Phenylpiperidines

Phenylpiperidines are chemical compounds with a phenyl moiety directly attached to piperidine. Of particular interest are a variety of derivatives of 4-phenylpiperidine, which have pharmacological effects including morphine-like activity[1] or other central nervous system effects.

4-Phenylpiperidine derivatives
CompoundN4-position3-position4'-positionType of pharmacology
MPPPMePhH–OCOEtOpioid analgesic
ProdineMePhMe–OCOEtOpioid analgesic
PEPAPCH2CH2PhPhH–OCOMeOpioid analgesic
PethidineMePhH–CO2EtOpioid analgesic with monoamine reuptake inhibitor activity
Budipinet-BuPhHPhAntiparkinsonian agent
ProdipineiPrPhHPhAntiparkinsonian agent
KetobemidoneMe3-HO–PhH–COEtOpioid analgesic and NMDA receptor antagonist
ParoxetineH4-F–Ph–CH2OAr[a]HSelective serotonin reuptake inhibitor
EnefexineH4-Et–PhHHAntidepressant
FemoxetineMePh–CH2O(4-MeOPh)HSelective serotonin reuptake inhibitor
CPCAMe4-Cl–Ph–CO2MeHMonoamine reuptake inhibitor
  1. ↑ Ar denotes an aryl group; here specifically being benzodioxol-3-yl.

Some of the butyrophenone antipsychotics, including aceperone, bromperidol, haloperidol, moperone, and trifluperidol, as well as the related diphenylbutylpiperidine antipsychotic penfluridol, are also 4-phenylpiperidine derivatives.

Certain other opioids, including alvimopan, loperamide, and diphenoxylate, are 4-phenylpiperidine derivatives as well.

See also

  • Benzylpiperidine
  • Phenylpiperazine

References

  1. ↑ Janssen, PA (April 1962). "A Review of the Chemical Features Associated with Strong Morphine-Like Activity". British Journal of Anaesthesia. 34 (4): 260–268. doi:10.1093/bja/34.4.260. PMID 14451235.


This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.