alpha-Pyrrolidinopropiophenone

α-Pyrrolidinopropiophenone

Systematic (IUPAC) name
(RS)-1-Phenyl-2-(1-pyrrolidinyl)-1-propanone
Identifiers
CAS Number	19134-50-0
PubChem	CID 209045
ChemSpider	181124
UNII	01DP8CH58H
Chemical data
Formula	C13H17NO
Molar mass	203.28 g/mol
SMILES O=C(C(C)N1CCCC1)C2=CC=CC=C2
InChI InChI=1S/C13H17NO/c1-11(14-9-5-6-10-14)13(15)12-7-3-2-4-8-12/h2-4,7-8,11H,5-6,9-10H2,1H3 Key:KPUJAQRFIJAORQ-UHFFFAOYSA-N
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α-Pyrrolidinopropiophenone (α-PPP),^[1] 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.^[2][3]

α-PPP is illegal in the UK under the blanket ban on substituted cathinones, and 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.^[4][5]

See also

• 4'-Methyl-α-pyrrolidinopropiophenone (MePPP)
• 4'-Methoxy-α-pyrrolidinopropiophenone (MOPPP)
• 3,4-Methylenedioxy-α-pyrrolidinopropiophenone (MDPPP)
• 3',4'-Methylenedioxy-α-pyrrolidinobutiophenone (MDPBP)
• Alpha-Pyrrolidinopentiophenone (α-PVP)
• α-Pyrrolidinopentiothiophenone (α-PVT)
• α-Pyrrolidinohexiophenone (α-PHP)

References

1. Iwao, J.; Kowaki, C.; Kakemi, H. (1954). "Studies on Alkanolamines. II Synthesis of N-Methylephedrone and Its Derivatives. Application of the Voigt Reaction" (pdf). Yakugaku Zasshi 74 (5): 551–553.
2. Staack R. F.; Maurer, H. H. (2005). "Metabolism of Designer Drugs of Abuse". Current Drug Metabolism 6 (3): 259–274. doi:10.2174/1389200054021825. PMID 15975043.
3. Springer, D.; Fritschi, G.; Maurer, H. H. (2003). "Metabolism of the New Designer Drug α-Pyrrolidinopropiophenone (PPP) and the Toxicological Detection of PPP and 4'-Methyl-α-Pyrrolidinopropiophenone (MPPP) Studied in Rat Urine Using Gas Chromatography-Mass Spectrometry". Journal of Chromatography B 796 (2): 253–266. doi:10.1016/j.jchromb.2003.07.008. PMID 14581066.
4. Maurer, H. H.; Kraemer, T.; Springer, D.; Staack, R. F. (2004). "Chemistry, Pharmacology, Toxicology, and Hepatic Metabolism of Designer Drugs of the Amphetamine (Ecstasy), Piperazine, and Pyrrolidinophenone Types: A Synopsis". Therapeutic Drug Monitoring 26 (2): 127–131. doi:10.1097/00007691-200404000-00007. PMID 15228152.
5. Meltzer, P. C.; Butler, D.; Deschamps, J. R.; Madras, B. K. (2006). "1-(4-Methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (Pyrovalerone) Analogues: A Promising Class of Monoamine Uptake Inhibitors" (pdf). Journal of Medicinal Chemistry 49 (4): 1420–1432. doi:10.1021/jm050797a. PMC 2602954. PMID 16480278.