident to
travel or curtail the free exchange of personal
communications, humanitarian aid, or “information or
informational materials.” Id. § 1702(b). Moreover, criminal
penalties under IEEPA are reserved exclusively for those who
“willfully commit[ ], willfully attempt[ ] to commit, or
willfully conspire[ ] to commit” a violation of any license,
order or regulation issued pursuant to IEEPA. Id. § 1705(c).
And the Act exempts those who act in “good faith” reliance
on IEEPA, or on “any regulation, instruction, or direction”
issued under IEEPA, from both civil and criminal liability. Id.
§ 1702(a)(3).

On March 15, 1995, President Bill Clinton issued
Executive Order 12957, which declared a national emergency
to deal with the “unusual and extraordinary threat” posed to
the national security, foreign policy and economy of the

18
United States by “the actions and policies of the Government
of Iran,” and which prohibited United States involvement
with petroleum development in Iran. 60 Fed. Reg. 14615
(Mar. 17, 1995). 14 On May 6, 1995, President Clinton signed
Executive Order 12959, which fortified the sanctions regime
by banning U.S. firms from exporting to Iran, importing from
Iran, or investing in Iran, subject to the exemptions provided
in IEEPA. See 60 Fed. Reg. 24757 (May 9, 1995); see also
Exec. Order No. 13059, 62 Fed. Reg. 44531 (Aug. 21, 1997)
(clarifying the preceding Orders). The Executive Orders
authorized the Secretary of the Treasury, in consultation with
the Secretary of State, “to take such actions, including the
promulgation of rules and regulations . . . as may be
necessary to carry out the purposes” of the Orders. See, e.g.,
60 Fed. Reg. 14615 at § 3. The Treasury Department
subsequently issued the Iranian Transactions Regulations
(ITR). See generally 31 C.F.R. Part 560.

Subject to limited exemptions and to licenses issued by
OFAC, the ITR prohibits, in part, the “exportation,
reexportation, sale, or supply, directly or indirectly, from the
United States, or by a United States person, wherever located,
of any goods, technology, or services to Iran or the
Government of Iran,” 31 C.F.R. § 560.204, and “any new
investment by a United States person in Iran or in property

14
The national emergency with respect to Iran has been
extended annually through presidential notices. See Executive
Documents summarized in the annotations to 50 U.S.C. §
1701.

19
(including entities) owned or controlled by the Government
of Iran,” id. § 560.207; see also id. § 560.206(a) (generally
prohibiting “any transaction or dealing in or related to . . .
[g]oods, technology, or services for exportation,
reexportation, sale or supply, directly or indirectly, to Iran or
the Government of Iran”). 15 The regulations also incorporate
the statutory exemption permitting the exportation of
“informational materials.” Id. § 560.210(c). Critically, this
exemption does not apply to informational materials “not
fully created and in existence at the date of the transactions,
or to the substantive or artistic alteration or enhancement of
informational materials.” Id.

B.

15
OFAC authorizes otherwise proscribed transactions
through general licenses set forth in the ITR and through
specific licenses issued pursuant to the procedures outlined in
31 C.F.R. Part 560, Subpart E. Whereas a general license
categorically authorizes “a particular type of transaction for a
class of persons without the need to apply for a license,” a
specific license is a “written document issued by OFAC to a
particular person or entity, authorizing a particular transaction
in response to a written license application.” OFAC,
Frequently Asked Questions and Answers,
http://www.treasury.gov/resource-
center/faqs/Sanctions/Pages/answer.aspx (last visited April
29, 2011).

20
 The maxim that Congress may not delegate legislative
power to the President is “universally recognized as vital to
the integrity and maintenance of the system of government
ordained by the Constitution.” Field v. Clark, 143 U.S. 649,
692 (1892). Nevertheless, the Supreme Court has invoked the
unconstitutional delegation doctrine—which derives its
constitutional underpinning from Article I’s vesting of “all
legislative powers” with Congress 16—to strike down a law
only twice in its history. See Panama Ref. Co. v. Ryan, 293
U.S. 388 (1935) (invalidating delegation under section 9(c) of
the National Industrial Recovery Act permitting the President
to prohibit the interstate transportation of petroleum goods);
A.L.A. Schechter Poultry Corp. v. United States, 295 U.S. 495
(1935) (striking down section 3 of the same Act, which
authorized trade and industrial associations to propose “codes
of fair competition” that would become legally binding if
approved by the President). The Court’s jurisprudence has
been animated by a “practical understanding that in our
increasingly complex society, replete with ever changing and
more technical problems, Congress simply cannot do its job
absent an ability to delegate power under broad general
directives.” Mistretta v. United States, 488 U.S. 361, 372
(1989). Accordingly, in assessing a permissible delegation,
the Court has decreed it will be “‘constitutionally sufficient if
Congress clearly delineates the general policy, the public
agency which is to apply it, and the boundaries of this
delegated authority.’” Id. at 372-73 (quoting Am. Power &
Light Co. v. SEC, 329 U.S. 90, 105 (1946)).

16
U.S. Const. art. I, § 1.

21
 Congress’s ability to endow a coordinate branch of
government with a measure of discretion is circumscribed by
the requirement that it must “lay down by legislative act an
intelligible principle to which the person or body authorized
to [exercise the delegated authority] is directed to conform.”
J.W. Hampton, Jr. & Co. v. United States, 276 U.S. 394, 409
(1928). Whereas Congress must itself elucidate “the standards
of legal obligation” in order to fulfill its “essential legislative
function,” it may devolve to “selected instrumentalities
[responsibility for] the making of subordinate rules within
prescribed limits and the determination of facts to which the
policy as declared by the legislature is to apply.” Schechter
Poultry, 295 U.S. at 530. Because no one standard can
account for the range of contexts in which Congress
legislates, “the degree of agency discretion that is acceptable
varies according to the scope of the power congressionally
conferred.” Whitman v. Am. Trucking Ass’ns, Inc., 531 U.S.
457, 475 (2001).

The Supreme Court has upheld Congress’s delegation
to the President of civil authority to nullify certain
attachments and transfers of assets under IEEPA. Dames &
Moore, 453 U.S. at 675. But Amirnazmi contends IEEPA’s
delegation of authority to define criminal conduct is
inherently more suspect and that, consequently, only a lesser
degree of executive discretion is constitutionally permissible
in this context. The Court has expressly refrained from
deciding whether Congress must provide stricter guidance
than a mere “intelligible principle” when authorizing the
Executive “to promulgate regulations that contemplate
criminal sanctions.” Touby v. United States, 500 U.S. 160,

22
165-66 (1991). After concluding the contested delegation
would pass constitutional muster even under a heightened
standard, the Court refrained from resolving the petitioner’s
argument that criminal regulations promulgated under
congressional delegations of authority should be subject to
more searching scrutiny on account of the “heightened risk to
individual liberty” they pose. Id. at 166. 17

C.

17
In Touby, the Court held section 201(h) of the Controlled
Substances Act, which delegated to the Attorney General the
authority to temporarily designate a substance as “controlled”
without submitting to the full complement of procedural
requirements for permanent scheduling, “meaningfully
constrain[ed] the Attorney General’s discretion to define
criminal conduct.” Id. at 166. The Court pointed to “multiple
specific restrictions on the Attorney General’s discretion”
that, together, satisfied the nondelegation doctrine. Id. at 167.
To schedule a drug temporarily, the Attorney General was
required to find that doing so would be “necessary to avoid an
imminent hazard to the public safety.” Id. at 166 (citing 21
U.S.C. § 811(h)(1)). In rendering this determination, the
Attorney General was “required to consider” three specific
factors, ordered to publish 30-day notice of the proposed
scheduling in the Federal Register and to transmit notice to
the Secretary of Health and Human Services, and bound by
several of the strictures for permanent scheduling (“high
potential for abuse,” “no currently accepted medical use”). Id.
at 166-67.

23
 1.

Two of our sister circuits have analyzed IEEPA’s
delegation of authority to criminalize conduct in light of
Touby and have concluded the Act withstands constitutional
scrutiny. In United States v. Arch Trading Co., 987 F.2d
1087, 1092-94 (4th Cir. 1993), the Fourth Circuit discerned
“constraining factors” in IEEPA comparable to those found
sufficient in Touby and concluded the President’s powers are
“explicitly defined and circumscribed.” And in United States
v. Dhafir, 461 F.3d 211, 217 (2d Cir. 2006), the Second
Circuit adopted the Fourth Circuit’s logic, concluding IEEPA
would satisfy even a heightened standard because “the
authorities delegated are defined and limited.” 18

We too conclude that IEEPA “meaningfully
constrains” the President’s discretion. See Touby, 500 U.S. at
166. Under the Controlled Substance Act provision examined
in Touby, the Attorney General could not temporarily
schedule a drug without first finding that doing so would be
“necessary to avoid an imminent hazard to the public safety.”
Id. Similarly, to activate IEEPA, the President must find that
an “unusual and extraordinary threat . . . to the national

18
District Courts have followed suit. See United States v.
Mirza, No. H-06-421, 2010 U.S. Dist. LEXIS 34556, at *3-4
(S.D. Tex. Apr. 7, 2010); United States v. Esfahani, No. 05-
CR-0255, 2006 U.S. Dist. LEXIS 1839, at *11-12 (N.D. Ill.
Jan. 17, 2006); United States v. Anvari-Hamedani, 378 F.
Supp. 2d 821, 829-30 (N.D. Ohio 2005).

24
security, foreign policy, or economy of the United States”
originating on foreign soil has reached “national emergency”
proportions. See 50 U.S.C. § 1701. In Touby, the Court found
the Attorney General was constrained by the requirement that
he abide by several of the more rigorous features of the
permanent scheduling process designating illegal drugs. 500
U.S. at 166-67. Likewise, IEEPA prohibits the President from
regulating certain exempt transactions, 50 U.S.C. § 1702(b),
from prosecuting unwitting violators or holding liable those
who act in good faith reliance on the statute and regulations,
id. §§ 1705(c), 1702(a)(3), and from obviating Congress’s
role as ultimate arbiter of emergency trade policy, see id. §§
1622(b), 1703, 1706; 19 see also Mistretta, 488 U.S. at 372-73
(explaining Congress must “clearly delineate[ ] the general
policy . . . and the boundaries of this delegated authority”).

In effecting the shift of peacetime authority from
TWEA to IEEPA, Congress “placed several procedural
restrictions on the President’s exercise of the national-
emergency powers, including congressional consultation,
review, and termination.” Regan, 468 U.S. at 249 (Blackmun,
J., dissenting). In so doing, Congress reaffirmed its “essential
legislative function,” see Schechter Poultry, 295 U.S. at 530,
and struck a careful balance between affording the President a
degree of authority to address the exigencies of national
emergencies and restraining his ability to perpetuate

19
The Constitution vests the power to regulate commerce
with foreign nations in the hands of Congress. U.S. Const. art.
I, § 8.

25
emergency situations indefinitely by creating more
opportunities for congressional input, cf. Panama Ref. Co.,
293 U.S. at 430 (“Congress has declared no policy, has
established no standard, has laid down no rule”). 20 Therefore,
IEEPA meets the same standard of constraint outlined in
Touby; that is, IEEPA meaningfully constrains the
Executive’s discretion. Accordingly, it is unnecessary for us
to address the unsettled question of whether something more
demanding than an “intelligible principle” is necessitated
within the context of delegating authority to define criminal
conduct.

2.

Second, Amirnazmi claims Congress has violated
fundamental separation-of-powers precepts by neglecting its
statutory responsibility to monitor the implementation of the

20
Amirnazmi unconvincingly attempts to distinguish Touby
by arguing the power to classify newly designed drugs is “far
narrower” than the powers conferred by the IEEPA. The
petitioner in Dhafir raised a similar argument, contending the
Touby court upheld a “temporary power” to schedule
controlled substances whereas IEEPA confers authority that
can persist indefinitely. 461 F.3d at 217. The Second Circuit
rejected this position, pointing to the need for the President to
reaffirm the national emergency at regular intervals and
Congress’s ability to terminate the declaration as indicia of
proper limitation. Id. We find no material durational
difference between the delegations at issue here and in Touby.

26
Iranian sanctions regime established under IEEPA. In so
doing, Amirnazmi claims, the legislature has allowed the
President to arrogate “virtually unlimited power over foreign
trade,” thereby fomenting a “serious threat to public liberty
[that] necessitates judicial intervention.” This allegation
implicates interrelated issues of foreign policy, congressional
authorization, and statutorily mandated oversight. Because
these considerations are intertwined, we consider them in
concert.

The linchpin of Amirnazmi’s claim is 50 U.S.C. §
1622(b), which reads: “Not later than six months after a
national emergency is declared, and not later than the end of
each six-month period thereafter that such emergency
continues, each House of Congress shall meet to consider a
vote on a joint resolution to determine whether that
emergency shall be terminated.” In Dhafir, the Second Circuit
noted in passing that Congress’s failure to fulfill its oversight
responsibilities might conceivably raise “complicated and
sensitive issues concerning separation of powers” but
declined to expound in light of an inadequate factual record.
461 F.3d at 217 n.3. Given the conventional wisdom that the
shift in authority from TWEA to IEEPA was inspired in part
by a prevailing sentiment that Congress’s role in devising
emergency trade policy warranted strengthening, see supra

27
Section III.A, its failure to police executive conduct would
appear counterintuitive. 21

As a threshold matter, we must determine whether a
national emergency properly declared under NEA terminates
automatically when Congress fails to meet in conformance
with the language of § 1622(b). In Beacon Products Corp. v.
Reagan, 814 F.2d 1, 4 (1st Cir. 1987), the First Circuit
answered that question in the negative. The court reasoned
that the disparity between § 1622(d), which explicitly
provides for the automatic termination of a national
emergency should the President fail to extend it, and §
1622(b), which is devoid of a parallel congressional
provision, suggests Congress deliberately withheld automatic
termination as a remedy for violation of the “periodic
meeting” clause. Id. at 4. Next, the court noted Congress
eliminated a sunset provision from an earlier draft of NEA,
reserving for itself “the burden of acting affirmatively” by
substituting in that provision’s place the requirement that it
pass a resolution to end an emergency. Id. (referencing 50
U.S.C. § 1622(a)). The court then concluded Congress likely
intended “to give those who want to end the emergency the
chance to force a vote on the issue, rather than to require
those who do not want to end the emergency to force
congressional action to prevent automatic termination.” Id. at
5. We agree that Congress did not effectively terminate the

21
The parties agree that Congress has not met regularly to
consider terminating the national emergency with respect to
Iran.

28
emergency against Iran simply by virtue of its failure to hold
the periodic meetings addressed in § 1622(b).

Amirnazmi contends Beacon Products should not
control our analysis because the issue here is not merely one
of statutory interpretation but instead one that requires us to
consider whether Congress’s failure to regularly convene to
evaluate the desirability of a continued emergency trade
regime violates the power-sharing program contemplated by
IEEPA. That is, Amirnazmi would have us hold that
Congress’s assumption of a silent partner role transforms a
limited delegation into a blank check that confers upon the
Executive unbridled power to create trade policy. In Dames v.
Moore, the Court wrote that IEEPA “constitutes specific
congressional authorization to the President” to take certain
emergency measures. 453 U.S. at 675. Following
Amirnazmi’s logic, the issue would then become whether
protracted inaction vitiates this authorization. If this were the
case, we would likely consider whether, after express
authorization has ostensibly lapsed, the President’s continued
criminalization of certain commercial conduct has either been
implicitly countenanced or whether he is in fact acting
pursuant to some form of inherent authority.

The constitutionality of IEEPA’s delegation of
criminal authority does not rest on Congress affirmatively
renewing its approval of each ongoing emergency at regular
six-month intervals. Equating inaction with a withdrawal of
authorization would be particularly improper with a statute
that concerns foreign affairs, “a sphere in which delegation is
afforded even broader deference.” Dhafir, 461 F.3d at 215.

29
“Congress—in giving the Executive authority over matters of
foreign affairs—must of necessity paint with a brush broader
than that it customarily wields in domestic areas.” Zemel v.
Rusk, 381 U.S. 1, 17 (1965); see also Veterans & Reservists
for Peace in Vietnam v. Reg. Comm’r of Customs, 459 F.2d
676, 679 (3d Cir. 1972) (“Ordinarily, when dealing with
matters of foreign relations, Congress may lawfully delegate
to the President broader discretion than would be permissible
with regard to domestic affairs.”); United States v. Curtiss-
Wright Exp. Corp., 299 U.S. 304, 319-20 (1936) (upholding
Congress’s ability to delegate the power to prohibit the sale of
arms to certain countries designated by the President and
explaining that it was “important to bear in mind that we are
here dealing not alone with an authority vested in the
President by an exertion of legislative power, but with such
an authority plus the very delicate, plenary and exclusive
power of the President as the sole organ of the federal
government in the field of international relations”). Mindful
of the heightened deference accorded the Executive in this
field, we decline to interpret the legislative grant of authority
parsimoniously. Congress may act to terminate the national
emergency; NEA does not necessarily compel Congress to
take affirmative steps to prolong the President’s charted
course. See Beacon Prods., 814 F.2d at 4; 50 U.S.C. § 1622.

Congress’s failure to satisfy the periodic meeting
requirements of § 1622(b) does not ineluctably lead to a
conclusion that the President’s continued prosecution of trade
sanctions under IEEPA has ceased to be “pursuant to an
express or implied authorization.” See Youngstown Sheet &
Tube Co. v. Sawyer, 343 U.S. 579, 635 (1952) (Jackson, J.,

30
concurring) (setting forth the familiar tripartite framework for
evaluating executive action and explaining the President’s
power is “at its maximum” when he acts according to
congressional directive). In Haig v. Agee, 453 U.S. 280, 300-
01 (1981), the Court inferred congressional approval of a
“longstanding and officially promulgated” executive policy
from both inaction and statutory developments that “‘left
completely untouched the broad rule-making authority
granted in the earlier Act.’” Id. (quoting Zemel, 381 U.S. at
12). Under Agee, we must generally defer to a consistent
administrative construction of a statute. Id. at 291. “This is
especially so in the areas of foreign policy and national
security, where congressional silence is not to be equated
with congressional disapproval.” Id. The Court’s analysis in
Agee was buttressed by its determination that Congress had
“endorsed not only the underlying premise of Executive
authority in the areas of foreign policy and national security,
but also its specific application” to the subject matter at issue.
Id. at 294.

Similarly, this regulatory embargo against Iran has
been in place since 1995. Far from sitting by as successive
Presidents maintained a sweeping sanctions regime, Congress
has expanded, deepened and formalized the sanctions in a
comprehensive legislative effort to target Iran through
economic measures. In 1996, Congress passed the Iran
Sanctions Act, Pub. L. No. 104-172, 110 Stat. 1541 (1996)
(codified in part at 50 U.S.C. § 1701 (note)), which mandated
the imposition of specified sanctions against foreign firms
that reached threshold levels of involvement with Iran’s

31
energy sector. 22 Subsequently, in 2006, Congress passed the
Iran Freedom Support Act. Pub L. No. 109-293, 120 Stat.
1344 (2006) (codified in part at 50 U.S.C. § 1701 (note)). In
addition to appropriating funds earmarked for the support of
persons and organizations “working for the purpose of
supporting and promoting democracy for Iran,” id. § 302, the
Act placed Congress’s imprimatur on executive sanctions
against Iran. Under the heading “Codification of Sanctions,”
Congress wrote:

United States sanctions with respect to Iran
imposed pursuant to sections 1 and 3 of
Executive Order No. 12957, sections 1(e),
(1)(g) and (3) of Executive Order No. 12959,

22
See id. at § 3 (“The Congress declares that it is the policy of
the United States to deny Iran the ability to support acts of
international terrorism and to fund the development and
acquisition of weapons of mass destruction and the means to
deliver them by limiting the development of Iran’s ability to
explore for, extract, refine, or transport by pipeline petroleum
resources of Iran.”). Iran has been designated a state sponsor
of terrorism continuously since January 19, 1984. Prevatt v.
Islamic Republic of Iran, 421 F. Supp. 2d 152, 156 (D.D.C.
2006). This classification has restricted the flow of goods into
Iran under section 6(j) of the Export Administration Act of
1979 (codified at 50 U.S.C. App’x § 2405(j)), section 620A
of the Foreign Assistance Act of 1961 (codified at 22 U.S.C.
§ 2371), and sections 38 and 40 of the Arms Export Control
Act (codified at 22 U.S.C. § 2780).

32
 and sections 2, 3, and 5 of Executive Order No.
13059 (relating to exports and certain other
transactions with Iran) as in effect on January 1,
2006, shall remain in effect. The President may
terminate such sanctions, in whole or in part, if
the President notifies Congress at least 15 days
in advance of such termination.

Id. at § 101(a). Notably, one of the provisions incorporated by
reference (section 2 of Executive Order 13059) specifically
prohibited “the exportation, reexportation, sale, or supply,
directly or indirectly, from the United States, or by a United
States person, wherever located, of any goods, technology, or
services to Iran or the Government of Iran.” 62 Fed. Reg.
44531.

And in 2010, Congress passed the Comprehensive Iran
Sanctions, Accountability, and Divestment Act of 2010. Pub.
L. No. 111-195, 124 Stat. 1312 (2010) (codified in part at 50
U.S.C § 1701 (note)). CISADA expanded the Iran Sanctions
Act by targeting Iran’s ability to make or import gasoline and
placing new restrictions on financial institutions. Id. Most
significantly for our purposes, however, is § 103(b)(2), in
which Congress codified the prohibitions on the exportation
of goods, services and technology of United States origin to
Iran that were then in effect under executive orders
promulgated pursuant to IEEPA. Id. at Tit. I, § 103, 124 Stat.
at 1328-31. 23 Therefore, when Amirnazmi was tried and

23
CISADA incorporated the exemptions provided in 50
U.S.C. § 1702(b), including the informational-materials

33
convicted, Congress had already ratified the OFAC
regulations under which he was charged. And, in the
aftermath of his conviction, Congress once more manifested
its approval of executive conduct by again codifying the
extant prohibitions on exports issued pursuant to IEEPA.
These measures demonstrate Congress’s approval of the
emergency measures undertaken against Iran notwithstanding
its failure to adhere to the meeting requirements of §
1622(b). 24

Far from being unaware or indifferent, in the case of
Iran, Congress has clearly and consistently demonstrated its
support of the Executive’s agenda. This is not a scenario in
which we are compelled to divine the significance—if any—
of congressional silence. Nevertheless, given the number of
countries against which trade sanctions have been leveled

exemption, into this blanket codification. Pub. L. No. 111-195
at Tit. I, § 103(b)(2)(B)(i), 124 Stat. at 1328-29.
24
Unsurprisingly, Congress’s enactment of legislative
sanctions against Iran coincided with its eschewing of
periodic meetings to review the Executive’s IEEPA-based
sanctions. This reality corroborates the First Circuit’s
supposition in Beacon Products that “[f]ailure to vote likely
means that few legislators wish to end the emergency. It
would be odd to think that Congress would make it easier to
terminate a popular emergency than an unpopular one.” 814
F.2d at 4-5.

34
pursuant to IEEPA, 25 it is not difficult to envisage a situation
in which Congress’s position is less robustly documented.
Although Congress’s failure to periodically meet neither
automatically terminates an emergency nor bespeaks its
dissatisfaction with the President’s policies, § 1622(b)
provides a regularized mechanism for disquieted
representatives to initiate a dialogue about or even contest the
wisdom of continuing on with the President’s strategy. Once
the President has invoked his power to criminalize certain
conduct under IEEPA, Congress retains an ongoing part in
ensuring the Executive’s actions remain “meaningfully
constrained” so as to satisfy the requirements of Touby. 26

25
Since the statute’s inception, Presidents have found
“unusual and extraordinary” threats emanating from
Afghanistan, Angola, Belarus, Burma, Colombia, Cote
d’Ivoire, the Democratic Republic of the Congo, Haiti, Iran,
Iraq, Liberia, Libya, Nicaragua, North Korea, Panama, Sierra
Leone, South Africa, Sudan, Syria, the Western Balkans, and
Zimbabwe. See Executive Documents summarized in the
annotations to 50 U.S.C. § 1701.
26
Originally, NEA provided for termination of an emergency
state by “concurrent resolution” of Congress. See Beacon
Products v. Reagan, 633 F. Supp. 1191, 1194 (D. Mass.
1986) (citing the first iteration of 50 U.S.C. § 1622(a)).
However, in INS v. Chadha, 462 U.S. 919, 959 (1983), the
Supreme Court invalidated a similar provision as an
unconstitutional “legislative veto” insofar as it allowed
Congress to act without obtaining the President’s signature.

35
 The Supreme Court has held that “[m]atters intimately
related to foreign policy and national security are rarely
proper subjects for judicial intervention,” Agee, 453 U.S. at
292, and federal courts have historically declined to review
“the essentially political questions surrounding the
declaration or continuance of a national emergency,” United
States v. Spawr Optical Research, Inc., 685 F.2d 1076, 1080
(9th Cir. 1982) (internal quotation marks omitted). Although
such considerations do not preclude enforcing compliance
with statutory dictates, NEA places the onus on Congress to
ensure emergency situations remain anomalous and do not
quietly evolve into default norms. See Youngstown, 343 U.S.
at 654 (Jackson, J., concurring) (“[P]ower to legislate for
emergencies belongs in the hands of Congress, but only

Subsequently, Congress amended NEA and the
unconstitutional clause with one that called for termination of
an emergency by “joint resolution.” Pub. L. No. 99-93, Tit.
VIII, § 801, 99 Stat. 405, 448 (1985) (amending 50 U.S.C. §
1622 by striking each use of the word “concurrent” and
inserting in its place the word “joint”). IEEPA, on its face,
permits a national emergency to be “terminated by the
Congress by concurrent resolution pursuant to section 202 of
the National Emergencies Act [50 U.S.C. § 1622].” See 50
U.S.C. § 1706(b) (2011). Chadha and the amendment to the
cross-referenced section in NEA would appear to have
rendered the words “by concurrent resolution” in § 1706(b)
ineffective. “[P]ursuant to section 202 of the National
Emergencies Act,” Congress may only terminate an
emergency via joint resolution.

36
Congress itself can prevent power from slipping through its
fingers.”).

IV.

Next, Amirnazmi argues the government failed to
prove beyond a reasonable doubt that ChemPlan does not fall
within the scope of IEEPA’s informational-materials
exemption. He contends that Congress intended to insulate
transactions incident to the free flow of information from
regulation and that the sale of ChemPlan, which conveys
pricing information and scientific information, falls within
this category of presumptively exempt activity. He urges us to
vacate his convictions on Counts Two and Five of the
superseding indictment, which charged him with ChemPlan-
related IEEPA violations, because, he argues, OFAC’s
interpretation of this exemption both flouts congressional
intent and is unconstitutionally vague.

Congress proscribes the Executive from regulating,
pursuant to IEEPA,

the importation from any country, or the
exportation to any country, whether commercial
or otherwise, regardless of format or medium of
transmission, of any information or
informational materials, including but not
limited to, publications, films, posters,
phonograph records, photographs, microfilms,
microfiche, tapes, compact disks, CD ROMs,
artworks, and news wire feeds . . . .

37
50 U.S.C. § 1702(b)(3). OFAC has incorporated the statutory
exemption into the ITR; the regulations provide a general
license authorizing transactions involving “information and
informational materials.” See 31 C.F.R. § 560.210(c)(1).
Although not enumerated in the statute, technology and
software are capable of qualifying as “informational
materials” under the regulations. See id. § 560.418 (“The
release of technology or software in the United States . . . to
any person violates the [ITR] if made with knowledge or
reason to know the technology is intended for Iran or the
Government of Iran, unless that technology or software meets
the definition of information and informational materials in §
560.315.”). However, under OFAC’s interpretation, the
general license is not applicable to “transactions related to
information and informational materials not fully created and
in existence at the date of the transactions, or to the
substantive or artistic alteration or enhancement of
informational materials, or to the provision of marketing and
business consulting services.” Id. § 560.210(c)(2) (emphasis
added).

At trial, the parties agreed to submit the issue of
whether ChemPlan fell within the exemption to the jury as a
factual matter, and the jury was instructed that the
government had the burden of proving beyond a reasonable
doubt the exemption did not apply. In his Rule 29 motion,
Amirnazmi appeared to challenge the sufficiency of the
evidence supporting his conviction on the IEEPA counts. The
District Court, viewing the evidence in the light most
favorable to the government, concluded a reasonable
factfinder could have found the government had proven

38
beyond a reasonable doubt that ChemPlan was “not fully
created and in existence at the date of the [relevant]
transactions” and thus could have found the informational-
materials exemption inapplicable. Amirnazmi, 2009 U.S. Dist.
LEXIS 74833, at *18. In reaching this conclusion, the District
Court cited Amirnazmi’s description of ChemPlan as a
“dynamic tool, which allows the user to generate ‘what if’
scenarios,” as well as testimony indicating that ChemPlan
packages were specifically tailored to end users and that the
program allowed users to enter their own data in order to
generate customized reports.

Ordinarily, our review of whether a jury verdict rests
on legally sufficient evidence is “particularly deferential.”
United States v. Dent, 149 F.3d 180, 187 (3d Cir. 1998). We
must “view the evidence in the light most favorable to the
Government . . . and will sustain the verdict if any rational
trier of fact could have found the essential elements of the
crime beyond a reasonable doubt.” Id. (internal quotation
marks omitted). The government argues Amirnazmi has
waived any claim that the exemption applies as a matter of
law by accepting the proposed jury instruction. See United
States ex rel. O’Connor v. New Jersey, 405 F.2d 632, 634 n.2
(3d Cir. 1969) (quoting Johnson v. Zerbst, 304 U.S. 458, 464
(1938) (defining a waiver as “an intentional relinquishment or
abandonment of a known right or privilege”)).

But because the jury returned a guilty verdict without
specific interrogatories, we cannot say with any certainty
whether it concluded ChemPlan simply did not qualify as
“informational materials” or whether, as the District Court

39
surmised, it concluded the exemption was inapplicable on
account of the regulatory carve-out. In federal criminal cases,
a general verdict will be upheld if the government has
adduced sufficient evidence in support of at least one of the
alternative theories on which the jury was charged. Griffin v.
United States, 502 U.S. 46, 49 (1991). 27 We agree with the
District Court that a reasonable factfinder could have found
the government proved beyond a reasonable doubt that
ChemPlan was “not fully created and in existence at the date
of the transactions,” and was therefore subject to OFAC
regulation under the ITR. 28

27
In its jury charge, the District Court quoted both IEEPA’s
informational-materials exemption and the regulatory carve-
out within the ITR. It then stressed that “the defendant has
raised this [informational-materials] exemption as an issue
during trial. The government has the burden to prove beyond
a reasonable doubt that the exemption does not apply.”
28
We will thus assume without deciding that the ChemPlan
software could conceivably satisfy the definition of
“information and informational materials” in 31 C.F.R. §
560.315. See 31 C.F.R. § 560.418. Nevertheless, it bears
noting that OFAC has consistently treated software as
conceptually distinct from other forms of informational
materials. See id. § 560.210(c)(3) (“This section does not
exempt from regulation or authorize transactions incident to
the exportation of software subject to the Export
Administration Regulations (15 CFR parts 730-774).”); id. §
560.210(c)(4) (“This section does not exempt from regulation

40
 Amirnazmi argues reliance on this regulatory language
is fatally misplaced for two reasons. First, he claims OFAC’s
interpretation of the informational-materials exemption is
ultra vires. As Congress has structured IEEPA to disempower
the Executive from imposing trade sanctions that impinge
upon certain conduct, he argues, a regulation that undercuts
this legislative charge by purporting to criminalize such
conduct would be unenforceable. Second, he argues this
regulation fails to inform those potentially affected by IEEPA
that certain conduct is proscribed. Because the regulation did
not announce with unmistakable clarity that a product of
ChemPlan’s nature would not fall within the general license
for “informational materials,” he contends, it is
unconstitutionally vague.

A.

First, Amirnazmi contends OFAC’s regulation
removing informational materials “not fully created and in
existence at the date of the transactions” from the scope of the
statutory exemption reflects an impermissible agency
interpretation that should be struck down under the principles
enunciated in Chevron U.S.A. v. Natural Resources Defense
Council, Inc., 467 U.S. 837, 842-43 (1984). We disagree.

or authorize the exportation of goods (including software) . . .
where such exportation . . . is for use in the transmission of
any data.”).

41
 Prior to 1988, trade sanctions that hampered the
exchange of informational materials were routinely justified
under TWEA and IEEPA as incidental to the broader
commercial purpose of these trade measures. See, e.g.,
Teague v. Regional Comm’r of Customs, 404 F.2d 441, 445
(2d Cir. 1968) (upholding TWEA regulations that effected a
categorical prohibition on importation of informational
materials from China, North Korea and North Vietnam
because the limitation was “incidental to the proper general
purpose of the regulations: restricting the dollar flow to
hostile nations”). In Veterans & Reservists for Peace in
Vietnam, we wrote:

[A] statute is not overly broad and thus
violative of the First Amendment merely
because it regulates incident to its scheme
protected activities or property. It is only where
the statute directly regulates speech or
expression arguably protected by the First
Amendment, or where as its mechanism the
statute has granted discretion to a delegatee to
determine whether particular items of
expression may be prohibited on the basis of
their content, that the question of overbreadth
arises. [TWEA] Section 5(b) does not directly
regulate First Amendment protected material,
rather it controls transactions concerning
property in which an enemy has an economic
interest. The purport of the statute is clear on its
face, and therefore provides guidance to the

42
 delegatee with regard to the exercise of his
functions.

459 F.2d at 681. Until 1988, this line of reasoning held sway.
The regulations “nominally allowed the importation of
informational materials . . . but in reality banned it by
requiring that the importers make payment into blocked U.S.
accounts.” Walsh v. Brady, 927 F.2d 1229, 1230 (D.C. Cir.
1991) (citing 31 C.F.R. § 515.545 (1987)).

Congress amended section 5 of TWEA and section
203(b) of IEEPA in 1988 to exempt the regulation of
informational materials from the Executive’s congeries of
powers. See Omnibus Trade and Competitiveness Act of
1988, Pub. L. No. 100-418, § 2502, 102 Stat. 1107, 1371
(1988) (codified at 50 U.S.C. app. § 5(b), 50 U.S.C. §
1072(b)). 29 The amendment specifically removed from the
29
The amendment restricted the Executive from regulating or
prohibiting, directly or indirectly,

the importation from any country, or the
exportation to any country, whether commercial
or otherwise, of publications, films, posters,
phonograph records, photographs, microfilms,
microfiche, tapes, or other informational
materials, which are not otherwise controlled
for export under section 5 of the Export
Administration Act of 1979 or with respect to
which no acts are prohibited by chapter 37 of
title 18, United States Code.

43
Executive’s purview the authority to regulate or prohibit such
transactions “directly or indirectly.” Id. This Berman
Amendment was considered “a reaction to several seizures by
the United States of shipments of magazines and books from
embargoed countries and to the Treasury Department’s
restrictions on the permissible forms of payment for
informational materials purchased from Cuba.” Kalantari v.
NITV, Inc., 352 F.3d 1202, 1205 (9th Cir. 2003) (footnotes
omitted).

In the wake of the Berman Amendment, OFAC
amended its regulations to conform with the new statutory
language. See Foreign Assets Control Regulations and Cuban
Assets Control Regulations, 54 Fed. Reg. 5229 (Feb. 2, 1989)
(codified at 31 C.F.R. §§ 500.206, 500.332). Paralleling the
statute, the new regulations exempted informational
materials, “whether commercial or otherwise,” from
prohibition or regulation. Id. Notably, however, OFAC took a
narrow view of what constituted “informational materials.”
From the outset, OFAC reserved the right to regulate
transactions related to “informational materials not fully
created and in existence at the date of the transaction” and
those concerning “the substantive or artistic alteration or
enhancement of informational materials.” Id. OFAC also
excluded “intangible items, such as telecommunications
transmissions,” from the definition of “informational
materials.” Id.

Pub. L. No. 100-418, § 2502(b)(1)(C).

44
 A divergence in views soon developed with regard to
how expansively OFAC was required to interpret the Berman
Amendment. In Cernuda v. Heavey, 720 F. Supp. 1544, 1549-
51 (S.D. Fla. 1989), the District Court for the Southern
District of Florida discerned from the legislative history of the
Berman Amendment an “obvious First Amendment
orientation.” In holding OFAC’s exclusion of original
artwork from the definition of “informational materials”
unreasonable, the court determined Congress had amended
TWEA and IEEPA “to prevent the statute from running afoul
of the First Amendment.” Id. at 1551-53. Because original
artwork merits First Amendment protection, the court
concluded, OFAC could not exclude it from the sweep of
“informational materials.” In dictum, the court theorized that
the Berman Amendment “totally exempts from prohibition or
regulation the import of ideas and information protected by
the First Amendment.” Id. at 1550 n.10.

By contrast, in Capital Cities/ABC, Inc. v. Brady, 740
F. Supp. 1007, 1011-13 (S.D.N.Y. 1990), the District Court
for the Southern District of New York concluded OFAC’s
exclusion of intangibles was consistent with the amendment’s
“other informational materials” language. Capital Cities had
purchased the exclusive rights to televise the 1991 Pan
American Games from Havana, Cuba for $ 8.7 million and
agreed to remit seventy-five percent of this sum to the host
organizer of the games. Id. at 1009-10. OFAC informed
Capital Cities the proposed transaction would not fall within a
general license provision and that it would not issue a specific
license so long as the transaction would result in a substantial
sum being transferred to Cuba. Id. The court found the

45
Berman Amendment was susceptible of multiple reasonable
interpretations and found the agency’s interpretation that
excluded intangibles such as telecommunications worthy of
deference under Chevron. Id. at 1011. In contrast to the
Cernuda court, the Capital Cities court found “the legislative
history reflects, at best, a general purpose to foster the
exchange of ideas across national borders.” Id. 30

In 1994, Congress expanded this limitation on
executive authority by enacting the Free Trade in Ideas Act.
Pub. L. No. 103-236, § 525, 108 Stat. 382, 474 (1994)
(codified as amended at 12 U.S.C. § 95a, 50 U.S.C. §
1702(b)). In part, Congress responded to OFAC’s exclusion
of intangible materials from the definition of “informational
materials” by amending IEEPA’s exemption to restrict the
Executive from regulating transactions concerning
informational materials “regardless of format or medium of
transmission.” Id. § 525(c)(1) (amending 50 U.S.C.
§1702(b)(3)). Congress also added “compact disks, CD
ROMS, artworks, and news wire feeds” to the nonexclusive

30
In analyzing Capital Cities’ First Amendment arguments,
the court noted that “the Berman Amendment is in derogation
of the Executive’s constitutional authority to conduct foreign
affairs by the use of embargoes on trade with hostile nations.”
Id. at 1013. Balancing this constitutional prerogative with the
First Amendment issues implicated by deference to OFAC’s
interpretation, the court found OFAC’s narrowing
interpretation prudentially avoided a separation-of-powers
problem. Id.

46
litany of enumerated media that could qualify as
“informational materials.” Id. The House Conference Report
stated:

[N]o embargo may prohibit or restrict directly
or indirectly the import or export of information
that is protected under the First Amendment to
the U.S. Constitution. The language was
explicitly intended, by including the words
“directly or indirectly,” to have a broad scope.
However, the Treasury Department has
narrowly and restrictively interpreted the
language in ways not originally intended. The
present amendment is only intended to address
some of those restrictive interpretations, for
example limits on the type of information that is
protected or on the medium or method of
transmitting the information.

H.R. Conf. Rep. No. 103-482, at 239 (1994), reprinted in
1994 U.S.C.C.A.N. 398, 483. Significantly, although
Congress overrode OFAC’s interpretation to the extent that it
excluded intangible materials from the definition of
“informational materials,” it did not disabuse OFAC of its
belief that it could permissibly regulate “informational
materials not fully created and in existence at the date of the
transaction.” That carve-out remained in place and, to date,
has not been challenged as ultra vires.

Before this Court, Amirnazmi relies on Cernuda to
argue that, because ChemPlan is a product that would merit

47
First Amendment protection, it necessarily falls outside the
scope of OFAC’s regulatory capabilities. Although it suffused
its opinion with constitutional considerations, the Cernuda
court refrained from reaching the merits of the petitioner’s
First Amendment challenge to the regulations, opting instead
to rest on “statutory construction and the legislative history of
the [Berman] [A]mendment.” 720 F. Supp. at 1553.
Similarly, Amirnazmi stresses he “is not challenging his
conviction under the IEEPA on First Amendment grounds.”
Consequently, whether ChemPlan theoretically could qualify
for First Amendment protection is not the dispositive
inquiry. 31 Instead, we must determine whether OFAC’s
31
Amirnazmi endeavors to bring ChemPlan within the ambit
of First Amendment protection by analogy to two categories
of speech. First, he argues ChemPlan functionally resembles
the prescription drug pricing information classified as
protected by Virginia State Bd. of Pharmacy v. Virginia
Citizens Consumer Council, 425 U.S. 748, 770 (1976), in that
it enables consumers to make more educated decisions and
thus serves the free market system by steering resources to
their most productive ends. Second, he characterizes
ChemPlan as “scientific expression” protected under Miller v.
California, 413 U.S. 15, 34 (1973); see also Universal City
Studios, Inc. v. Corley, 273 F.3d 429, 454 (2d Cir. 2001)
(computer code capable of meriting First Amendment
protection). Because Amirnazmi has not pursued a First
Amendment challenge at any stage in this litigation, we need
not determine whether OFAC’s regulation would pass
constitutional muster.

48
interpretation of the “informational materials” exemption
comports with congressional intent. See Chevron, 467 U.S. at
843 n.9 (“The judiciary is the final authority on issues of
statutory construction and must reject administrative
constructions which are contrary to clear congressional
intent.”).

We are satisfied that OFAC’s interpretation of
IEEPA’s informational-materials exemption is “based on a
permissible construction of the statute.” Chevron, 467 U.S. at
843. With the Berman Amendment and the Free Trade in
Ideas Act, Congress sought to ensure the robust exchange of
informational materials would not be unduly inhibited by
OFAC. When OFAC enacted regulations that Congress
considered at odds with this overarching purpose, the
legislature intervened and modified the statutory language to
rectify OFAC’s perceived missteps. Critically, although
Congress addressed one facet of OFAC’s 1989 interpretation
of the informational-materials exemption by stressing in 1994
that the Executive may not regulate informational materials
“regardless of format or medium of transmission,” it did not
counteract the component of that interpretation at issue here.
Presumably cognizant of OFAC’s narrowing interpretations,
Congress could have inserted text stipulating that the
Executive may not regulate informational materials regardless
of whether fully created and in existence at the date of the
transactions. Although the legislative history obliquely
alludes to other ways in which OFAC had interpreted the
exemption in an unforeseen manner, it chose to “only . . .
address some of those restrictive interpretations.” See H.R.
Conf. Rep. No. 103-482, at 239. “[W]hen Congress is aware

49
of an agency’s interpretation of a statute and takes no action
to correct it while amending other portions of the statute, it
may be inferred that the agency’s interpretation is consistent
with congressional intent.” Barrera-Echavarria v. Rison, 44
F.3d 1441, 1444-45 (9th Cir. 1995) (en banc) (citing North
Haven Bd. of Educ. v. Bell, 456 U.S. 512, 535 (1982)),
superseded by statute on other grounds as stated in Kwai Fun
Wong v. United States INS, 373 F.3d 952, 972 n.26 (9th Cir.
2004).

Moreover, there is ample evidence to suggest Congress
has accepted OFAC’s decision to permit the circulation of
informational materials already in existence while
concomitantly regulating transactions that contemplate the
creation of new materials. In the ITR, OFAC has fleshed out
the scope of the regulatory carve-out by explaining:

Transactions that are prohibited notwithstanding
this section include, but are not limited to,
payment of advances for information and
informational materials not yet created and
completed (with the exception of prepaid
subscriptions for widely circulated magazines
and other periodical publications), and
provision of services to market, produce or co-
produce, create or assist in the creation of
information and informational materials.

50
31 C.F.R. § 560.210(c)(2). 32 OFAC has made a reasoned
determination that Congress’s paramount concern for
facilitating transactions and activities incident to the flow of
informational materials in-being does not reach goods and
events that would not be produced but for financing from the
United States (in the case of imports) or financing from
purchasers in embargoed countries (in the case of exports). In
the case of commercial goods, the key distinction rests
between informational materials that are widely circulated in
a standardized format and those that are bespoke. Whereas
OFAC may not regulate the sale or transfer of prefabricated

32
OFAC’s general interpretation of the informational-
materials exemption, in place when Congress amended the
informational-materials exemption in 1994, reads:

[P]rohibited transactions include, without
limitation, payment of advances for
informational materials not yet created and
completed, provision of services to market,
produce or co-produce, create or assist in the
creation of informational materials, and
payment or royalties to a designated national
with respect to income received for
enhancements or alterations made by persons
subject to the jurisdiction of the United States to
informational materials imported from a
designated national.

54 Fed. Reg. 5229 (codified at 31 C.F.R. § 500.206(c)).

51
or mass-produced informational materials, custom-made
materials crafted to suit the unique specifications of a
particular purchaser are not sacrosanct. This distinction is
sensible, and it reflects a permissible implementation of the
statutory exemption in light of IEEPA’s competing
imperatives (i.e. restricting material support for hostile
regimes while encouraging the robust interchange of
information).

At trial, the government adduced sufficient evidence to
convince a reasonable factfinder beyond a reasonable doubt
that ChemPlan was not “fully created and in existence” at the
date of the relevant transactions. Amirnazmi trumpeted the
software’s dynamism. Joseph Mehl, a computer network
support technician who provided services to TranTech,
testified to his belief that each ChemPlan package was
“specifically tailored to the end user, depending on what
industry they worked in.” In aggressively pursuing
commercial ties with NPC, Amirnazmi attempted to stoke his
counterparty’s interest by proposing several options for
calibrating the software to NPC’s unique needs. As explained
below, the sale of ChemPlan to NPC was the cornerstone of
Amirnazmi’s conspiracy to bring his technical expertise to
Iran for that country’s aggrandizement. Consequently, the
transfer of ChemPlan to Iranian purchasers does not fit neatly
into the paradigm of informational exchange envisioned by
Congress. Quite clearly, Amirnazmi envisioned ChemPlan as
being of singular functional utility to Iranian users. Since the
inception of the informational-materials exemption, OFAC
has excepted such transactions from the scope of the general
license.

52
 Accordingly, we conclude that 31 C.F.R. §
560.210(c)(2) is a permissible construction of IEEPA’s
informational-materials exemption and is worthy of deference
under Chevron. See 467 U.S. at 843. Therefore, a reasonable
factfinder could have found the government proved beyond a
reasonable doubt that the sale of ChemPlan to Iranian
purchasers did not qualify for exemption from IEEPA as a
matter of law.

B.

Next, Amirnazmi contends OFAC’s regulations are
imprecisely drafted and consequently void for vagueness. His
core argument is that the carve-outs to the informational-
materials exemption fail to provide “clear principles.”
According to him, it is impossible to determine whether a
work is “fully created and in existence” without necessarily
invoking “an untethered subjective judgment.” Again, we find
Amirnazmi’s argument unconvincing. 33

33
Amirnazmi has challenged all four of his IEEPA
convictions on the theory that OFAC’s regulations are
unconstitutionally vague. He argues that the alleged
vagueness of the informational-materials exemption is
“exacerbated by the vagueness of other provisions in the
regulations.” Specifically, he argues that the amorphousness
of 31 C.F.R. § 560.206(a) allowed the government to convict
him for engaging “solely in preliminary negotiations with
Iranian entities.” However, that regulation prohibits “any
transaction or dealing.” Id. This language flatly proscribes the

53
 “A statute is void on vagueness grounds if it: (1) ‘fails
to provide people of ordinary intelligence a reasonable
opportunity to understand what conduct it prohibits’; or (2)
‘authorizes or even encourages arbitrary and discriminatory
enforcement.’” United States v. Stevens, 533 F.3d 218, 249
(3d Cir. 2008) (quoting Hill v. Colorado, 530 U.S. 703, 732
(2000)). In the criminal context, “since vagueness attacks are
based on lack of notice, ‘they may be overcome in any
specific case where reasonable persons would know their
conduct puts [them] at risk’ of punishment under the statute.”
San Filippo v. Bongiovanni, 961 F.2d 1125, 1138 (3d Cir.
1992) (quoting Maynard v. Cartwright, 486 U.S, 356, 361
(1988) (alteration in original)). Criminal statutes need only
give “fair warning that certain conduct is prohibited” to
survive constitutional challenges. Id. (internal quotation
marks omitted).

Furthermore, the Supreme Court has stated that:

[E]conomic regulation is subject to a less strict
vagueness test because its subject matter is

conduct for which Amirnazmi was convicted. See United
States v. Parise, 159 F.3d 790, 797 (3d Cir. 1998)
(concluding that the “plain meaning” of the term “dealings”
encompassed “all interactions or contacts” that a jury could
have considered as “proof of the requisite association”
between a RICO defendant and an illicit enterprise).
Therefore, we will confine our analysis to the regulatory
carve-out and Amirnazmi’s ChemPlan-related IEEPA
convictions.

54
 often more narrow, and because businesses,
which face economic demands to plan behavior
carefully, can be expected to consult relevant
legislation in advance of action [and may]
clarify the meaning of the regulation by [their]
own inquiry, or by resort to an administrative
process.

Village of Hoffman Estates v. Flipside, Hoffman Estates, Inc.,
455 U.S. 489, 498 (1982). And, significantly, “the Court has
recognized that a scienter requirement may mitigate a law’s
vagueness, especially with respect to the adequacy of notice
to the complainant that his conduct is proscribed.” Id. at 499;
see also United States v. Hescorp, Heavy Equip. Sales Corp.,
801 F.2d 70, 77 (2d Cir. 1986) (“[A] requirement of
willfulness makes a vagueness challenge especially difficult
to sustain. . . . ‘A mind intent upon willful evasion is
inconsistent with surprised innocence.’” (quoting United
States v. Ragen, 314 U.S. 513, 524 (1942))).

The District Court rested its conclusion that the
regulation is not unconstitutionally vague on two grounds.
First, it reasoned that the sophisticated nature of those
required to consult the IEEPA regulations coupled with the
availability of guidance from OFAC officials on electronic
and telephone hotlines negated any notice concerns. And
second, it noted that IEEPA’s scienter requirement counseled

55
against a vagueness finding. See Amirnazmi, 2009 U.S. Dist.
LEXIS 74833, at *4-8. 34

As to the latter point, the government had to prove
beyond a reasonable doubt that Amirnazmi willfully violated
the trade restrictions. See 50 U.S.C. § 1705(c) (restricting
IEEPA convictions to those who “willfully commit[ ],
willfully attempt[ ] to commit, or willfully conspire[ ] to
commit” a violation of any license, order or regulation issued
pursuant to IEEPA); see also id. § 1702(a)(3) (“No person
shall be held liable in any court for or with respect to
anything done or omitted in good faith in connection with the
administration of, or pursuant to and in reliance on, this title,
or any regulation, instruction, or direction issued under this
title.”). As the District Court noted, “this is a case where
34
Without explicitly pronouncing on the constitutionality of
the informational-materials exemption, federal courts have
uniformly upheld the regulations in the face of vagueness
challenges. See, e.g., United States v. Soussi, 316 F.3d 1095,
1101-03 (10th Cir. 2002); United States v. Quinn, 401 F.
Supp. 2d 80, 100 (D.D.C. 2005) (“[T]he Iran trade embargo
laws . . . are not apt to sweep within their coverage the
everyday acts of average citizens. Rather, they govern the
activities of relatively sophisticated individuals who are
deliberately engaged in international commerce and,
therefore, must be familiar with (if not expert in) various legal
regimes . . . in multiple countries.”); Anvari-Hamedani, 378
F. Supp. 2d at 830-31; United States v. Lindh, 212 F. Supp.
2d 541, 573-74 (E.D. Va. 2002); United States v. Geissler,
731 F. Supp. 93, 100-01 (E.D.N.Y. 1990).

56
ignorance of the law is a defense; the inability to appreciate
the meaning of the law negatives the mens rea required for
conviction, and Defendant was free to, and did, argue this to
the jury.” Amirnazmi, 2009 U.S. Dist. LEXIS 74833, at *7
(internal quotation marks omitted). The jury unanimously
concluded Amirnazmi knew his conduct was unlawful.

And, as to the former point, the record reveals
Amirnazmi only halfheartedly availed himself of the
opportunity to receive definitive guidance from OFAC.
Amirnazmi first contacted OFAC upon his return from Iran
on June 3, 2008. He indicated he was curious as to whether
consolidating publicly available documents in a single
location to increase the ease of access for individuals in Iran
would fall within the informational-materials exemption, and
he alluded to the possibility of exporting a good to Iran. He
did not mention the computations that could be done with the
data, nor did he ask if confidential trade secrets were exempt.
On June 10, after FBI and IRS officials had executed the
search warrant for TranTech, Amirnazmi again contacted the
OFAC hotline, this time to complain his office had been
searched, but without making any inquiries about the
interplay between ChemPlan and the Iranian sanctions. On
June 11, he sent a letter to OFAC confirming his unsupported
understanding that ChemPlan fell within the exemption but
again failed to disclose how ChemPlan functioned as a
dynamic planning tool. Amirnazmi once more contacted
OFAC on June 17 and was told to submit a “detailed
explanation of the transactions he wanted to carry out” if he
wanted authoritative guidance. One month later, he was
indicted. The District Court concluded Amirnazmi did not

57
contact OFAC “in good faith or with the intention of actually
procuring guidance in complying with the OFAC
regulations.” Amirnazmi, 2009 U.S. Dist. LEXIS 74833, at *6
n.17. Amirnazmi’s refusal to provide OFAC with the detailed
information that might have allowed the agency to offer
reasoned guidance supports the District Court’s conclusion.

Moreover, OFAC’s interpretive rulings do not cast
doubt on the ability of reasonable persons to appreciate
whether their conduct was prohibited. Amirnazmi points to a
sequence of rulings in which OFAC attempted to demarcate
the scope of permissible editing of Iranian-authored works to
be published in the United States. After OFAC ruled on
September 30, 2003, that “collaboration on and editing of
manuscripts submitted by persons in Iran, including activities
such as the reordering of paragraphs or sentences, correction
of syntax, grammar, and replacement of inappropriate words
by U.S. persons, prior to publication, may result in a
substantively altered or enhanced product,” it revisited this
broad statement after meeting with publishing representatives,
concluding on April 2, 2004, that “style and copy editing,”
such as correcting grammar and spelling and reformatting the
document for publication, was exempt activity. On July 19,
2004, OFAC addressed how these prior rulings would apply
to U.S. newspapers seeking to publish Iranian-authored
articles. It wrote that “substantive edits to the work’s content
to make the work more cohesive, efficient, argumentative or
effective . . . and to make the work conform to the
newspaper’s editorial standards would not constitute

58
substantive or artistic alteration or enhancement of the article
or commentary.” 35

Although Amirnazmi would read this publishing
trilogy as indicating the regulations are so convoluted as to
render them incomprehensible even to those charged with
administering the sanctions, the salient lesson is that
representatives of the publishing entities actually met with
OFAC officials to proactively and candidly discuss how the
regulations should apply to their line of work. 36 OFAC, for its

35
On the heels of this series of interpretive rulings, OFAC
created a general license for transactions “necessary and
ordinarily incident to publishing.” See 69 Fed. Reg. 75468,
75471 (Dec. 17, 2004) (codified at 31 C.F.R. § 560.538).
36
Amirnazmi fails to grapple with other OFAC rulings that
are arguably more germane to ChemPlan’s status as
informational material. A February 3, 2003, ruling specified
that, with respect to the “provision of access to a database, the
inclusion of an electric [sic] search function that does no
more than search and sort the exempt information in the
database is . . . exempt from the prohibitions of the ITR.” It
further noted that such guidance did “not address any
additional product that may be offered in connection with the
use of the database; nor does it apply to technical support,
customer support, or any other services that might be
provided.” On December 11, 2003, OFAC distinguished
between the provision of basic information and the provision
of services “beyond the mere dissemination of information in-
being.” As explained above in Section IV.A, this line of

59
part, demonstrated its willingness to partake in productive
consultations with businesses that approached it. If
Amirnazmi had been perplexed by the applicability of the
regulations, he had abundant opportunity to obtain
clarification. See Village of Hoffman Estates, 455 U.S. at 498
(noting that the ability of sophisticated businesses to obtain
clarification “by resort to an administrative process” provides
one of the rationales for according economic regulations
greater latitude upon a review for vagueness).

In sum, we agree with the District Court’s conclusion
that, in light of the “narrow subject matter and reach of the
IEEPA regulations, as well as the sophisticated nature of the
persons they affect and the ability of such persons to obtain
guidance from OFAC itself, the IEEPA regulations are not
unconstitutionally vague.” Amirnazmi, 2009 U.S. Dist.
LEXIS 74833, at *6. 37 Because OFAC’s regulations are

demarcation encourages the inference that products falling
within this latter category, such as ChemPlan, would fail to
find refuge in the exemption.
37
Amirnazmi’s challenge to the constitutionality of the
regulations takes the form of a facial challenge. However, the
Supreme Court has written that a petitioner “who engages in
some conduct that is clearly proscribed cannot complain of
the vagueness of the law as applied to the conduct of others.
A court should therefore examine the complainant’s conduct
before analyzing other hypothetical applications of the law.”
Village of Hoffman Estates, 455 U.S. at 495 (footnote
omitted). Because Amirnazmi had ample notice that his

60
neither ultra vires nor unconstitutionally vague, we will deny
Amirnazmi’s request to vacate his IEEPA convictions on
these grounds.

V.

Finally, Amirnazmi’s appeal requires us to address two
further issues: (1) whether there was a variance between the
indictment, which charged Amirnazmi with one continuous
conspiracy, and the facts established at trial; and (2) whether
the District Court abused its discretion in admitting tape
recordings of Amirnazmi’s prison telephone calls. We
conclude Amirnazmi is not entitled to relief on either of these
grounds.

A.

Amirnazmi contends there was a variance between the
indictment and the facts established at trial, and that this
variance caused evidence to be admitted that would otherwise
have been barred by the statute of limitations. 38 Namely,

conduct was captured by the regulations, his facial vagueness
challenge, which would be upheld “only if the enactment is
impermissibly vague in all of its applications,” must fail. See
id.
38
We exercise plenary review over claims of variance. United
States v. Daraio, 445 F.3d 253, 259 (3d Cir. 2006). When,
however, the petitioner does not raise a claim in a timely
fashion, our review is for plain error. United States v.
Williams, 464 F.3d 443, 445 (3d Cir. 2006). In the District

61
Court, Amirnazmi moved for a new trial on the ground that
the court erroneously admitted evidence of conduct that fell
outside the statute of limitations period on the faulty premise
that he had engaged in one continuous course of conduct. On
appeal, he has converted this argument into a claim of
prejudicial variance. Although both require us to determine
whether Amirnazmi’s pre-2003 conduct was part of the same
continuing course of action that precipitated the 2008
conspiracy charge, the variance claim would allow us to
undertake a plenary review of the District Court’s decision
whereas resubmitting the evidentiary claim would constrain
our review by limiting us to the deferential abuse of
discretion standard. Whether or not we review Amirnazmi’s
variance claim de novo or for plain error, he must
demonstrate that the District Court prejudiced a substantial
right. See United States v. Kemp, 500 F.3d 257, 287 (3d Cir.
2007) (“A conviction must be vacated when (1) there is a
variance between the indictment and the proof presented at
trial and (2) the variance prejudices a substantial right of the
defendant.”) (internal quotation marks omitted) (emphases
added); Williams, 464 F.3d at 445 (“Under the plain error
standard, before an appellate court can correct an error not
raised at trial, there must be (1) error, (2) that is plain, and (3)
that affect[s] substantial rights.”) (internal quotation marks
omitted) (alteration in original) (emphases added). Because
Amirnazmi cannot prove a substantial right was unfairly
prejudiced, the dispute over the appropriate standard is
immaterial.

62
Amirnazmi alleges the evidence, “if anything,” proved he
engaged in two separate conspiracies, one of which
terminated before the limitations period. The statute of
limitations for violations of IEEPA is five years. See 18
U.S.C. § 3282(a) (setting the default statute of limitations for
non-capital federal offenses). But, because the District Court
concluded Amirnazmi’s actions dating back to 1997 were part
of a single, continuous conspiracy, it admitted evidence of
acts occurring prior to 2003. Amirnazmi contends, as he did
in his Rule 33 motion, that the introduction of evidence
relating to his activities outside the limitations period tainted
his trial.

“There is a variance if the indictment charges a single
conspiracy while the evidence presented at trial proves only
the existence of multiple conspiracies.” United States v.
Kemp, 500 F.3d 257, 287 (3d Cir. 2007). The rule against
variance “protects the defendant’s right to an indictment
sufficiently inform[ing] [him] of the charges against him so
that he may prepare his defense and not be misled or
surprised at trial.” United States v. Schurr, 775 F.2d 549, 553-
54 (3d Cir. 1985) (internal quotation marks omitted)
(alterations in original). Conspiracy “is a continuing offense
and a jury may consider each and all of a defendant’s actions
in furtherance of the conspiracy so long as the indictment is
brought within five years of the last overt act.” United States
v. Jake, 281 F.3d 123, 130 n.6 (3d Cir. 2002). “[T]he crucial
question in determining whether the statute of limitations has
run is the scope of the conspiratorial agreement, for it is that
which determines both the duration of the conspiracy, and
whether the act relied on as an overt act may properly be

63
regarded as in furtherance of the conspiracy.” Grunewald v.
United States, 353 U.S. 391, 397 (1957).

The government’s superseding indictment charged
Amirnazmi with conspiring to violate IEEPA from 1996
through July 2008 by engaging in transactions with
companies located in Iran despite knowing such conduct was
prohibited. When the District Court analyzed Amirnazmi’s
claim within the statute of limitations context, it defined
Amirnazmi’s conspiracy as a plot “to bring his technical
wherewithal, especially the ChemPlan system, back to Iran
for the benefit of that country.” Amirnazmi, 648 F. Supp. 2d
at 723. The superseding indictment set forth six pre-2003
overt acts that allegedly contributed to the advancement of
this conspiracy, and the court concluded that the evidence
adduced by the government at trial demonstrated this conduct
was “closely tied” to his “continuing efforts to sell his
ChemPlan software to the [NPC].” 39

39
Specifically, the court cited evidence that Amirnazmi (1)
signed a 1997 agreement with NPC to sell the ChemPlan
software and traveled to Iran to conduct demonstrations and
training; (2) sold NPC a ChemPlan update in 1998; (3) helped
secure the BoxScore software for NPC in 2000; (4) met with
NPC personnel in Iran in 2000 and subsequently sent NPC
officials a fax that included a subscription order form and
other ChemPlan materials and which suggested the formation
of a joint venture; (5) attended the same conference in 2001
and sent a letter to NPC with an offer for a ChemPlan
program that would be designed to meet its ends; (6) sent a

64
 The District Court concluded Amirnazmi had
“resolved on achieving certain goals for the betterment of
Iran” prior to 2003 and that, although he failed to make
significant headway until well later, “there is no evidence that
[he] ever abandoned or renounced” the plan he had hatched in
the late 1990s. Id. After his encounter with President
Ahmadinejad in 2006, Amirnazmi’s efforts began to bear
fruit. He successfully negotiated another licensing agreement
with NPC in 2008 (after representing that the 1997 agreement
was still valid), and he signed memoranda of understanding
with IBACO and NITD. In the court’s estimation,
Amirnazmi’s efforts to sell ChemPlan to NPC were integral
to his goal of turning Iran into a “chemical powerhouse.”
Thus, it concluded, Amirnazmi’s pre-2003 acts fell squarely
within the scope of his conspiracy to bolster Iran’s chemical
capacities, and evidence of these acts was properly presented
to the jury on the theory that they contributed to a continuing
course of conduct. Id.

Amirnazmi now offers two alternative arguments: (1)
the government failed to prove his pre-2003 conduct was part
of any conspiracy, and (2) even if his early sales to the NPC
were part of a conspiracy to violate IEEPA, that purported

second letter discussing the 2001 conference and urging NPC
to contact him with respect to the proposed joint venture; and
(7) attempted to drum up business in 2002 with his
unsuccessful attempt to have brochures printed in Iran for his
software. Amirnazmi, 648 F. Supp. 2d at 722.

65
conspiracy terminated “well before the subsequent 2008 sale
of ChemPlan.”

The gravamen of Amirnazmi’s contention that his pre-
2003 conduct was not conspiratorial in any way is that the
government failed to demonstrate the existence of an
agreement to violate the statute. See United States v. Gebbie,
294 F.3d 540, 544 (3d Cir. 2002) (listing “an agreement
between two or more persons” as an essential element of a
conspiracy charge under 18 U.S.C. § 371). Amirnazmi claims
the government failed to demonstrate he shared a common
enterprise with NPC “beyond occasionally buying and selling
computer software.” He attempts to divorce his pre-2003 acts
from the overriding contextual narrative and style them as
intermittent transactions between a buyer and a seller working
at arms’ length and without any nefarious joint objective.
However, Amirnazmi declines to confront the evidence that
demonstrates he worked in conjunction with various officials
to provide ChemPlan and BoxScore and had ongoing, regular
contact with assorted NPC agents. The jury may reasonably
infer these business relationships would not have persisted
without at least an understanding in place between the parties
that Amirnazmi would be willing to provide goods and
services in violation of the embargo. See United States v.
McGlory, 968 F.2d 309, 326 (3d Cir. 1992) (concluding that a
reasonable jury could infer from the totality of the evidence
“that the activities of the participants . . . could not have been
carried on except as the result of a preconceived scheme or
common understanding” (internal quotation marks omitted)
(alteration in original)).

66
 And Amirnazmi’s alternative contention—that, at best,
the government proved the existence of two separate
conspiracies—is similarly unpersuasive. It miscasts his
unrequited efforts to spark renewed interest in ChemPlan
prior to 2006 as evidence the conspiracy could not have been
“continuing.” This slackening may reveal a disparity in the
vigor with which each side pursued the object of the
conspiracy; NPC seems to have been a somewhat reluctant
collaborator for most of the early part of the past decade.
Nevertheless, the resumption of concerted activity in 2007
came on the heels of Amirnazmi’s continuous efforts to
preserve and strengthen TranTech’s Iranian ties. The
temporary lull in sales does not detract from the District
Court’s conclusion that Amirnazmi’s later actions were part
of the same conspiracy that had begun in the 1990s.
Amirnazmi’s recurrent efforts to strengthen the relationship
were sandwiched between two periods of concerted activity
in which the parties pursued the same unlawful end. The
unaltered nature of the parties’ interests both prior to and after
2003 belies Amirnazmi’s depiction of the facts as evidencing
one conspiracy ceasing and another commencing.

Amirnazmi would have to demonstrate that, even if a
variance led to evidence being admitted that otherwise would
have been barred by the statute of limitations, such evidence
prejudiced a substantial right. As noted, this holds true
whether we conduct a plenary review or review for plain
error. “An error affects substantial rights when it is
prejudicial: It must have affected the outcome of the district
court proceedings.” United States v. Vazquez-Lebron, 582
F.3d 443, 446 (3d Cir. 2009) (internal quotation marks

67
omitted). Here, it appears as though Amirnazmi’s variance
argument is targeted primarily, if not exclusively, at his
conviction for conspiracy in Count One. Because limiting the
jury’s consideration to evidence of Amirnazmi’s post-2006
activities would not have resulted in a different outcome,
Amirnazmi cannot demonstrate his substantial rights were
prejudiced by introduction of this evidence.

Because the District Court neither misinterpreted the
law of conspiracy nor prejudiced a substantial right of
Amirnazmi’s, it did not err in admitting evidence of
Amirnazmi’s pre-2003 conduct.

B.

Lastly, Amirnazmi appeals the District Court’s
decision to allow the government to introduce into evidence
tape recordings and translated transcripts of telephone calls
placed by Amirnazmi to certain family members during his
pretrial imprisonment at the Federal Detention Center
(FDC). 40 Amirnazmi argues the government violated Fed. R.
40
We review a district court’s decision to admit or exclude
evidence, “if premised on a permissible view of the law,” for
an abuse of discretion. United States v. Sokolow, 91 F.3d 396,
402 (3d Cir. 1996). Amirnazmi initially challenged the tape
recordings under the Wiretap Act, 18 U.S.C. § 2510 et seq.
The District Court rejected this argument in its Feb. 6, 2009
Order admitting the tapes, and Amirnazmi declined to renew
this objection in either his Rule 33 motion or in the briefing
materials he has submitted in support of his current appeal.

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Crim. P. 17(c) by impermissibly using subpoenas as
discovery devices. Rule 17(c), which governs the issuance of
subpoenas duces tecum in federal criminal proceedings, is
“not intended to provide a means of discovery for criminal
cases.” United States v. Nixon, 418 U.S. 683, 698 (1974),
superseded by statute on other grounds as stated in Bourjaily
v. United States, 483 U.S. 171, 177-79 (1987); see also
United States v. Cuthbertson, 630 F.2d 139, 144 (3d Cir.
1980). Rather, the rule was designed “to expedite [a] trial by
providing a time and place before trial for the inspection of
the subpoenaed materials.” Bowman Dairy Co. v. United
States, 341 U.S. 214, 220 (1951). Notably, the Rule 17(c) test
outlined in Nixon pertains to the production of documents in
advance of trial. 418 U.S. at 698-700.

Here, the government served a series of trial subpoenas
on the FDC’s Custodian of Records requiring him to appear
on a specified date and to bring with him copies of
Amirnazmi’s telephonic communications aside from those
shielded by attorney-client privilege. Critically, the dates
returnable of the subpoenas paralleled the then-scheduled trial
dates and noted that the witness was “subject to call.”
Because the subpoenas did not require pre-trial production,
the District Court concluded Nixon was not controlling and
the government had not run afoul of Rule 17(c). Amirnazmi,
however, argues the government implicitly understood that
the FDC would expedite its production of the requested
evidence. That is, based on the alacrity with which the FDC
habitually responds to subpoenas received from the United
States Attorney’s Office, Amirnazmi believes the government
anticipated the FDC turning around the subpoenas in short

69
order and consequently having access to the communications
well in advance of trial. Thus, he argues the protections
embodied in Nixon against the misuse of pre-trial subpoenas
should apply notwithstanding the formal returnable dates on
the subpoenas.

Although the District Court rejected Amirnazmi’s
invitation to adopt a broad reading of Rule 17(c) both at the
suppression hearing and in its denial of his Rule 33 motion,
Amirnazmi again seeks a ruling that Nixon’s gloss on Rule
17(c) applies with equal force to trial subpoenas likely to
yield pre-trial production. Amirnazmi discerns support in
United States v. Noriega, 764 F. Supp. 1480, 1494 (S.D. Fla.
1991), for the broad proposition that trial subpoenas may not
be used to procure advance production of a defendant’s
prison-recorded conversations without first obtaining leave of
court. Significantly, in Noriega, the subpoenas directed the
custodian of records to appear and testify on various dates,
none of which corresponded with scheduled hearings in the
case. Id. at 1482. Because no proceedings were scheduled on
the dates indicated in the subpoenas, the court found it
unmistakable that the subpoenas “constituted a broad
dragnet” designed to “enable the prosecution to examine
these recordings prior to trial in order to obtain additional
discovery against the defendant.” Id. at 1492-93.
Additionally, the court noted that subpoenas are more likely
to be used for impermissible discovery purposes “when
advance production of materials is sought instead of the usual
production at time of trial or other proceeding in which they
are to be used in evidence.” Id. at 1493.

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 Here, the government issued subpoenas that complied
with the facial requirements of trial subpoenas. On other
facts, such formalistic compliance may be insufficient to
mask the government’s efforts to make an end run around
Nixon. However, the record before us does not demonstrate
such an impermissible discovery motive. We therefore
conclude that the District Court did not abuse its discretion in
admitting the recordings as evidence. 41

41
Furthermore, Amirnazmi claims the trial was tainted by the
admission of these telephone recordings but does not explain
how the result would have been different were they to have
been excluded. As the District Court astutely noted,

The probative value of these tape recordings
lies in their value as evidence of Defendant’s
state of mind. Yet, the jury was presented with a
plethora of other evidence from which
Defendant’s state of mind could be determined,
including Defendant’s repeated contradictory
statements about his business dealings in Iran,
and the multiple times he was put on notice of
the restrictions on trade with Iran. Therefore,
even assuming the Court erred in admitting
these tape recordings, such error would not have
had a substantial impact on the verdict and
would not warrant a new trial.

648 F. Supp. 2d at 720 n.18.

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 VI.

For the foregoing reasons, we will affirm the jury’s
verdict and the District Court’s imposition of a four-year
prison sentence.

72