Tryptamine (CHEM021725)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:11:01 UTC
Update Date2016-11-09 01:17:21 UTC
Accession NumberCHEM021725
Identification
Common NameTryptamine
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical 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 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
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot 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
Bioavailability1ChemAxon
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
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
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