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N-Methyl-DOET
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| Clinical data | |
|---|---|
| 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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| 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]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]
History
[edit]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]
Analogues
[edit]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]
See also
[edit]- 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
[edit]- ^ a b c d e f g h i j Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. pp. 834–835, 878. ISBN 978-3-03788-700-4. OCLC 858805226.
8.5.26. N-Substitution von 2,4,5-trisubstituierten Phenylalkylaminen: Einerseits wurde der Einfluss von N-Alkyl-, andererseits derjenige von N-Heterogruppen-Substituenten geprüft. Allgemein ist bekannt, dass das Einführen von Alkylsubstituenten am Stickstoff von psychedelischen Phenylalkylaminen eine Abnahme der HT2-Rezeptoraffinitäten zur Folge hat [29, 150, 151]. Die Wirkungsabschwächung konnte mit den potenten Substanzen DOB (2) und DOM (8) im Menschen bestätigt werden [8]: N-Methyl-DOM (316; BEATRICE) und METHYL-DOB (317) erwiesen sich im Vergleich zu den beiden unmethylierten Verbindungen als massiv weniger aktiv; die aktive Dosis wurde dabei noch nicht eruiert. METHYL-DOET (318; DOETM) erwies sich bei einer Dosierung von 18mg bereits als deutlich aktiv [140]; die Wirkungen wurden im Vergleich zu DOET (14) als ruhiger und angenehmer beschrieben. [...] 318; METHYL-DOET, 18mg, 8-10h. [...] [140] P. Rausch. Persönliche Mitteilung, 2009.
- ^ Nichols DE (2018). Chemistry and Structure-Activity Relationships of Psychedelics. Current Topics in Behavioral Neurosciences. Vol. 36. pp. 1–43. doi:10.1007/7854_2017_475. ISBN 978-3-662-55878-2. PMID 28401524.
Although the most active tryptamine hallucinogens are N,N-dialkylated, the phenethylamines generally cannot tolerate even a single N-substitution. Even small groups such as methyl or ethyl (see Table 2) abolish their hallucinogenic activity.
- ^ a b Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. "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."
- ^ a b Shulgin AT (1980). "Hallucinogens". In Burger A, Wolf ME (eds.). Burger's Medicinal Chemistry. Vol. 3 (4 ed.). New York: Wiley. pp. 1109–1137. ISBN 978-0-471-01572-7. OCLC 219960627.
Of all the variously substituted phenylisopropylamines that have been N-methylated and titrated in man (including the homologs of TMA-2, 2,5-DMA, DOM, and DOB: 60.22b, 60.22i, 60.22aa, and 60.22ff, respectively), it is only the methylenedioxy compound 60.23a that has maintained quantitative potency (94). As with mescaline itself, dimethylation of this compound eliminates any central action.
- ^ a b Jacob P, Shulgin AT (1994). "Structure-Activity Relationships of the Classic Hallucinogens and Their Analogs". In Lin GC, Glennon RA (eds.). Hallucinogens: An Update (PDF). National Institute on Drug Abuse Research Monograph Series. Vol. 146. National Institute on Drug Abuse. pp. 74–91. PMID 8742795. Archived from the original on 13 July 2025.
[MDA] is also remarkable because the N-methyl homolog 3,4 (MDMA) has biological activity, although the nature of its action places it outside of this review. No other phenethylamine hallucinogen retains central activity on N-methylation.