AL-38022A

Last updated
AL-38022A
AL-38022A Structure.svg
AL-38022A 3D.png
Clinical data
Other namesAL38022A; Indazole-4,5-DHP-AMT
Drug class Serotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Identifiers
  • (S)-2-(8,9-Dihydro-7H-pyrano[2,3-g]indazol-1-yl)-1-methylethylamine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C13H17N3O
Molar mass 231.299 g·mol−1
3D model (JSmol)
Melting point 106 to 107 °C (223 to 225 °F)
  • c13CCCOc3ccc(cn2)c1n2CC(C)N
  • InChI=1S/C13H17N3O/c1-9(14)8-16-13-10(7-15-16)4-5-12-11(13)3-2-6-17-12/h4-5,7,9H,2-3,6,8,14H2,1H3/t9-/m0/s1 Yes check.svgY
  • Key:FJRIVFVALIEIOY-VIFPVBQESA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

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]

Contents

See also

References

  1. 1 2 3 4 Nichols DE (2018). "Chemistry and Structure-Activity Relationships of Psychedelics". Curr Top Behav Neurosci. 36: 1–43. 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. 1 2 Duan W, Cao D, Wang S, Cheng J (January 2024). "Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants". Chem Rev. 124 (1): 124–163. 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. 1 2 3 May JA, Sharif NA, Chen HH, Liao JC, Kelly CR, Glennon RA, et al. (January 2009). "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-g]indazol-1-yl)-1-methylethylamine]". Pharmacology, Biochemistry, and Behavior. 91 (3): 307–314. doi:10.1016/j.pbb.2008.07.015. PMC   3763814 . PMID   18718483.
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