| Class: | Non-hallucinogenic serotonin 5-HT2A receptor agonist; Psychoplastogen |
| Pubchem: | 44287166 |
| Chemspiderid: | 23136125 |
| Chembl: | 41806 |
| Synonyms: | 5-MeO-iso-DMT; 5-Methoxy-isoDMT; 5-OMe-isoDMT; 5-OMe-iso-DMT; 5-Methoxy-iso-DMT; 5-Methoxy-N,N-dimethylisotryptamine |
| Iupac Name: | 2-(5-methoxyindol-1-yl)-N,N-dimethylethanamine |
| C: | 13 |
| H: | 18 |
| N: | 2 |
| O: | 1 |
| Smiles: | CN(C)CCN1C=CC2=C1C=CC(=C2)OC |
| Stdinchi: | 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 |
| Stdinchikey: | 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-HT2A receptor agonist and psychoplastogen of the isotryptamine group.[1] [2] [3] [4] [5] It is the isotryptamine analogue of the non-hallucinogenic 6-MeO-DMT and is a positional isomer of the psychedelic 6-MeO-isoDMT.
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. Hence, it appears to be non-hallucinogenic. On the other hand, 5-MeO-isoDMT has comparable psychoplastogenic potency and effects compared to the psychedelic 5-MeO-DMT. These effects are blocked by the serotonin 5-HT2A receptor antagonist ketanserin. 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. Hence, these analogues appear to be less or fully non-hallucinogenic similarly to 5-MeO-isoDMT. In addition, like 5-MeO-isoDMT, they retain potent psychoplastogenic effects.
5-MeO-isoDMT was first described in the scientific literature by 1984.[6] It was subsequently further characterized in 2020. Confusingly, the drug has been referred to as "6-MeO-isoDMT" (or rather "6-OMe-isoDMT") in some publications.[7]