5-MeO-isoDMT

Not to be confused with 5-MeO-DMT or 6-MeO-isoDMT.

5-MeO-isoDMT

Clinical data
Other names	5-MeO-iso-DMT; 5-Methoxy-isoDMT; 5-OMe-isoDMT; 5-OMe-iso-DMT; 5-Methoxy-iso-DMT; 5-Methoxy-N,N-dimethylisotryptamine
Drug class	Non-hallucinogenic serotonin 5-HT2A receptor agonist; Psychoplastogen
Identifiers
IUPAC name 2-(5-methoxyindol-1-yl)-N,N-dimethylethanamine
PubChem CID	44287166
ChemSpider	23136125
ChEMBL	ChEMBL41806
Chemical and physical data
Formula	C13H18N2O
Molar mass	218.300 g·mol^−1
3D model (JSmol)	Interactive image
SMILES CN(C)CCN1C=CC2=C1C=CC(=C2)OC
InChI 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, or 5-OMe-isoDMT, also known as 5-methoxy-N,N-dimethylisotryptamine, is a putatively non-hallucinogenic serotonin 5-HT_2A 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-HT_2A receptor antagonist ketanserin.[4][5] Certain analogues and derivatives of 5-MeO-isoDMT, like isoDMT and the α-methylated AAZ-A-154 (DLX-001; (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

• 2-Bromo-LSD
• Ariadne (drug)
• ITI-1549
• Lisuride
• Tabernanthalog

References

1. Duan W, Cao D, Wang S, Cheng J (January 2024). "Serotonin 2A Receptor (5-HT_2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants". Chemical Reviews. 124 (1): 124–163. doi:10.1021/acs.chemrev.3c00375. PMID 38033123.
2. 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. doi:10.1007/s00213-024-06599-5. PMID 38743110.
3. Glennon 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. ISBN 978-0-470-43352-2.
4. Dunlap LE (2022). "Development of Non-Hallucinogenic Psychoplastogens". eScholarship. Retrieved 19 November 2024.
5. Dunlap LE, Azinfar A, Ly C, Cameron LP, Viswanathan J, Tombari RJ, et al. (February 2020). "Identification of Psychoplastogenic N,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. Glennon 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. Glennon 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.