Ethylketazocine

Ethylketazocine

Systematic (IUPAC) name
(1S,9R)-10-(cyclopropylmethyl)-1-ethyl-4-hydroxy-13-methyl-10-azatricyclo[7.3.1.0^2,7]trideca-2,4,6-trien-8-one
Identifiers
CAS Number	36292-66-7
ATC code	None
PubChem	CID 644273
ChemSpider	559289
Chemical data
Formula	C19H25NO2
Molar mass	299.407
SMILES O=C2c1c(cc(O)cc1)[C@@]3(C([C@H]2N(CC3)CC4CC4)C)CC
InChI 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

Ethylketazocine (WIN-35,197-2), also known as ethylketocyclazocine (EKC), 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]

See also

• Benzomorphan
• Ketazocine

References

1. William O. Foye; Thomas L. Lemke (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. Edythe D. London (1993). Imaging Drug Action in the Brain. CRC Press. p. 130. ISBN 978-0-8493-8843-9. Retrieved 22 April 2012.
3. Enno Freye (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.