Talk:Substituted pyrrolidinophenone

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Generic structure of pyrrolidinophenone molecule.

Substituted pyrrolidinophenones are a chemical class of psychoactive compounds that are based on the structure of alpha-pyrrolidinopropiophenone (α-PPP). Pyrrolidinophenones have stimulant effects and are presumed to be more potent and addictive than others stimulants of class amphetamine and cathinone.[1]

Chemistry

Pyrrolidinophenones are a chemical class releated to cathinones, and they differs from other cathinones in that they contains a pyrrolidine ring in amino group.

Pharmacology

Presence of a pyrrolidine ring in any cathinone-like compound confers potent uptake blocking properties at DAT and NET. Thus, pyrrolidinophenones are mechanistically distinct from ring-substituted cathinones, such as mephedrone and methylone, which act as non-selective substrates for monoamine transporters and trigger transmitter release. Importantly, MDPV and α-PVP are similar in potency and transporter selectivity, indicating that the presence of the 3,4-methylenedioxy substituent in MDPV does not exert much influence on the profile of transporter activity. By contrast, alkyl chain length extending from the α-carbon is a critical structural feature, with shorter chain length (i.e., α-PPP, methyl) yielding less potent transporter-blocking properties when compared to longer chain length (i.e., α-PVP, propyl).[1]

List of substituted pyrrolidinophenones

Compound R2 R3 R4 R5 Rα Structure
α-PPP H H H H H Α-PPP.svg
α-PVP H H H H CH2CH3 Α-PVP.svg
α-PHP H H H H CH2CH2CH3 Α-PHP.svg
α-PHpP H H H H CH2CH2CH2CH3 Α-PHpP.svg
MDPV H OCH2- O- H CH2CH3 MDPV.svg
MDPHP H OCH2- O- H CH2CH2CH3 MDPHP.svg

See also


External links

References

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  1. 1.0 1.1 Pharmacology of novel synthetic stimulants structurally related to the “bath salts” constituent 3,4-methylenedioxypyrovalerone (MDPV) | https://www.sciencedirect.com/science/article/pii/S002839081400080X