AFCDB: Tryptamine (FDB000917)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:46 UTC

Update date

2020-09-17 15:38:35 UTC

Primary ID

FDB000917

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Tryptamine

Description

Tryptamine, 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 Number

61-54-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	1.34 g/L	ALOGPS
logP	1.21	ALOGPS
logP	1.49	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	17.17	ChemAxon
pKa (Strongest Basic)	9.73	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	41.81 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	50.37 m³·mol⁻¹	ChemAxon
Polarizability	18.34 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C10H12N2

IUPAC name

2-(1H-indol-3-yl)ethan-1-amine

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 Key

APJYDQYYACXCRM-UHFFFAOYSA-N

Isomeric SMILES

NCCC1=CNC2=CC=CC=C12

Average Molecular Weight

160.2157

Monoisotopic Molecular Weight

160.100048394

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Tryptamines and derivatives

Direct Parent

Tryptamines 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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

indole alkaloid (CHEBI:16765 )
aminoalkylindole (CHEBI:16765 )
tryptamines (CHEBI:16765 )
aralkylamino compound (CHEBI:16765 )
Indole alkaloids (C00398 )

Ontology

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 74.97%; H 7.55%; N 17.48%	DFC
Melting Point	Mp 118°	DFC
Boiling Point	Bp0.15 137°	DFC
Experimental Water Solubility	Not Available
Experimental logP	1.55	HANSCH,C ET AL. (1995)
Experimental pKa	pKa2 10.2 (25°)	DFC
Isoelectric point	Not Available
Charge	+1
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-001i-2900000000-6a48efe719d0f7482467	2015-03-01	View Spectrum
GC-MS	Tryptamine, 2 TMS, GC-MS Spectrum	splash10-00dr-2900000000-037af42e76613b924496	Spectrum
GC-MS	Tryptamine, 3 TMS, GC-MS Spectrum	splash10-00di-1900000000-0f82cbf608e15678c41e	Spectrum
GC-MS	Tryptamine, non-derivatized, GC-MS Spectrum	splash10-00di-2900000000-a7c4e80f196945c43f38	Spectrum
GC-MS	Tryptamine, 2 TMS, GC-MS Spectrum	splash10-00di-7900000000-3900b703ce7b512e882b	Spectrum
GC-MS	Tryptamine, 3 TMS, GC-MS Spectrum	splash10-00di-8900000000-f45a71db0a2ef37bb21e	Spectrum
GC-MS	Tryptamine, 3 TMS, GC-MS Spectrum	splash10-00di-2900000000-bd00339c48e04ebcf419	Spectrum
GC-MS	Tryptamine, 2 TMS, GC-MS Spectrum	splash10-00di-2900000000-830c8a076e1bd787d36b	Spectrum
GC-MS	Tryptamine, non-derivatized, GC-MS Spectrum	splash10-001i-2900000000-b39aa63579c1df55320b	Spectrum
GC-MS	Tryptamine, non-derivatized, GC-MS Spectrum	splash10-00di-1900000000-ac580ff9d9d90ed4712f	Spectrum
GC-MS	Tryptamine, non-derivatized, GC-MS Spectrum	splash10-00dr-2900000000-037af42e76613b924496	Spectrum
GC-MS	Tryptamine, non-derivatized, GC-MS Spectrum	splash10-00di-1900000000-0f82cbf608e15678c41e	Spectrum
GC-MS	Tryptamine, non-derivatized, GC-MS Spectrum	splash10-00di-2900000000-a7c4e80f196945c43f38	Spectrum
GC-MS	Tryptamine, non-derivatized, GC-MS Spectrum	splash10-00di-7900000000-3900b703ce7b512e882b	Spectrum
GC-MS	Tryptamine, non-derivatized, GC-MS Spectrum	splash10-00di-8900000000-f45a71db0a2ef37bb21e	Spectrum
GC-MS	Tryptamine, non-derivatized, GC-MS Spectrum	splash10-00di-2900000000-bd00339c48e04ebcf419	Spectrum
GC-MS	Tryptamine, non-derivatized, GC-MS Spectrum	splash10-00di-2900000000-830c8a076e1bd787d36b	Spectrum
GC-MS	Tryptamine, non-derivatized, GC-MS Spectrum	splash10-00di-2900000000-bd00339c48e04ebcf419	Spectrum
GC-MS	Tryptamine, non-derivatized, GC-MS Spectrum	splash10-00di-2900000000-830c8a076e1bd787d36b	Spectrum
Predicted GC-MS	Tryptamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-001i-6900000000-9eba5d47042c8fee1aeb	Spectrum
Predicted GC-MS	Tryptamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-03di-0900000000-b73564ce7b9f5f38af40	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00kf-0900000000-24ae4f71c6de13d45134	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-014l-7900000000-630a258032b083d5d676	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (MX-1303) , Positive	splash10-001i-2900000000-b39aa63579c1df55320b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0006-0900000000-0572e0c6753816d29646	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-0006-0900000000-a3617243f16ac1d19ca3	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-0006-0900000000-5198dc18989eb021ff2b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-014l-2900000000-3b3b79050401c23f0c22	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-014l-7900000000-b62047ba50e6464b146c	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0002-9500000000-692ccea6512d337d1e9b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0006-0900000000-0572e0c6753816d29646	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0006-0900000000-a3617243f16ac1d19ca3	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0006-0900000000-5198dc18989eb021ff2b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-014l-2900000000-3b3b79050401c23f0c22	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-014l-7900000000-b62047ba50e6464b146c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0006-0900000000-bb34ead00b4bce5008dc	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-0006-0900000000-bb699b23c5872ac8e0fd	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0900000000-0584fe53e5bb04749635	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0900000000-10334c65fa0049224d2b	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03dl-0900000000-7bc3b97123326f275789	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0900000000-5905ea387430fa86aaf0	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014l-2900000000-efe6e15de34968102591	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-c52fec329f216423ec97	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-274ddaffc49a15406923	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014l-2900000000-11fbc4d015c37419fca0	2015-05-27	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)	Spectrum
1D NMR	¹³C 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

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

DB08653

HMDB ID

HMDB00303

CRC / DFC (Dictionary of Food Compounds) ID

BMS99-K:BMS99-K

EAFUS ID

Not Available

Dr. Duke ID

BIGG ID

KNApSAcK ID

HET ID

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
anti amebic	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
hypertensive			DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
vasopressor			DUKE

Enzymes

Name	Gene Name	UniProt ID
Aromatic-L-amino-acid decarboxylase	DDC	P20711
Serotonin N-acetyltransferase	AANAT	Q16613

Pathways

Name	SMPDB Link	KEGG Link
Tryptophan Metabolism	SMP00063	map00380

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not 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.

Tryptamine (FDB000917)

Structure for FDB000917 (Tryptamine)