2-(1H-INDOL-3-YL)ETHANAMINE

Identification

Name
2-(1H-INDOL-3-YL)ETHANAMINE
Accession Number
DB08653
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
External IDs
NSC-165212
Categories
Not Available
UNII
422ZU9N5TV
CAS number
Not Available
Weight
Average: 160.2157
Monoisotopic: 160.100048394
Chemical Formula
C10H12N2
InChI Key
APJYDQYYACXCRM-UHFFFAOYSA-N
InChI
InChI=1S/C10H12N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6,11H2
IUPAC Name
2-(1H-indol-3-yl)ethan-1-amine
SMILES
NCCC1=CNC2=CC=CC=C12

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UAralkylamine dehydrogenase light chainNot AvailableAlcaligenes faecalis
UAralkylamine dehydrogenase heavy chainNot AvailableAlcaligenes faecalis
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
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
Tryptophan MetabolismMetabolic
Tryptophan MetabolismMetabolic
Tryptophan MetabolismMetabolic
Indole Alkaloid BiosynthesisMetabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0000303
KEGG Compound
C00398
PubChem Compound
1150
PubChem Substance
99445124
ChemSpider
1118
BindingDB
50024210
ChEBI
16765
ChEMBL
CHEMBL6640
IUPHAR
125
Guide to Pharmacology
GtP Drug Page
HET
TSS
PDB Entries
2agw / 2fpb / 2iuq / 2pql / 3atm / 3rxi / 4ge1

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
Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.34 mg/mLALOGPS
logP1.21ALOGPS
logP1.49ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)17.17ChemAxon
pKa (Strongest Basic)9.73ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area41.81 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity50.37 m3·mol-1ChemAxon
Polarizability18.34 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9967
Blood Brain Barrier+0.9771
Caco-2 permeable-0.532
P-glycoprotein substrateNon-substrate0.5458
P-glycoprotein inhibitor INon-inhibitor0.9767
P-glycoprotein inhibitor IINon-inhibitor0.8394
Renal organic cation transporterInhibitor0.5764
CYP450 2C9 substrateNon-substrate0.8841
CYP450 2D6 substrateNon-substrate0.5059
CYP450 3A4 substrateNon-substrate0.7669
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.5648
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.8346
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6446
Ames testNon AMES toxic0.9303
CarcinogenicityNon-carcinogens0.9255
BiodegradationNot ready biodegradable0.9211
Rat acute toxicity2.4108 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9337
hERG inhibition (predictor II)Non-inhibitor0.7437
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
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-00dr-2900000000-037af42e76613b924496
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)GC-MSsplash10-00di-1900000000-0f82cbf608e15678c41e
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-00di-2900000000-a7c4e80f196945c43f38
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-00di-7900000000-3900b703ce7b512e882b
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)GC-MSsplash10-00di-8900000000-f45a71db0a2ef37bb21e
GC-MS Spectrum - GC-MS (3 TMS)GC-MSsplash10-00di-2900000000-bd00339c48e04ebcf419
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-00di-2900000000-830c8a076e1bd787d36b
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-001i-2900000000-b39aa63579c1df55320b
GC-MS Spectrum - EI-BGC-MSsplash10-00di-1900000000-ac580ff9d9d90ed4712f
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00dr-2900000000-037af42e76613b924496
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00di-1900000000-0f82cbf608e15678c41e
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00di-2900000000-a7c4e80f196945c43f38
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00di-7900000000-3900b703ce7b512e882b
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00di-8900000000-f45a71db0a2ef37bb21e
GC-MS Spectrum - GC-MSGC-MSsplash10-00di-2900000000-bd00339c48e04ebcf419
GC-MS Spectrum - GC-MSGC-MSsplash10-00di-2900000000-830c8a076e1bd787d36b
GC-MS Spectrum - GC-MSGC-MSsplash10-00di-2900000000-bd00339c48e04ebcf419
GC-MS Spectrum - GC-MSGC-MSsplash10-00di-2900000000-830c8a076e1bd787d36b
Mass Spectrum (Electron Ionization)MSsplash10-001i-2900000000-6a48efe719d0f7482467
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-03di-0900000000-b73564ce7b9f5f38af40
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-00kf-0900000000-24ae4f71c6de13d45134
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-014l-7900000000-630a258032b083d5d676
MS/MS Spectrum - EI-B (MX-1303) , PositiveLC-MS/MSsplash10-001i-2900000000-b39aa63579c1df55320b
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-0006-0900000000-0572e0c6753816d29646
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-0006-0900000000-a3617243f16ac1d19ca3
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-0006-0900000000-5198dc18989eb021ff2b
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-014l-2900000000-3b3b79050401c23f0c22
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-014l-7900000000-b62047ba50e6464b146c
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03dl-0900000000-7bc3b97123326f275789
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0900000000-5905ea387430fa86aaf0
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-014l-2900000000-efe6e15de34968102591
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0900000000-c52fec329f216423ec97
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0900000000-274ddaffc49a15406923
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-014l-2900000000-11fbc4d015c37419fca0
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0002-9500000000-692ccea6512d337d1e9b
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0006-0900000000-0572e0c6753816d29646
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0006-0900000000-a3617243f16ac1d19ca3
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0006-0900000000-5198dc18989eb021ff2b
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014l-2900000000-3b3b79050401c23f0c22
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014l-7900000000-b62047ba50e6464b146c
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0006-0900000000-bb34ead00b4bce5008dc
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0006-0900000000-bb699b23c5872ac8e0fd
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as tryptamines and derivatives. These are compounds containing the tryptamine backbone, which is structurally characterized by an indole ring substituted at the 3-position by an ethanamine.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Indoles and derivatives
Sub Class
Tryptamines and derivatives
Direct Parent
Tryptamines and derivatives
Alternative Parents
3-alkylindoles / 2-arylethylamines / Aralkylamines / Substituted pyrroles / Benzenoids / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Monoalkylamines / Hydrocarbon derivatives
Substituents
Tryptamine / 3-alkylindole / Indole / 2-arylethylamine / Aralkylamine / Substituted pyrrole / Benzenoid / Pyrrole / Heteroaromatic compound / Azacycle
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
indole alkaloid, aminoalkylindole, tryptamines, aralkylamino compound (CHEBI:16765) / Indole alkaloids (C00398)

Targets

Kind
Protein
Organism
Alcaligenes faecalis
Pharmacological action
Unknown
General Function
Aralkylamine dehydrogenase (azurin) activity
Specific Function
Oxidizes primary aromatic amines and, more slowly, some long-chain aliphatic amines, but not methylamine or ethylamine. Uses azurin as an electron acceptor to transfer electrons from the reduced tr...
Gene Name
aauA
Uniprot ID
P84887
Uniprot Name
Aralkylamine dehydrogenase light chain
Molecular Weight
19651.915 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Alcaligenes faecalis
Pharmacological action
Unknown
General Function
Aralkylamine dehydrogenase (azurin) activity
Specific Function
Oxidizes primary aromatic amines and, more slowly, some long-chain aliphatic amines, but not methylamine or ethylamine. Uses azurin as an electron acceptor to transfer electrons from the reduced tr...
Gene Name
aauB
Uniprot ID
P84888
Uniprot Name
Aralkylamine dehydrogenase heavy chain
Molecular Weight
42924.595 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Drug created on September 15, 2010 15:33 / Updated on November 02, 2018 06:52