Chiral resolution and absolute configuration of the enantiomers of the psychoactive "designer drug" 3,4-methylenedioxypyrovalerone.
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.
Drug Design and Synthesis Section, Molecular Targets and Medications Discovery Branch, National Institute on Drug Abuse, National Institutes of Health, Department of Health and Human Services, Bethesda, Maryland.
Masaki
M
Suzuki
Jeffrey R
JR
Deschamps
Arthur E
AE
Jacobson
Kenner C
KC
Rice
D052117:Benzodioxoles / Q000032:analysis / Q000737:chemistry* / Q000302:isolation & purification; D015198:Designer Drugs / Q000032:analysis / Q000737:chemistry* / Q000302:isolation & purification; D006851:Hydrochloric Acid / Q000737:chemistry; D057230:Limit of Detection; D011619:Psychotropic Drugs / Q000032:analysis / Q000737:chemistry* / Q000302:isolation & purification; D011759:Pyrrolidines / Q000032:analysis / Q000737:chemistry* / Q000302:isolation & purification; D013237:Stereoisomerism; D000094982:Synthetic Cathinone
D052117:Benzodioxoles; D015198:Designer Drugs; D011619:Psychotropic Drugs; D011759:Pyrrolidines; D006851:Hydrochloric Acid; D000094982:Synthetic Cathinone
3,4-methylenedioxypyrovalerone (MDPV); bath salts; designer drug; euphoric stimulant; non-chromatographic chiral resolution; synthesis