![]() | |
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 |
|
Identifiers | |
| |
Chemical and physical data | |
Formula | C14H23NO2 |
Molar mass | 237.343 g·mol−1 |
3D model (JSmol) | |
| |
|
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]
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]
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]
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]
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.
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.
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.
[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.