7-MeO-DMT was only briefly mentioned inAlexander Shulgin's bookTiHKAL (Tryptamines I Have Known and Loved) and its properties and effects were not described.[2]
In an early study using the isolated rat stomach fundus strip, the drug showed very lowserotonin receptoraffinity (A2 = 4,677nM) that was about 56-fold lower than that of 5-MeO-DMT.[3][4][5] However, this assay was subsequently found to be an unreliable predictor ofhallucinogenic activity.[6] The receptor in this tissue may correspond to the serotonin5-HT2B receptor.[7]
In subsequent studies, 7-MeO-DMT bound to theserotonin5-HT2A receptor (Ki = 5,400–5,440nM) and had 9- to 59-fold lower affinity than 5-MeO-DMT and 5- to 17-fold lower affinity than DMT.[1][8][9] It showed no detectable affinity for the serotonin5-HT2C receptor (Ki = >10,000nM), but did show affinity for the serotonin5-HT1A receptor (Ki = 1,760nM).[9] Its affinity for the serotonin 5-HT1A receptor was 160-fold lower than that of 5-MeO-DMT and was 9-fold lower than that of DMT.[9] 7-MeO-DMT has also been assessed at the serotonin5-HT1E and5-HT1F receptors (Ki = >10,000nM and 2,620nM, respectively).[10]
7-MeO-DMT substitutes for the atypical psychedelic 5-MeO-DMT in rodentdrug discrimination tests.[5] The drug was only briefly mentioned inAlexander Shulgin's 1997 bookTiHKAL and is not known to have been tested in humans.[3][2] Hence, it is unknown whether 7-MeO-DMT produces psychedelic effects in humans.[3][2]
^abcdDuan 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.PMID38033123.Nevertheless, substitutions at positions 6 or 7 were reported to reduce or even abolish the binding ability to 5-HT2 receptors. For example, 6-OMe-DMT (35, Ki = 7300 nM) and 7-OMe-DMT (36, Ki = 5400 nM) exhibited reduced affinity compared to that of DMT (Ki = 1200 nM) at [3H]-ketanserin-labeled 5-HT2Rs.124
^abcGlennon RA, Rosecrans JA (1982). "Indolealkylamine and phenalkylamine hallucinogens: a brief overview".Neuroscience and Biobehavioral Reviews.6 (4):489–497.doi:10.1016/0149-7634(82)90030-6.PMID6757811.
^Glennon RA, Gessner PK (April 1979). "Serotonin receptor binding affinities of tryptamine analogues".Journal of Medicinal Chemistry.22 (4):428–432.doi:10.1021/jm00190a014.PMID430481.
^abGlennon RA, Young R, Rosecrans JA, Kallman MJ (1980). "Hallucinogenic agents as discriminative stimuli: a correlation with serotonin receptor affinities".Psychopharmacology.68 (2):155–158.doi:10.1007/BF00432133.PMID6776558.
^Nichols DE, Schooler D, Yeung MC, Oberlender RA, Zabik JE (September 1984). "Unreliability of the rat stomach fundus as a predictor of hallucinogenic activity in substituted phenethylamines".Life Sciences.35 (13):1343–1348.doi:10.1016/0024-3205(84)90390-4.PMID6482656.
^abcGlennon RA, Dukat M, Grella B, Hong S, Costantino L, Teitler M, et al. (August 2000). "Binding of beta-carbolines and related agents at serotonin (5-HT(2) and 5-HT(1A)), dopamine (D(2)) and benzodiazepine receptors".Drug and Alcohol Dependence.60 (2):121–132.doi:10.1016/s0376-8716(99)00148-9.hdl:11380/17721.PMID10940539.
