Picenadol
From Self-sufficiency
| 160px | |
| Systematic (IUPAC) name | |
|---|---|
|
3-(1,3-dimethyl-4-propylpiperidin-4-yl)phenol | |
| Identifiers | |
| CAS Number | 79201-85-7 |
| ATC code | none |
| PubChem | CID 53077 |
| Chemical data | |
| Formula | C16H25NO |
| Molar mass | 247.38 g/mol[[Script error: No such module "String".]] |
| Script error: No such module "collapsible list". | |
Picenadol (LY-150720) is a 4-phenylpiperidine derivative that is an opioid analgesic drug.
Picenadol is an effective analgesic with similar efficacy to pethidine (meperidine). It has been investigated for some applications such as obstetrics[1] and dentistry,[2] but never commercialised.
It is unusual in that one enantiomer is a pure μ-opioid agonist, while the other is an antagonist.[3] The (3R,4R) isomer is the agonist, while (3S,4S) is antagonist.[4] 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.[5]
References
- ↑ 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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