United States District Court, D. Maine
ORDER ON TREATMENT OF ALPHA-PVP UNDER UNITED STATES
A. WOODCOCK, JR. UNITED STATES DISTRICT JUDGE.
Brewer pleaded guilty to one count of engaging in a
conspiracy to distribute and possess
alpha-pyrrolidinopentiophenone (Alpha-PVP), a controlled
substance not listed in the United States Sentencing
Guideline Drug Quantity Table or the Drug Equivalency Tables.
He now asks the Court to use pyrovalerone, a schedule V
substance, not methcathinone, a schedule I substance, to
calculate his drug quantity and base offense level under the
Sentencing Guidelines, on the ground that Alpha-PVP is more
closely related to pyrovalerone. The Court denies Mr.
Brewer’s request, first because the statute requires a
comparison only to a controlled substance in schedules I or
II, and also because as a matter of fact Alpha-PVP is more
closely related to methcathinone than to pyrovalerone.
The Charge and Conviction
January 23, 2015, Nathan Brewer waived his right to
prosecution by indictment and pleaded guilty to Count 1 of an
information, charging him with conspiracy to distribute and
possess: (1) prior to March 7, 2014, a mixture or substance
containing a detectable amount of Alpha-PVP, a controlled
substance analogue as defined in 21 U.S.C. § 802(32);
and (2) from March 7, 2014 until a date unknown, but no
earlier than June 1, 2014, a mixture or substance containing
a detectable amount of Alpha-PVP, a schedule I controlled
substance, all in violation of 21 U.S.C. §§ 813,
841(a)(1), and 846. Waiver of Indictment (ECF No.
3); Information (ECF No. 4); Entry (ECF No.
The Presentence Report
17, 2015, the Probation Office (PO) prepared a revised
presentence investigation report, which set forth its
guideline calculations. Presentence
Investigation Report (PSR). Based on a total drug
quantity of 989.1 kilograms of marijuana equivalent, the PO
concluded that Mr. Brewer had a base offense level of 28.
Id. at 6. To determine drug quantity, the PO
attributed to Mr. Brewer: (1) 1.008 kilograms of Alpha-PVP
discovered on February 26, 2014, when Mr. Brewer’s
younger brother picked up a package of bath salts at the post
office; (2) 120.8 grams of Alpha-PVP from a June 16, 2014
package also picked up at a post office; and (3) 2, 603 grams
of Alpha-PVP that reflect sales Mr. Brewer made to a source
of information from November 2013 to February 2014.
Id. at 4-5.
The Presentence Conference and Subsequent Memoranda
August 5, 2015, during a pre-sentence conference, defense
counsel argued that the PO and the Drug Enforcement Agency
(DEA) had wrongly determined that Alpha-PVP was more closely
related to methcathinone for drug quantity purposes, and that
instead pyrovalerone – a schedule V controlled
substance – was more closely related. See
Entry (ECF No. 29); Mot. to Extend Time to Obtain
Expert Op. Re: Alpha- PVP and Pyrovalerone (ECF
No. 30). The Government filed a memorandum on February 12,
2016, submitting that Alpha-PVP should be compared to
methcathinone, not pyrovalerone, for sentencing purposes.
Gov’t’s Mem. in Aid of Sentencing Re:
Alpha-PVP, Methcathinone, and Pyrovalerone (ECF No. 63)
(Gov’t’s Mot.). Mr. Brewer responded in
opposition to the Government’s memorandum on March 11,
2016. Def.’s Sentencing Mem. in Resp. to
Gov’t’s Mem. Re: the Appl. of Pyrovalerone under
the Sentencing Guidelines (ECF No. 70) (Def.’s
Opp’n). The Government replied on March 25, 2016.
Gov’t’s Resp. Mem. in Aid of Sentencing Re:
Alpha-PVP, Methcathinone, and Pyrovalerone (ECF No. 74)
THE PARTIES’ POSITIONS
The Government’s Memorandum in Aid of
Sentencing Regarding Alpha-PVP,
Methcathinone, and Pyrovalerone
Government argues that Alpha-PVP is substantially similar to
methcathinone, a schedule I controlled substance, in both
chemical structure and stimulant effect on the central
nervous system, and pursuant to 21 U.S.C. § 802(32)(A),
under the United States Sentencing Guidelines (U.S.S.G.)
should be compared to methcathinone for activity occurring
prior to March 7, 2014. Gov’t’s Mot. at
2. In response to Mr. Brewer’s claim that pyrovalerone,
a schedule V controlled substance, should be used as a
controlled substance analogue to Alpha-PVP for sentencing
purposes, the Government asserts that a controlled substance
analogue can only be compared to substances in schedule I or
II, and thus, even if pyrovalerone were more similar in
structure and physiological effect, methcathinone is the most
appropriate analogue to Alpha-PVP for sentencing.
the Government argues that after March 7, 2014, when
Alpha-PVP was designated as a schedule I controlled substance
but not specifically referenced in the Sentencing Guidelines,
in order to determine the correct drug comparison for
sentencing purposes, it is necessary to refer to U.S.S.G.
§ 2D1.1, Application Note 6. Id. at 4;
see Section III(C), infra. Applying the
Application Note 6 rubric, the Government contends that,
based on the reports provided by its experts, Alpha-PVP is
substantially similar in chemical structure and physiological
effect to methcathinone, and “is at least as potent if
not more potent than methcathinone in drug discrimination
Government also points to United States v. Moreno,
No. 15-cr-15-jdp, 2015 WL 6071680 (E.D. Wis. Oct. 15, 2015)
to counter Mr. Brewer’s assertion that pyrovalerone is
the more closely related analogue to Alpha-PVP. Id.
at 5. The Eastern District of Wisconsin held:
The guideline does not instruct the court, as defendants ask,
to sentence defendants based on the most closely related
controlled substance from among the (expanding) universe of
controlled substances. Rather, Application Note 6 tells the
court to find the most closely related controlled substance
from among those referenced in the guideline.
Pyrovalerone is not listed in either the Drug Quantity Table
or the Drug Equivalency Table. Thus, it is irrelevant how
closely analogous Alpha– PVP is to pyrovalerone because
pyrovalerone is not an available comparator under the
Id. (citing Moreno, 2015 WL 6071680 at *2)
(emphasis in original).
to rebuff any argument that Alpha-PVP has only minor effects
on its users, the Government turns to the testimony from
Moreno of three Alpha-PVP users, which includes,
inter alia, that the drug made them paranoid, unable to
sleep, made other users violent, and was more exhilarating
and addictive than methamphetamine. Id. at 5-6.
Nathan Brewer’s Response to the Government
Brewer does not dispute that Alpha-PVP was a controlled
substance analogue prior to March 7, 2014. Def.’s
Opp’n at 1 n.1. Instead, his argument is that
pyrovalerone is more closely related to Alpha-PVP, and
pyrovalerone should be considered for sentencing purposes in
setting the base offense level under the Sentencing
disprove the Government’s experts, Mr. Brewer puts
forth two expert opinions to support the assertion that
pyrovalerone, not methcathinone, “is the most closely
related controlled substance to Alpha-PVP, ” both
structurally and in its effects on the body. Id. at
2-3. One expert opinion explicitly states that methcathinone
is not to be considered “most similar”
structurally to Alpha-PVP, as it has significant molecular
differences when compared to Alpha-PVP, while pyrovalerone is
almost identical to Alpha-PVP. Id. at 2. Mr. Brewer
also provides a report that he contends supports that the
dosage of pyrovalerone needed to effect the body is no
different from Alpha-PVP or methcathinone. Id. at 5.
Mr. Brewer argues that there is ambiguity regarding whether
pyrovalerone can be considered under the Sentencing
Guidelines, and as such the rule of lenity “should tip
the balance in favor of the application of
pyrovalerone.” Id. at 6. Specifically, Mr.
Brewer turns to the language in Application Note 6 which
states: “In the case of a controlled substance that is
not specifically referenced in this guideline,
determine the base offense level using the marihuana
equivalency of the most closely related controlled
substance referenced in this guideline.”
Id. at 8 (citing U.S.S.G. § 2D1.1, app. n.6)
(emphasis provided by Defendant). From this, he argues that
because schedule V controlled substances are
“referenced” in the Sentencing Guidelines, and
that pyrovalerone is a schedule V controlled substance, there
is ambiguity as to whether pyrovalerone is actually a
“controlled substance referenced in the
guideline.” Id. Moreover, Mr. Brewer contends
that the Government’s argument that the “most
closely” related controlled substance must be
specifically listed in the Sentencing Guideline Table is not
supported by the language of Application Note 6. Id.
at 9. He argues that the Government’s position would
render meaningless the Sentencing Guidelines’
conversion rate of a schedule V controlled substance to
marijuana. Id. at 10-11.
Mr. Brewer submits that following the Government’s
argument would create an unwarranted sentencing disparity
under 18 U.S.C. § 3553(a), because he would be sentenced
using methcathinone, when pyrovalerone is more similar to
Alpha-PVP. Id. at 13.
The Government’s Reply
Government notes that when considering Mr. Brewer’s
concession that Alpha-PVP was a controlled substance analogue
prior to March 7, 2014 (making it an analogue to a controlled
substance in schedule I or II), and the fact that Alpha-PVP
became a schedule I substance after March 7, 2014, it is
illogical for Alpha-PVP to be compared to a schedule V
controlled substance. Gov’t’s Reply at
1. This point, the Government argues, is further emphasized
when the effects of Alpha-PVP on users are taken into
consideration, such as paranoia, propensity for violence, and
addiction on a level equal to or greater than
methamphetamine. Id. at 1-2.
the Government disagrees with Mr. Brewer’s reading of
Application Note 6, and specifically that had the Sentencing
Commission intended for “referenced” to apply to
an entire schedule of drugs (schedule V), it would have
written language to that effect. Id. at 2. Likewise,
the Government points out that Mr. Brewer’s assessment
of Application Note 6 ignores Application Note 8(a), which
makes it unnecessary to use Application Note 6 for schedule V
controlled substances like pyrovalerone because all schedule
V controlled substances receive the same marijuana
equivalency pursuant to Application Note 8(a). Id.
while the Government agrees that the chemical compositions of
pyrovalerone, methcathinone, and Alpha-PVP are similar, with
respect to the pharmacological effects of pyrovalerone, it
contends that Mr. Brewer’s expert has provided limited
and confusing evidence on the issue, equivocating on the
actual physiological effects of pyrovalerone. Id. at
3. The Government’s expert, it contends, has provided
evidence on the actual physiological effects of using
methcathinone and Alpha-PVP, specifically that both produce
stimulus effects similar to methamphetamine or cocaine.
Id. at 4.
STATUTORY AND REGULATORY BACKGROUND
The Controlled Substance Analogue Enforcement Act of 1986:
Application to Pre–March 7, 2014 Conduct
enacted the Controlled Substance Analogue Enforcement Act of
1986 (Analogue Act) “to prevent ‘underground
chemists’ from creating new drugs that have similar
effects on the human body as drugs explicitly prohibited
under the federal drug laws.” United States v.
Ketchen, No. 1:13-CR-00133-JAW, 2015 WL 3649486, at *6
(D. Me. June 11, 2015) (citing United States v.
McFadden, 753 F.3d 432, 436 (4th Cir. 2014), vacated
and remanded, 135 S.Ct. 2298 (2015); United
States v. Hodge, 321 F.3d 429, 437 (3d Cir. 2003)
(purpose of the Analogue Act is to “make illegal the
production of designer drugs and other chemical variants of
listed controlled substances that otherwise would escape the
reach of the drug laws”)). The Analogue Act provides:
A controlled substance analogue shall, to the extent intended
for human consumption, be treated, for the purposes of any
Federal law as a controlled substance in schedule I.
21 U.S.C. § 813. Except as provided in subparagraph (C)
of 21 U.S.C. § 802(32),  the term “controlled
substance analogue” means a substance:
(i) the chemical structure of which is substantially similar
to the chemical structure of a controlled substance in
schedule I or II;
(ii) which has a stimulant, depressant, or hallucinogenic
effect on the central nervous system that is substantially
similar to or greater than the stimulant, depressant, or
hallucinogenic effect on the central nervous system of a
controlled substance in schedule I or II; or
(iii) with respect to a particular person, which such person
represents or intends to have a stimulant, depressant, or
hallucinogenic effect on the central nervous system that is
substantially similar to or greater than the stimulant,
depressant, or hallucinogenic effect on the central nervous
system of a controlled substance in schedule I or II.
21 U.S.C. § 802(32)(A). Together, these provisions have
been interpreted to require the Government prove three
elements: (1) substantial chemical similarity between the
analogue and the controlled substance (the chemical structure
element), see 21 U.S.C. § 802(32)(A)(i); (2)
substantially similar actual, intended, or represented
physiological effects on the central nervous system (the
pharmacological similarity element), see 21 U.S.C.
§ 802(32)(A)(i), (ii); and, (3) intent that the
substance be consumed by humans (the human consumption
element), see id. § 813. See
McFadden, 753 F.3d at 436 (citing United States
v. Klecker, 348 F.3d 69, 71 (4th Cir. 2003)).
have routinely upheld the application of the Analogue Act to
analogue chemicals. See United States v. Sullivan,
714 F.3d 1104 (8th Cir. 2013) (4– methylmethcathinone);
United States v. Berger, 553 F.3d 1107 (8th Cir.
2009) (1, 4– butanediol); United States v.
Roberts, 363 F.3d 118 (2d Cir. 2004) (1,
4–butanediol); United States v. Klecker, 348
F.3d 69 (4th Cir. 2003) (5–methoxy–N,
N-diisopropyltryptamine); United States v. Washam,
312 F.3d 926 (8th Cir. 2002) (1, 4– butanediol);
United States v. Fisher, 289 F.3d 1329 (11th Cir.
2002) (gamma-butyrolactone); United States v.
Carlson, 87 F.3d 440 (11th Cir. 1996) (3, 4–
methylenedioxymethamphetamine); United States v.
Hofstatter, 8 F.3d 316 (6th Cir. 1993) (ephedrine and
Designating Alpha-PVP as a Schedule 1 Controlled
March 7, 2014, the Deputy Administrator of the DEA issued a
final order to temporarily schedule 10 synthetic cathinones
into schedule I pursuant to the temporary scheduling
provisions of the Controlled Substances Act (CSA). Schedules
of Controlled Substances: Temporary Placement of 10 Synthetic
Cathinones Into Schedule I, 79 Fed. Reg. 12938 (Mar. 7,
2014). Among the 10 substances, Alpha-PVP was included.
Id. The DEA further stated that “[t]his action
is based on a finding by the Deputy Administrator that the
placement of these synthetic cathinones . . . into schedule I
of the CSA is necessary to avoid an imminent hazard to the
public safety.” Id. The DEA went on to state:
Many synthetic cathinones produce pharmacological effects
substantially similar to the schedule I substances cathinone,
methcathinone, and 3, 4-methylenedioxymethamphetamine (MDMA)
and schedule II stimulants amphetamine, methamphetamine, and
cocaine. [Alpha-PVP is a] synthetic cathinone and [is]
structurally and pharmacologically similar to amphetamine,
MDMA, cathinone, and other related substances. Accordingly,
these synthetic cathinone substances share substantial
similarities with schedule I and schedule II substances with
respect to desired and adverse effects. In general, desired
effects reported by abusers of synthetic cathinone substances
include euphoria, sense of well-being, increased sociability,
energy, empathy, increased alertness, and improved
concentration and focus. Abusers also report experiencing
unwanted effects such as tremor, vomiting, agitation,
sweating, fever, and chest pain. . . . These synthetic
cathinone substances have no known medical use in the United
States but evidence demonstrates that these substances are
being abused by individuals. There have been documented
reports of emergency room admissions and deaths associated
with the abuse of synthetic cathinone substances.
The Guideline Analysis: U.S.S.G. § 2D1.1
§ 2D1.1 applies at sentencing for violations of 21
U.S.C. § 841(a). The first step in the drug quantity
analysis under U.S.S.G. § 2D1.1 is to determine whether
the drug at issue is listed in the Drug Quantity Table (DQT).
U.S.S.G. § 2D1.1(c). However, the DQT covers only a
small number of controlled substances, and as is the case
with Alpha-PVP, when the controlled substance is not in the
DQT, the second step is to check the Drug Equivalency Tables
(DETs). U.S.S.G. § 2D1.1, app. n.8(D). The DETs convert
a larger number of controlled substances into marijuana
equivalent weights for purposes of determining the offense
level. Alpha– PVP is also not listed in the DETs.
substance is not listed in either the DQT or the DETs,
Application Note 6 requires that the base offense level be
determined using the marijuana equivalency of “the most
closely related controlled substance referenced in this
guideline.” U.S.S.G. § 2D1.1, app. n.6.
Application Note 6 reads in relevant part:
For purposes of this guideline "analogue" has the
meaning given the term "controlled substance
analogue" in 21 U.S.C. § 802(32). In determining
the appropriate sentence, the court also may consider whether
the same quantity of analogue produces a greater effect on
the central nervous system than the controlled substance for
which it is an analogue.
In the case of a controlled substance that is not
specifically referenced in this guideline, determine the base
offense level using the marihuana equivalency of the most
closely related controlled substance referenced in this
guideline. In determining the most closely related controlled
substance, the court shall, to the extent practicable,
consider the following:
(A) Whether the controlled substance not referenced in this
guideline has a chemical structure that is substantially
similar to a controlled ...