Chemistry:Picenadol
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| Formula | C16H25NO |
| Molar mass | 247.382 g·mol−1 |
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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 (3S,4R) isomer is the agonist, while (3R,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]
Synthesis
See also
References
- ↑ Zimmerman DM, "1,3,4-Trisubstituted-4-arylpiperidines and their preparation", US patent 4081450, issued 28 April 1978, assigned to Eli Lilly & Company
- ↑ "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 147 (4): 404–6. October 1983. doi:10.1016/s0002-9378(16)32234-7. PMID 6624809.
- ↑ "Picenadol in a large multicenter dental pain study". Pharmacotherapy 14 (1): 54–9. 1994. doi:10.1002/j.1875-9114.1994.tb02789.x. PMID 8159602.
- ↑ "Effects of picenadol and its agonist and antagonist isomers on schedule-controlled behavior". The Journal of Pharmacology and Experimental Therapeutics 227 (3): 671–5. December 1983. PMID 6655562.
- ↑ Froimowitz M, Cody V. Absolute configurations and conformations of the opioid agonist and antagonist enantiomers of picenadol. Chirality. 1995;7(7):518-25.
- ↑ "Picenadol". Drug and Alcohol Dependence 14 (3–4): 381–401. February 1985. doi:10.1016/0376-8716(85)90069-9. PMID 2986931.
- ↑ Feth G, Mills JE, "Process for preparation of substituted formamidine and substituted N-iminomethyl piperidine", US patent 4499274, published 1985-02-12, assigned to McNeil Lab Inc.
- ↑ "A concise, stereoselective synthesis of picenadol". Tetrahedron Letters 31 (38): 5401–5404. 1990. doi:10.1016/S0040-4039(00)97857-2.
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