Α-Methylisotryptamine Explained

Drug Name:α-Methylisotryptamine
Width:175px
Class:Serotonin–norepinephrine releasing agent
Serotonin receptor agonist
Cas Number:1227465-67-9
Pubchem:20806570
Chemspiderid:19644583
Synonyms:isoAMT; iso-αMT; α-Me-isoT; PAL-569; 1-α-Methyltryptamine; 1-API; 1-IT; α-Methyl-isotryptamine
Iupac Name:1-indol-1-ylpropan-2-amine
C:11
H:14
N:2
Smiles:CC(CN1C=CC2=CC=CC=C21)N
Stdinchi:1S/C11H14N2/c1-9(12)8-13-7-6-10-4-2-3-5-11(10)13/h2-7,9H,8,12H2,1H3
Stdinchikey:OZPPCCIRSILHOZ-UHFFFAOYSA-N

α-Methylisotryptamine (isoAMT or α-Me-isoT) is a synthetic compound belonging to the tryptamine class, 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] 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. As the (–)-enantiomer, it specifically acts as a preferential serotonin and norepinephrine releasing agent (SNRA), with values of 177nM for serotonin release, 81nM for norepinephrine release, and 1,062nM for dopamine release. 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). In addition to its monoamine release, α-methylisotryptamine shows affinity for serotonin 5-HT2 receptors.

Analogs

A derivative of α-methylisotryptamine, AAZ-A-154 (DLX-001; (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

Notes and References

  1. Bauer CT . Determinants of Abuse-Related Effects of Monoamine Releasers in Rats . VCU Scholars Compass . 5 July 2014 . 10.25772/AN08-SZ65 . 24 November 2024.
  2. Banks ML, Bauer CT, Blough BE, Rothman RB, Partilla JS, Baumann MH, Negus SS . 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 . 24796848 . 4067459 . 10.1037/a0036595 .
  3. Lyon RA, Titeler M, Seggel MR, Glennon RA . Indolealkylamine analogs share 5-HT2 binding characteristics with phenylalkylamine hallucinogens . European Journal of Pharmacology . 145 . 3 . 291–297 . January 1988 . 3350047 . 10.1016/0014-2999(88)90432-3 .
  4. Web site: 1-(1H-Indol-1-yl)propan-2-amine . PubChem . 24 November 2024.
  5. Oeri HE . Beyond ecstasy: Alternative entactogens to 3,4-methylenedioxymethamphetamine with potential applications in psychotherapy . Journal of Psychopharmacology . 35 . 5 . 512–536 . May 2021 . 32909493 . 8155739 . 10.1177/0269881120920420 .
  6. Glennon RA, Dukat MG . α-Ethyltryptamine: A Ratiocinatory Review of a Forgotten Antidepressant . ACS Pharmacology & Translational Science . 6 . 12 . 1780–1789 . December 2023 . 38093842 . 10714429 . 10.1021/acsptsci.3c00139 .
  7. Duan W, Cao D, Wang S, Cheng J . Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants . Chemical Reviews . 124 . 1 . 124–163 . January 2024 . 38033123 . 10.1021/acs.chemrev.3c00375 .
  8. Atiq MA, Baker MR, Voort JL, Vargas MV, Choi DS . Disentangling the acute subjective effects of classic psychedelics from their enduring therapeutic properties . Psychopharmacology . May 2024 . 38743110 . 10.1007/s00213-024-06599-5 . free .
  9. Web site: DLX 1 . AdisInsight . 11 December 2023 . 2 November 2024.
  10. Web site: Delving into the Latest Updates on DLX-001 with Synapse . Synapse . 1 November 2024 . 2 November 2024.
  11. Rasmussen K, Engel S, Chytil M, Koenig A, Meyer R, Rus M, Olson D, Salinas E . 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 . 38040810 . 10729596 . 10.1038/s41386-023-01756-4 .
  12. Chang-Fong J, Addo J, Dukat M, Smith C, Mitchell NA, Herrick-Davis K, Teitler M, Glennon RA . Evaluation of isotryptamine derivatives at 5-HT(2) serotonin receptors . Bioorganic & Medicinal Chemistry Letters . 12 . 2 . 155–158 . January 2002 . 11755343 . 10.1016/s0960-894x(01)00713-2 .
  13. Nilsson BM . 5-Hydroxytryptamine 2C (5-HT2C) receptor agonists as potential antiobesity agents . Journal of Medicinal Chemistry . 49 . 14 . 4023–4034 . July 2006 . 16821762 . 10.1021/jm058240i .
  14. Bishop MJ, Nilsson BM . New 5-HT2C receptor agonists . Expert Opinion on Therapeutic Patents . 13 . 11 . 2003 . 1354-3776 . 10.1517/13543776.13.11.1691 . 1691–1705.
  15. Isaac M . Serotonergic 5-HT2C receptors as a potential therapeutic target for the design antiepileptic drugs . Current Topics in Medicinal Chemistry . 5 . 1 . 59–67 . 2005 . 15638778 . 10.2174/1568026053386980 .
  16. Bös M, Jenck F, Martin JR, Moreau JL, Sleight AJ, Wichmann J, Widmer U . 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 . 9276022 . 10.1021/jm970030l .

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