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the discovery of an unacceptable incidence of agranulocytosis, the development of Monase was halted and the drug was withdrawn from potential market use.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
PubChem Compound
8366
ChemSpider
8063
ChEMBL
CHEMBL1412355
Predicted Properties
PropertyValueSource
Water Solubility0.481 mg/mLALOGPS
logP2.55ALOGPS
logP2.43Chemaxon
logS-2.6ALOGPS
pKa (Strongest Acidic)17.13Chemaxon
pKa (Strongest Basic)9.99Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count1Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area41.81 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity59.32 m3·mol-1Chemaxon
Polarizability22.13 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon