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| ECHA InfoCard | 100.020.998 |
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| Formula | C15H21NO |
| Molar mass | 231.339 g·mol−1 |
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Metazocine is anopioidanalgesic related topentazocine. While metazocine has significant analgesic effects,[2] mediated through a mixedagonist–antagonist action[3] at themu opioid receptor,[4] its clinical use is limited bydysphoric andhallucinogenic effects which are most likely caused by activity atkappa opioid receptors (where it is a high-efficacy agonist)[5] and/orsigma receptors.[6][7]
Metazocine is in Schedule II of the Controlled Substances Act 1970 of the United States as a Narcotic with ACSCN 9240 with a 19 gram aggregate manufacturing quota as of 2014. The free base conversion ratio for salts includes 0.81 for the hydrochloride and 0.74 for the hydrobromide.[8] It is listed under the Single Convention for the Control of Narcotic Substances 1961 and is controlled in most countries in the same fashion as is morphine.
Thebenzomorphan, metazocine (6), can be obtained from a variation of themorphinansynthesis.
Reaction of theGrignard reagent fromp-methoxybenzyl chloride (1) with thelutidine methiodide (2) affords the benzylated dihydropyridine (3). Reduction of theenamineπ-bond leads to thetetrahydropyridine (4). Cyclization by means of acid leads directly to the benzomorphan ring system (5).Demethylation of the aromatic ring system gives thephenol. Although this last compound is in fact a relatively potent analgesic, it is not available commercially as adrug.[9][10] Also see:[11]
