From Infogalactic: the planetary knowledge core
Jump to: navigation, search
Moxazocine structure.svg
Systematic (IUPAC) name
CAS Number 58239-89-7
ChemSpider 16737008
Chemical data
Formula C18H25NO2
Molecular mass 287.397 g/mol

Moxazocine (BL-4566) is an opioid analgesic of the benzomorphan family which was never marketed.[1] It acts as a partial agonist or mixed agonist/antagonist of the opioid receptors and binds preferentially to the κ-opioid receptor.[2] Despite its failure to reach the market, clinical studies demonstrated moxazocine to be approximately 10x as potent by weight as morphine as an analgesic.[3]


Moxazocine synthesis:[4]

Reduction of the carbonyl group in oxygenated benzomorphan 1 affords the corresponding alcohol (2). This intermediate is then N-demethylated by means of BrCN. Acylation with cyclopropylcarbonyl chloride[5][6] gives the amide (3). The alcohol is then converted to the ether by treatment with MeI and base (4). Treatment with LiAlH4 serves to reduce the amide function. Cleavage of the phenolic ether by one of the standard schemes affords moxazocine (6).

See also


  1. Dictionary of Pharmacological Agents Volume 2. CRC Press. p. 1382. ISBN 978-0-412-46630-4. Retrieved 22 April 2012.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
  2. Lua error in Module:Citation/CS1/Identifiers at line 47: attempt to index field 'wikibase' (a nil value).
  3. Dobkin, Allen B; Esposito, Barbara F; Noveck, Robert J; Caruso, Frank S (October 1977). "Moxazocine and morphine in patients with severe postoperative pain". Current Therapeutic Research. 22 (4): 469–478. <templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
  4. T. A. Montzka and J. D. Matiskella, DE 2517220  Chem. Abstr. 84, 59832k (1976).
  6. U.S. Patent 5,504,245