N-Methyl-DOET

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

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	None
Identifiers
IUPAC name 1-(4-ethyl-2,5-dimethoxyphenyl)-N-methylpropan-2-amine
Chemical and physical data
Formula	C14H23NO2
Molar mass	237.343 g·mol−1
3D model (JSmol)	Interactive image
SMILES CNC(Cc1cc(OC)c(cc1OC)CC)C
InChI InChI=1S/C14H23NO2/c1-6-11-8-14(17-5)12(7-10(2)15-3)9-13(11)16-4/h8-10,15H,6-7H2,1-5H3 Key:RQQHOPRRBXCSOF-UHFFFAOYSA-N

Use and effects

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

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

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

• 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