Chemistry:5-MeO-isoDMT

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5-MeO-isoDMT, or 5-OMe-isoDMT, also known as 5-methoxy-N,N-dimethylisotryptamine, is a putatively non-hallucinogenic serotonin 5-HT2A receptor agonist and psychoplastogen of the isotryptamine group.[1][2][3][4][5][6] It is the isotryptamine analogue of the non-hallucinogenic 6-MeO-DMT and is a positional isomer of the psychedelic 6-MeO-isoDMT.[3][5][6]

The drug does not substitute for serotonergic psychedelics in animal drug discrimination tests and does not produce the head-twitch response, a behavioral of psychedelic effects, at any dose.[1][3][5][7][6] Hence, it appears to be non-hallucinogenic.[3][5][6] On the other hand, 5-MeO-isoDMT has comparable psychoplastogenic potency and effects compared to the psychedelic 5-MeO-DMT.[1][2][4][5] These effects are blocked by the serotonin 5-HT2A receptor antagonist ketanserin.[4][5] Certain analogues and derivatives of 5-MeO-isoDMT, like isoDMT and the α-methylated zalsupindole (DLX-001; AAZ-A-154; (R)-5-MeO-α-methyl-isoDMT), likewise produce no head-twitch response, whereas 6-MeO-isoDMT produces a reduced head-twitch response.[1][4][5][6] Hence, these analogues appear to be less or fully non-hallucinogenic similarly to 5-MeO-isoDMT.[1][4][5][6] In addition, like 5-MeO-isoDMT, they retain potent psychoplastogenic effects.[1][4][5]

5-MeO-isoDMT was first described in the scientific literature by 1984.[6][7] It was subsequently further characterized in 2020.[4][5] Confusingly, the drug has been referred to as "6-MeO-isoDMT" (or rather "6-OMe-isoDMT") in some publications.[3]

See also

References

  1. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 "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. 
  2. ↑ 2.0 2.1 "Disentangling the acute subjective effects of classic psychedelics from their enduring therapeutic properties". Psychopharmacology. May 2024. doi:10.1007/s00213-024-06599-5. PMID 38743110. 
  3. ↑ 3.0 3.1 3.2 3.3 3.4 "Role of stereochemistry in drug discrimination studies". Drug Discrimination: Applications to Medicinal Chemistry and Drug Studies. Wiley. 5 August 2011. pp. 129–161. doi:10.1002/9781118023150.ch4. ISBN 978-0-470-43352-2. 
  4. ↑ 4.0 4.1 4.2 4.3 4.4 4.5 4.6 "Development of Non-Hallucinogenic Psychoplastogens". 2022. https://escholarship.org/uc/item/5qr3w0gm. 
  5. ↑ 5.00 5.01 5.02 5.03 5.04 5.05 5.06 5.07 5.08 5.09 "Identification of Psychoplastogenic N,N-Dimethylaminoisotryptamine (isoDMT) Analogues through Structure-Activity Relationship Studies". Journal of Medicinal Chemistry 63 (3): 1142–1155. February 2020. doi:10.1021/acs.jmedchem.9b01404. PMID 31977208. 
  6. ↑ 6.0 6.1 6.2 6.3 6.4 6.5 6.6 "Synthesis and evaluation of a novel series of N,N-dimethylisotryptamines". Journal of Medicinal Chemistry 27 (1): 41–45. January 1984. doi:10.1021/jm00367a008. PMID 6581313. 
  7. ↑ 7.0 7.1 "The Study of Structure-Activity Relationships Using Drug Discrimination Methodology". Methods of Assessing the Reinforcing Properties of Abused Drugs. New York, NY: Springer New York. 1987. pp. 373–390. doi:10.1007/978-1-4612-4812-5_18. ISBN 978-1-4612-9163-3. https://books.google.com/books?id=CIXlBwAAQBAJ&pg=PA379. 



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