View source for N-(S)-Fenchyl-1-(2-morpholinoethyl)-7-methoxyindole-3-carboxamide

7-methoxy-1-(2-morpholinoethyl)-N-((1S,4R)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl)-1H-indole-3-carboxamide (N-[(S)-fenchyl]-1-[2-(morpholin-4-yl)ethyl]-7-methoxyindole-3-carboxamide, UR-12, MN-25) is a drug invented by Bristol-Myers Squibb, that acts as a reasonably selective agonist of peripheral cannabinoid receptors. It has moderate affinity for CB2 receptors with a Ki of 11nM, but 22x lower affinity for the psychoactive CB1 receptors with a Ki of 245nM. The indole 2-methyl derivative has the ratio of affinities reversed however, with a Ki of 8nM at [[CB1]] and 29nM at [[CB2]], which contrasts with the usual trend of 2-methyl derivatives having increased selectivity for CB2 (cf. [[JWH-018]] vs [[JWH-007]], [[JWH-081]] vs [[JWH-098]]).


== 2-methyl derivative ==

Chemically, it is closely related to another indole-3-carboxamide synthetic cannabinoid, Org 28611, but with a different cycloalkyl substitution on the carboxamide, and the cyclohexylmethyl group replaced by morpholinylethyl, as in [[JWH-200]] or [[A-796,260]]. Early compounds such as these have subsequently led to the development of a large number of related indole-3-carboxamide cannabinoid ligands.


==See also==

* [[A-834,735]]
* [[AB-001]]
* [[AM-1221]]
* [[JTE 7-31]]
* [[JWH-203]]
* [[MDA-19]]
* [[SR-144,528]]
* [[UR-144]]