4-MeO-DMT
Chemical compound
From Wikipedia, the free encyclopedia
4-MeO-DMT, or 4-methoxy-DMT, also known as 4-methoxy-N,N-dimethyltryptamine or as O-methylpsilocin (PSOM), is a serotonin receptor modulator and possible psychedelic drug of the tryptamine and 4-hydroxytryptamine families.[1][2][3][4][5] It is the O-methylated analogue of psilocin (4-HO-DMT) and a positional isomer of 5-MeO-DMT.[1][5]
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| Other names | 4-OMe-DMT; 4-Methoxy-DMT; 4-Methoxy-N,N-dimethyltryptamine; O-Methylpsilocin; PSOM |
| Drug class | Serotonin receptor modulator |
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| Formula | C13H18N2O |
| Molar mass | 218.300 g·mol−1 |
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Use and effects
Interactions
Pharmacology
Pharmacodynamics
| Target | Affinity (Ki, nM) |
|---|---|
| 5-HT1A | 235 (Ki) 352 (EC50) 103% (Emax) |
| 5-HT2A | 68–1,300 (Ki) 21 (EC50) 76% (Emax) |
| 5-HT2B | 9 (EC50) 58% (Emax) |
| 5-HT2C | 340 (Ki) 4 (EC50) 100% (Emax) |
| SERT | 903 (IC50) |
| NET, DAT | >10,000 |
| Notes: The smaller the value, the more avidly the drug interacts with the site. Sources:[7][8][9] | |
4-MeO-DMT has shown high affinity for several serotonin receptors, including the serotonin 5-HT1A receptor, the serotonin 5-HT2A receptor, and the serotonin 5-HT2C receptor.[7][8] Compared to 5-MeO-DMT, 4-MeO-DMT had similar affinity for the serotonin 5-HT2A receptor, but showed much lower affinity (21-fold) for the serotonin 5-HT1A receptor.[7][8] The drug shows pronounced biased agonism at the serotonin 5-HT2C receptor.[10]
4-MeO-DMT produces serotonergic psychedelic-like effects in animals, including rodents and monkeys.[1][2][3][4][5] It has been found to disrupt object size discrimination performance in monkeys, suggesting that it may have psychedelic effects in humans.[1][11] However, whereas 5-MeO-DMT has greater potency than bufotenin (5-HO-DMT), 4-MeO-DMT has lower potency than psilocybin (4-PO-DMT).[1] This may be due to the fact that the lipophilicity of psilocin is not importantly enhanced by O-methylation, in contrast to the case of bufotenin, which has associated limitations in terms of blood–brain barrier permeability.[1] Besides psilocin/psilocybin, 4-MeO-DMT is also less potent than 5-MeO-DMT.[2]
4-MeO-DMT fully substituted for DOM in rodent drug discrimination tests, with an ED50 of about 3.53 mg/kg and about 3-fold lower potency than 5-MeO-DMT.[12] 4-MeO-DMT also substituted for 5-MeO-DMT in rodent drug discrimination tests, with an ED50 of 3.47 μmol/kg and about 2.7-fold lower potency than 5-MeO-DMT.[13] Despite its activity in drug discrimination tests however, 4-MeO-DMT fails to produce the head-twitch response in rodents.[9] This may in part be related to the drug's unusually potent serotonin 5-HT1A receptor agonism.[9]
Chemistry
Analogues
Analogues of 4-MeO-DMT include dimethyltryptamine (DMT), 4-methoxytryptamine (4-MT or 4-MeO-T), psilocin (4-HO-DMT), 4-AcO-DMT (psilacetin), 4-MeO-DET, 4-MeO-DiPT, 4-MeO-MiPT, 4-methyl-DMT, 5-MeO-DMT, 6-MeO-DMT, and 7-MeO-DMT, among others.[6]
History
4-MeO-DMT was first described in the scientific literature by at least 1968.[1][14]
Society and culture
Legal status
Canada
4-MeO-DMT is not a controlled substance in Canada.[15]
United States
In the United States, 4-MeO-DMT is a Schedule I controlled substance as it is a positional isomer of 5-MeO-DMT.[16][17]