7-MeO-DMT
Pharmaceutical compound
From Wikipedia, the free encyclopedia
7-MeO-DMT, or 7-OMe-DMT, also known as 7-methoxy-N,N-dimethyltryptamine, is a serotonin receptor modulator of the tryptamine family.[1] It is the 7-methoxy derivative of the serotonergic psychedelic dimethyltryptamine (DMT) and is a positional isomer of 5-MeO-DMT, 4-MeO-DMT, and 6-MeO-DMT.[1]
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| Other names | 7-OMe-DMT; 7-Methoxy-DMT; 7-Methoxy-N,N-dimethyltryptamine |
| Drug class | Serotonin receptor modulator; Possible serotonergic psychedelic or hallucinogen |
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| Formula | C13H18N2O |
| Molar mass | 218.300 g·mol−1 |
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Use and effects
7-MeO-DMT was only briefly mentioned in Alexander Shulgin's book TiHKAL (Tryptamines I Have Known and Loved) and its properties and effects were not described.[2]
Pharmacology
Pharmacodynamics
In an early study using the isolated rat stomach fundus strip, the drug showed very low serotonin receptor affinity (A2 = 4,677 nM) 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 of hallucinogenic activity.[6] The receptor in this tissue may correspond to the serotonin 5-HT2B receptor.[7]
In subsequent studies, 7-MeO-DMT bound to the serotonin 5-HT2A receptor (Ki = 5,400–5,440 nM) 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 serotonin 5-HT2C receptor (Ki = >10,000 nM), but did show affinity for the serotonin 5-HT1A receptor (Ki = 1,760 nM).[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 serotonin 5-HT1E and 5-HT1F receptors (Ki = >10,000 nM and 2,620 nM, respectively).[10]
7-MeO-DMT substitutes for the atypical psychedelic 5-MeO-DMT in rodent drug discrimination tests.[5] The drug was only briefly mentioned in Alexander Shulgin's 1997 book TiHKAL 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]
Chemistry
Analogues
Analogues of 7-MeO-DMT include 7-methoxytryptamine, dimethyltryptamine (DMT), 4-MeO-DMT, 5-MeO-DMT, and 6-MeO-DMT, among others.[2][1]
History
7-MeO-DMT was first described in the scientific literature by at least 1968.[11]
Society and culture
Legal status
United States
7-MeO-DMT is not an explicitly controlled substance in the United States, but may be considered a Schedule I controlled substance in this country as it is a positional isomer of 5-MeO-DMT.[12][13]