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Eleventh Circuit Rules DEA’s Definition of Positional Isomer Does Not Apply to Substances on Temporary Schedule, Vacates Possession Conviction

by Matt Clarke 

The U.S. Court of Appeals for the Eleventh Circuit held that neither the definition of “positional isomer” set forth in 21 C.F.R. § 1300.0l(b) nor the specific inclusion of ethylone as a positional isomer of the temporary-scheduled substance butylone on the website of the Drug Enforcement Agency (“DEA”) suffice to legally define ethylone as a positional isomer of butylone in a prosecution for violations of the Controlled Substances Act, 21 U.S.C. §§ 841(a)(l) and 84l(b)(l)(C). Thus, the Court vacated Jason Phifer’s conviction for possession with intent to distribute a controlled substance in violation of the foregoing statutes.

Phifer was convicted of possession with intent to distribute ethylone. At the time he was arrested, ethylone was not on the DEA’s permanent schedule of controlled substance, 21 C.F.R. § 1308.l(a). Instead, the prosecution took place under the theory that ethylone was a “positional isomer” of butylone, a substance also absent from the permanent schedule but which the DEA had placed on its temporary schedule of controlled substances, 21 C.F.R. § 1308.ll(h), along with “its optical, positional, and geometric isomers.” The issue at trial and on appeal was whether ethylone is a positional isomer of butylone. As the Court observed, if ethylone is, then Phifer’s conviction stands, but if it isn’t, then “we must set aside Phifer’s conviction.” 

Isomers are molecules that share the same chemical formula but differ in the spatial position of, or connections between, their constituent atoms. Isomers differ in chemical and physical properties. It is clear that ethylone is an isomer of butylone. Whether it is a “positional isomer” is less clear. 

In 21 C.F.R. § 1300.0l(b), the DEA defines “positional isomers” as substances with the same molecular formula, core structure, and functional groups or substituents. The parties agreed that, under that definition, ethylone is a positional isomer of butylone. However, by its own terms, the definitions in § 1300.0l(b) are limited in application to the substances listed on the permanent schedule in 21 CF.R. § 1308.ll(d). Neither butylone nor ethylone were listed on the permanent schedule at the time of Phifer’s arrest. Butylone has since been permanently scheduled, but that cannot be applied retroactively to an alleged possession that occurred before the permanent listing took place. 

At trial and outside the jury’s presence, Phifer offered testimony from a professor recognized by both parties as an expert in organic chemistry. The professor testified that, under a widely accepted definition of the types of isomers, ethylone was a skeletal isomer of butylone, not a positional isomer. The trial court refused to present that definition to the jury. 

On appeal, the DEA pointed out that its website listed ethylone as a positional isomer of butylone and asserted that its definition should apply to the prosecution both under § 1300.0l(b) and its website, pursuant to the deference the Supreme Court gives promulgating agencies under Auer v. Robbins, 519 U.S. 452 (1997). Phifer countered that § 1300.0l(b) excludes itself from applying to substances listed in § 1308.ll(h), and the rule of lenity trumps Auer in criminal cases. Under the rule of lenity, a court must resolve ambiguous criminal law in favor of the defendant. 

The Eleventh Circuit held that § 1300.0l(b)’s definition does not govern the meaning of “positional isomer” in § 1308.ll(h), and the rule of lenity overrides Auer. In addition, the DEA’s website does not govern it. 

The Court could not determine what definition does apply. Accordingly, it reversed Phifer’s conviction and remanded the case with instructions for the trial court to hold a hearing to determine all of the generally accepted scientific definitions of “positional isomer” to provide the jury with those definitions and instructions to find Phifer not guilty should ethylone not be a positional isomer of butylone under any definition presented. See: United States v. Phifer, 909 F.3d 372 (11th Cir. 2018). 

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United States v. Phifer



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