Chemistry:AL-38022A

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AL-38022A is a serotonin receptor agonist and psychedelic drug of the indazolethylamine family related to the psychedelic tryptamine 5-MeO-AMT.[1] It is one of a range of similar drugs developed for scientific research and with some possible clinical applications such as in the treatment of glaucoma.[1][2][3] The drug acts as a potent and selective agonist for the 5-HT2 family of serotonin receptors, with highest binding affinity for the 5-HT2C subtype and around four times less affinity for 5-HT2A and 5-HT2B.[1][2][4] In drug discrimination tests in animals, it fully substituted for the psychedelic drugs 5-MeO-DMT and DOM.[1][4] AL-38022A was first described in the scientific literature by Richard Glennon and colleagues in 2009.[4]

See also

References

  1. ↑ 1.0 1.1 1.2 1.3 "Chemistry and Structure-Activity Relationships of Psychedelics". Curr Top Behav Neurosci 36: 1–43. 2018. doi:10.1007/7854_2017_475. PMID 28401524. "A variation on ring-substitution patterns was the discovery of indazole ligands with potent 5-HT2A agonist activity (May et al. 2003a, 2006). For example, AL-38022A 15 was developed as a highly potent 5-HT2A agonist that had efficacy in reducing intraocular pressure in glaucoma. Compound 15 was a full agonist at all three 5-HT2 family receptors, with EC50 values between 0.5 and 2.2 nM for several functional responses (May et al. 2009). In a drug discrimination assay in rats trained to discriminate the hallucinogen DOM from saline, 15 produced full substitution, with an ED50 of 0.05 mg/kg. Similarly, it produced full substitution in monkeys trained to discriminate DOM from saline, with an ED50 of 0.04 mg/kg, comparable to the potent 5-HT2A/2C agonist DOI.". 
  2. ↑ 2.0 2.1 "Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants". Chem Rev 124 (1): 124–163. January 2024. doi:10.1021/acs.chemrev.3c00375. PMID 38033123. "Later, May et al. also reported compound AL-38022A (30), which has the same benzopyrazole scaffold and an additional pyran ring fused to the bicyclic core, as a high affinity (Ki = 0.13 nM, [ 125I]-DOI) and potent agonist (EC50 = 22.5 nM, Emax = 87%) at the r5-HT2AR.141 Compound AL-38022A also exhibited high selectivity for 5-HT2 receptors against other related receptors.141". 
  3. ↑ Chen HH, May JA, Severns BS. Pyranoindazoles and their use for the treatment of glaucoma. US 6881749
  4. ↑ 4.0 4.1 4.2 "Pharmacological properties and discriminative stimulus effects of a novel and selective 5-HT2 receptor agonist AL-38022A [(S)-2-(8,9-dihydro-7H-pyrano[2,3-gindazol-1-yl)-1-methylethylamine]"]. Pharmacology, Biochemistry, and Behavior 91 (3): 307–314. January 2009. doi:10.1016/j.pbb.2008.07.015. PMID 18718483. 



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