Showing Compound Card for Tryptamine (CDB004844)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (6) Show 8 proteinsXML
Record Information
Version1.0
Created at2020-04-17 18:42:37 UTC
Updated at2020-11-18 16:38:50 UTC
CannabisDB IDCDB004844
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common 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. Tryptamine is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
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 Weight160.22
Monoisotopic Molecular Weight160.1
IUPAC Name2-(1H-indol-3-yl)ethan-1-amine
Traditional Nametryptamine
CAS Registry Number61-54-1
SMILES
NCCC1=CNC2=C1C=CC=C2
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
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting Point114 - 119 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logP1.55HANSCH,C ET AL. (1995)
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-001i-2900000000-6a48efe719d0f74824672015-03-01View Spectrum
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-b73564ce7b9f5f38af402012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00kf-0900000000-24ae4f71c6de13d451342012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014l-7900000000-630a258032b083d5d6762012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (MX-1303) , Positivesplash10-001i-2900000000-b39aa63579c1df55320b2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0006-0900000000-0572e0c6753816d296462012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0006-0900000000-a3617243f16ac1d19ca32012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0006-0900000000-5198dc18989eb021ff2b2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-014l-2900000000-3b3b79050401c23f0c222012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-014l-7900000000-b62047ba50e6464b146c2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0002-9500000000-692ccea6512d337d1e9b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-0900000000-0572e0c6753816d296462017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-0900000000-a3617243f16ac1d19ca32017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-0900000000-5198dc18989eb021ff2b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014l-2900000000-3b3b79050401c23f0c222017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014l-7900000000-b62047ba50e6464b146c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0006-0900000000-bb34ead00b4bce5008dc2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-0006-0900000000-bb699b23c5872ac8e0fd2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-0584fe53e5bb047496352021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-10334c65fa0049224d2b2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-0900000000-7bc3b97123326f2757892015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-5905ea387430fa86aaf02015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-2900000000-efe6e15de349681025912015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-c52fec329f216423ec972015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-274ddaffc49a154069232015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-2900000000-11fbc4d015c37419fca02015-05-27View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 15.09 MHz, DMSO-d6, experimental)Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Serotonin N-acetyltransferaseAANAT17q25Q16613 details
Amine oxidase [flavin-containing] BMAOBXp11.23P27338 details
Amine oxidase [flavin-containing] AMAOAXp11.3P21397 details
Aromatic-L-amino-acid decarboxylaseDDC7p12.2P20711 details
Amiloride-sensitive amine oxidase [copper-containing]ABP17q36.1P19801 details
Indolethylamine N-methyltransferaseINMT7p14.3O95050 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Amiloride-sensitive amine oxidase [copper-containing]ABP17q36.1P19801 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
Amiloride-sensitive amine oxidase [copper-containing]ABP17q36.1P19801 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0000303
DrugBank IDDB08653
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000917
KNApSAcK IDC00001434
Chemspider ID1118
KEGG Compound IDC00398
BioCyc IDTRYPTAMINE
BiGG IDNot Available
Wikipedia LinkTryptamine
METLIN IDNot Available
PubChem Compound1150
PDB IDNot Available
ChEBI ID16765
References
General ReferencesNot Available

Enzymes

Enzyme Details
1. Serotonin N-acetyltransferase
General function:
Involved in N-acetyltransferase activity
Specific function:
Controls the night/day rhythm of melatonin production in the pineal gland. Catalyzes the N-acetylation of serotonin into N-acetylserotonin, the penultimate step in the synthesis of melatonin.
Gene Name:
AANAT
Uniprot ID:
Q16613
Molecular weight:
23343.8
Enzyme Details
2. Amine oxidase [flavin-containing] B
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:
MAOB
Uniprot ID:
P27338
Molecular weight:
58762.475
Enzyme Details
3. Amine oxidase [flavin-containing] A
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:
MAOA
Uniprot ID:
P21397
Molecular weight:
59681.27
Enzyme Details
4. Aromatic-L-amino-acid decarboxylase
General function:
Involved in carboxy-lyase activity
Specific function:
Catalyzes the decarboxylation of L-3,4-dihydroxyphenylalanine (DOPA) to dopamine, L-5-hydroxytryptophan to serotonin and L-tryptophan to tryptamine.
Gene Name:
DDC
Uniprot ID:
P20711
Molecular weight:
53893.755
Enzyme Details
5. Amiloride-sensitive amine oxidase [copper-containing]
General function:
Involved in copper ion binding
Specific function:
Catalyzes the degradation of compounds such as putrescine, histamine, spermine, and spermidine, substances involved in allergic and immune responses, cell proliferation, tissue differentiation, tumor formation, and possibly apoptosis. Placental DAO is thought to play a role in the regulation of the female reproductive function.
Gene Name:
ABP1
Uniprot ID:
P19801
Molecular weight:
85377.1
Enzyme Details
6. Indolethylamine N-methyltransferase
General function:
Involved in methyltransferase activity
Specific function:
Functions as thioether S-methyltransferase and is active with a variety of thioethers and the corresponding selenium and tellurium compounds, including 3-methylthiopropionaldehyde, dimethyl selenide, dimethyl telluride, 2-methylthioethylamine, 2-methylthioethanol, methyl-n-propyl sulfide and diethyl sulfide. Plays an important role in the detoxification of selenium compounds (By similarity). Catalyzes the N-methylation of tryptamine and structurally related compounds.
Gene Name:
INMT
Uniprot ID:
O95050
Molecular weight:
28833.695