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

• 2-Phenylpiperidine
• 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.