Etryptamine
Identification
- Name
- Etryptamine
- Accession Number
- DB01546
- 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the discovery of an unacceptable incidence of agranulocytosis, the development of Monase was halted and the drug was withdrawn from potential market use.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.
- Type
- Small Molecule
- Groups
- Illicit, Investigational, Withdrawn
- Structure
Structure for Etryptamine (DB01546)
- Weight
- Average: 188.2688
Monoisotopic: 188.131348522 - Chemical Formula
- C12H16N2
- Synonyms
- 3-(2-aminobutyl)indole
- alpha-ethyltryptamine
- α-ethyltryptamine
- αET
Pharmacology
- Indication
Developed in the 1960's for use as an antidepressant before market withdrawal in 1962.
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- 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
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
- Not Available
- Affected organisms
- 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
- Product Ingredients
Ingredient UNII CAS InChI Key Alpha-ethyltryptamine acetate 3RY07R55EE 118-68-3 TUQLBJAHRWROHB-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
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
- 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]
- 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]
- 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]
- 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]
- Link [Link]
- External Links
- 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
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 221 Young, E.H.P.; British Patent 933,786; August 14,1963; assigned to Imperial Chemical Industries Ltd. water solubility 510 mg/L YALKOWSKY,SH & DANNENFELSER,RM (1992) logS -2.57 ADME Research, USCD - 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 22.14 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 - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9747 Caco-2 permeable - 0.581 P-glycoprotein substrate Substrate 0.5596 P-glycoprotein inhibitor I Non-inhibitor 0.9707 P-glycoprotein inhibitor II Non-inhibitor 0.957 Renal organic cation transporter Non-inhibitor 0.7206 CYP450 2C9 substrate Non-substrate 0.8464 CYP450 2D6 substrate Non-substrate 0.6558 CYP450 3A4 substrate Non-substrate 0.7638 CYP450 1A2 substrate Inhibitor 0.7011 CYP450 2C9 inhibitor Non-inhibitor 0.7816 CYP450 2D6 inhibitor Non-inhibitor 0.5981 CYP450 2C19 inhibitor Non-inhibitor 0.6405 CYP450 3A4 inhibitor Non-inhibitor 0.6545 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.5318 Ames test Non AMES toxic 0.839 Carcinogenicity Non-carcinogens 0.8728 Biodegradation Not ready biodegradable 0.9804 Rat acute toxicity 2.2219 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9799 hERG inhibition (predictor II) Non-inhibitor 0.8727
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Drug created on July 31, 2007 07:10 / Updated on January 03, 2021 09:49