United States v. Brewer, 1:15-cr-00003-JAW

CourtUnited States District Courts. 1st Circuit. United States District Court (Maine)
Docket Number1:15-cr-00003-JAW
Decision Date28 June 2016




June 28, 2016


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.


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

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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-

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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).


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.

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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

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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.

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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

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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.


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