In the
United States Court of Appeals
For the Seventh Circuit
____________________
No. 15‐3312
UNITED STATES OF AMERICA,
Plaintiff‐Appellee,
v.
MICHAEL R. MORENO,
Defendant‐Appellant.
____________________
Appeal from the United States District Court for the
Western District of Wisconsin.
No. 15‐cr‐00015 — James D. Peterson, Judge.
____________________
ARGUED DECEMBER 9, 2016 — DECIDED AUGUST 30, 2017
____________________
Before WILLIAMS and HAMILTON, Circuit Judges, and
CHANG, District Judge.
CHANG, District Judge. Alpha‐PVP is a designer drug that
produces a powerful stimulant effect in its users. This effect,
plus the drug’s high potential for abuse, landed Alpha‐PVP
on the federal government’s Schedule I of controlled sub‐
Of the Northern District of Illinois, sitting by designation.
2 No. 15‐3312
stances. Michael Moreno pled guilty to importing Alpha‐
PVP from China and dealing the drug in northwestern Wis‐
consin. He now appeals the 80‐month prison sentence im‐
posed by the district court for that drug trafficking. Specifi‐
cally, Moreno argues that the district court assigned the
wrong offense level to Alpha‐PVP when calculating the Sen‐
tencing Guidelines range. Alpha‐PVP is not specifically
listed in the Sentencing Guidelines drug‐quantity tables, so
the Guidelines required the district court to determine the
“most closely related” controlled substance, U.S.S.G.
§ 2D1.1, appl. n.6, and then use that drug’s offense level for
Alpha‐PVP. After holding an evidentiary hearing, the district
court found that the most closely related drug is methcathi‐
none, which is another Schedule I controlled substance. Alt‐
hough we have a different take than the district court on the
legal question of how to apply the pertinent Guideline, we
affirm because the district court’s careful and thorough factu‐
al finding was correct.
I.
Moreno began selling Alpha‐PVP (which is shorthand for
Alpha‐pyrrolidinovalerophenone) back in 2012, Presentence
Report (PSR) ¶ 14, even before the designer drug was listed
on any Schedule of controlled substances. On March 7, 2014,
the federal government listed Alpha‐PVP as a Schedule I
controlled substance. Schedule I is reserved for those drugs
that have a “high potential for abuse,” have “no currently
accepted medical use in treatment in the United States,” and
“lack … accepted safety for use,” even under medical super‐
vision. 21 U.S.C. § 812(b)(1)(A)‐(C). After Alpha‐PVP made it
onto Schedule I, Moreno conspired to sell at least 2.1 kilo‐
No. 15‐3312 3
grams of it in northwestern Wisconsin. PSR ¶ 78. (For a sense
of what that quantity means in practical terms, an individual
dose of Alpha‐PVP is around half a gram. Sentencing Tr. at
93.)
After Moreno pled guilty, the case headed to sentencing,
with the primary dispute being what offense level to assign
to Alpha‐PVP. As noted earlier, because the Sentencing
Guidelines do not explicitly set an offense level for Alpha‐
PVP, the district court had to figure out which controlled
substance is “most closely related” to Alpha‐PVP. U.S.S.G.
§ 2D1.1, appl. n.6. The government proposed methcathinone,
which is another Schedule I controlled substance. In support
of that proposal, the government offered the testimony of
two DEA scientists and three users of Alpha‐PVP. Against
this, and in order to argue that a substance called pyro‐
valerone was more closely related, the defense proffered ex‐
pert‐witness declarations of a forensic scientist and a phar‐
macologist. (The defense declarations had been submitted in
other cases; a fuller description of the parties’ evidence is
discussed later in this opinion.) After holding an evidentiary
hearing, the district court found that the most closely related
drug is, as proposed by the government, methcathinone.
With that finding in place, the district court calculated the
advisory Sentencing Guidelines range, considered the 18
U.S.C. § 3553(a) factors, and imposed a sentence of 80
months’ imprisonment.
4 No. 15‐3312
II.
Usually, it is easy to figure out what Sentencing Guide‐
lines offense level to assign to a particular quantity of drugs,
because Guideline § 2D1.1 contains two tables that explicitly
tell us the answer for the most commonly prosecuted drugs.
U.S.S.G. § 2D1.1(c) (Drug Quantity Table), § 2D1.1, appl.
n.8(D) (Drug Equivalency Tables). When a controlled sub‐
stance does not appear on either table, the Guidelines re‐
quire that the district court determine which controlled sub‐
stance is “most closely related” to the drug at issue, and then
use that controlled substance’s offense level:
In the case of a controlled substance that is not
specifically referenced in this guideline, deter‐
mine the base offense level using the marihua‐
na equivalency of the most closely related con‐
trolled substance referenced in this guideline.
U.S.S.G. § 2D1.1, appl. n.6. The application note goes on and
provides guidance on how to determine which controlled
substance is most closely related to the one at issue. In es‐
sence, courts must look for similarities in chemical structure
and in effects:
In determining the most closely related con‐
trolled substance, the court shall, to the extent
practicable, consider the following:
(A) Whether the controlled substance not ref‐
erenced in this guideline has a chemical struc‐
ture that is substantially similar to a controlled
substance referenced in this guideline.
No. 15‐3312 5
(B) Whether the controlled substance not refer‐
enced in this guideline has a stimulant, depres‐
sant, or hallucinogenic effect on the central
nervous system that is substantially similar to
the stimulant, depressant, or hallucinogenic ef‐
fect on the central nervous system of a con‐
trolled substance referenced in this guideline.
(C) Whether a lesser or greater quantity of the
controlled substance not referenced in this
guideline is needed to produce a substantially
similar effect on the central nervous system as
a controlled substance referenced in this guide‐
line.
Id.
In this appeal, the threshold question is whether More‐
no’s proposed comparator, pyrovalerone, is even—as a mat‐
ter of law—eligible to be considered as the most closely re‐
lated substance to Alpha‐PVP. The government argues that
only those substances that explicitly appear—by name—on
one of the Guidelines’ drug tables (either the Drug Quantity
Table, § 2D1.1(c), or the Drug Equivalency Table, § 2D1.1,
appl. n.8(D)), can serve as a “most closely related” substance.
The government grounds this argument on a clause in appli‐
cation note 6, which says that the district court should search
for the “most closely related controlled substance referenced
in this guideline.” U.S.S.G. § 2D1.1, appl. n.6 (emphasis add‐
ed). Also, each of the three considerations listed in the appli‐
cation note require the district court to compare the drug at
issue with “a controlled substance referenced in this guideline.”
Id., appl. n.6(A)‐(C) (emphasis added). The government then
points out that pyrovalerone is not expressly listed, by spe‐
6 No. 15‐3312
cific name, on either table, so it is ineligible to serve as a
most closely related substance. Indeed, the Tables do not list
any Schedule V drugs by name; instead, the Drug Equiva‐
lency Table groups them all under one entry for “Schedule V
Substances.” U.S.S.G. § 2D1.1 cmt. n.8(D).
Although the government’s position has some force, it re‐
lies on too cramped a reading of the governing Guideline.
The operative text at issue uses a term—“referenced”—that
is broader in meaning than what the government proposes.
The application note does not say that the sentencing court
must search for the most closely related substance that is
specifically “listed” or “named” in the guideline. Instead, the
substance need only be “referenced” in the guideline. And
Schedule V controlled substances are “referenced” in Guide‐
line § 2D1.1: as noted earlier, the Drug Equivalency Table
groups them all under one entry for “Schedule V Substanc‐
es.” U.S.S.G. § 2D1.1 cmt. n.8(D). To make the same point, as
applied in this case: pyrovalerone is a Schedule V controlled
substance and the Drug Equivalency Table assigns a mari‐
huana equivalency to “Schedule V Substances,” so that Table
does refer to pyrovalerone. In light of the reference to Sched‐
ule V Substances, we hold that the application note allows
defendants to propose a Schedule V controlled substance as
the most closely related drug.1
Against this reading, the district court expressed concern
that opening the substance‐comparator analysis to all of the
1 The Sentencing Commission is of course free to revise (or clarify)
the application note so that the parties are limited to proposing only
those controlled substances specifically listed in the Drug Tables by
name.
No. 15‐3312 7
controlled substances on all five DEA Schedules would make
the decisional task all but unworkable, because there would
be too many potential comparators. D. Ct. Opinion at 4. But
there are already around 65 specifically named drugs on the
Drug Equivalency Table, so adding the five specifically
named Schedule V substances, 21 C.F.R. § 1308.15(d), (e),
would not measurably increase the difficulty of the analysis.
More to the point, expanding the potential comparators to
include all controlled substances will not render the task
unworkable. As a practical matter, the district court would
not need to evaluate every single controlled substance be‐
cause the government and the defendant will engage in an
adversarial presentation, proposing what each believes is the
most closely related substance—just as the parties did in this
case. Indeed, even if the defendant refrains from affirmative‐
ly offering a particular controlled substance and simply puts
the government to its burden of proof, still the district court
would not actually be considering every controlled sub‐
stance.
Remember too that the Guidelines instruct the parties
and the district court to consider, to the extent practicable,
three specific factors in determining the most closely related
substance—and those factors will themselves serve a nar‐
rowing function in limiting the field of potential compara‐
tors. The first factor is similarity of chemical structure, so an
expert immediately would be able to exclude substances
with dissimilar chemical structures. The second and third
factors—effect and potency—too will narrow down the po‐
tential comparators. Indeed, neither the government’s ex‐
8 No. 15‐3312
perts nor the experts relied on by Moreno2 expressed any
concerns that the search for a most closely related substance
was too difficult due to the number of controlled substances
available for comparison. So there is no practical hurdle that
undermines the plain‐meaning interpretation of the Guide‐
lines application note: Schedule V substances, like pyro‐
valerone, are “referenced” in the Drug Equivalency Table
and neither the parties nor the district court need cabin the
comparator search to the substances that are listed by specif‐
ic name in the Table.
There is no need, however, for a re‐do of the sentencing.
The district court wisely chose to address whether methcath‐
inone is in fact the most closely related substance to Alpha‐
PVP. To start, the district court noted how unusual it would
be for a Schedule V substance (like pyrovalerone) to be the
most closely related substance for a new Schedule I designer
drug. Sentencing Op. at 4 n.3. By statutory definition,
Schedule V substances must have a “currently accepted
medical use,” 21 U.S.C. § 812(b)(5)(B), which is a mismatch
for a new designer drug that almost surely would not yet
have undergone required testing for medical uses. Sentenc‐
ing Op. at 4 n.3. To be sure, it is possible for the disputed de‐
signer drug to have been created many years ago; indeed,
Alpha‐PVP itself was patented in 1967, as part of a patent on
a family of chemical compounds, so it is possible for a de‐
2 The expert reports offered by Moreno had been submitted in two
other Alpha‐PVP cases. United States v. Brett Lawton et al., Case No. 13‐cr‐
165 (D. Vt.) (Cozzi Declaration of Sept. 20, 2014); United States v. Ryan
Ellis et al., Case No. 13‐cr‐133 (D. Me.) (Bono Declaration of Sept. 22,
2014).
No. 15‐3312 9
signer drug to have undergone testing. More importantly,
however, Schedule V substances—again by statutory defini‐
tion—must have only a “low potential for abuse,” as well as
causing only “limited” physical or psychological depend‐
ence, when viewed relative to Schedule IV substances. 21
U.S.C. § 812(b)(5)(A), (C). It is unlikely that makers and dis‐
tributors of designer drugs would put in the resources to
make, import, or sell (and take on the risk of selling) drugs
with only the most limited potential for abuse. Unfortunate‐
ly, the success of the illegal drug market is premised on
promoting addiction in users to foster demand. So drug traf‐
fickers are not likely chomping at the bit to sell designer
drugs that only have the effects and potency of Schedule V
substances. It is true that, in light of the breadth of designer
drugs, there might still be instances when a Schedule V drug
ends up being the most closely related substance—but that is
likely going to be rare.
Although pyrovalerone started out with two strikes
against it, the district court also thoroughly considered each
of the three factors set forth in application note 6 to Guide‐
lines § 2D1.1. The first factor—similarity of chemical struc‐
ture—did not significantly tip the scales much one way or
the other (if anything, chemical‐structure similarity did serve
the narrowing function that we described earlier). DEA sci‐
entist Daniel Willenbring, whose job duties include analyz‐
ing drugs for assignment to the controlled substance Sched‐
ules, Sentencing Tr. at 14, explained that both methcathinone
and Alpha‐PVP share a “phenethylamine core structure,” id.
at 19‐21. And both substances are classified as cathinones.
Daniel Willenbring Report ¶ 7. At the same time, however,
the expert declarations offered by the defense also showed
10 No. 15‐3312
close structural similarity between pyrovalerone and Alpha‐
PVP. Among other things, pyrovalerone’s chemical formula
differed from Alpha‐PVP’s formula by only one methyl
group (CH3). Joseph Bono Report at 7‐8. Not surprisingly,
the district court correctly found that both the government
and Moreno had persuasively shown that their respective
proposed substances were both substantially similar in
structure to Alpha‐PVP.
So chemical structure alone did not answer the question
as between methcathinone and pyrovalerone. Indeed, when
the district court evaluated the scientific evidence on the
second and third factors—effect and potency—the court
concluded that the competing expert evidence did not con‐
clusively show which substance was more closely related to
Alpha‐PVP. The type of effect produced by methcathinone
use and pyrovalerone use is the same: they both have a
stimulant effect (as distinct from a depressant or hallucino‐
genic effect) on the central nervous system. But the parties
disputed the “maximum” effect of Alpha‐PVP, as well as its
potency. The maximum effect of a drug is the greatest phar‐
macological effect a drug can have, without regard to a limit
on how much the user takes. Potency is a different kind of
comparative measurement, specifically, the amount of a
drug that is needed to produce the same effect when com‐
pared to another drug. The government’s expert on these is‐
sues, Cassandra Prioleau, opined that Alpha‐PVP is similar
to methcathinone in effect and potency, but the opinion was
premised on animal‐based studies and review of some case
reports provided by physicians or law enforcement to the
DEA. And Prioleau did not examine the competing defense
expert report except to “read them briefly,” Sentencing Tr. at
No. 15‐3312 11
79, nor was she able to testify specifically about the data dis‐
cussed in the defense report, id. at 80‐81. But the defense ex‐
pert report too was flawed, as the district court found, be‐
cause the report relied on information reported in a patent
that aggregated data for a family of chemical compounds, ra‐
ther than for Alpha‐PVP specifically. D. Ct. Opinion at 8
(discussing U.S. Patent No. 3,314,970). Nor did the defense
report directly rebut the government expert’s opinion, be‐
cause the defense report was obtained from another sentenc‐
ing, rather than generated in this case.
Although the scientific evidence was a wash, the district
court did find reliable the live, in‐court testimony of three
users of Alpha‐PVP, and their testimony established that the
powerful stimulant effect of the drug was more like
methcathinone instead of the relatively mild pyrovalerone.
Sentencing Tr. at 127‐28 (“I think the stories of the witnesses
that we’ve heard here today really supports the conclusion
that we are not dealing with a drug as benign as ... pyro‐
valerone.”). The users described a litany of effects and addic‐
tion that went well beyond mild stimulus: “It just felt like
something was … coming out of my skin,” id. at 95; “I didn’t
sleep,” “I didn’t eat,” “I lost about 80 pounds in two
months,” id. at 105; “it made you feel like you were going
crazy,” “couldn’t think straight,” id. at 115. Indeed, all three
users testified that Alpha‐PVP had an even more powerful
effect than methamphetamine, id. at 96, 106, 115, which is
treated by the Guidelines even more seriously than
methcathinone, U.S.S.G. § 2D1.1, Drug Equivalency Table
(setting marihuana equivalency of 2 kilograms for one gram
of methamphetamine, and only 380 grams for one gram of
methcathinone) (cited by D. Ct. Op. at 9). Based on the rec‐
12 No. 15‐3312
ord evidence, the district court committed no clear error in
finding that methcathinone is the most closely related sub‐
stance to Alpha‐PVP.3
Moreno’s remaining contention is that the district court
supposedly treated the Sentencing Guidelines generally, and
application note 6 to Guideline § 2D1.1 in particular, as
“mandatory,” Def.’s Br. at 31, and that the district court erred
in doing so. It is not crystal clear where Moreno thinks the
district court went wrong. To the extent that Moreno is argu‐
ing that, in calculating the advisory Guidelines range, the
district court was not bound by the Guidelines, we reject that
notion. Yes, district courts enjoy the discretion, in appropri‐
ate cases, to disagree with the views of the Sentencing
Commission in deciding what the ultimate sentence ought to
be under the overarching sentencing statute, 18 U.S.C.
§ 3553(a). Peugh v. United States, 133 S. Ct. 2072, 2080 (2013)
(citing Pepper v. United States, 562 U.S. 476, 501 (2011)). But
the district court still must adhere to the Guidelines when
calculating the advisory range. Peugh, 133 S. Ct. at 2080
(“First, ‘a district court should begin all sentencing proceed‐
ings by correctly calculating the applicable Guidelines
range.’”) (quoting Gall v. United States, 552 U.S. 38, 49 (2007)).
3 The district court’s finding is consistent with the other sentencing
decisions issued after Alpha‐PVP was added to Schedule I. United States
v. Emerson, 2016 WL 1047006, at *4 (D. Vt. Mar. 10, 2016) (rejecting pyro‐
valerone in favor of methcathinone); United States v. Brewer, 2016 WL
3580614, at *15 (D. Me. June 28, 2016) (same). The Ninth Circuit also af‐
firmed a methcathinone finding in an unpublished order, United States v.
Lane, 616 Fed. App’x 328, 328 (9th Cir. Sept. 17, 2015), but the Ninth Cir‐
cuit’s local rules deem unpublished orders as non‐precedential, 9th Cir.
Rule 36‐3(a).
No. 15‐3312 13
So the district court correctly followed the Sentencing Guide‐
lines and application note 6—without overlaying other
§ 3553(a) considerations—when calculating the advisory
range.
To the extent that Moreno is arguing that the district
court treated the advisory Guidelines range as mandatory,
the record does not bear out that assertion. For one, the dis‐
trict court entertained defense counsel’s arguments for a sen‐
tence below the advisory Guidelines range. See Sentencing
Tr. at 146‐58. Then the district court explained, in detail, why
it was rejecting those arguments in imposing the sentence of
80 months’ imprisonment, and not once mentioned that the
Guidelines range required that sentence (nor did the court
mention that the Guidelines range was presumptively the
right sentence). Id. at 159‐62. What’s more, the district court
imposed a below‐Guidelines sentence on Moreno’s co‐
defendant at the same sentencing hearing in the same case.
See id. at 163. So there is no reason to think that the district
court treated the advisory range as mandatory.
There is one final possible variation of Moreno’s argu‐
ment that the district court treated the Guidelines as manda‐
tory: under 18 U.S.C. § 3553(a), the district court should have
considered pyrovalerone (and the Schedule V marihuana
equivalency) as the most closely related substance. But that
makes no sense because the district court rejected—as a fac‐
tual matter—that Alpha‐PVP had similar effects on users as
pyrovalerone. It would be one thing if the district court had
agreed that pyrovalerone was the right comparator but felt
constrained from applying a Schedule V equivalency due to
the court’s interpretation of the Guidelines that the most
closely related substance must be specifically named in the
14 No. 15‐3312
Drug Tables. But that is not our case: instead, the district
court carefully evaluated the evidence and found that pyro‐
valerone has effects that are dissimilar from Alpha‐PVP. So it
would not make sense for the district court to employ pyro‐
valerone in the § 3553(a) analysis at all. In no way did the
district court err in its consideration of how the Guidelines
interact with § 3553(a).
The judgment is affirmed.