4-MeO-DMT
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| Clinical data | |
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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; Serotonergic psychedelic; Hallucinogen |
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| E number | {{#property:P628}} |
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| ECHA InfoCard | {{#property:P2566}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value). |
| Chemical and physical data | |
| Formula | C13H18N2O |
| Molar mass | 218.300 g·mol−1 |
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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]
Use and effects
[edit | edit source]According to Alexander Shulgin in his book TiHKAL (Tryptamines I Have Known and Loved), 4-MeO-DMT is not known to have been tested in humans.[6] However, the N,N-diethyl analogue 4-MeO-DET has been tested in humans and was found to be completely inactive at doses of up to 30 mg orally or smoked.[6]
Interactions
[edit | edit source]Pharmacology
[edit | edit source]Pharmacodynamics
[edit | edit source]| Target | Affinity (Ki, nM) |
|---|---|
| 5-HT1A | 235 |
| 5-HT2A | 68–1,300 |
| 5-HT2C | 340 |
| Notes: The smaller the value, the more avidly the drug interacts with the site. Sources:[7][8] | |
4-MeO-DMT has shown high affinity for several serotonin receptors, including the serotonin 5-HT1A receptor (Ki = 235 nM), the serotonin 5-HT2A receptor (Ki = 68–1,300 nM), and the serotonin 5-HT2C receptor (Ki = 340 nM).[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.[9]
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][10] 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.[11] 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.[12]
Chemistry
[edit | edit source]Analogues
[edit | edit source]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, 5-MeO-DMT, 6-MeO-DMT, and 7-MeO-DMT, among others.[6]
History
[edit | edit source]4-MeO-DMT was first described in the scientific literature by at least 1968.[1][13]
Society and culture
[edit | edit source]Legal status
[edit | edit source]In the United States 4-MeO-DMT is a Schedule 1 controlled substance as it is a positional isomer of 5-MeO-DMT.[14]
See also
[edit | edit source]References
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- ^ a b c Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value). "The 4-methyl ether of psilocin, 4-MeO-DMT, is especially appealing, in that it is a simple homologue of psilocin and it is quite stable. But the methyl group as an ether link lacks the lability of the phosphate or acetate esters, and it cannot be easily hydrolyzed off to form psilocin. The immediate homologue is 4-MeO-DET which is completely without action either orally or by smoking at dosages up to 30 mgs. [...] The 5-MeO-DMT has already been mentioned, and the remaining two would be 4-MeO-DMT and 4-MeO-DIPT. The former is a known compound but has not been measured in man. The latter is not a known compound."
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