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Record Information
Version1.0
Creation Date2016-07-13 19:43:06 UTC
Update Date2016-07-19 23:17:01 UTC
LmdbLMDB00134
Secondary Accession NumbersNone
Metabolite Identification
Common NameTryptamine
DescriptionTryptamine is a monoamine compound that is common precursor molecule to many hormones and neurotransmitters. Biosynthesis generally proceeds from the amino acid tryptophan, with tryptamine in turn acting as a precursor for other compounds. Substitutions to the tryptamine molecule give rise to a group of compounds collectively known as tryptamines. The most well-known tryptamines are serotonin, an important neurotransmitter, and melatonin, a hormone involved in regulating the sleep-wake cycle.
Structure
Thumb
Synonyms
ValueSource
1H-Indole-3-ethanamineChEBI
2-(1H-indol-3-yl)ETHANAMINEChEBI
2-(3-Indolyl)ethylamineChEBI
3-(2-Aminoethyl)indoleChEBI
(3-Indolyl)ethylamineHMDB
2-(1H-indol-3-yl)EthylamineHMDB
2-indol-3-yl-AethylaminHMDB
2-indol-3-yl-EthylamineHMDB
3-(2-Aminoethyl)-1H-indoleHMDB
3-IndoleethanamineHMDB
3-IndoleethylamineHMDB
TryptaminHMDB
2-(1H-indol-3-yl)Ethan-1-amineHMDB
beta-(3-Indolyl)ethylamineHMDB
Β-(3-indolyl)ethylamineHMDB
TRPNHMDB
TryptamineHMDB
Chemical FormulaC10H12N2
Average Molecular Weight160.2157
Monoisotopic Molecular Weight160.100048394
IUPAC Name2-(1H-indol-3-yl)ethan-1-amine
Traditional Nametryptamine
CAS Registry Number61-54-1
SMILES
NCCC1=CNC2=CC=CC=C12
InChI Identifier
InChI=1S/C10H12N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6,11H2
InChI KeyAPJYDQYYACXCRM-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as tryptamines and derivatives. Tryptamines and derivatives are compounds containing the tryptamine backbone, which is structurally characterized by an indole ring substituted at the 3-position by an ethanamine.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassTryptamines and derivatives
Direct ParentTryptamines and derivatives
Alternative Parents
Substituents
  • Tryptamine
  • 3-alkylindole
  • Indole
  • 2-arylethylamine
  • Aralkylamine
  • Substituted pyrrole
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Azacycle
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Amine
  • Primary amine
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity50.37 m³·mol⁻¹ChemAxon
Polarizability18.34 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00dr-2900000000-037af42e76613b924496Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-1900000000-0f82cbf608e15678c41eSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00di-2900000000-a7c4e80f196945c43f38Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00di-7900000000-3900b703ce7b512e882bSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-8900000000-f45a71db0a2ef37bb21eSpectrum
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-00di-2900000000-bd00339c48e04ebcf419Spectrum
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00di-2900000000-830c8a076e1bd787d36bSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-2900000000-b39aa63579c1df55320bSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-1900000000-ac580ff9d9d90ed4712fSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00dr-2900000000-037af42e76613b924496Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-1900000000-0f82cbf608e15678c41eSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-2900000000-a7c4e80f196945c43f38Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-7900000000-3900b703ce7b512e882bSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-8900000000-f45a71db0a2ef37bb21eSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-2900000000-bd00339c48e04ebcf419Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-2900000000-830c8a076e1bd787d36bSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-2900000000-bd00339c48e04ebcf419Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-2900000000-830c8a076e1bd787d36bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-6900000000-9eba5d47042c8fee1aebSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0900000000-b73564ce7b9f5f38af40Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00kf-0900000000-24ae4f71c6de13d45134Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014l-7900000000-630a258032b083d5d676Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (MX-1303) , Positivesplash10-001i-2900000000-b39aa63579c1df55320bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0006-0900000000-0572e0c6753816d29646Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0006-0900000000-a3617243f16ac1d19ca3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0006-0900000000-5198dc18989eb021ff2bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-014l-2900000000-3b3b79050401c23f0c22Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-014l-7900000000-b62047ba50e6464b146cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0002-9500000000-692ccea6512d337d1e9bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-0900000000-0572e0c6753816d29646Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-0900000000-a3617243f16ac1d19ca3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-0900000000-5198dc18989eb021ff2bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014l-2900000000-3b3b79050401c23f0c22Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014l-7900000000-b62047ba50e6464b146cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0006-0900000000-bb34ead00b4bce5008dcSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0006-0900000000-bb699b23c5872ac8e0fdSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-0584fe53e5bb04749635Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-10334c65fa0049224d2bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-0900000000-7bc3b97123326f275789Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-5905ea387430fa86aaf0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-2900000000-efe6e15de34968102591Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-c52fec329f216423ec97Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-274ddaffc49a15406923Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-2900000000-11fbc4d015c37419fca0Spectrum
MSMass Spectrum (Electron Ionization)splash10-001i-2900000000-6a48efe719d0f7482467Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Ruminal Fluid
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
Ruminal FluidDetected and Quantified145 uMNot AvailableCaprine details
Ruminal FluidDetected and Quantified148 uMNot AvailableCaprine details
Ruminal FluidDetected and Quantified284.08 uMNot AvailableCaprine details
DrugBank IDDB08653
HMDB IDHMDB0000303
FooDB IDFDB000917
Phenol Explorer IDNot Available
KNApSAcK IDC00001434
BiGG IDNot Available
BioCyc IDTRYPTAMINE
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTryptamine
Chemspider ID1118
ChEBI ID16765
PubChem Compound ID1150
Kegg Compound IDC00398
YMDB IDNot Available
ECMDB IDM2MDB004849
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available