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Talk:Substituted pyrrolidinophenones: Difference between revisions
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[[File:Α-PPP.svg|thumb|right|301px||Generic structure of pyrrolidinophenone molecule.]] | [[File:Α-PPP.svg|thumb|right|301px||Generic structure of pyrrolidinophenone molecule.]] | ||
'''Substituted pyrrolidinophenones''' are a chemical class of psychoactive compounds... | '''Substituted pyrrolidinophenones''' (or simply '''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">Marusich, J. A., Antonazzo, K. R., Wiley, J. L., Blough, B. E., Partilla, J. S., & Baumann, M. H. (2014). Pharmacology of novel synthetic stimulants structurally related to the “bath salts” constituent 3, 4-methylenedioxypyrovalerone (MDPV). Neuropharmacology, 87, 206-213. https://doi.org/10.1016/j.neuropharm.2014.02.016</ref> | ||
==Chemistry== | ==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== | ==Pharmacology== | ||
Presence of a [[pyrrolidine]] ring in any [[cathinone]]-like compound confers potent uptake blocking properties at DAT ([[dopamine]] transporter) and NET ([[norepinephrine]] transporter). 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"/> | |||
==List of substituted pyrrolidinophenones == | ==List of substituted pyrrolidinophenones == | ||
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! scope="col" | '''Structure''' | ! scope="col" | '''Structure''' | ||
|- | |- | ||
| [[α-PPP]] || H || H || H || H || | | [[α-PPP]] || H || H || H || H || CH<sub>3</sub> || [[File:Α-PPP.svg|171px]] | ||
|- | |- | ||
| [[a-PVP|α-PVP]] || H || H || H || H || CH<sub>2</sub>CH<sub>3</sub> || [[File:α-PVP.svg|171px]] | | [[a-PVP|α-PVP]] || H || H || H || H || CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> || [[File:α-PVP.svg|171px]] | ||
|- | |- | ||
| [[ | | [[5-DBFPV]] || H || CH<sub>2</sub>- || OCH<sub>2</sub>- || H || CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> || [[File:5-DBFPV.svg|171px]] | ||
|- | |- | ||
| [[ | | [[MDPV]] || H || OCH<sub>2</sub>- || O- || H || CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> || [[File:MDPV.svg|171px]] | ||
|- | |- | ||
| [[ | | [[a-PHP|α-PHP]] || H || H || H || H || CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> || [[File:α-PHP.svg|171px]] | ||
|- | |- | ||
| [[MDPHP]] || H || OCH<sub>2</sub>- || O- || H || CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> || [[File:MDPHP.svg|171px]] | | [[MDPHP]] || H || OCH<sub>2</sub>- || O- || H || CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> || [[File:MDPHP.svg|171px]] | ||
|- | |||
| [[α-PHpP]] || H || H || H || H || CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> || [[File:α-PHpP.svg|171px]] | |||
|- | |- | ||
|} | |} | ||
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*[[Stimulants]] | *[[Stimulants]] | ||
*[[Cathinones]] | *[[Cathinones]] | ||
==External links== | ==External links== | ||
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==References== | ==References== | ||
[[Category:Chemical class]] | [[Category:Chemical class]][[Category:Pyrrolidinophenone|*]][[Category:Approval]] | ||