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α-Ethyltryptamine

Clinical data
Other names	3-(2-aminobutyl)indole
ATC code	none
Legal status
Legal status	US: Schedule I
Identifiers
IUPAC name 1-(1H-indol-3-yl)butan-2-amine
CAS Number	2235-90-7 118-68-3
PubChem CID	8367
DrugBank	DB01546
ChemSpider	8064
CompTox Dashboard (EPA)	DTXSID1046764
Chemical and physical data
Formula	C12H16N2
Molar mass	188.27 g/mol g·mol
3D model (JSmol)	Interactive image
Melting point	222 to 223 °C (432 to 433 °F)
SMILES c1cccc2c1c(c2)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 Key:ZXUMUPVQYAFTLF-UHFFFAOYSA-N
(verify)

α-ethyltryptamine (αET, AET, "Monase"), also known as etryptamine, is a psychedelic, stimulant and entactogen of the tryptamine chemical class.

History

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was developed as an antidepressant by Upjohn chemical company in the United States under the name "Monase" but was withdrawn from potential commercial use due to an unacceptable incidence of agranulocytosis.

αET 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.

Pharmacology

αET is structurally and pharmacologically related to α-methyltryptamine (αMT), but its effects are slightly different. In contrast to αMT, αET is less stimulating and hallucinogenic, its effects resembling more those of entactogens like MDMA ("Ecstasy").

Similarly to MDMA, αET has been demonstrated to be a releasing agent of serotonin, norepinephrine and dopamine (with serotonin being the primary neurotransmitter affected); in addition, it acts as a non-selective serotonin receptor agonist. Scientific research has shown that alpha-ethyltryptamine is a serotonergic neurotoxin.

See also

• α-methyltryptamine
• 4-Methyl-αET

References

1. α-ET TiHKAL entry • Erowid.
2. Huang XM, Johnson MP, Nichols DE (1991). "Reduction in brain serotonin markers by alpha-ethyltryptamine (Monase)". European Journal of Pharmacology. 200 (1): 187–190. doi:10.1016/0014-2999(91)90686-K. PMID 1722753. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)

External links

• Erowid.org (2009). "TiHKAL #11. a-ET". Retrieved 2010-02-10.

• α-ET TiHKAL entry • Isomer Design
• α-ET Vault on Erowid