Phenylpiperidines arechemical compounds with aphenylmoiety directly attached topiperidine. Of particular interest are a variety ofderivatives of4-phenylpiperidine, which havepharmacological effects includingmorphine-like activity[1] or othercentral nervous system effects.
| 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 withmonoamine 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 andNMDA 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 |
Some of thebutyrophenoneantipsychotics, includingaceperone,bromperidol,haloperidol,moperone, andtrifluperidol, as well as the relateddiphenylbutylpiperidine antipsychoticpenfluridol, are also 4-phenylpiperidine derivatives.
Certain other opioids, includingalvimopan,loperamide, anddiphenoxylate, are 4-phenylpiperidine derivatives as well.
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