Cyclazocine

Cyclazocine
Clinical data
Routes of
administration
Oral
ATC code
  • none
Identifiers
IUPAC name
  • 3-(Cyclopropylmethyl)-6,11-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocin-8-ol
    or
    2-Cyclopropylmethyl-2'-hydroxy-5,9-dimethyl-6,7-benzomorphan
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.020.627
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Chemical and physical data
FormulaC18H25NO
Molar mass271.404 g·mol−1
3D model (JSmol)
SMILES
  • Oc1ccc4c(c1)C2(C(C(N(CC2)CC3CC3)C4)C)C
InChI
  • InChI=1S/C18H25NO/c1-12-17-9-14-5-6-15(20)10-16(14)18(12,2)7-8-19(17)11-13-3-4-13/h5-6,10,12-13,17,20H,3-4,7-9,11H2,1-2H3 checkY
  • Key:YQYVFVRQLZMJKJ-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Cyclazocine is a mixed opioid agonist/antagonist related to dezocine, pentazocine and phenazocine. This family of opioid drugs is called the benzomorphans or benzazocines.[1] It is a KOR agonist and MOR partial agonist, and also has high affinity for the DOR.[2]

Use

Research into the use of cyclazocine for the treatment of bipolar patients with depression was undertaken by Fink and colleagues (1970). It showed that 8 out of 10 patients experienced moderate improvement.

Research during the 1960s and 1970s into the possible use of cyclazocine for management of pain, and later for assisting treatment of narcotic addiction was severely hampered by the drug's psychotomimetic, dysphoric, and hallucinatory effects.[3] The dysphoric/anxiety inducing effects of the drug correlate with increasing dosage and would likely reduce the risk of abuse in the same manner as other opioids which preferentially act on the KOR versus the DOR and MOR, although the side-effect threshold is often lower than the lowest effective dose.

See also

  • Benzomorphan

References

  1. Archer, S.; Glick, S. D.; Bidlack, J. M. (1996). "Cyclazocine Revisited". Neurochemical Research. 21 (11): 1369–1373. doi:10.1007/BF02532378. PMID 8947927. S2CID 680860.
  2. Bidlack JM, Cohen DJ, McLaughlin JP, Lou R, Ye Y, Wentland MP (July 2002). "8-Carboxamidocyclazocine: a long-acting, novel benzomorphan". J. Pharmacol. Exp. Ther. 302 (1): 374–80. doi:10.1124/jpet.302.1.374. PMID 12065740. S2CID 15864569.
  3. Freedman, A. M.; Fink, M.; Sharoff, R.; Zaks, A. (1967). "Cyclazocine and Methadone in Narcotic Addiction". The Journal of the American Medical Association. 202 (3): 191–194. doi:10.1001/jama.1967.03130160065011. PMID 6072354.


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