8-Carboxamidocyclazocine

8-Carboxamidocyclazocine

Identifiers
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
CAS Number	911207-68-6 Y
PubChem CID	10086063
ChemSpider	30845204
CompTox Dashboard (EPA)	DTXSID40726979
Chemical and physical data
Formula	C19H26N2O
Molar mass	298.430 g·mol−1
3D model (JSmol)	Interactive image
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, discovered 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this discovery has subsequently been used to develop many novel opioid derivatives where the phenolic hydroxy group has been replaced by either carboxamide or a variety of larger groups.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

• Tianeptine, an atypical, selective MOR full-agonist licensed for major depression since 1989.
• Samidorphan, an opioid preferring the MOR, which is under development for major depression.