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United States v. Brewer

United States District Court, D. Maine

June 28, 2016

UNITED STATES OF AMERICA
v.
NATHAN BREWER

          ORDER ON TREATMENT OF ALPHA-PVP UNDER UNITED STATES SENTENCING GUIDELINES

          JOHN A. WOODCOCK, JR. UNITED STATES DISTRICT JUDGE.

         Nathan 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.

         I. BACKGROUND

         A. The Charge and Conviction

         On 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. 12).

         B. The Presentence Report

         On June 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.

         C. The Presentence Conference and Subsequent Memoranda

         On 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) (Gov’t’s Reply).

         II. THE PARTIES’ POSITIONS

         A. The Government’s Memorandum in Aid of Sentencing Regarding Alpha-PVP, Methcathinone, and Pyrovalerone

         The 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. Id.

         Further, 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 studies.” Id.

         The 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 guideline.

Id. (citing Moreno, 2015 WL 6071680 at *2) (emphasis in original).

         Finally, 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.

         B. Nathan Brewer’s Response to the Government

         Mr. 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 Guidelines.[1] Id.

         To 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.

         Additionally, 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.

         Finally, 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.

         C. The Government’s Reply

         The 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.

         Furthermore, 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. at 2-3.

         Finally, 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.

         III. STATUTORY AND REGULATORY BACKGROUND

         A. The Controlled Substance Analogue Enforcement Act of 1986: Application to Pre–March 7, 2014 Conduct

         Congress 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)[2]; 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), [3] 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)).

         Courts 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 phenylpropanolamine).

         B. Designating Alpha-PVP as a Schedule 1 Controlled Substance

         On 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.

Id.

         C. The Guideline Analysis: U.S.S.G. § 2D1.1

         U.S.S.G. § 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.

         When a 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 ...

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