11-Methoxyasimilobine
Pharmaceutical compound
From Wikipedia, the free encyclopedia
11-Methoxyasimilobine, also known as 1,11-dimethoxy-2-hydroxynoraporphine, is a serotonin 5-HT2 receptor agonist of the noraporphine family related to the noraporphine alkaloid asimilobine.[1][2] It is the 11-methoxy derivative of asimilobine.[1][2]
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| Other names | 1,11-Dimethoxy-2-hydroxynoraporphine; Compound 16l; Compound S31 |
| Drug class | Serotonin 5-HT2 receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonin 5-HT2C receptor agonist |
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| Formula | C18H19NO3 |
| Molar mass | 297.354 g·mol−1 |
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Whereas asimilobine is a selective, lower-potency, high-efficacy partial agonist of the serotonin 5-HT2C receptor,[3] 11-methoxyasimilobine is a highly potent and selective full agonist of both the serotonin 5-HT2A and 5-HT2C receptors, with approximately 8-fold preferential activation of the serotonin 5-HT2C receptor over the serotonin 5-HT2A receptor.[1] Its EC50 (Emax) values were 18 nM (98%) at the serotonin 5-HT2A receptor and 2.3 nM (100%) at the serotonin 5-HT2C receptor.[1] The drug is a biased agonist of the serotonin 5-HT2C receptor, favoring Gq signaling over β-arrestin recruitment by approximately 6.3-fold.[1] It was among the most potent dual serotonin 5-HT2A and 5-HT2C receptor agonists of a large series of assessed noraporphines.[1]
Besides the serotonin 5-HTA and 5-HT2C receptors, the drug also showed weak agonism of the serotonin 5-HT2B receptor, but only at very high concentrations (EC50 = >10,000 nM).[1][2] It showed little activity at a selection of other serotonin receptors.[1]
The chemical synthesis of 11-methoxyasimilobine has been described.[1][2] A variety of analogues of the drug with similar activity have also been described.[1][2]
11-Methoxyasimilobine was described in the scientific literature by Wangzhi Qin and colleagues in 2025.[1] It had previously been patented in 2022.[2] There is interest in 11-methoxyasimilobine and related compounds for potential medical use, such as treatment of anxiety, obsessive–compulsive disorder (OCD), and substance use disorders.[1][2]