Record Information
Version1.0
Creation date2010-04-08 22:04:46 UTC
Update date2020-09-17 15:38:35 UTC
Primary IDFDB000917
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameTryptamine
DescriptionTryptamine, also known as TRPN, 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. Tryptamine is a very strong basic compound (based on its pKa). Tryptamine exists in all living organisms, ranging from bacteria to humans. Outside of the human body, Tryptamine has been detected, but not quantified in, several different foods, such as rocket salad, ohelo berries, cashew nuts, chia, and japanese walnuts. This could make tryptamine a potential biomarker for the consumption of these foods. An aminoalkylindole consisting of indole having a 2-aminoethyl group at the 3-position.
CAS Number61-54-1
Structure
Thumb
Synonyms
SynonymSource
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
β-(3-Indolyl)ethylaminebiospider
1H-Indole-3-ethanamine, 9CIdb_source
TryptaminiumHMDB
Predicted Properties
PropertyValueSource
Water Solubility1.34 g/LALOGPS
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
Chemical FormulaC10H12N2
IUPAC name2-(1H-indol-3-yl)ethan-1-amine
InChI IdentifierInChI=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
Isomeric SMILESNCCC1=CNC2=CC=CC=C12
Average Molecular Weight160.2157
Monoisotopic Molecular Weight160.100048394
Classification
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
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 74.97%; H 7.55%; N 17.48%DFC
Melting PointMp 118°DFC
Boiling PointBp0.15 137°DFC
Experimental Water SolubilityNot Available
Experimental logP1.55HANSCH,C ET AL. (1995)
Experimental pKapKa2 10.2 (25°)DFC
Isoelectric pointNot Available
Charge+1
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-001i-2900000000-6a48efe719d0f7482467Spectrum
GC-MSTryptamine, 2 TMS, GC-MS Spectrumsplash10-00dr-2900000000-037af42e76613b924496Spectrum
GC-MSTryptamine, 3 TMS, GC-MS Spectrumsplash10-00di-1900000000-0f82cbf608e15678c41eSpectrum
GC-MSTryptamine, non-derivatized, GC-MS Spectrumsplash10-00di-2900000000-a7c4e80f196945c43f38Spectrum
GC-MSTryptamine, 2 TMS, GC-MS Spectrumsplash10-00di-7900000000-3900b703ce7b512e882bSpectrum
GC-MSTryptamine, 3 TMS, GC-MS Spectrumsplash10-00di-8900000000-f45a71db0a2ef37bb21eSpectrum
GC-MSTryptamine, 3 TMS, GC-MS Spectrumsplash10-00di-2900000000-bd00339c48e04ebcf419Spectrum
GC-MSTryptamine, 2 TMS, GC-MS Spectrumsplash10-00di-2900000000-830c8a076e1bd787d36bSpectrum
GC-MSTryptamine, non-derivatized, GC-MS Spectrumsplash10-001i-2900000000-b39aa63579c1df55320bSpectrum
GC-MSTryptamine, non-derivatized, GC-MS Spectrumsplash10-00di-1900000000-ac580ff9d9d90ed4712fSpectrum
GC-MSTryptamine, non-derivatized, GC-MS Spectrumsplash10-00dr-2900000000-037af42e76613b924496Spectrum
GC-MSTryptamine, non-derivatized, GC-MS Spectrumsplash10-00di-1900000000-0f82cbf608e15678c41eSpectrum
GC-MSTryptamine, non-derivatized, GC-MS Spectrumsplash10-00di-2900000000-a7c4e80f196945c43f38Spectrum
GC-MSTryptamine, non-derivatized, GC-MS Spectrumsplash10-00di-7900000000-3900b703ce7b512e882bSpectrum
GC-MSTryptamine, non-derivatized, GC-MS Spectrumsplash10-00di-8900000000-f45a71db0a2ef37bb21eSpectrum
GC-MSTryptamine, non-derivatized, GC-MS Spectrumsplash10-00di-2900000000-bd00339c48e04ebcf419Spectrum
GC-MSTryptamine, non-derivatized, GC-MS Spectrumsplash10-00di-2900000000-830c8a076e1bd787d36bSpectrum
GC-MSTryptamine, non-derivatized, GC-MS Spectrumsplash10-00di-2900000000-bd00339c48e04ebcf419Spectrum
GC-MSTryptamine, non-derivatized, GC-MS Spectrumsplash10-00di-2900000000-830c8a076e1bd787d36bSpectrum
Predicted GC-MSTryptamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-6900000000-9eba5d47042c8fee1aebSpectrum
Predicted GC-MSTryptamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0900000000-b73564ce7b9f5f38af40Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00kf-0900000000-24ae4f71c6de13d45134Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014l-7900000000-630a258032b083d5d676Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (MX-1303) , Positivesplash10-001i-2900000000-b39aa63579c1df55320bSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0006-0900000000-0572e0c6753816d29646Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0006-0900000000-a3617243f16ac1d19ca3Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0006-0900000000-5198dc18989eb021ff2bSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-014l-2900000000-3b3b79050401c23f0c22Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-014l-7900000000-b62047ba50e6464b146cSpectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0002-9500000000-692ccea6512d337d1e9bSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-0900000000-0572e0c6753816d29646Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-0900000000-a3617243f16ac1d19ca3Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-0900000000-5198dc18989eb021ff2bSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014l-2900000000-3b3b79050401c23f0c22Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014l-7900000000-b62047ba50e6464b146cSpectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0006-0900000000-bb34ead00b4bce5008dcSpectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-0006-0900000000-bb699b23c5872ac8e0fdSpectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-0584fe53e5bb04749635Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-10334c65fa0049224d2bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-0900000000-7bc3b97123326f275789Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-5905ea387430fa86aaf0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-2900000000-efe6e15de34968102591Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-c52fec329f216423ec97Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-274ddaffc49a15406923Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-2900000000-11fbc4d015c37419fca0Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
2D NMR[1H,1H] 2D NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID1118
ChEMBL IDCHEMBL6640
KEGG Compound IDC00398
Pubchem Compound ID1150
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB08653
HMDB IDHMDB00303
CRC / DFC (Dictionary of Food Compounds) IDBMS99-K:BMS99-K
EAFUS IDNot Available
Dr. Duke IDTRYPTAMINE
BIGG ID34864
KNApSAcK IDC00001434
HET IDTSS
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti amebic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
hypertensiveDUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
vasopressorDUKE
Enzymes
NameGene NameUniProt ID
Aromatic-L-amino-acid decarboxylaseDDCP20711
Serotonin N-acetyltransferaseAANATQ16613
Pathways
NameSMPDB LinkKEGG Link
Tryptophan MetabolismSMP00063 map00380
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.