Isotryptamine, the parent compound of the substituted isotryptamines and the simplest isotryptamine.

Substituted isotryptamines, or simply isotryptamines, also known as 2-(1-indolyl)ethylamines, are a group of indoles closely related to the tryptamines but with the ethylamine side chain located at the 1 position of the indole ring system rather than at the 3 position as in tryptamines. Hence, they are positional isomers of tryptamines.

A variety of isotryptamines have been studied and described, including serotonergic psychedelics and psychoplastogens like 6-MeO-isoDMT;[1][2] non-hallucinogenic psychoplastogens like isoDMT, 5-MeO-isoDMT, and zalsupindole (DLX-001; AAZ-A-154);[3][4][5][6] serotonin 5-HT2C receptor agonists like (S)-5,6-difluoro-isoAMT, Ro60-0175 ((S)-5-fluoro-6-chloro-isoAMT), and PNU-181731;[7][8][9][10][11] serotonin 5-HT6 receptor modulators;[12][13][14] and dual monoamine releasing agents and serotonin receptor agonists like isoAMT (PAL-569).[15][16][17]

JRT is the isotryptamine analogue of LSD and may be considered a cyclized isotryptamine.[18][19]

Chemical structures of selected isotryptamines

See also

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References

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  1. ^ Glennon RA, Jacyno JM, Young R, McKenney JD, Nelson D (January 1984). "Synthesis and evaluation of a novel series of N,N-dimethylisotryptamines". J Med Chem. 27 (1): 41โ€“45. doi:10.1021/jm00367a008. PMIDย 6581313.
  2. ^ Dunlap LE, Azinfar A, Ly C, Cameron LP, Viswanathan J, Tombari RJ, Myers-Turnbull D, Taylor JC, Grodzki AC, Lein PJ, Kokel D, Olson DE (February 2020). "Identification of Psychoplastogenic N,N-Dimethylaminoisotryptamine (isoDMT) Analogues through Structure-Activity Relationship Studies". J Med Chem. 63 (3): 1142โ€“1155. doi:10.1021/acs.jmedchem.9b01404. PMCย 7075704. PMIDย 31977208.
  3. ^ 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): 124โ€“163. doi:10.1021/acs.chemrev.3c00375. PMIDย 38033123.
  4. ^ Atiq MA, Baker MR, Voort JL, Vargas MV, Choi DS (May 2024). "Disentangling the acute subjective effects of classic psychedelics from their enduring therapeutic properties". Psychopharmacology (Berl). doi:10.1007/s00213-024-06599-5. PMIDย 38743110.
  5. ^ Rasmussen K, Chytil M, Agrawal R, Leach P, Gillie D, Mungenast A, Vancutsem P, Engel S, Meyer R, Koenig A, Rus M (2024). "14. Preclinical Pharmacology of DLX-001, a Novel Non-Hallucinogenic Neuroplastogen With the Potential for Treating Neuropsychiatric Diseases". Biological Psychiatry. 95 (10). Elsevier BV: S80. doi:10.1016/j.biopsych.2024.02.192. ISSNย 0006-3223.
  6. ^ Rasmussen K, Engel S, Chytil M, Koenig A, Meyer R, Rus M, Olson D, Salinas E (December 2023). "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): 211โ€“354 (274โ€“275). doi:10.1038/s41386-023-01756-4. PMCย 10729596. PMIDย 38040810.
  7. ^ Chang-Fong J, Addo J, Dukat M, Smith C, Mitchell NA, Herrick-Davis K, Teitler M, Glennon RA (January 2002). "Evaluation of isotryptamine derivatives at 5-HT(2) serotonin receptors". Bioorg Med Chem Lett. 12 (2): 155โ€“158. doi:10.1016/s0960-894x(01)00713-2. PMIDย 11755343.
  8. ^ Bishop, Michael J; Nilsson, Bjรถrn M (2003). "New 5-HT2C receptor agonists". Expert Opinion on Therapeutic Patents. 13 (11): 1691โ€“1705. doi:10.1517/13543776.13.11.1691. ISSNย 1354-3776.
  9. ^ Dutton, Alice C.; Barnes, Nicholas M. (2006). "Anti-obesity pharmacotherapy: Future perspectives utilising 5-HT2C receptor agonists". Drug Discovery Today: Therapeutic Strategies. 3 (4): 577โ€“583. doi:10.1016/j.ddstr.2006.11.005.
  10. ^ Nilsson BM (July 2006). "5-Hydroxytryptamine 2C (5-HT2C) receptor agonists as potential antiobesity agents". J Med Chem. 49 (14): 4023โ€“4034. doi:10.1021/jm058240i. PMIDย 16821762.
  11. ^ Lee J, Jung ME, Lee J (November 2010). "5-HT2C receptor modulators: a patent survey". Expert Opin Ther Pat. 20 (11): 1429โ€“1455. doi:10.1517/13543776.2010.518956. PMIDย 20849206.
  12. ^ Geldenhuys WJ, Van der Schyf CJ (2008). "Serotonin 5-HT6 receptor antagonists for the treatment of Alzheimer's disease". Curr Top Med Chem. 8 (12): 1035โ€“1048. doi:10.2174/156802608785161420. PMIDย 18691131.
  13. ^ Glennon RA, Siripurapu U, Roth BL, Kolanos R, Bondarev ML, Sikazwe D, Lee M, Dukat M (2010). "The medicinal chemistry of 5-HT6 receptor ligands with a focus on arylsulfonyltryptamine analogs". Curr Top Med Chem. 10 (5): 579โ€“595. doi:10.2174/156802610791111542. PMCย 5839515. PMIDย 20166945.
  14. ^ Siddiqui N, Andalip, Bawa S, Ali R, Afzal O, Akhtar MJ, Azad B, Kumar R (April 2011). "Antidepressant potential of nitrogen-containing heterocyclic moieties: An updated review". J Pharm Bioallied Sci. 3 (2): 194โ€“212. doi:10.4103/0975-7406.80765. PMCย 3103913. PMIDย 21687347.
  15. ^ Bauer, Clayton T. (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.
  16. ^ Banks ML, Bauer CT, Blough BE, Rothman RB, Partilla JS, Baumann MH, Negus SS (June 2014). "Abuse-related effects of dual dopamine/serotonin releasers with varying potency to release norepinephrine in male rats and rhesus monkeys". Exp Clin Psychopharmacol. 22 (3): 274โ€“284. doi:10.1037/a0036595. PMCย 4067459. PMIDย 24796848.
  17. ^ Lyon RA, Titeler M, Seggel MR, Glennon RA (January 1988). "Indolealkylamine analogs share 5-HT2 binding characteristics with phenylalkylamine hallucinogens". Eur J Pharmacol. 145 (3): 291โ€“297. doi:10.1016/0014-2999(88)90432-3. PMIDย 3350047.
  18. ^ Tuck JR, Dunlap LE, Khatib YA, Hatzipantelis CJ, Weiser Novak S, Rahn RM, Davis AR, Mosswood A, Vernier AM, Fenton EM, Aarrestad IK, Tombari RJ, Carter SJ, Deane Z, Wang Y, Sheridan A, Gonzalez MA, Avanes AA, Powell NA, Chytil M, Engel S, Fettinger JC, Jenkins AR, Carlezon WA, Nord AS, Kangas BD, Rasmussen K, Liston C, Manor U, Olson DE (April 2025). "Molecular design of a therapeutic LSD analogue with reduced hallucinogenic potential". Proceedings of the National Academy of Sciences of the United States of America. 122 (16) e2416106122. doi:10.1073/pnas.2416106122. PMCย 12037037. PMIDย 40228113.
  19. ^ Dunlap L (2022). "Chapter 5. An Analog of LSD With Antipsychotic Potential". Development of Non-Hallucinogenic Psychoplastogens (PDF) (Ph.D. thesis). University of California, Davis. pp.ย 105โ€“114.


๐Ÿ“š Artikel Terkait di Wikipedia

Isotryptamine

variety of isotryptamine derivatives, or substituted isotryptamines, have been studied and described. Substituted isotryptamine Substituted tryptamine

Substituted tryptamine

Arylalkylamine Substituted ฮฒ-carboline Ibogalog Iboga alkaloid Lysergamide TiHKAL List of miscellaneous 5-HT2A receptor agonists Substituted isotryptamine Indazolylethylamine

JRT (drug)

JRT, also known as isotryptamine-LSD, is a serotonin receptor modulator, psychoplastogen, and serotonergic psychedelic related to lysergic acid diethylamide

ฮ‘-Methylisotryptamine

ฮฑ-Methylisotryptamine (isoAMT or ฮฑ-Me-isoT) is a synthetic compound belonging to the isotryptamine family, known for its psychoactive properties. As a structural analogue

Zalsupindole

has been cleared by the FDA for at home administration. Substituted isotryptamine Substituted tryptamine ยง Related compounds Non-hallucinogenic 5-HT2A

Substituted methoxyphenethylamine

ASR-2001 (2CB-5PrO)) Scalines (4-substituted 3,5-DMPEAs) (e.g., 4-desoxymescaline (DESOXY; 4-Me-3,5-DMPEA)) ฮจ-PEAs (4-substituted 2,6-DMPEAs) (e.g., ฮจ-2C-T-4)

IsoDMT

serotonin 5-HT2A receptor agonist and psychoplastogen of the isotryptamine group. It is the isotryptamine homologue of dimethyltryptamine (DMT), a more well-known

DOx

4-Substituted-2,5-dimethoxyamphetamines (DOx) is a chemical class of substituted amphetamine derivatives featuring methoxy groups at the 2- and 5- positions