NAV

Etryptamine

Identification

Generic Name
Etryptamine
DrugBank Accession Number
DB01546
Background

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the discovery of an unacceptable incidence of agranulocytosis, the development of Monase was halted and the drug was withdrawn from potential market use.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

Type
Small Molecule
Groups
Illicit, Investigational, Withdrawn
Structure
3D
Similar Structures
Weight
Average: 188.2688
Monoisotopic: 188.131348522
Chemical Formula
C12H16N2
Synonyms
  • 3-(2-aminobutyl)indole
  • alpha-ethyltryptamine
  • Etryptamine
  • α-ethyltryptamine
  • αET

Pharmacology

Indication

Developed in the 1960's for use as an antidepressant before market withdrawal in 1962.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

αET is a stimulant and psychedelic with MDMA like physiological effects. Like MDMA, increases in locomotor activity and mood elevation can be seen post administration. [2]

Mechanism of action

The mechanism of action responsible for its antidepressant activity was believed to lie in its ability to inhibit monoamine oxidase, while its stimulant activity on the central nervous system appeared to result from its structural similarity to indole-based psychedelics. [5]

Research discovered αET to be both a monoamine oxidase inhibitor and a potent monoamine releasing agent capable of serotonergic neurotoxicity. [3]

The ability to release serotonin was linked to αET's MDMA like properties. [2] αET has been shown to release serotonin pre-synaptically, as well as lesser amounts of norepinephrine and dopamine.

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Alpha-ethyltryptamine acetate3RY07R55EE118-68-3TUQLBJAHRWROHB-UHFFFAOYSA-N
International/Other Brands
Monase (Upjohn)

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as 3-alkylindoles. These 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
Aralkylamines / Substituted pyrroles / Benzenoids / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Monoalkylamines / Hydrocarbon derivatives
Substituents
3-alkylindole / Amine / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Heteroaromatic compound / Hydrocarbon derivative / Organic nitrogen compound / Organonitrogen compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
GR181O3R32
CAS number
2235-90-7
InChI Key
ZXUMUPVQYAFTLF-UHFFFAOYSA-N
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
IUPAC Name
1-(1H-indol-3-yl)butan-2-amine
SMILES
CCC(N)CC1=CNC2=CC=CC=C12

References

Synthesis Reference

α-ET TiHKAL entry • Isomer Design: http://isomerdesign.com/PiHKAL/read.php?domain=tk&id=11

General References
  1. Huang XM, Johnson MP, Nichols DE: Reduction in brain serotonin markers by alpha-ethyltryptamine (Monase). Eur J Pharmacol. 1991 Jul 23;200(1):187-90. [Article]
  2. Krebs KM, Geyer MA: Behavioral characterization of alpha-ethyltryptamine, a tryptamine derivative with MDMA-like properties in rats. Psychopharmacology (Berl). 1993;113(2):284-7. [Article]
  3. Martinez DL, Geyer MA: Characterization of the disruptions of prepulse inhibition and habituation of startle induced by alpha-ethyltryptamine. Neuropsychopharmacology. 1997 Mar;16(3):246-55. [Article]
  4. STEINER WG, PSCHEIDT GR, COSTA E, HIMWICH HE: ALPHA-ETHYLTRYPTAMINE (ETRYPTAMINE): AN ELECTROENCEPHALOGRAPHIC, BEHAVIORAL AND NEUROCHEMICAL ANALYSIS. Psychopharmacologia. 1963 Jul 2;4:354-66. [Article]
  5. Link [Link]
KEGG Drug
D04092
KEGG Compound
C06213
PubChem Compound
8367
PubChem Substance
46507084
ChemSpider
8064
BindingDB
50025198
ChEBI
134838
ChEMBL
CHEMBL1619758
Wikipedia
Alpha-Ethyltryptamine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)221Young, E.H.P.; British Patent 933,786; August 14,1963; assigned to Imperial Chemical Industries Ltd.
water solubility510 mg/LYALKOWSKY,SH & DANNENFELSER,RM (1992)
logS-2.57ADME Research, USCD
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
Polarizability22.14 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9747
Caco-2 permeable-0.581
P-glycoprotein substrateSubstrate0.5596
P-glycoprotein inhibitor INon-inhibitor0.9707
P-glycoprotein inhibitor IINon-inhibitor0.957
Renal organic cation transporterNon-inhibitor0.7206
CYP450 2C9 substrateNon-substrate0.8464
CYP450 2D6 substrateNon-substrate0.6558
CYP450 3A4 substrateNon-substrate0.7638
CYP450 1A2 substrateInhibitor0.7011
CYP450 2C9 inhibitorNon-inhibitor0.7816
CYP450 2D6 inhibitorNon-inhibitor0.5981
CYP450 2C19 inhibitorNon-inhibitor0.6405
CYP450 3A4 inhibitorNon-inhibitor0.6545
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5318
Ames testNon AMES toxic0.839
CarcinogenicityNon-carcinogens0.8728
BiodegradationNot ready biodegradable0.9804
Rat acute toxicity2.2219 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9799
hERG inhibition (predictor II)Non-inhibitor0.8727
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Drug created at July 31, 2007 13:10 / Updated at February 03, 2022 21:15