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Chiral Resolution and Absolute Configuration of the Enantiomers of the Psychoactive “Designer Drug” 3,4‐Methylenedioxypyrovalerone
Author(s) -
Suzuki Masaki,
Deschamps Jeffrey R.,
Jacobson Arthur E.,
Rice Kenner C.
Publication year - 2015
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22423
Subject(s) - enantiomer , chemistry , designer drug , absolute configuration , stimulant , drug , stereochemistry , chirality (physics) , pharmacology , physics , quantum mechanics , quark , medicine , nambu–jona lasinio model , chiral symmetry breaking
Illicit rac ‐MDPV (3,4‐methylenedioxypyrovalerone), manufactured in clandestine labs, has become widely abused for its cocaine‐like stimulant properties. It has recently been found as one of the toxic materials in the so‐called “bath salts,” producing, among other effects, psychosis and tachycardia in humans when introduced by any of the several routes of administration (e.g., intravenous, oral, etc.). The considerable toxicity of this “designer drug” probably resides in one of the enantiomers of the racemate. In order to obtain a sufficient amount of the enantiomers of rac ‐MDPV to determine their activity, we improved the known synthesis of rac ‐MDPV and found chemical resolving agents, (+)‐ and (–)‐2’‐bromotetranilic acid, that gave the MDPV enantiomers in >96% enantiomeric excess as determined by 1 H nuclear magnetic resonance and chiral high‐performance liquid chromatography . The absolute stereochemistry of these enantiomers was determined by single‐crystal X‐ray diffraction studies. Chirality 27:287‐293, 2015 . Published 2015. This article is a U.S. Government work and is in the public domain in the USA.