Phenylethylpyrrolidine

Phenylethylpyrrolidine

Names
Preferred IUPAC name 1-(2-Phenylethyl)pyrrolidine
Identifiers
CAS Number	6273-83-2
3D model (JSmol)	Interactive image
ChemSpider	364511
PubChem CID	411735
CompTox Dashboard (EPA)	DTXSID701029426
InChI 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
SMILES c1c(cccc1)CCN2CCCC2
Properties
Chemical formula	C12H17N
Molar mass	175.275 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

1-(2-Phenylethyl)pyrrolidine (PEP) is a chemical compound of the phenethylamine family. It is an analogue of 2-phenylethylamine where the amine has been replaced by a pyrrolidine ring.

Derivatives

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

PEP is the base chemical structure for a series of stimulant drugs, including: ^[1]

• α-PBP
• α-PHP
• α-PPP
• α-PVP
• MDPBP
• MDPPP
• MDPV
• MOPPP
• MPBP
• MPHP
• MPPP
• Naphyrone
• Prolintane
• Pyrovalerone
• TH-PVP

All of these compounds differ from PEP in that the alpha carbon is extended and a ketone is attached to the beta carbon (with the exception of prolintane), among other modifications. ^[1]

A cyclized phenethylamine and 2-aminoindane derivative is Pyr-AI ((2-indanyl)pyrrolidine). ^[2] It is the analogue of 2-aminoindane (2-AI) in which the amine has been replaced with a pyrrolidine group. ^[2] The drug has been described as having strong and long-lasting amphetamine-like effects in rodents. ^{[2] [3]}

See also

• Phenethylamine
• Amphetamine
• Cathinone

References

1. Glennon 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. Brandt, 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 . Retrieved 2 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.