Phenylpiperidines

Chemical structure of 4-phenylpiperidine.

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
Compound N 4-position 3-position 4'-position Type of pharmacology
MPPP Me Ph H –OCOEt Opioid analgesic
Prodine Me Ph Me –OCOEt Opioid analgesic
PEPAP CH2CH2Ph Ph H –OCOMe Opioid analgesic
Pethidine Me Ph H –CO2Et Opioid analgesic with monoamine reuptake inhibitor activity
Budipine t-Bu Ph H Ph Antiparkinsonian agent
Prodipine iPr Ph H Ph Antiparkinsonian agent
Ketobemidone Me 3-HO–Ph H –COEt Opioid analgesic and NMDA receptor antagonist
Paroxetine H 4-F–Ph –CH2OAr[a] H Selective serotonin reuptake inhibitor
Enefexine H 4-Et–Ph H H Antidepressant
Femoxetine Me Ph –CH2O(4-MeOPh) H Selective serotonin reuptake inhibitor
CPCA Me 4-Cl–Ph –CO2Me H Monoamine 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

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.


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