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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-11-09 23:13:19 UTC
HMDB IDHMDB0000303
Secondary Accession Numbers
  • HMDB00303
  • HMDB0060064
  • HMDB60064
Metabolite Identification
Common NameTryptamine
DescriptionTryptamine, also known as TrpN, is a catabolite of tryptophan converted by the gut microbiota. After absorption through the intestinal epithelium, tryptophan catabolites enter the bloodstream and are later excreted in the urine. Both Clostridium sp. and Ruminococcus sp. have been found to convert tryptophan into tryptamine (PMID: 30120222 ). Tryptamine is a monoamine compound that is a common precursor molecule to many hormones and neurotransmitters. Biosynthesis generally proceeds from the amino acid tryptophan, with tryptamine 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. Tryptamine has been detected, but not quantified in, several different foods, such as onion-family vegetables, acerola, Japanese walnuts, custard apples, and green zucchinis. This could make tryptamine a potential biomarker for the consumption of these foods.
Structure
Data?1582752122
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=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
Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point114 - 119 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.55HANSCH,C ET AL. (1995)
Experimental Spectral Properties

Experimental Collision Cross Sections

PredictorAdduct TypeData SourceCCS Value (Å2)Reference
DeepCCS[M-H]-MetCCS_train_neg131.54630932474
DeepCCS[M+H]+Baker128.4230932474
AllCCS[M-H]-Not Available131.546http://allccs.zhulab.cn/database/detail?ID=AllCCS00000322
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.34 g/LALOGPS
logP10(1.21) g/LALOGPS
logP10(1.49) g/LChemAxon
logS10(-2.1) g/LALOGPS
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
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+134.30731661259
DarkChem[M-H]-132.42831661259
AllCCS[M+H]+135.28232859911
AllCCS[M-H]-137.08732859911

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Tryptamine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00dr-2900000000-037af42e76613b9244962014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Tryptamine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-1900000000-0f82cbf608e15678c41e2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Tryptamine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00di-2900000000-a7c4e80f196945c43f382014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Tryptamine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00di-7900000000-3900b703ce7b512e882b2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Tryptamine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-8900000000-f45a71db0a2ef37bb21e2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Tryptamine GC-MS (3 TMS)splash10-00di-2900000000-bd00339c48e04ebcf4192014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Tryptamine GC-MS (2 TMS)splash10-00di-2900000000-830c8a076e1bd787d36b2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Tryptamine EI-B (Non-derivatized)splash10-001i-2900000000-b39aa63579c1df55320b2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Tryptamine EI-B (Non-derivatized)splash10-00di-1900000000-ac580ff9d9d90ed4712f2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Tryptamine GC-EI-TOF (Non-derivatized)splash10-00dr-2900000000-037af42e76613b9244962017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Tryptamine GC-EI-TOF (Non-derivatized)splash10-00di-1900000000-0f82cbf608e15678c41e2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Tryptamine GC-EI-TOF (Non-derivatized)splash10-00di-2900000000-a7c4e80f196945c43f382017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Tryptamine GC-EI-TOF (Non-derivatized)splash10-00di-7900000000-3900b703ce7b512e882b2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Tryptamine GC-EI-TOF (Non-derivatized)splash10-00di-8900000000-f45a71db0a2ef37bb21e2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Tryptamine GC-MS (Non-derivatized)splash10-00di-2900000000-bd00339c48e04ebcf4192017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Tryptamine GC-MS (Non-derivatized)splash10-00di-2900000000-830c8a076e1bd787d36b2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Tryptamine GC-MS (Non-derivatized)splash10-00di-2900000000-bd00339c48e04ebcf4192017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Tryptamine GC-MS (Non-derivatized)splash10-00di-2900000000-830c8a076e1bd787d36b2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tryptamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-6900000000-9eba5d47042c8fee1aeb2017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tryptamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-001i-2900000000-6a48efe719d0f74824672015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Tryptamine Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-03di-0900000000-b73564ce7b9f5f38af402012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tryptamine Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-00kf-0900000000-24ae4f71c6de13d451342012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tryptamine Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-014l-7900000000-630a258032b083d5d6762012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tryptamine EI-B (MX-1303) , Positive-QTOFsplash10-001i-2900000000-b39aa63579c1df55320b2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tryptamine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOFsplash10-0006-0900000000-0572e0c6753816d296462012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tryptamine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOFsplash10-0006-0900000000-a3617243f16ac1d19ca32012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tryptamine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOFsplash10-0006-0900000000-5198dc18989eb021ff2b2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tryptamine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOFsplash10-014l-2900000000-3b3b79050401c23f0c222012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tryptamine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOFsplash10-014l-7900000000-b62047ba50e6464b146c2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tryptamine Linear Ion Trap , negative-QTOFsplash10-0002-9500000000-692ccea6512d337d1e9b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tryptamine LC-ESI-QQ , positive-QTOFsplash10-0006-0900000000-0572e0c6753816d296462017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tryptamine LC-ESI-QQ , positive-QTOFsplash10-0006-0900000000-a3617243f16ac1d19ca32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tryptamine LC-ESI-QQ , positive-QTOFsplash10-0006-0900000000-5198dc18989eb021ff2b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tryptamine LC-ESI-QQ , positive-QTOFsplash10-014l-2900000000-3b3b79050401c23f0c222017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tryptamine LC-ESI-QQ , positive-QTOFsplash10-014l-7900000000-b62047ba50e6464b146c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tryptamine Linear Ion Trap , positive-QTOFsplash10-0006-0900000000-bb34ead00b4bce5008dc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tryptamine , positive-QTOFsplash10-0006-0900000000-bb699b23c5872ac8e0fd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tryptamine 10V, Positive-QTOFsplash10-0006-0900000000-0584fe53e5bb047496352021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tryptamine 20V, Positive-QTOFsplash10-0006-0900000000-10334c65fa0049224d2b2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tryptamine 10V, Positive-QTOFsplash10-03dl-0900000000-7bc3b97123326f2757892015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tryptamine 20V, Positive-QTOFsplash10-0006-0900000000-5905ea387430fa86aaf02015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tryptamine 40V, Positive-QTOFsplash10-014l-2900000000-efe6e15de349681025912015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tryptamine 10V, Negative-QTOFsplash10-0a4i-0900000000-c52fec329f216423ec972015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tryptamine 20V, Negative-QTOFsplash10-0a4i-0900000000-274ddaffc49a154069232015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tryptamine 40V, Negative-QTOFsplash10-014l-2900000000-11fbc4d015c37419fca02015-05-27Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 1H]-TOCSY 2D NMR Spectrum (experimental)2012-12-04Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Brain
  • Intestine
  • Neuron
  • Platelet
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not AvailableNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not Specified
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.026 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.098 (0.03-0.15) umol/mmol creatinineChildren (1-13 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
UrineDetected and Quantified0.03 (0.01-0.049) umol/mmol creatinineAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
UrineDetected and Quantified0.02 (0.02-0.03) umol/mmol creatinineAdult (>18 years old)FemaleNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Irritable bowel syndrome
details
UrineDetected and Quantified0.926 umol/mmol creatinineAdult (>18 years old)Female
Pregnancy
details
Associated Disorders and Diseases
Disease References
Irritable bowel syndrome
  1. Ponnusamy K, Choi JN, Kim J, Lee SY, Lee CH: Microbial community and metabolomic comparison of irritable bowel syndrome faeces. J Med Microbiol. 2011 Jun;60(Pt 6):817-27. doi: 10.1099/jmm.0.028126-0. Epub 2011 Feb 17. [PubMed:21330412 ]
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDDB08653
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDTRYPTA
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceAbramovitch, R. A.; Shapiro, D. Tryptamines, carbolines, and related compounds. II. A convenient synthesis of tryptamines and b-carbolines. Journal of the Chemical Society (1956), 4589-92.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Radulovacki P, Djuricic-Nedelson M, Chen EH, Radulovacki M: Human tryptamine metabolism decreases during night sleep. Brain Res Bull. 1983 Jan;10(1):43-5. [PubMed:6186344 ]
  2. Mathew RJ, Ho BT, Kralik P, Weinman M, Claghorn JL: Anxiety and platelet MAO levels after relaxation training. Am J Psychiatry. 1981 Mar;138(3):371-3. [PubMed:7008633 ]
  3. Gilboa-Garber N, Katz-Bergman Y, Pinsky A: Comparative study of the sensitivity of acetylcholinesterases and cholinesterases from animal and bacterial sources to inhibition by serotonin and its derivatives. Experientia. 1978 Aug 15;34(8):992-3. [PubMed:100343 ]
  4. Tsuchiya H, Ohtani S, Yamada K, Tajima K, Sato M: Formation of tetrahydro-beta-carbolines in human saliva. Biochem Pharmacol. 1995 Dec 22;50(12):2109-12. [PubMed:8849340 ]
  5. Tam WY, Chan MY, Lee PH: The menstrual cycle and platelet 5-HT uptake. Psychosom Med. 1985 Jul-Aug;47(4):352-62. [PubMed:4023163 ]
  6. Friedl W, Kruger J, Propping P: Intraindividual stability and extent of genetic determination of platelet monoamine oxidase activity. Pharmacopsychiatria. 1981 May;14(3):83-6. [PubMed:7196052 ]
  7. Sullivan JP, McDonnell L, Hardiman OM, Farrell MA, Phillips JP, Tipton KF: The oxidation of tryptamine by the two forms of monoamine oxidase in human tissues. Biochem Pharmacol. 1986 Oct 1;35(19):3255-60. [PubMed:3094536 ]
  8. al Mardini H, Harrison EJ, Ince PG, Bartlett K, Record CO: Brain indoles in human hepatic encephalopathy. Hepatology. 1993 Jun;17(6):1033-40. [PubMed:7685732 ]
  9. Young SN, Gauthier S: Effect of tryptophan administration on tryptophan, 5-hydroxyindoleacetic acid and indoleacetic acid in human lumbar and cisternal cerebrospinal fluid. J Neurol Neurosurg Psychiatry. 1981 Apr;44(4):323-8. [PubMed:6165809 ]
  10. Siwers B, Ringberger VA, Tuck JR, Sjoqvist F: Initial clinical trial based on biochemical methodology of zimelidine (a serotonin uptake inhibitor) in depressed patients. Clin Pharmacol Ther. 1977 Feb;21(2):194-200. [PubMed:837638 ]
  11. Sullivan JL, Coffey CE, Basuk B, Cavenar JO, Maltbie AA, Zung WW: Urinary tryptamine excretion in chronic schizophrenics with low platelet MAO activity. Biol Psychiatry. 1980 Feb;15(1):113-20. [PubMed:7357050 ]
  12. Tsuchiya H, Hayashi T, Tatsumi M, Hoshino Y, Ohtani S, Takagi N: High-performance liquid-chromatographic analysis for serotonin and tryptamine excreted in urine after oral loading with L-tryptophan. Clin Chem. 1989 Jan;35(1):43-7. [PubMed:2910580 ]
  13. Anderson GM, Gerner RH, Cohen DJ, Fairbanks L: Central tryptamine turnover in depression, schizophrenia, and anorexia: measurement of indoleacetic acid in cerebrospinal fluid. Biol Psychiatry. 1984 Oct;19(10):1427-35. [PubMed:6518200 ]
  14. Gaszner P, Miklya I: The use of the synthetic enhancer substances (-)-deprenyl and (-)-BPAP in major depression. Neuropsychopharmacol Hung. 2004 Dec;6(4):210-20. [PubMed:15825677 ]
  15. Dolusic E, Kowalczyk M, Magnus V, Sandberg G, Normanly J: Biotinylated indoles as probes for indole-binding proteins. Bioconjug Chem. 2001 Mar-Apr;12(2):152-62. [PubMed:11312675 ]
  16. Demisch L, von der Muhlen H, Bochnik HJ, Seiler N: Substrate-typic changes of platelet monoamine oxidase activity in sub-types of schizophrenia. Arch Psychiatr Nervenkr (1970). 1977 Dec 28;224(4):319-29. [PubMed:606205 ]
  17. Gaszner P, Miklya I: Major depression and the synthetic enhancer substances, (-)-deprenyl and R-(-)-1-(benzofuran-2-yl)-2-propylaminopentane. Prog Neuropsychopharmacol Biol Psychiatry. 2006 Jan;30(1):5-14. Epub 2005 Jul 14. [PubMed:16023777 ]
  18. Mousseau DD, Layrargues GP, Butterworth RF: Region-selective decreases in densities of [3H]tryptamine binding sites in autopsied brain tissue from cirrhotic patients with hepatic encephalopathy. J Neurochem. 1994 Feb;62(2):621-5. [PubMed:8294925 ]
  19. Anthenelli RM, Tipp J, Li TK, Magnes L, Schuckit MA, Rice J, Daw W, Nurnberger JI Jr: Platelet monoamine oxidase activity in subgroups of alcoholics and controls: results from the Collaborative Study on the Genetics of Alcoholism. Alcohol Clin Exp Res. 1998 May;22(3):598-604. [PubMed:9622437 ]
  20. Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]
  21. Roager HM, Licht TR: Microbial tryptophan catabolites in health and disease. Nat Commun. 2018 Aug 17;9(1):3294. doi: 10.1038/s41467-018-05470-4. [PubMed:30120222 ]

Enzymes

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
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
Reactions
Tryptamine + Water + Oxygen → Indoleacetaldehyde + Ammonia + Hydrogen peroxidedetails
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
Reactions
Tryptamine + Water + Oxygen → Indoleacetaldehyde + Ammonia + Hydrogen peroxidedetails
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
Reactions
L-Tryptophan → Tryptamine + Carbon dioxidedetails
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
Reactions
Tryptamine + Water + Oxygen → Indoleacetaldehyde + Ammonia + Hydrogen peroxidedetails
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
Reactions
S-Adenosylmethionine + Tryptamine → S-Adenosylhomocysteine + N-Methyltryptaminedetails