8-Carboxamidocyclazocine

8-Carboxamidocyclazocine

Systematic (IUPAC) name
(1S,10R,13R)-10-(Cyclopropylmethyl)-1,13-dimethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-triene-4-carboxamide
Identifiers
CAS Number	911207-68-6 Y
PubChem	CID: 10086063
ChemSpider	30845204
Chemical data
Formula	C19H26N2O
Molecular mass	298.205 g/mol
SMILES C[C@H]1[C@H]2Cc3ccc(cc3[C@]1(CCN2CC4CC4)C)C(=O)N
InChI InChI=1S/C19H26N2O/c1-12-17-10-14-5-6-15(18(20)22)9-16(14)19(12,2)7-8-21(17)11-13-3-4-13/h5-6,9,12-13,17H,3-4,7-8,10-11H2,1-2H3,(H2,20,22)/t12-,17+,19-/m0/s1 Key:FAVQVALXVLMHLE-WILYLXEWSA-N
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8-Carboxamidocyclazocine (8-CAC) is an opioid analgesic drug related to cyclazocine, invented by medicinal chemist Mark P. Wentland and co-workers in Cogswell Laboratory at Rensselaer Polytechnic Institute. Similarly to cyclazocine, 8-CAC acts as an agonist at both the μ and κ opioid receptors, but has a much longer duration of action than cyclazocine, and does not have μ antagonist activity. Unexpectedly it was discovered that the phenolic hydroxyl group of cyclazocine could be replaced by a carboxamido group with only slight loss of potency at opioid receptors, and this discovery has subsequently been used to develop a large number of novel opioid derivatives where the phenolic hydroxy group has been replaced by either carboxamide or a variety of larger groups. Due to their strong κ-opioid agonist activity, these drugs are not suited for use as analgesics in humans, but have instead been researched as potential drugs for the treatment of cocaine addiction.

See also

• Samidorphan