United States v. Jason Phifer (11th Cir. September 2018)

The Federal Docket

September 26, 2018

Drug Offenses – The definition of “positional isomer” under 21 C.F.R. § 1300.01(b) does not apply to substances temporarily classified as controlled substances under 21 C.F.R. 1308.11(h).

Rule of LenityAuer deference does not apply to criminal regulations and that courts must decide whether a criminal regulation unambiguously prohibits the acts charged.

Jason Phifer was convicted after a trial of possession with intent to distribute a controlled substance, namely a substance called “ethylone.” At issue for the Court was whether ethylone is a “positional isomer” of butylone, and therefore an illegal controlled substance. The Court reversed Phifer’s conviction, holding that the DEA’s definition of a “positional isomer” did not unambiguously apply to ethylone.

In a highly technical opinion, the Eleventh Circuit was tasked with determining whether the DEA’s “regulatory definition” for the phrase “positional isomer” unambiguously applied to ethlyone, which the DEA asserted was a positional isomer of butylone, a known designer drug.

Under 21 C.F.R. § 1308.11(h), certain substances may be scheduled as controlled substances on a temporary basis while awaiting eventual permanent scheduling. In March 2014, the DEA issued an order temporarily scheduling butylone as a Schedule I controlled substance, along with “its optical, positional, and geometric isomers…”

The DEA defines “positional isomer” under 21 C.F.R. § 1300.01(b), as “any substance possessing the same molecular formula and core structure and having the same functional group and/or substitute as those found in the respective Schedule I hallucinogen, attacked at any position on the core structure.”

The government and Phifer agreed that, under the DEA’s preferred definition, butylone and ethylone would be positional isomers of each other. However, Phifer argued that the DEA’s definition of “positional isomer” under § 1300.01(b) does not apply to temporarily scheduled substances. Indeed, according to the text of § 1300.01(b), its definition applies to the term “as used in § 1308.11(d),” the statute governing permanently, not temporarily, scheduled controlled substances.

Since the DEA’s regulatory definition applied only to permanently scheduled drugs, Phifer contended that “positional isomer” should be defined by its commonly understood scientific meaning. Applying this definition, Phifer had an expert witness testify at trial that butylone and ethylone would not be commonly understood as positional isomers to each other because they lack the same carbon skeleton. The trial court, however, refused to instruct the jury on Phifer’s proposed definition of “positional isomers” and instead instructed the jury on the DEA’s preferred definition.

On appeal, the Court first held that the definition of “positional isomer” under § 1300.01(b) did not unambiguously apply to temporarily scheduled controlled substances under § 1308.11(h). In light of that ambiguity, the Court weighed whether to defer to the DEA’s definition under Auer v. Robbins, 519 U.S. 452 (1997).

The Court acknowledged that there were several factors indicating it should defer to the DEA’s interpretation under Auer. Nonetheless, the Court declined to apply Auer deference because the law in question was a criminal regulation, not a typical agency regulation. Citing the Rule of Lenity, the Court held that “Auer deference does not apply in criminal cases.” Rather, the Court should look “solely at the language of the regulatory provision at issue to determine whether it unambiguously prohibits the act charged.”

The Court remanded the case to the district court with instructions to conduct a Daubert hearing and define “positional isomer” in its jury instructions “in all ways that [the court] has found are generally accepted within the scientific community.” Only if the jury finds that ethylone satisfies one of those definitions can Phifer be convicted.

Appeal from Middle District of Florida

Opinion by Rosenbaum, joined by Jordan and Dubina

Concurrence by Jordan

Click here to read the opinion.

Tom Church - Tom is a trial and appellate lawyer focusing on criminal defense and civil trials. Tom is the author of "The Federal Docket" and is a contributor to Mercer Law Review's Annual Survey in the areas of federal sentencing guidelines and criminal law. Tom graduated with honors from the University of Georgia Law School where he served as a research assistant to the faculty in the areas of constitutional law and civil rights litigation. Read Tom's reviews on AVVO. Follow Tom on Linkedin.

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