Alpha-ethyltryptamine

α-Ethyltryptamine
Clinical data


ATC code	none
Legal status
Legal status	CA: Schedule III DE: Anlage I (Controlled) UK: Class A US: Schedule I
Identifiers
IUPAC name 1-(1H-indol-3-yl)butan-2-amine
Synonyms	3-(2-aminobutyl)indole
CAS Number	2235-90-7^Y
PubChem CID	8367
DrugBank	DB01546^Y
ChemSpider	8064^Y
Chemical and physical data
Formula	C₁₂H₁₆N₂
Molar mass	188.27 g/mol
3D model (Jmol)	Interactive image
Melting point	222 to 223 °C (432 to 433 °F)
SMILES c1cccc2c1c(c[nH]2)CC(N)CC
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^Y Key:ZXUMUPVQYAFTLF-UHFFFAOYSA-N^Y

α-Ethyltryptamine (αET, AET), also known as etryptamine (INN, BAN, USAN), is a psychedelic, stimulant, and entactogenic drug of the tryptamine class. It was originally developed and marketed as an antidepressant under the brand name Monase by Upjohn in the 1960s.

Originally believed to exert its effects predominantly via monoamine oxidase inhibition, alpha-ethyltryptamine was developed during the 1960s as an antidepressant by Upjohn chemical company in the United States under the name Monase, but was withdrawn from potential commercial use due to incidence of idiosyncratic agranulocytosis.

α-ET gained limited recreational popularity as a designer drug in the 1980s. Subsequently, in the USA it was added to the Schedule I list of illegal substances in 1993.

αET is structurally and pharmacologically related to αMT, α-methyltryptamine, and it is believed its central stimulant activity is probably not due to its activity as an MAOI, but appears to stem from its structural relationship to the indolic psychedelics. In contrast to αMT, αET is less stimulating and hallucinogenic, its effects resembling more those of entactogens like MDMA ("Ecstasy").

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