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Indopan

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Identification

Generic Name
Indopan
DrugBank Accession Number
DB01446
Background

Indopan (alpha-methyltryptamine) is 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, indopan became regulated as a Schedule I controlled substance in the United states.

Type
Small Molecule
Groups
Experimental, Illicit
Structure
3D
Similar Structures
Weight
Average: 174.2423
Monoisotopic: 174.115698458
Chemical Formula
C11H14N2
Synonyms
  • 1-(1H-Indol-3-yl)-2-propanamine
  • 3-(2-Aminopropyl)indole
  • alpha-Methyl-1H-indole-3-ethanamine
  • alpha-Methyl-beta-indoleethylamine
  • alpha-methyltryptamine
  • AMT
  • DL-3-(2-Aminopropyl)indole
  • Indopan
  • α-Methyl-3-indoleethanamine
  • α-methyltryptamine
  • αMT
External IDs
  • 164 E
  • DEA No. 7432
  • RO 3-0926
  • U 14
  • U-14
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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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

Adverse Effects
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Toxicity

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

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

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
tryptamines (CHEBI:59020)
Affected organisms
Not Available

Chemical Identifiers

UNII
BIK35ACJ0Q
CAS number
299-26-3
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

References

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

Clinical Trials

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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-MSsplash10-0006-8900000000-3e6ea7e25929a31274e9
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a6r-0900000000-b4e9932ad4c413ba93f0
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0900000000-6ad78633ff39a8d20bc5
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-05gi-1900000000-c25164ccbba5b9a247b2
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0900000000-955893c02372fe037940
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-2900000000-d5c0659e1a59ee9bbe82
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0fr6-0900000000-d8208342e9af008ced2d
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-135.24388
predicted
DeepCCS 1.0 (2019)
[M+H]+139.0721
predicted
DeepCCS 1.0 (2019)
[M+Na]+148.12053
predicted
DeepCCS 1.0 (2019)

Drug created at July 31, 2007 13:09 / Updated at June 12, 2020 16:51