Alpha-pyrrolidinopropiophenone

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ImageFile =a-PPP.png ImageSize = 180px
IUPACName = 1-Phenyl-2-(1-pyrrolidinyl)-1-propanone
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CASNo = 19134-50-0
PubChem = 209045
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MeSHName = alpha-pyrrolidinopropiophenone
Section2 = Chembox Properties
Formula = C13H17NO
MolarMass = 203.28
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Alpha-pyrrolidinopropiophenone (α-PPP) is a stimulant drug. It is similar in structure to the appetite suppressant diethylpropion and has analogous effects in animals. Little is known about this compound, but it has been detected by laboratories in Germany as an ingredient in "ecstasy" tablets seized by law enforcement authorities. This drug has been found to produce stimulant effects in animals and presumably also produces these effects in humans, based on the context in which it has been found. [ Staack RF, Maurer HH. Metabolism of Designer Drugs of Abuse. Current Drug Metabolism. 2005 Jun; 6(3): 259-74. ] [ Springer D, Fritschi G, Maurer HH. Metabolism of the new designer drug alpha-pyrrolidinopropiophenone (PPP) and the toxicological detection of PPP and 4'-methyl-alpha-pyrrolidinopropiophenone (MPPP) studied in rat urine using gas chromatography-mass spectrometry. Journal of Chromatography B, Analytical Technologies in the Biomedical and Life Sciences. 2003 Nov 5; 796(2): 253-66. ]

α-PPP is not illegal in any country, but due to its structural similarity to illegal drugs such as methcathinone and pyrovalerone it might be considered a controlled substance analogue in some countries such as the USA, Australia and New Zealand. Analogues of α-PPP such as pyrovalerone and MDPV have been more widely used and are presumed to be more potent and addictive than α-PPP itself. Structure-activity relationships of these drugs suggest that a variety of ring-substituted analogues are likely to be potential drugs of abuse, and stimulant activity has been found for analogues with between 3 and 6 carbon atoms in the alkyl chain. [ Maurer HH, Kraemer T, Springer D, Staack RF. Chemistry, pharmacology, toxicology, and hepatic metabolism of designer drugs of the amphetamine (ecstasy), piperazine, and pyrrolidinophenone types: a synopsis. Therapeutic Drug Monitoring. 2004 Apr; 26(2): 127-31. ] [ Meltzer PC, Butler D, Deschamps JR, Madras BK. 1-(4-Methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (Pyrovalerone) analogues: a promising class of monoamine uptake inhibitors. Journal of Medicinal Chemistry. 2006 Feb 23;49(4):1420-32. ]

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