Moxazocine

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Moxazocine
Identifiers
  • (1S,9R,13S)-10-(cyclopropylmethyl)-13-methoxy-1-methyl-10-azatricyclo[7.3.1.02,7]trideca-2,4,6-trien-4-ol
JSmol)
  • Oc1ccc2C[C@H]3N(CC[C@@](C)(c2c1)[C@@H]3OC)CC4CC4
  • InChI=1S/C18H25NO2/c1-18-7-8-19(11-12-3-4-12)16(17(18)21-2)9-13-5-6-14(20)10-15(13)18/h5-6,10,12,16-17,20H,3-4,7-9,11H2,1-2H3/t16-,17-,18+/m1/s1
  • Key:IOZWXJXXVLARQC-KURKYZTESA-N

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]

Synthesis

Moxazocine synthesis:[4][5]

Reduction of the carbonyl group in oxygenated

LiAlH4
serves to reduce the amide function. Cleavage of the phenolic ether by one of the standard schemes affords moxazocine (6).

See also

References

  1. . Retrieved 22 April 2012.
  2. .
  3. ^ Dobkin AB, Esposito BF, Noveck RJ, Caruso FS (October 1977). "Moxazocine and morphine in patients with severe postoperative pain". Current Therapeutic Research. 22 (4): 469–478.
  4. ^ DE 2517220, Montzka TA, Matiskella JD, "9-Alkoxy-5-methyl-6,7-benzomophane, VerfahrenE zu ihrer Herstellung und sie enthaltende Mittel [9-Alkoxy-5-methyl-6,7-benzomophanes, processes for their preparation and compositions containing them]", published 1975-11-06, assigned to Bristol-Myers Co. 
  5. ^ Montzka TA, Matiskella JD, Chem. Abstr. 84, 59832k (1976).
  6. ^ Zhang K, Lu M, Li Y (2003). "Synthesis of Cyclopropanecarbonyl chloride". Chemical Industry Times. 17 (7): 36–38.
  7. ^ U.S. patent 5,504,245