Chiral resolution and absolute configuration of the enantiomers of the psychoactive "designer drug" 3,4-methylenedioxypyrovalerone

Chirality
Masaki SuzukiKenner C Rice

Abstract

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.

References

Jul 14, 2011·General Hospital Psychiatry·Joseph L AntonowiczSai L Ramanujam
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Citations

Nov 28, 2015·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Tiina LaaksonenKristiina Wähälä
Dec 15, 2015·Organic & Biomolecular Chemistry·Mahesh H Shinde, Umesh A Kshirsagar
Sep 5, 2015·Organic & Biomolecular Chemistry·Tiina LaaksonenKristiina Wähälä
Oct 5, 2017·Journal of Analytical Toxicology·Bárbara SilvaFernando Remião
Jan 16, 2016·The Journal of Pharmacology and Experimental Therapeutics·Brenda M GannonWilliam E Fantegrossi
Mar 14, 2017·Analytical Methods : Advancing Methods and Applications·Michael D HambuchenS Michael Owens

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