Methylenedioxypyrovalerone

MDPV
Clinical data
Other names	MDPV; 3′,4′-Methylenedioxy-α-(pyrrolidin-1-yl)valerophenone; MDPK; MD-α-PVP
Routes of; administration	Oral, insufflation, intravenous, rectal, vaporization
Drug class	Stimulant; Norepinephrine–dopamine reuptake inhibitor
Legal status
Legal status	AU: S9 (Prohibited substance); BR: Class F1 (Prohibited narcotics); CA: Schedule I; DE: Anlage II (Authorized trade only, not prescriptible); UK: Class B; US: Schedule I; UN: Psychotropic Schedule II; Illegal in Austria, Belgium, Bulgaria, Croatia, Cyprus, Czech Republic, Denmark, Estonia, France, Hungary, Ireland, Finland, Italy, Latvia, Luxembourg, Norway, Poland, Portugal, Romania, Russia, Slovakia, Slovenia, Sweden, Turkey, Ukraine.;
Pharmacokinetic data
Metabolism	Hepatic
Excretion	Primarily urine (renal)
Identifiers
	IUPAC name 1-(1,3-Benzodioxol-5-yl)-2-(pyrrolidin-1-yl)pentan-1-one;
CAS Number	687603-66-3 ; 24622-62-6 (HCl);
PubChem CID	20111961;
ChemSpider	16788110 ;
UNII	E7LD6JMR0L;
KEGG	C22808 ;
CompTox Dashboard (EPA)	DTXSID90897461 ;
Chemical and physical data
Formula	C16H21NO3
Molar mass	275.348 g·mol−1
3D model (JSmol)	Interactive image;
Chirality	Racemic mixture
	SMILES O=C(C(CCC)N1CCCC1)C2=CC=C3C(OCO3)=C2;
	InChI InChI=1S/C16H21NO3/c1-2-5-13(17-8-3-4-9-17)16(18)12-6-7-14-15(10-12)20-11-19-14/h6-7,10,13H,2-5,8-9,11H2,1H3 ; Key:SYHGEUNFJIGTRX-UHFFFAOYSA-N ;
	(verify)

Methylenedioxypyrovalerone (abbreviated MDPV) is a stimulant of the cathinone class that acts as a norepinephrine–dopamine reuptake inhibitor (NDRI).^[3]^[4]^[5]^[6]

^ "Substance Details 3,4-Methylenedioxypyrovalerone". Retrieved January 22, 2024.
^ Cite error: The named reference EMCDDA was invoked but never defined (see the help page).
^ Baumann MH, Bukhari MO, Lehner KR, Anizan S, Rice KC, Concheiro M, Huestis MA (2017). "Neuropharmacology of 3,4-Methylenedioxypyrovalerone (MDPV), Its Metabolites, and Related Analogs". Neuropharmacology of New Psychoactive Substances (NPS). Curr Top Behav Neurosci. Vol. 32. pp. 93–117. doi:10.1007/7854_2016_53. ISBN 978-3-319-52442-9. PMC 5392131. PMID 27830575.
^ Simmons SJ, Leyrer-Jackson JM, Oliver CF, Hicks C, Muschamp JW, Rawls SM, Olive MF (October 2018). "DARK Classics in Chemical Neuroscience: Cathinone-Derived Psychostimulants". ACS Chem Neurosci. 9 (10): 2379–2394. doi:10.1021/acschemneuro.8b00147. PMC 6197900. PMID 29714473.
^ Baumann MH, Partilla JS, Lehner KR, Thorndike EB, Hoffman AF, Holy M, et al. (March 2013). "Powerful cocaine-like actions of 3,4-methylenedioxypyrovalerone (MDPV), a principal constituent of psychoactive 'bath salts' products". Neuropsychopharmacology. 38 (4): 552–62. doi:10.1038/npp.2012.204. PMC 3572453. PMID 23072836.
^ Simmler LD, Buser TA, Donzelli M, Schramm Y, Dieu LH, Huwyler J, et al. (January 2013). "Pharmacological characterization of designer cathinones in vitro". British Journal of Pharmacology. 168 (2): 458–70. doi:10.1111/j.1476-5381.2012.02145.x. PMC 3572571. PMID 22897747.