title: Isolation and characterization of a newly identified impurity in methamphetamine synthesized via reductive amination of 1-phenyl-2-propanone (P2P) made from phenylacetic acid/lead (II) acetate.
abstract: A trace processing impurity found in certain methamphetamine exhibits was isolated and identified as trans-N-methyl-4-methyl-5-phenyl-4-penten-2-amine hydrochloride (1). It was determined that this impurity was produced via reductive amination of trans-4-methyl-5-phenyl-4-penten-2-one (4), which was one of a cluster of related ketones generated during the synthesis of 1-phenyl-2-propanone (P2P) from phenylacetic acid and lead (II) acetate. This two-step sequence resulted in methamphetamine containing elevated levels of 1. In contrast, methamphetamine produced from P2P made by other methods produced insignificant (ultra-trace or undetectable) amounts of 1. These results confirm that 1 is a synthetic marker compound for the phenylacetic acid and lead (II) acetate method. Analytical data for 1 and 4, and a postulated mechanism for the production of 4, are presented. Copyright © 2015 John Wiley & Sons, Ltd.
authors.affiliation: Special Testing and Research Laboratory, US Drug Enforcement Administration, 22624 Dulles Summit Court, Dulles, VA, 20166-9509, USA.
authors.forename: Steven G
authors.initials: SG
authors.lastname: Toske
authors.affiliation: North Carolina State Crime Laboratory, 121 East Tryon Road, Raleigh, NC, 27603, USA.
authors.forename: Jennifer B
authors.initials: JB
authors.lastname: McConnell
authors.affiliation: Special Testing and Research Laboratory, US Drug Enforcement Administration, 22624 Dulles Summit Court, Dulles, VA, 20166-9509, USA.
authors.forename: Jaclyn L
authors.initials: JL
authors.lastname: Brown
authors.affiliation: Special Testing and Research Laboratory, US Drug Enforcement Administration, 22624 Dulles Summit Court, Dulles, VA, 20166-9509, USA.
authors.forename: Jennifer M
authors.initials: JM
authors.lastname: Tuten
authors.affiliation: Special Testing and Research Laboratory, US Drug Enforcement Administration, 22624 Dulles Summit Court, Dulles, VA, 20166-9509, USA.
authors.forename: Erin E
authors.initials: EE
authors.lastname: Miller
authors.affiliation: Special Testing and Research Laboratory, US Drug Enforcement Administration, 22624 Dulles Summit Court, Dulles, VA, 20166-9509, USA.
authors.forename: Monica Z
authors.initials: MZ
authors.lastname: Phillips
authors.affiliation: Special Testing and Research Laboratory, US Drug Enforcement Administration, 22624 Dulles Summit Court, Dulles, VA, 20166-9509, USA.
authors.forename: Etienne R
authors.initials: ER
authors.lastname: Vazquez
authors.affiliation: Department of Forensic Sciences, The George Washington University, Washington, DC, 20007, USA.
authors.forename: Ira S
authors.initials: IS
authors.lastname: Lurie
authors.affiliation: Special Testing and Research Laboratory, US Drug Enforcement Administration, 22624 Dulles Summit Court, Dulles, VA, 20166-9509, USA.
authors.forename: Patrick A
authors.initials: PA
authors.lastname: Hays
authors.affiliation: Special Testing and Research Laboratory, US Drug Enforcement Administration, 22624 Dulles Summit Court, Dulles, VA, 20166-9509, USA.
authors.forename: Elizabeth M
authors.initials: EM
authors.lastname: Guest
mesh_terms: D000096:Acetone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D000586:Amination; D000697:Central Nervous System Stimulants / Q000138:chemical synthesis* / Q000737:chemistry; D004340:Drug Contamination; D013287:Illicit Drugs / Q000138:chemical synthesis* / Q000737:chemistry; D008694:Methamphetamine / Q000138:chemical synthesis* / Q000737:chemistry; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D010084:Oxidation-Reduction; D010648:Phenylacetates / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D000697:Central Nervous System Stimulants; D013287:Illicit Drugs; D009942:Organometallic Compounds; D010648:Phenylacetates; D000096:Acetone; D008694:Methamphetamine; C008863:1-phenyl-2-propanone; C008261:lead acetate
keywords: 1-phenyl-2-propanone; Dakin-West; forensic chemistry; impurity profiling; lead (II) acetate; methamphetamine; phenylacetic acid; synthetic marker