Methylenedioxypyrovalerone

Methylenedioxypyrovalerone (MDPV) is a stimulant of the cathinone class that acts as a norepinephrine–dopamine reuptake inhibitor (NDRI). It was first developed in the 1960s by a team at Boehringer Ingelheim. Its activity at the dopamine transporter is six times stronger than at the norepinephrine transporter and it is virtually inactive at the serotonin transporter. MDPV remained an obscure stimulant until around 2004 when it was reportedly sold as a designer drug. In the US, products containing MDPV and labeled as bath salts were sold as recreational drugs in gas stations, similar to the marketing for Spice and K2 as incense, until it was banned in 2011.

Methylenedioxypyrovalerone
Clinical data
Routes of
administration		Oral, insufflation, intravenous, rectal, vaporization
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
MetabolismHepatic
ExcretionPrimarily urine (renal)
Identifiers
  • 1-(1,3-Benzodioxol-5-yl)-2-(pyrrolidin-1-yl)pentan-1-one
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC16H21NO3
Molar mass275.348 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
  • O=C(C(CCC)N1CCCC1)C2=CC=C3C(OCO3)=C2
  • 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 Y
  • Key:SYHGEUNFJIGTRX-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)
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