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5-MeO-isoDMT

From Wikipedia, the free encyclopedia
Serotonergic psychoplastogen

Not to be confused with5-MeO-DMT or6-MeO-isoDMT.
Pharmaceutical compound
5-MeO-isoDMT
Clinical data
Other names5-MeO-iso-DMT; 5-Methoxy-isoDMT; 5-OMe-isoDMT; 5-OMe-iso-DMT; 5-Methoxy-iso-DMT; 5-Methoxy-N,N-dimethylisotryptamine
Drug classNon-hallucinogenicserotonin5-HT2A receptoragonist;Psychoplastogen
Identifiers
  • 2-(5-methoxyindol-1-yl)-N,N-dimethylethanamine
CAS Number
PubChemCID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC13H18N2O
Molar mass218.300 g·mol−1
3D model (JSmol)
  • CN(C)CCN1C=CC2=C1C=CC(=C2)OC
  • InChI=1S/C13H18N2O/c1-14(2)8-9-15-7-6-11-10-12(16-3)4-5-13(11)15/h4-7,10H,8-9H2,1-3H3
  • Key:HRCTXPIFQNOZCQ-UHFFFAOYSA-N

5-MeO-isoDMT, or5-OMe-isoDMT, also known as5-methoxy-N,N-dimethylisotryptamine, is a putatively non-hallucinogenicserotonin5-HT2A receptoragonist andpsychoplastogen of theisotryptamine group.[1][2][3][4][5][6] It is the isotryptamineanalogue of the non-hallucinogenic6-MeO-DMT and is apositional isomer of the psychedelic6-MeO-isoDMT.[3][5][6]

The drug does not substitute forserotonergic psychedelics in animaldrug discrimination tests and does not produce thehead-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 psychoplastogenicpotency and effects compared to the psychedelic5-MeO-DMT.[1][2][4][5] These effects are blocked by the serotonin 5-HT2A receptorantagonistketanserin.[4][5] Certain analogues andderivatives of 5-MeO-isoDMT, likeisoDMT and the α-methylatedzalsupindole (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 thescientific 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

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References

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  1. ^abcdefDuan W, Cao D, Wang S, Cheng J (January 2024). "Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants".Chemical Reviews.124 (1):124–163.doi:10.1021/acs.chemrev.3c00375.PMID 38033123.
  2. ^abAtiq 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.doi:10.1007/s00213-024-06599-5.PMC 12226698.PMID 38743110.
  3. ^abcdeGlennon RA, Young R (5 August 2011). "Role of stereochemistry in drug discrimination studies". In Glennon RA, Young R (eds.).Drug Discrimination: Applications to Medicinal Chemistry and Drug Studies. Wiley. pp. 129–161.doi:10.1002/9781118023150.ch4.ISBN 978-0-470-43352-2.
  4. ^abcdefgDunlap LE (2022)."Development of Non-Hallucinogenic Psychoplastogens".eScholarship. Retrieved19 November 2024.
  5. ^abcdefghijDunlap LE, Azinfar A, Ly C, Cameron LP, Viswanathan J, Tombari RJ, et al. (February 2020)."Identification of PsychoplastogenicN,N-Dimethylaminoisotryptamine (isoDMT) Analogues through Structure-Activity Relationship Studies".Journal of Medicinal Chemistry.63 (3):1142–1155.doi:10.1021/acs.jmedchem.9b01404.PMC 7075704.PMID 31977208.
  6. ^abcdefgGlennon RA, Jacyno JM, Young R, McKenney JD, Nelson D (January 1984). "Synthesis and evaluation of a novel series of N,N-dimethylisotryptamines".Journal of Medicinal Chemistry.27 (1):41–45.doi:10.1021/jm00367a008.PMID 6581313.
  7. ^abGlennon RA, Young R (1987)."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. pp. 373–390.doi:10.1007/978-1-4612-4812-5_18.ISBN 978-1-4612-9163-3.
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