ContaminantDB: Etryptamine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 05:56:13 UTC

Update Date

2016-11-09 01:15:57 UTC

Accession Number

CHEM019234

Identification

Common Name

Etryptamine

Class

Small Molecule

Description

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the discovery of an unacceptable incidence of agranulocytosis, the development of Monase was halted and the drug was withdrawn from potential market use.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.

Contaminant Sources

STOFF IDENT Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Etryptamine hydrochloride	MeSH
Etryptamine monoacetate	MeSH
2-Ethyltryptamine	MeSH
Etryptamine monoacetate, (-)-isomer	MeSH
Etryptamine, (+)-isomer	MeSH
3-(2-Aminobutylindole)	MeSH
Etryptamine acetate, (+-)-isomer OF etryptamine	MeSH
Etryptamine monoacetate, (+)-isomer	MeSH
Etryptamine monoacetate, (+-)-isomer	MeSH
alpha-Ethyltryptamine	MeSH

Chemical Formula

C₁₂H₁₆N₂

Average Molecular Mass

188.269 g/mol

Monoisotopic Mass

188.131 g/mol

CAS Registry Number

2235-90-7

IUPAC Name

1-(1H-indol-3-yl)butan-2-amine

Traditional Name

α-ethyltryptamine

SMILES

CCC(N)CC1=CNC2=CC=CC=C12

InChI Identifier

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

InChI Key

ZXUMUPVQYAFTLF-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as 3-alkylindoles. 3-alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

3-alkylindoles

Alternative Parents

Substituents

3-alkylindole
Aralkylamine
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Azacycle
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organonitrogen compound
Primary aliphatic amine
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.48 g/L	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	22.14 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

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0079-0900000000-7b365aafe0f30a53544f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0079-2900000000-7fb14ccf4af4885c1ee3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05o0-5900000000-fbb39e6b9e60df156bab	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-cabd33e14eb8f5528a87	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-724890bb23775725be4e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-8900000000-23981666d0033a07a0a0	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB01546

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Alpha-Ethyltryptamine

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

8367

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Etryptamine (CHEM019234)

Structure for CHEM019234: Etryptamine