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Identification
NameAlpha-methyltryptamine
Accession NumberDB01446
TypeSmall Molecule
GroupsExperimental, Illicit
DescriptionA 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 Identifiers
  • U-14
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIBIK35ACJ0Q
CAS number299-26-3
WeightAverage: 174.2423
Monoisotopic: 174.115698458
Chemical FormulaC11H14N2
InChI KeyInChIKey=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
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
IndicationNot Available
PharmacodynamicsWith 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 actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityLong lasting serotonin neuro-toxicity at high doses is potentially possible, and is seen with a close analogue of alpha-methyltryptmaine: alpha-ethyltryptamine.
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+0.9856
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point98-100 °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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
Comments
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Drug created on July 31, 2007 07:09 / Updated on August 17, 2016 12:23