Chemistry:Asimilobine

Asimilobine, also known as (R)-1-methoxy-2-hydroxynoraporphine, is a noraporphine alkaloid with various known pharmacological actions. It has been found to act as a selective biased partial agonist of the serotonin 5-HT_2C receptor, with an EC₅₀ of 308 nM and E_max of 86% for activation of G_q signaling and no β-arrestin2 recruitment. Conversely, asimilobine was inactive as an agonist of the serotonin 5-HT_2A and 5-HT_2B receptors, but did show weak antagonism of these receptors at very high concentrations (IC₅₀ = >10,000 nM). Derivatives and analogues of asimilobine with more potent serotonin 5-HT_2C receptor agonism, such as 11-chloroasimilobine, have been studied and described. In addition, derivatives with dual highly potent serotonin 5-HT_2A and 5-HT_2C receptor agonism, such as 11-methoxyasimilobine, have been described.

(RS)-Asimilobine.

Although asimilobine is inactive as an agonist of the serotonin 5-HT_2A and 5-HT_2C receptors, the racemic form of the compound has been found to act as an agonist of the serotonin 5-HT_2A, 5-HT_2B, and 5-HT_2C receptors, with EC₅₀ (E_max) values of 318 nM (55%), 794 nM (25%), and 51 nM (94%), respectively. The 1-propoxy homologue shows more potent serotonin 5-HT_2A and 5-HT_2B receptor agonism and less potent serotonin 5-HT_2C receptor agonism (EC₅₀ (E_max) = 43 nM (91%), 53 nM (81%), and 197 nM (98%), respectively).

See also

• Noraporphine
• Aporphine alkaloid
• Nornuciferine
• 11-Chloroasimilobine
• 11-Methoxyasimilobine
• MQ02-439