Picenadol

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IUPAC_name = 3-(1,3-dimethyl-4-propylpiperidin-4-yl)phenol

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CAS_number = 79201-85-7
synonyms = Picenadol
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PubChem = 53077
smiles = CCCC1(CCN(C)CC1C)c1cccc(O)c1
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C = 16 | H = 25 | N = 1 | O = 1
molecular_weight = 247.38 g/mol
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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 [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.] and dentistry, [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.] but never commercialised.

It is unusual in that one enantiomer is a pure μ-opioid agonist, while the other is an antagonist. [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.] The (3R,4R) isomer is the agonist, while (3S,4S) is antagonist. [Froimowitz M, Cody V. Absolute configurations and conformations of the opioid agonist and antagonist enantiomers of picenadol. "Chirality". 1995;7(7):518-25.] 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. [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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