Talk:Substituted pyrrolidinophenones: Difference between revisions

'''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 [[Substituted amphetamine|amphetamine]] and [[cathinone]].<ref name="Bath salts">Pharmacology of novel synthetic stimulants structurally related to the “bath salts” constituent 3,4-methylenedioxypyrovalerone (MDPV) | https://www.sciencedirect.com/science/article/pii/S002839081400080X</ref>

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).<ref name="Bath salts"/>

| [[α-PPP]] || H || H || H || H || H || [[File:Α-PPP.svg|171px]]

| [[a-PVP|α-PVP]] || H || H || H || H || CH₂CH₃ || [[File:α-PVP.svg|171px]]

| [[a-PHP|α-PHP]] || H || H || H || H || CH₂CH₂CH₃ || [[File:α-PHP.svg|171px]]

| [[α-PHpP]] || H || H || H || H || CH₂CH₂CH₂CH₃ || [[File:α-PHpP.svg|171px]]

| [[MDPV]] || H || OCH₂- || O- || H || CH₂CH₃ || [[File:MDPV.svg|171px]]

| [[MDPHP]] || H || OCH₂- || O- || H || CH₂CH₂CH₃ || [[File:MDPHP.svg|171px]]

[[Category:Chemical class]]