Alpha-methyltryptamine

Identification

Name
Alpha-methyltryptamine
Accession Number
DB01446
Type
Small Molecule
Groups
Experimental, Illicit
Description

A stimulant and psychoactive drug which produces effects similar to 3,4-methylenedioxy-N-methylamphetamine (MDMA), despite being structurally dissimilar. It was developed in the 1960's by Upjohn with the intention for use as an antidepressant. In the 1990's, alpha-methyltryptamine became regulated as a Schedule I controlled substance in the United states.

Structure
Thumb
Synonyms
  • 164E
  • 3-IT
  • AMT
  • Indopan
  • IT-290
  • IT-403
  • αMT
External IDs
U-14
Categories
UNII
BIK35ACJ0Q
CAS number
299-26-3
Weight
Average: 174.2423
Monoisotopic: 174.115698458
Chemical Formula
C11H14N2
InChI Key
QSQQQURBVYWZKJ-UHFFFAOYSA-N
InChI
InChI=1S/C11H14N2/c1-8(12)6-9-7-13-11-5-3-2-4-10(9)11/h2-5,7-8,13H,6,12H2,1H3
IUPAC Name
1-(1H-indol-3-yl)propan-2-amine
SMILES
CC(N)CC1=CNC2=CC=CC=C12

Pharmacology

Indication
Not Available
Pharmacodynamics

With 20-30 milligrams, euphoria, empathy and psychedelic effects are noticeable. Side effects reported have included anxiety, restlessness, tachycardia, muscle tension, jaw tightness, headache, nausea, vomiting, and pupil dilation.

Mechanism of action
Not Available
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
Toxicity

Long lasting serotonin neuro-toxicity at high doses is potentially possible, and is seen with a close analogue of alpha-methyltryptmaine: alpha-ethyltryptamine.

Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
9287
PubChem Substance
46507024
ChemSpider
8930
BindingDB
50014210
ChEBI
59020
ChEMBL
CHEMBL30713
Wikipedia
Alpha-Methyltryptamine

Clinical Trials

Clinical Trials
Not Available

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)98-100 °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility1.15 mg/mLALOGPS
logP2ALOGPS
logP1.9ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)17.14ChemAxon
pKa (Strongest Basic)9.96ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area41.81 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity54.79 m3·mol-1ChemAxon
Polarizability20.19 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+0.9856
Caco-2 permeable-0.6033
P-glycoprotein substrateNon-substrate0.5372
P-glycoprotein inhibitor INon-inhibitor0.9732
P-glycoprotein inhibitor IINon-inhibitor0.884
Renal organic cation transporterNon-inhibitor0.7162
CYP450 2C9 substrateNon-substrate0.8415
CYP450 2D6 substrateNon-substrate0.6107
CYP450 3A4 substrateNon-substrate0.7401
CYP450 1A2 substrateNon-inhibitor0.5192
CYP450 2C9 inhibitorNon-inhibitor0.7333
CYP450 2D6 inhibitorNon-inhibitor0.5346
CYP450 2C19 inhibitorNon-inhibitor0.6425
CYP450 3A4 inhibitorNon-inhibitor0.6172
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5077
Ames testNon AMES toxic0.7655
CarcinogenicityNon-carcinogens0.9039
BiodegradationNot ready biodegradable0.9737
Rat acute toxicity2.2108 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9729
hERG inhibition (predictor II)Non-inhibitor0.8778
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 GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
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

Taxonomy

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 / Aralkylamine / Benzenoid / Substituted pyrrole / Heteroaromatic compound / Pyrrole / Azacycle / Organic nitrogen compound / Organopnictogen compound / Hydrocarbon derivative
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
tryptamines (CHEBI:59020)

Drug created on July 31, 2007 07:09 / Updated on November 02, 2018 05:01