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Α-Methylisotryptamine

Topic: Chemistry

 From HandWiki - Reading time: 12 min

α-Methylisotryptamine (isoAMT or α-Me-isoT) is a synthetic compound belonging to the isotryptamine family, known for its psychoactive properties. As a structural analog of α-methyltryptamine (αMT), isoAMT exhibits entactogenic and psychedelic effects.

Pharmacology

α-Methylisotryptamine is a monoamine releasing agent and serotonin receptor agonist of the isotryptamine group.[1][2][3][4] It is the isotryptamine homologue of α-methyltryptamine (αMT), which is a more well-known serotonergic psychedelic, entactogen, and stimulant of the tryptamine family with similar pharmacological actions.[4][5][6]

Like αMT, α-methylisotryptamine is a monoamine releasing agent.[1][2] As the (–)-enantiomer, it specifically acts as a preferential serotonin and norepinephrine releasing agent (SNRA), with EC50 values of 177 nM for serotonin release, 81 nM for norepinephrine release, and 1,062 nM for dopamine release.[1][2] In contrast to amphetamine and similar agents acting as potent and selective dopamine and norepinephrine releasing agents, (–)-α-methylisotryptamine showed no misuse potential in animal studies, including no cocaine-like effects in drug discrimination tests and no facilitation of intracranial self-stimulation (ICSS).[1][2] In addition to its monoamine release, α-methylisotryptamine shows affinity for serotonin 5-HT2 receptors.[3]

Analogs

A derivative of α-methylisotryptamine, zalsupindole (DLX-001; AAZ-A-154; (R)-5-MeO-N,N-dimethyl-isoAMT), is a non-hallucinogenic serotonin 5-HT2A receptor agonist and is being developed for potential medical use in the treatment depression and other neuropsychiatric disorders.[7][8][9][10][11] Other derivatives of α-methylisotryptamine have also been developed, such as the selective serotonin 5-HT2C receptor agonists (S)-5,6-difluoro-isoAMT and Ro60-0175 ((S)-5-fluoro-6-chloro-isoAMT), among others.[12][13][14][15][16]

See also

References

  1. ↑ 1.0 1.1 1.2 1.3 Bauer CT (5 July 2014). Determinants of Abuse-Related Effects of Monoamine Releasers in Rats. VCU Scholars Compass (Thesis). doi:10.25772/AN08-SZ65. Retrieved 24 November 2024.
  2. ↑ 2.0 2.1 2.2 2.3 "Abuse-related effects of dual dopamine/serotonin releasers with varying potency to release norepinephrine in male rats and rhesus monkeys". Experimental and Clinical Psychopharmacology 22 (3): 274–284. June 2014. doi:10.1037/a0036595. PMID 24796848. 
  3. ↑ 3.0 3.1 "Indolealkylamine analogs share 5-HT2 binding characteristics with phenylalkylamine hallucinogens". European Journal of Pharmacology 145 (3): 291–297. January 1988. doi:10.1016/0014-2999(88)90432-3. PMID 3350047. 
  4. ↑ 4.0 4.1 "1-(1H-Indol-1-yl)propan-2-amine". https://pubchem.ncbi.nlm.nih.gov/compound/20806570. 
  5. ↑ "Beyond ecstasy: Alternative entactogens to 3,4-methylenedioxymethamphetamine with potential applications in psychotherapy". Journal of Psychopharmacology 35 (5): 512–536. May 2021. doi:10.1177/0269881120920420. PMID 32909493. 
  6. ↑ "α-Ethyltryptamine: A Ratiocinatory Review of a Forgotten Antidepressant". ACS Pharmacology & Translational Science 6 (12): 1780–1789. December 2023. doi:10.1021/acsptsci.3c00139. PMID 38093842. 
  7. ↑ "Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants". Chemical Reviews 124 (1): 124–163. January 2024. doi:10.1021/acs.chemrev.3c00375. PMID 38033123. 
  8. ↑ "Disentangling the acute subjective effects of classic psychedelics from their enduring therapeutic properties". Psychopharmacology 242 (7): 1481–1506. May 2024. doi:10.1007/s00213-024-06599-5. PMID 38743110. 
  9. ↑ "DLX 1". 11 December 2023. https://adisinsight.springer.com/drugs/800063576. 
  10. ↑ "Delving into the Latest Updates on DLX-001 with Synapse". 1 November 2024. https://synapse.patsnap.com/drug/853f1446b79348adad375cc77a9efb7e. 
  11. ↑ "ACNP 62nd Annual Meeting: Poster Abstracts P251 - P500: P361. Preclinical Pharmacology of DLX-001, a Novel Non-Hallucinogenic Neuroplastogen With the Potential for Treating Neuropsychiatric Diseases". Neuropsychopharmacology 48 (Suppl 1): 211–354 (274–275). December 2023. doi:10.1038/s41386-023-01756-4. PMID 38040810. 
  12. ↑ "Evaluation of isotryptamine derivatives at 5-HT(2) serotonin receptors". Bioorganic & Medicinal Chemistry Letters 12 (2): 155–158. January 2002. doi:10.1016/s0960-894x(01)00713-2. PMID 11755343. 
  13. ↑ "5-Hydroxytryptamine 2C (5-HT2C) receptor agonists as potential antiobesity agents". Journal of Medicinal Chemistry 49 (14): 4023–4034. July 2006. doi:10.1021/jm058240i. PMID 16821762. 
  14. ↑ "New 5-HT2C receptor agonists". Expert Opinion on Therapeutic Patents 13 (11): 1691–1705. 2003. doi:10.1517/13543776.13.11.1691. ISSN 1354-3776. 
  15. ↑ "Serotonergic 5-HT2C receptors as a potential therapeutic target for the design antiepileptic drugs". Current Topics in Medicinal Chemistry 5 (1): 59–67. 2005. doi:10.2174/1568026053386980. PMID 15638778. 
  16. ↑ "Novel agonists of 5HT2C receptors. Synthesis and biological evaluation of substituted 2-(indol-1-yl)-1-methylethylamines and 2-(indeno[1,2-b]pyrrol-1-yl)-1-methylethylamines. Improved therapeutics for obsessive compulsive disorder". J Med Chem 40 (17): 2762–2769. August 1997. doi:10.1021/jm970030l. PMID 9276022. 



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