Alpha-ethyltryptamine acetateProduct ingredient for Etryptamine
- Name
- Alpha-ethyltryptamine acetate
- Drug Entry
- Etryptamine
In the 1960's, alpha-ethyltryptamine (αET), a non hydrazine reversible monoamine oxidase inhibitor, was developed in the United States by the Upjohn chemical company for use as an antidepressant. αET was an FDA approved antidepressant under the name Monase. However, in 1962, after the discovery of an unacceptable incidence of agranulocytosis, the development of Monase was halted and the drug was withdrawn from potential market use.
In 1993, the US Drug Enforcement Administration added αET to Schedule I of its Schedules of Controlled Substances, after an increasing incidence of its use as a recreational drug in the 1980's. Currently, αET is an illegal substance; however, it's activity is still under scientific investigation.
αET is a stimulant and hallucinogen, but it is less stimulating and hallucinogenic than alpha-methyltryptamine, a closely related compound. Instead, the effects of αET, a tryptamine derivative, more closely resemble the amphetamine derived drug 3,4-methylenedioxy-N-methylamphetamine (MDMA). Similarly to MDMA, αET has been shown to release serotonin pre-synaptically, as well as lesser amounts of norepinephrine and dopamine. Like MDMA, increases in locomotor activity and mood elevation can be seen post administration.
- Accession Number
- DBSALT000188
- Structure
- Synonyms
- Not Available
- UNII
- 3RY07R55EE
- CAS Number
- 118-68-3
- Weight
- Average: 248.3208
Monoisotopic: 248.152477894 - Chemical Formula
- C14H20N2O2
- InChI Key
- TUQLBJAHRWROHB-UHFFFAOYSA-N
- InChI
- InChI=1S/C12H16N2.C2H4O2/c1-2-10(13)7-9-8-14-12-6-4-3-5-11(9)12;1-2(3)4/h3-6,8,10,14H,2,7,13H2,1H3;1H3,(H,3,4)
- IUPAC Name
- 1-(1H-indol-3-yl)butan-2-amine; acetic acid
- SMILES
- CC(O)=O.CCC(N)CC1=CNC2=CC=CC=C12
- External Links
- PubChem Compound
- 8366
- ChemSpider
- 8063
- ChEMBL
- CHEMBL1412355
- Predicted Properties
Property Value Source Water Solubility 0.481 mg/mL ALOGPS logP 2.55 ALOGPS logP 2.43 Chemaxon logS -2.6 ALOGPS pKa (Strongest Acidic) 17.13 Chemaxon pKa (Strongest Basic) 9.99 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 41.81 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 59.32 m3·mol-1 Chemaxon Polarizability 22.13 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon