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

7-methoxy-1--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) is a drug invented by Bristol-Myers Squibb

Bristol-Myers Squibb

Bristol-Myers Squibb , often referred to as BMS, is a pharmaceutical company, headquartered in New York City. The company was formed in 1989, following the merger of its predecessors Bristol-Myers and the Squibb Corporation...

, that acts as a reasonably selective agonist

Agonist

An agonist is a chemical that binds to a receptor of a cell and triggers a response by that cell. Agonists often mimic the action of a naturally occurring substance...

of peripheral cannabinoid receptor

Cannabinoid receptor

The cannabinoid receptors are a class of cell membrane receptors under the G protein-coupled receptor superfamily. As is typical of G protein-coupled receptors, the cannabinoid receptors contain seven transmembrane spanning domains...

s. It has moderate affinity for CB₂ receptors with a K_i of 11nM, but 22x lower affinity for the psychoactive CB₁ receptors with a K_i of 245nM. The indole 2-methyl derivative has the ratio of affinities reversed however, with a K_i 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

JWH-018

JWH-018 or AM-678 is an analgesic chemical from the naphthoylindole family, which acts as a full agonist at both the CB1 and CB2 cannabinoid receptors, with some selectivity for CB2...

vs JWH-007

JWH-007

JWH-007 is an analgesic chemical from the naphthoylindole family, which acts as a cannabinoid agonist at both the CB1 and CB2 receptors. It was the most active of the first group of N-alkyl naphoylindoles discovered by the team led by John W Huffman, several years after the family was initially...

, JWH-081

JWH-081

JWH-081 is an analgesic chemical from the naphthoylindole family, which acts as a cannabinoid agonist at both the CB1 and CB2 receptors. With a Ki of 1.2nM it is fairly selective for the CB1 subtype, its affinity at this subtype approximately 10x the affinity at CB2. It was discovered by and named...

vs JWH-098

JWH-098

JWH-098 is a synthetic cannabinoid receptor agonist from the naphthoylindole family. It is the indole 2-methyl derivative of a closely related compound JWH-081, but has markedly different affinity for the CB1 and CB2 receptors...

).
Chemically, it is closely related to another indole-3-carboxamide synthetic cannabinoid, Org 28611

Org 28611

Org 28611 is a drug developed by Organon International which acts as a potent cannabinoid receptor full agonist at both the CB1 and CB2 receptors...

, but with a different cycloalkyl substitution on the carboxamide, and the cyclohexylmethyl group replaced by morpholinylethyl, as in JWH-200

JWH-200

JWH-200 is an analgesic chemical from the aminoalkylindole family, which acts as a cannabinoid receptor agonist. Its binding affinity at the CB1 receptor is 42nM, around the same as that of THC, but its analgesic potency in vivo was higher than that of other analogues with stronger CB1 binding...

or A-796,260

A-796,260

A-796,260 is a drug developed by Abbott Laboratories which acts as a potent and selective cannabinoid CB2 receptor agonist. Replacing the aromatic 3-benzoyl or 3-naphthoyl group found in most indole derived cannabinoids with the 3-tetramethylcyclopropylmethanone group, imparts significant...

. Early compounds such as these have subsequently led to the development of a large number of related indole-3-carboxamide cannabinoid ligands.

See also

Further reading