N-Methyl-DOET
| File:N-methyl-DOET structure.png | |
| Clinical data | |
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| Other names | METHYL-DOET; DOETM; 4-Ethyl-2,5-dimethoxy-N-methylamphetamine; 2,5-Dimethoxy-4-ethyl-N-methylamphetamine; 4-Ethyl-2,5-dimethoxymethamphetamine |
| Routes of administration | Oral[1] |
| Drug class | Serotonergic psychedelic; Hallucinogen |
| ATC code |
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| Identifiers | |
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| E number | {{#property:P628}} |
| CompTox Dashboard (EPA) |
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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 | C14H23NO2 |
| Molar mass | 237.343 g·mol−1 |
| 3D model (JSmol) | |
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N-Methyl-DOET, also known as DOETM, as well as 4-ethyl-2,5-dimethoxy-N-methylamphetamine, is a psychedelic drug of the phenethylamine, amphetamine, and DOx families.[1] It is the N-methyl derivative of the serotonergic psychedelic 4-ethyl-2,5-dimethoxyamphetamine (DOET).[1]
Use and effects
[edit | edit source]N-Methyl-DOET is said to be significantly active at a dose of 18 mg and to have a duration of 8 to 10 hours in humans.[1] However, it appears to be several times less potent than DOET, which is active at doses of 2 to 6 mg with a duration of 14 to 20 hours.[1] The effects of N-methyl-DOET were not specifically described but were said to be calmer and more pleasant compared to those of DOET.[1]
Interactions
[edit | edit source]Chemistry
[edit | edit source]Analogues
[edit | edit source]N-Methylation of psychedelic phenethylamines has invariably greatly reduced or eliminated their hallucinogenic activity.[2][3][4][5] Examples of this include related compounds like Beatrice (N-methyl-DOM) and methyl-DOB (N-methyl-DOB), which at assessed doses appear to be inactive as psychedelics in humans.[1][3][4][5] However, N-methyl-DOET, though much less potent than DOET, is an apparent exception to this rule, in that it has been found to be clearly psychedelic and to retain decent potency.[1]
History
[edit | edit source]N-Methyl-DOET was first described in the scientific literature by Daniel Trachsel in 2013.[1] It was synthesized and evaluated by P. Rausch, who provided the information on its properties and effects to Trachsel via personal communication.[1]
See also
[edit | edit source]- DOx (psychedelics)
- Beatrice (N-methyl-DOM)
- N-Methyl-TMA-2
- N-Methyl-DOI
- Methyl-DOB (N-methyl-DOB)
- N-Methyl-2C-B
- N-Methyl-2C-I
- IDNNA (N,N-dimethyl-DOI)
- Methyl-TMA (N-methyl-TMA)
- N-Methylmescaline
- Trichocereine
- Ariadne
References
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- ^ a b Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value). "None of [the N-methyl homologues of the psychedelics] seem to produce stuff of elegance. It is clear that the adding of an N-methyl group onto DOM certainly cuts down the activity by a factor of ten-fold, and even then results in something that is not completely good. Three [mg] of DOM is a winner, but even ten times this, [30 mg] of N-methyl-DOM, is somewhat fuzzy. In the rabbit hyperthermia studies, this compound was some 25 times less active than DOM, so even animal tests say this is way down there in value. This particular measure suggests that the active level in man might be 75 [mg]. Well, maybe, but I am not at all comfortable in trying it at that level. In fact I do not intend to explore this any further whatsoever, unless there is a compelling reason, and I see no such reason. For the moment, let us leave this one to others, who might be more adventurous but less discriminating. [...] Three additional N-methylated homologues of known psychedelics warrant mention, but do not really deserve separate recipes. This is because they have had only the most cursory assaying, which I have learned about by personal correspondence. All three were synthesized by the reduction of the formamide of the parent primary amine with LAH. METHYL-TMA [...] had been run up in several trials to a maximum of 240 [mg], with some mental disturbances mentioned only at this highest level. METHYL-TMA-2 [...] had been tried at up to 120 [mg] without any effects. METHYL-TMA-6 [...] had been tried at up to 30 [mg] and it, too, was apparently without effects. These are reports that I have heard from others, but I have had no personal experience with them. Those that I can describe from personal experience are entered separately as recipes of their own. [...] So far, however, the only consistent thing seen is that, with N-methylation, the potency of the psychedelics is decreased, but the potency of the stimulants appears to be pretty much maintained. [...] The bottom line with METHYL-DOB is, as with the other N-methylated psychedelics, that it is way down in potency, and probably not worth pursuing."
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