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Identification
NameAlpha-ethyltryptamine
Accession NumberDB01546
TypeSmall Molecule
GroupsIllicit, Investigational, Withdrawn
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the discovery of an unacceptable incidence of agranulocytosis, the development of Monase was halted and the drug was withdrawn from potential market use.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.

Structure
Thumb
Synonyms
Etryptamine
α-ethyltryptamine
αET
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
Monase Upjohn
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Alpha-ethyltryptamine acetate
118-68-3
Thumb
  • InChI Key: TUQLBJAHRWROHB-UHFFFAOYNA-N
  • Monoisotopic Mass: 248.152477894
  • Average Mass: 248.3208
DBSALT000188
Categories
UNIIGR181O3R32
CAS number2235-90-7
WeightAverage: 188.2688
Monoisotopic: 188.131348522
Chemical FormulaC12H16N2
InChI KeyInChIKey=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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as indoles. These are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndoles
Direct ParentIndoles
Alternative Parents
Substituents
  • Indole
  • Aralkylamine
  • Benzenoid
  • Substituted pyrrole
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationDeveloped in the 1960's for use as an antidepressant before market withdrawal in 1962.
PharmacodynamicsαET 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 actionThe 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.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point221Young, 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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
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. [PubMed:1722753 ]
  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. [PubMed:7855195 ]
  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. [PubMed:9138441 ]
  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. [PubMed:14048556 ]
  5. Link [Link]
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
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Drug created on July 31, 2007 07:10 / Updated on September 16, 2013 17:15