O-Methyl-AL-34662
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| Other names | Indazole-5-MeO-AMT |
| Drug class | Serotonin 5-HT2 receptor agonist; Serotonergic psychedelic; Hallucinogen |
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| Chemical and physical data | |
| Formula | C11H15N3O |
| Molar mass | 205.261 g·mol−1 |
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O-Methyl-AL-34662 is a serotonin receptor agonist and putative serotonergic psychedelic of the indazole family related to the psychedelic tryptamine 5-MeO-AMT. It is an analogue of 5-MeO-AMT in which the indole ring has been replaced with an indazole ring and the active enantiomer has been purified.
The drug is a potent agonist of the serotonin 5-HT2 receptors, including of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors. It is a partial to full agonist of the serotonin 5-HT2A receptor and a full agonist of the serotonin 5-HT2C receptor. Both O-methyl-AL-34662 and 5-MeO-AMT showed around 10-fold lower potency as agonists of the serotonin 5-HT2A receptor compared to the serotonin 5-HT2B and 5-HT2C receptors. The drug has roughly the same activational potencies and efficacies at the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors as 5-MeO-AMT.
It potently induces the head-twitch response, a behavioral proxy of psychedelic effects, in mice, and hence may have hallucinogenic effects in humans. Its effective dose for induction of the head-twitch response was 0.16 mg/kg, which was about the same as that of (R)-DOI (0.13 mg/kg) and was about 6-fold more potent than 5-MeO-AMT (1.0 mg/kg).
O-Methyl-AL-34662 was first described in the scientific literature by 2006.
In contrast to the case of O-methyl-AL-34662, the corresponding flipped indazole analogue of 5-MeO-DMT has profoundly reduced potency as a serotonin 5-HT2A receptor agonist relative to 5-MeO-DMT (~1,250-fold lower activational potency).