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Phenylethylpyrrolidine

From Wikipedia, the free encyclopedia
Phenylethylpyrrolidine
Names
Preferred IUPAC name
1-(2-Phenylethyl)pyrrolidine
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C12H17N/c1-2-6-12(7-3-1)8-11-13-9-4-5-10-13/h1-3,6-7H,4-5,8-11H2
  • c1c(cccc1)CCN2CCCC2
Properties
C12H17N
Molar mass175.275 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

1-(2-Phenylethyl)pyrrolidine (PEP) is achemical compound of thephenethylamine family. It is ananalogue of2-phenylethylamine where theamine has been replaced by apyrrolidinering.

Derivatives

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The α-methyl (i.e.,amphetaminederivative is1-(α-methylphenethyl)pyrrolidine (MPEP), the β-keto derivative isphenacylpyrrolidine, and the combined α-methyl and β-keto (i.e.,cathinone) derivative isα-pyrrolidinopropiophenone (α-PPP).[1]Prolintane is the α-propyl derivative of PEP.[1]

PEP is the basechemical structure for a series ofstimulantdrugs, including:[1]

All of these compounds differ from PEP in that thealpha carbon is extended and aketone is attached to thebeta carbon (with the exception ofprolintane), among other modifications.[1]

Acyclized phenethylamine and2-aminoindane derivative isPyr-AI ((2-indanyl)pyrrolidine).[2] It is theanalogue of2-aminoindane (2-AI) in which theamine has been replaced with apyrrolidine group.[2] The drug has been described as having strong and long-lastingamphetamine-like effects in rodents.[2][3]

See also

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References

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  1. ^abcdGlennon RA (2014)."Bath salts, mephedrone, and methylenedioxypyrovalerone as emerging illicit drugs that will need targeted therapeutic intervention".Adv Pharmacol.69:581–620.doi:10.1016/B978-0-12-420118-7.00015-9.PMC 4471862.PMID 24484988.
  2. ^abcBrandt, Simon D.; Braithwaite, Robin A.; Evans-Brown, Michael; Kicman, Andrew T. (2013). "Aminoindane Analogues".Novel Psychoactive Substances. Elsevier. p. 261–283.doi:10.1016/b978-0-12-415816-0.00011-0.ISBN 978-0-12-415816-0. Retrieved2 November 2025.A 'strong amphetamine-type activity' has been reported for the pyrrolidine derivative of 2-AI (26, Fig. 11.10) [41] and 'a long duration' of activity was observed at the 10mg/kg dose in mice. Details about the procedure were not provided but neuropharmacological screenings were based on observational methods [48]. A piperidine derivative (27, PIP-AI), on the other hand, showed analgesic properties comparable to meperidine [41].
  3. ^Solomons E, Sam J (December 1973). "2-Aminoindans of pharmacological interest".J Med Chem.16 (12):1330–1333.doi:10.1021/jm00270a004.PMID 4765859.
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