Gemazocine

Gemazocine (R-15,497), also known as cyclogemine, is a non-selective opioid antagonist of the benzomorphan class.[1][2][3] It may have partial agonist properties at some of the opioid receptors, such as at the kappa receptor (as it induces dysphoric effects in humans), but seems to be generally antagonistic in its actions.[4]

Gemazocine
Clinical data
ATC code
  • None
Identifiers
IUPAC name
  • 10-(cyclopropylmethyl)-1-ethyl-13,13-dimethyl-10-azatricyclo[7.3.1.02,7]trideca-2,4,6-trien-4-ol
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC20H29NO
Molar mass299.458 g·mol−1
3D model (JSmol)
SMILES
  • Oc1ccc4c(c1)C2(C(C(N(CC2)CC3CC3)C4)(C)C)CC
InChI
  • InChI=1S/C20H29NO/c1-4-20-9-10-21(13-14-5-6-14)18(19(20,2)3)11-15-7-8-16(22)12-17(15)20/h7-8,12,14,18,22H,4-6,9-11,13H2,1-3H3
  • Key:AFZOCGNTFCGOEE-UHFFFAOYSA-N

References
  1. Macdonald, F. (1997). Dictionary of Pharmacological Agents. CRC Press. p. 955. ISBN 978-0-412-46630-4. Retrieved 22 April 2012.
  2. Gelders, Y. G.; de Ranter, C. J.; Schenk, H. (1979). "Structural Studies of Substituted 6,7-Benzomorphan Compounds. I. The Absolute Configuration of (−)-2-Cyclopropylmethyl-2'-hydroxy-5-ethyl-9,9-dimethyl-6,7-benzomorphan (Gemazocine) Hydrobromide". Acta Crystallographica B. 35 (3): 699–703. doi:10.1107/S0567740879004477.{{cite journal}}: CS1 maint: uses authors parameter (link)
  3. Verlinde C, De Ranter C (August 1988). "Assessment of the kappa-opioid activity of a series of 6,7-benzomorphans in the rabbit vas deferens". Eur. J. Pharmacol. 153 (1): 83–7. doi:10.1016/0014-2999(88)90590-0. PMID 2850928.
  4. Freye, E.; Hartung, E.; Schenk, G. K. (1983). "Bremazocine: An Opiate That Induces Sedation and Analgesia without Respiratory Depression" (PDF). Anesthesia and Analgesia. 62 (5): 483–488. doi:10.1213/00000539-198305000-00005. PMID 6301311.


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