Chemistry:Phenylpiperidines

From HandWiki

Phenylpiperidines are chemical compounds with a phenyl moiety directly attached to piperidine. There are a variety of pharmacological effects associated with phenylpiperidines including morphine-like activity[1] or other central nervous system effects.

"Phenyl"piperidines
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 mu-Agonist with serotonin reuptake inhibitor properties
Budipine t-Bu Ph H Ph Antiparkinson agent
Ketobemidone Me 3-HO–Ph H –COEt Opioid and NMDA antagonist
Paroxetine H 4-F–Ph –CH2OAr[lower-alpha 1] H Selective serotonin reuptake inhibitor (and norepinephrine transporter)
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.

Methylphenidate is a benzylpiperidine.

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.