3,4-Methylenedioxy Pyrovalerone

Pyrovalerone and its analogs are inhibitors of the transporters for certain monoamine neurotransmitters, including dopamine and norepinephrine, preventing their uptake.^1,2 3,4-Methylenedioxy Pyrovalerone (3,4-MDPV) is an analog of pyrovalerone which includes the 3,4-methylenedioxy moiety found on 3,4-methylenedioxymethamphetamine, a DEA Schedule I controlled substance. While its physiological, neurological, and toxicological actions have not been characterized, 3,4-MDPV has been reported by the DEA to be abused as a central nervous system stimulant.³ Its effective dose and chemical interactions are unknown, but it has been used alone and in combination with other stimulating compounds. Products containing 3,4-MDPV have been marketed in Europe and Australia; they have also been seized by law enforcement in several states.³ 3,4-MDPV and some of its metabolites have recently been characterized by spectroscopic analysis.^4,5,6,7 3,4-MDPV is to be used in the forensic analysis of samples that may contain this compound. This product, the free base of 3,4-MDPV, has superior solubility in organic solvents, compared to the hydrochloride salt .

1.Heron, C., Costentin, J., and Bonnet, J.J.Evidence that pure uptake inhibitors including cocaine interact slowly with the dopamine neuronal carrierEur. J. Pharmacol.264(3)391-398(1994) 2.Meltzer, P.C., Butler, D., Deschamps, J.R., et al.1-(4-methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (pyrovalerone) analogs. A promising class of monoamine uptake inhibitorsJ. Med. Chem.49(4)1420-1432(2006) 3.Drug Enforcement Admin.Office of Diversion, C.Methylenedioxypyrovalerone [(MDPV) 1-(1,3-benzodioxol-5-yl)-2-(1-pyrrolidinyl)-1-pentanone]() 4.Westphal, F., Junge, T., Rosner, P., et al.Mass and NMR spectroscopic characterization of 3,4-methylenedioxypyrovalerone: A designer drug with α-pyrrolidinophenone structureForensic Sci. Int.1901-8(2009) 5.Meyer, M.R., Du, P., Schuster, F., et al.Studies on the metabolism of the α-pyrrolidinophenone designer drug methylenedioxy-pyrovalerone (MDPV) in rat and human urine and human liver microsomes using GC-MS and LC-high-resolution MS and its detectability in urine by GC-MSJ. Mass Spectrom.45(12)1426-1442(2010) 6.Yohannan, J.C., and Bozenko, J.S.The characterization of 3,4-methylenedioxypyrovalerone (MDPV)Microgram Journal7(1)12-15(2010) 7.Strano-Rossi, S., Cadwallader, A.B., de la Torre, X., et al.Toxicological determination and in vitro metabolism of the designer drug methylenedioxypyrovalerone (MPDV) by gas chromatography/mass spectrometry and liquid chromatography/quadrupole time-of-flight mass spectrometryRapid Commun. Mass Spectrom.242706-2714(2010)