2,5-Dimethoxy-4-ethylamphetamine

2,5-Dimethoxy-4-ethylamphetamine
Clinical data
Other names	DOET; DOEt; DOE; HECATE; Hecate; DMEA; 2,5-Dimethoxy-4-ethylamphetamine; 4-Ethyl-2,5-dimethoxyamphetamine; Dimethoxyethylamphetamine; Ethyldimethoxyamphetamine
Drug class	Serotonergic psychedelic; Serotonin 5-HT2 receptor agonist; Antidepressant; Psychic energizer; Cognitive enhancer
Legal status
Legal status	AU: S9 (Prohibited substance); BR: Class F2 (Prohibited psychotropics); CA: Schedule I; DE: Anlage I (Authorized scientific use only); UK: Class A; US: Schedule I; UN: Psychotropic Schedule I;
Pharmacokinetic data
Metabolism	Oxidation of the 4-position ethyl group
Onset of action	1–3 hours
Duration of action	5–20 hours
Excretion	Urine (10–40% unchanged within 24 hours)
Identifiers
	IUPAC name 1-(4-Ethyl-2,5-dimethoxyphenyl)propan-2-amine;
CAS Number	22004-32-6 ;
PubChem CID	27402;
DrugBank	DB01467 ;
ChemSpider	25499 ;
UNII	9SK6K682UL;
KEGG	C22714 ;
ChEMBL	ChEMBL8224 ;
CompTox Dashboard (EPA)	DTXSID00860585 ;
Chemical and physical data
Formula	C13H21NO2
Molar mass	223.316 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O(c1cc(c(OC)cc1CC(N)C)CC)C;
	InChI InChI=1S/C13H21NO2/c1-5-10-7-13(16-4)11(6-9(2)14)8-12(10)15-3/h7-9H,5-6,14H2,1-4H3 ; Key:HXJKWPGVENNMCC-UHFFFAOYSA-N ;
	(verify)

2,5-Dimethoxy-4-ethylamphetamine (DOET) is a psychedelic drug of the phenethylamine, amphetamine, and DOx families. It is closely related to DOM and is a synthetic analogue of the naturally occurring phenethylamine psychedelic mescaline. The drug acts as a selective agonist of the serotonin 5-HT₂ receptors, including of the serotonin 5-HT_2A, 5-HT_2B, and 5-HT_2C receptors.

DOET was first discovered by Alexander Shulgin in the 1960s. It was clinically studied at low and sub-hallucinogenic doses for potential use as a pharmaceutical drug acting as a "psychic energizer" by Dow Chemical Company in the 1960s. However, its development was terminated after DOM emerged as a street drug and caused a public health crisis in San Francisco in 1967. Nonetheless, DOET's effects at low doses were extensively characterized in small clinical trials. The psychedelic effects of DOET at higher doses were subsequently described by Shulgin in his book PiHKAL in 1991.

DOET is taken by mouth. It has a slow onset of 1 to 3 hours, a delayed peak of 3 to 5 hours, and a dose-dependent and potentially very long duration of 5 to 20 hours. Effects at low doses include mild euphoria, enhanced self-awareness, and talkativeness, among others. Mild closed-eye visuals can also occur. At higher doses, DOET produces psychedelic effects including heightened emotions, sensory enhancement, rich closed-eye visuals, and open-eye visuals, among others. Physical effects include pupil dilation, increased heart rate, and increased blood pressure.