Picenadol
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|---|---|
| Systematic (IUPAC) name | |
| 3-(1,3-dimethyl-4-propylpiperidin-4-yl)phenol | |
| Clinical data | |
| Pregnancy cat. | ? |
| Legal status | ? |
| Identifiers | |
| CAS number | 79201-85-7  |
| ATC code | None |
| PubChem | CID 53077 |
| ChemSpider | 47943 |
| UNII | TV3535QWTJ |
| Chemical data | |
| Formula | C16H25NO |
| Mol. mass | 247.38 g/mol |
| SMILES | eMolecules & PubChem |
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Picenadol (LY-97435) is a 4-phenylpiperidine derivative that is an opioid analgesic drug developed by Eli Lilly in the 1970s[1].
Picenadol is an effective analgesic with similar efficacy to pethidine (meperidine). It has been investigated for some applications such as obstetrics[2] and dentistry,[3] but never commercialised.
It is unusual in that one enantiomer is a pure μ-opioid agonist, while the other is an antagonist.[4] The (3R,4R) isomer is the agonist, while (3S,4S) is antagonist.[5] This means that the racemic mix of the two enantiomers is a mixed agonist-antagonist, with relatively low abuse potential, and little of the κ-opioid activity that tends to cause problems with other opioid mixed agonist-antagonists such as pentazocine.[6]
[edit] References
- ^ US Patent 4081450 - 1,3,4-Trisubstituted-4-arylpiperidines and their preparation
- ^ Sherline DM. Picenadol (LY 150720) compared with meperidine and placebo for relief of post-cesarean section pain: a randomized double-blind study. American Journal of Obstetrics and Gynecology. 1983 Oct 15;147(4):404-6.
- ^ Goldstein DJ, Brunelle RL, George RE, Cooper SA, Desjardins PJ, Gaston GW, Jeffers GE, Gallegos LT, Reynolds DC. Picenadol in a large multicenter dental pain study. Pharmacotherapy. 1994 Jan-Feb;14(1):54-9.
- ^ Leander JD, Zimmerman DM. Effects of picenadol and its agonist and antagonist isomers on schedule-controlled behavior. Journal of Pharmacology and Experimental Therapeutics. 1983 Dec;227(3):671-5.
- ^ Froimowitz M, Cody V. Absolute configurations and conformations of the opioid agonist and antagonist enantiomers of picenadol. Chirality. 1995;7(7):518-25.
- ^ Zimmerman DM, Smits SE, Hynes MD, Cantrell BE, Leander JD, Mendelsohn LG, Nickander R. Picenadol. Drug and Alcohol Dependence. 1985 Feb;14(3-4):381-401.
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