Ethylketazocine

Ethylketazocine (WIN-35,197-2), is an opioid drug of the benzomorphan family which has been used extensively in scientific research in the last few decades as a tool to aid in the study of the κ-opioid receptor.[1] However, due to its relatively poor selectivity for the κ-opioid receptor over the μ- and δ-opioid receptors (of which it has approximately 80% and 20% of the affinity for, respectively, in comparison), as well as its relatively poor intrinsic activity at all sites (i.e., acts as a partial agonist with mixed agonist and antagonist properties), it has been mostly replaced in recent times by newer and more potent and selective compounds like U-50,488 and ICI-199,441.[1][2][3]

Ethylketazocine
Clinical data
Other namesethylketocyclazocine
ATC code
  • None
Identifiers
  • (1S,9R)-10-(cyclopropylmethyl)-1-ethyl-4-hydroxy-13-methyl-10-azatricyclo[7.3.1.02,7]trideca-2,4,6-trien-8-one
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H25NO2
Molar mass299.407 g·mol−1
3D model (JSmol)
  • O=C2c1c(cc(O)cc1)[C@@]3(C([C@H]2N(CC3)CC4CC4)C)CC
  • InChI=1S/C19H25NO2/c1-3-19-8-9-20(11-13-4-5-13)17(12(19)2)18(22)15-7-6-14(21)10-16(15)19/h6-7,10,12-13,17,21H,3-5,8-9,11H2,1-2H3/t12?,17-,19+/m1/s1
  • Key:SEJUQQOPVAUETF-MKFRLIFGSA-N

See also

References
  1. Foye WO, Lemke TL (24 September 2007). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. p. 657. ISBN 978-0-7817-6879-5. Retrieved 22 April 2012.
  2. London ED (1993). Imaging Drug Action in the Brain. CRC Press. p. 130. ISBN 978-0-8493-8843-9. Retrieved 22 April 2012.
  3. Freye E (3 April 2008). Opioids in Medicine: A Comprehensive Review on the Mode of Action and the Use of Analgesics in Different Clinical Pain States. Springer. p. 103. ISBN 978-1-4020-5946-9. Retrieved 22 April 2012.


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