Α-Ethyltryptamine

α-Ethyltryptamine
INN: Etryptamine
Clinical data
Trade names	Monase
Other names	alpha-Ethyltryptamine; αET; AET; α-ET; Etryptamine; PAL-125; 3-(2-Aminobutyl)indole; 3-Indolylbutylamine; U-17312E; U17312E; Ro 3-1932; NSC-63963; NSC-88061, Etryptamine (USAN US)
Routes of; administration	Oral
Drug class	Entactogen; Stimulant; Monoamine releasing agent; Serotonin receptor agonist; Monoamine oxidase inhibitor
ATC code	None;
Legal status
Legal status	BR: Class F2 (Prohibited psychotropics); CA: Schedule III; DE: Anlage I (Authorized scientific use only); UK: Class A; US: Schedule I; UN: Psychotropic Schedule I;
Pharmacokinetic data
Metabolism	Hydroxylation
Metabolites	• 6-Hydroxy-αET (inactive)
Onset of action	0.5–1.5 hours
Elimination half-life	~8 hours
Duration of action	6–8 hours (100–150 mg)
Excretion	Urine (majority)
Identifiers
	IUPAC name 1-(1H-indol-3-yl)butan-2-amine;
CAS Number	2235-90-7 ; 118-68-3 (acetate); 26330-11-0 (hydrochloride);
PubChem CID	8367;
PubChem SID	46507084;
DrugBank	DB01546 ;
ChemSpider	8064 ;
UNII	GR181O3R32;
KEGG	D04092;
ChEBI	CHEBI:134838;
ChEMBL	ChEMBL1619758;
CompTox Dashboard (EPA)	DTXSID1046764 ;
Chemical and physical data
Formula	C12H16N2
Molar mass	188.274 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	222 to 223 °C (432 to 433 °F)
	SMILES CCC(N)CC1=CNC2=CC=CC=C12;
	InChI InChI=1S/C12H16N2/c1-2-10(13)7-9-8-14-12-6-4-3-5-11(9)12/h3-6,8,10,14H,2,7,13H2,1H3 ; Key:ZXUMUPVQYAFTLF-UHFFFAOYSA-N ;
	(verify)

α-Ethyltryptamine (αET, AET), also known as etryptamine, is an entactogen and stimulant drug of the tryptamine family. It was originally developed and marketed as an antidepressant under the brand name Monase by Upjohn in the 1960s before being withdrawn due to toxicity.

Side effects of αET include facial flushing, headache, gastrointestinal distress, insomnia, irritability, appetite loss, and sedation, among others. A rare side effect of αET is agranulocytosis. αET acts as a releasing agent of serotonin, norepinephrine, and dopamine, as a weak serotonin receptor agonist, and as a weak monoamine oxidase inhibitor. It may also produce serotonergic neurotoxicity. αET is a substituted tryptamine and is closely related to α-methyltryptamine (αMT) and other α-alkylated tryptamines.

αET was first described in 1947. It was used as an antidepressant for about a year around 1961. The drug started being used recreationally in the 1980s and several deaths have been reported. αET is a controlled substance in various countries, including the United States and United Kingdom. There has been renewed interest in αET, for instance as an alternative to MDMA, with the development of psychedelics and entactogens as medicines in the 2020s.