Tryptamine (CED0001674)

Record Information
Version1.0
Creation Date2016-05-25 18:11:01 UTC
Update Date2026-05-14 18:59:01 UTC
Accession NumberCHEM021725
Identification
Common NameTryptamine
ClassSmall Molecule
Description
Tryptamine (C10H12N2) is an organic compound with an average molecular weight of 160.22 g/mol. Tryptamine belongs to the tryptamines and derivatives, a subclass of indoles and derivatives within the organic compounds. Biologically, it serves as a neurotransmitter (PMC8213022). It acts as an inhibitor for five recorded protein targets, including Aralkylamine dehydrogenase light chain (aauA), Aralkylamine dehydrogenase heavy chain (aauB), Amine oxidase [flavin-containing] B (MAOB), and 5-hydroxytryptamine receptor 2A (HTR2A). The compound is found in or released from 36 recorded sources across various sectors. These include Electrical & Electronic Equipment such as cell phones, capacitors, wires and cables, batteries, and printed circuit boards; Household cleaning & consumer products including perfumes within detergents and soaps, cigar cigarettes, non electric simulated smoking devices, other smoking requisites, and pipe accessories; Food, food processing & cookware including food packaging, food contact materials, food preservation, preparation of vinegar, and fermentation processes for beer; Textiles, leather & furnishings such as synthetic textiles, carpets and rugs; Healthcare, pharmaceuticals & veterinary products via medical devices; and Energy, oil & gas through lubricants. Recorded exposure routes include oral, inhalation, and touch. Tryptamine is a biomarker of hypothyroidism (PMC7009407). Blood levels are elevated in cases of obesity (PMC10372128), thyroid cancer (PMC7998837), and hypothyroidism (PMC6915086, PMC7009407). It is further associated with vomiting (PMC9775352), nausea (PMC9775352), hyperthyroidism (increase) (PMC10593800), thyroid cancer (decrease) (PMC10593800), and hypothyroidism (PMC2592280, PMC10593800, PMC12695664, PMC13024578). Conversely, blood levels are decreased in hyperthyroidism (PMC1492602, PMC6915086).
Contaminant Type
  • PFAS
  • Phytotoxin
Chemical Structure
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 Mass160.216 g/mol
Monoisotopic Mass160.100 g/mol
CAS Registry Number61-54-1
IUPAC Name2-(1H-indol-3-yl)ethan-1-amine
Traditional Nametryptamine
SMILESNCCC1=CNC2=CC=CC=C12
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
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-00dr-2900000000-037af42e76613b924496Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-00di-1900000000-0f82cbf608e15678c41eNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-00di-2900000000-a7c4e80f196945c43f38Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-00di-7900000000-3900b703ce7b512e882bNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-00di-8900000000-f45a71db0a2ef37bb21eNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-00di-2900000000-bd00339c48e04ebcf419Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-00di-2900000000-830c8a076e1bd787d36bNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-001i-2900000000-b39aa63579c1df55320bNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-00di-1900000000-ac580ff9d9d90ed4712fNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-00dr-2900000000-037af42e76613b924496Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-00di-1900000000-0f82cbf608e15678c41eNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-00di-2900000000-a7c4e80f196945c43f38Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-00di-7900000000-3900b703ce7b512e882bNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-00di-8900000000-f45a71db0a2ef37bb21eNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-00di-2900000000-bd00339c48e04ebcf419Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-00di-2900000000-830c8a076e1bd787d36bNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-00di-2900000000-bd00339c48e04ebcf419Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-00di-2900000000-830c8a076e1bd787d36bNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-001i-6900000000-9eba5d47042c8fee1aebNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0900000000-b73564ce7b9f5f38af40Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00kf-0900000000-24ae4f71c6de13d45134Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014l-7900000000-630a258032b083d5d676Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-2900000000-b39aa63579c1df55320bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0900000000-0572e0c6753816d29646Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0900000000-a3617243f16ac1d19ca3Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0900000000-5198dc18989eb021ff2bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014l-2900000000-3b3b79050401c23f0c22Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014l-7900000000-b62047ba50e6464b146cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-9500000000-692ccea6512d337d1e9bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0900000000-0572e0c6753816d29646Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0900000000-a3617243f16ac1d19ca3Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0900000000-5198dc18989eb021ff2bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014l-2900000000-3b3b79050401c23f0c22Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014l-7900000000-b62047ba50e6464b146cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0900000000-bb34ead00b4bce5008dcNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0900000000-bb699b23c5872ac8e0fdNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0900000000-0584fe53e5bb04749635Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0900000000-10334c65fa0049224d2bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0900000000-e2b178ca3a44030948adNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014l-5900000000-e43191817b05fd38fbbdNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03ec-0900000000-11688e9945b3dcaf20ffNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0900000000-981f5f5e9e465db911d1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0900000000-1558b7cae64ec50b70eeNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0900000000-621012c92ef5ec4b6aefNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0900000000-c92262a2915628fce25eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-9000000000-618edb85ae3bb3e449b0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014l-6900000000-6de3e78debbc5906a236Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-056r-0900000000-89f2b0fb4a6b2ec775abNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0900000000-79c298ab70ad53a4e1f0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03dl-0900000000-7bc3b97123326f275789Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0900000000-5905ea387430fa86aaf0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014l-2900000000-efe6e15de34968102591Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0900000000-c52fec329f216423ec97Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0900000000-274ddaffc49a15406923Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014l-2900000000-11fbc4d015c37419fca0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01ox-0900000000-692a3f21c188b8691c66Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0900000000-5b5a394e15a91e3242c4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00or-5900000000-43305fa918c8523d60ccNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0900000000-af8dccf6654d8703148aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0900000000-c3728f654d2dc9f8db97Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-1900000000-90d8f7689bfde0d8455fNot AvailableView Spectrum
MSMS Spectrumsplash10-001i-2900000000-6a48efe719d0f7482467Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
296.0Log mg/kg[170:530]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
obesityelevated_in_blood_inincreasePMC10372128
hypothyroidismis_biomarker_ofNot AvailablePMC7009407
hypothyroidismelevated_in_blood_inincreasePMC6915086 , PMC7009407
hypothyroidismassociated_withincreasePMC10593800 , PMC12695664 , PMC12695664 , PMC13024578
hypothyroidismassociated_withNot AvailablePMC2592280
nauseaassociated_withNot AvailablePMC9775352
vomitingassociated_withNot AvailablePMC9775352
Hyperthyroidismassociated_withincreasePMC10593800
Hyperthyroidismdecreased_in_blood_inNot AvailablePMC1492602 , PMC6915086
thyroid cancerassociated_withdecreasePMC10593800
thyroid cancerelevated_in_blood_inincreasePMC7998837
thyrotoxicosisassociated_withincreasePMC10593800
Exposure Sources
Source IDSourceSectorReference
7PesticidesAgriculture & land managementNot Available
10InsecticidesAgriculture & land managementNot Available
120Wires and cablesElectrical & Electronic EquipmentNot Available
121Printed circuit boardsElectrical & Electronic EquipmentNot Available
125BatteriesElectrical & Electronic EquipmentNot Available
130SemiconductorsElectrical & Electronic EquipmentNot Available
138LubricantsEnergy, oil & gasNot Available
147Food packagingFood, food processing & cookwareNot Available
174LubricantsIndustrial manufacturing & chemical processingNot Available
234Medical devicesHealthcare, pharmaceuticals & veterinary productsNot Available
451Carpets and RugsTextiles, leather & furnishingsNot Available
454Synthetic textilesTextiles, leather & furnishingsNot Available
490Personal care & cosmeticsNot Available
492Cell phonesElectrical & Electronic EquipmentNot Available
493CapacitorsElectrical & Electronic EquipmentNot Available
494Food contact materialsFood, food processing & cookwareNot Available
506AntennasElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
513Cores Yokes Or ArmaturesElectrical & Electronic EquipmentNot Available
514Discharge LampsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
550Preparation Of WortFood, food processing & cookwareNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
564Soap DispensersHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
607Rodenticides(1)Agriculture & land managementNot Available
608RodenticidesAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
652RopesTextiles, leather & furnishingsNot Available
Pathways
1 pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
5-hydroxytryptamine receptor 2A structureClick to view 3D structure5-hydroxytryptamine receptor 2AP28223HumansPredicted (SEA)2.64687
Click to view 3D structureSodium-dependent dopamine transporterP23977Rattus norvegicusPredicted (SEA)2.02408
Click to view 3D structureSodium-dependent serotonin transporterP31652Rattus norvegicusPredicted (SEA)1.86838
Click to view 3D structureNorepinephrine transporterQ9WTR4Rattus norvegicusPredicted (SEA)1.01204
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP28335HumansPredicted (SEA)2.88042
Click to view 3D structure5-hydroxytryptamine receptor 1AP19327Rattus norvegicusPredicted (SEA)3.73676
5-hydroxytryptamine receptor 1D structureClick to view 3D structure5-hydroxytryptamine receptor 1DP28221HumansPredicted (SEA)1.63483
5-hydroxytryptamine receptor 6 structureClick to view 3D structure5-hydroxytryptamine receptor 6P50406HumansPredicted (SEA)1.71268
5-hydroxytryptamine receptor 7 structureClick to view 3D structure5-hydroxytryptamine receptor 7P34969HumansPredicted (SEA)3.03612
5-hydroxytryptamine receptor 1B structureClick to view 3D structure5-hydroxytryptamine receptor 1BP28222HumansPredicted (SEA)1.47914
Click to view 3D structure5-hydroxytryptamine receptor 2BP30994Rattus norvegicusPredicted (SEA)0.311397
5-hydroxytryptamine receptor 1A structureClick to view 3D structure5-hydroxytryptamine receptor 1AP08908HumansPredicted (SEA)17.9053
Myeloperoxidase structureClick to view 3D structureMyeloperoxidaseP05164HumansPredicted (SEA)0.155698
Click to view 3D structure5-hydroxytryptamine receptor 1BP28564Rattus norvegicusPredicted (SEA)2.10193
5-hydroxytryptamine receptor 2B structureClick to view 3D structure5-hydroxytryptamine receptor 2BP41595HumansPredicted (SEA)7.16213
5-hydroxytryptamine receptor 5A structureClick to view 3D structure5-hydroxytryptamine receptor 5AP47898HumansPredicted (SEA)2.72472
D(2) dopamine receptor structureClick to view 3D structureD(2) dopamine receptorP14416HumansPredicted (SEA)50.6798
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP08909RatPredicted (SEA)7.86277
Click to view 3D structure5-hydroxytryptamine receptor 2AP14842Rattus norvegicusPredicted (SEA)15.5698
Sodium-dependent serotonin transporter structureClick to view 3D structureSodium-dependent serotonin transporterP31645HumansPredicted (SEA)23.4326
Click to view 3D structure5-hydroxytryptamine receptor 7P32305Rattus norvegicusPredicted (SEA)16.4262
D(3) dopamine receptor structureClick to view 3D structureD(3) dopamine receptorP35462HumansPredicted (SEA)58.0755
5-hydroxytryptamine receptor 1E structureClick to view 3D structure5-hydroxytryptamine receptor 1EP28566HumansPredicted (SEA)2.10193
Click to view 3D structure5-hydroxytryptamine receptor 1DP79400Sus scrofaPredicted (SEA)0.778492
Alpha-2A adrenergic receptor structureClick to view 3D structureAlpha-2A adrenergic receptorP08913HumansPredicted (SEA)19.618
Concentrations
Not Available
External Links
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
MSDSNot Available
General References
1. Abramovitch, 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.
2. Abramovitch, 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.
3. 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.
4. 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.
5. 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.
6. 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.
7. Tam WY, Chan MY, Lee PH: The menstrual cycle and platelet 5-HT uptake. Psychosom Med. 1985 Jul-Aug;47(4):352-62.
8. 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.
9. 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.
10. al Mardini H, Harrison EJ, Ince PG, Bartlett K, Record CO: Brain indoles in human hepatic encephalopathy. Hepatology. 1993 Jun;17(6):1033-40.
11. 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.
12. 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.
13. 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.
14. 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.
15. 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.
16. 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.
17. 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.
18. 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.
19. 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.
20. 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.
21. 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.
22. 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.
23. 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.
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=16126914
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=22770225
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=24345948
27. https://www.ncbi.nlm.nih.gov/pubmed/?term=24558969