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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:32:21 UTC

Update Date

2023-02-21 17:19:11 UTC

HMDB ID

HMDB0029740

Secondary Accession Numbers

HMDB29740

Metabolite Identification

Common Name

Indole-3-methanamine

Description

Indole-3-methanamine, also known as 3-aminomethylindole or 3-indolylmethylamine, belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. An aralkylamino compound that is indole substituted at position 3 by an aminomethyl group. Indole-3-methanamine is a very strong basic compound (based on its pKa). Outside of the human body, indole-3-methanamine has been detected, but not quantified in, barley, cereals, and cereal products. This could make indole-3-methanamine a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1H-indol-3-Ylmethanamine	ChEBI
3-Aminomethylindole	ChEBI
AMI	ChEBI
3-(Aminomethyl)indole	HMDB
3-Indolylmethylamine	HMDB
1-(1H-Indol-3-yl)methanamine	HMDB
1H-Indol-3-ylmethylamine	HMDB
1H-Indole-3-methanamine	HMDB
3-Indoylmethanamine	HMDB
Indole-3-methanamine	HMDB

Chemical Formula

C₉H₁₀N₂

Average Molecular Weight

146.1891

Monoisotopic Molecular Weight

146.08439833

IUPAC Name

(1H-indol-3-yl)methanamine

Traditional Name

1H-indol-3-ylmethanamine

CAS Registry Number

22259-53-6

SMILES

NCC1=CNC2=C1C=CC=C2

InChI Identifier

InChI=1S/C9H10N2/c10-5-7-6-11-9-4-2-1-3-8(7)9/h1-4,6,11H,5,10H2

InChI Key

JXYGLMATGAAIBU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

3-alkylindoles

Alternative Parents

Substituents

3-alkylindole
Aralkylamine
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Azacycle
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organonitrogen compound
Primary aliphatic amine
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aminoalkylindole (CHEBI:65009 )
aralkylamino compound (CHEBI:65009 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0029740)
Cytoplasm (HMDB: HMDB0029740)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029740)

Source

Endogenous

Endogenous (HMDB: HMDB0029740)

Plant

Poaceae (HMDB: HMDB0029740)

Exogenous

Food

Food (HMDB: HMDB0029740)

Cereal and cereal product

Cereal

Barley (FooDB: FOOD00088)

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereals and cereal products (FooDB: FOOD00858)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	104 - 107 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	1.55	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	4.03 g/L	ALOGPS
logP	1.03	ALOGPS
logP	1.2	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	15.98	ChemAxon
pKa (Strongest Basic)	9.53	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	1	ChemAxon
Refractivity	45.62 m³·mol⁻¹	ChemAxon
Polarizability	16.32 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	131.063	31661259
DarkChem	[M-H]-	128.623	31661259
DeepCCS	[M+H]+	129.644	30932474
DeepCCS	[M-H]-	126.041	30932474
DeepCCS	[M-2H]-	163.422	30932474
DeepCCS	[M+Na]+	138.561	30932474
AllCCS	[M+H]+	131.3	32859911
AllCCS	[M+H-H2O]+	126.6	32859911
AllCCS	[M+NH4]+	135.7	32859911
AllCCS	[M+Na]+	137.0	32859911
AllCCS	[M-H]-	131.4	32859911
AllCCS	[M+Na-2H]-	132.3	32859911
AllCCS	[M+HCOO]-	133.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Indole-3-methanamine	NCC1=CNC2=C1C=CC=C2	2755.3	Standard polar	33892256
Indole-3-methanamine	NCC1=CNC2=C1C=CC=C2	1645.5	Standard non polar	33892256
Indole-3-methanamine	NCC1=CNC2=C1C=CC=C2	1674.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Indole-3-methanamine,1TMS,isomer #1	C[Si](C)(C)NCC1=C[NH]C2=CC=CC=C12	1806.2	Semi standard non polar	33892256
Indole-3-methanamine,1TMS,isomer #1	C[Si](C)(C)NCC1=C[NH]C2=CC=CC=C12	1724.7	Standard non polar	33892256
Indole-3-methanamine,1TMS,isomer #2	C[Si](C)(C)N1C=C(CN)C2=CC=CC=C21	1766.3	Semi standard non polar	33892256
Indole-3-methanamine,1TMS,isomer #2	C[Si](C)(C)N1C=C(CN)C2=CC=CC=C21	1784.2	Standard non polar	33892256
Indole-3-methanamine,2TMS,isomer #1	C[Si](C)(C)N(CC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C	1984.4	Semi standard non polar	33892256
Indole-3-methanamine,2TMS,isomer #1	C[Si](C)(C)N(CC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C	1951.3	Standard non polar	33892256
Indole-3-methanamine,2TMS,isomer #2	C[Si](C)(C)NCC1=CN([Si](C)(C)C)C2=CC=CC=C12	1855.3	Semi standard non polar	33892256
Indole-3-methanamine,2TMS,isomer #2	C[Si](C)(C)NCC1=CN([Si](C)(C)C)C2=CC=CC=C12	1863.7	Standard non polar	33892256
Indole-3-methanamine,3TMS,isomer #1	C[Si](C)(C)N(CC1=CN([Si](C)(C)C)C2=CC=CC=C12)[Si](C)(C)C	2058.3	Semi standard non polar	33892256
Indole-3-methanamine,3TMS,isomer #1	C[Si](C)(C)N(CC1=CN([Si](C)(C)C)C2=CC=CC=C12)[Si](C)(C)C	2059.0	Standard non polar	33892256
Indole-3-methanamine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCC1=C[NH]C2=CC=CC=C12	2039.9	Semi standard non polar	33892256
Indole-3-methanamine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCC1=C[NH]C2=CC=CC=C12	1927.0	Standard non polar	33892256
Indole-3-methanamine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C=C(CN)C2=CC=CC=C21	1995.4	Semi standard non polar	33892256
Indole-3-methanamine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C=C(CN)C2=CC=CC=C21	1963.2	Standard non polar	33892256
Indole-3-methanamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C(C)(C)C	2404.7	Semi standard non polar	33892256
Indole-3-methanamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C(C)(C)C	2345.9	Standard non polar	33892256
Indole-3-methanamine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2289.8	Semi standard non polar	33892256
Indole-3-methanamine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2279.3	Standard non polar	33892256
Indole-3-methanamine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)[Si](C)(C)C(C)(C)C	2639.9	Semi standard non polar	33892256
Indole-3-methanamine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)[Si](C)(C)C(C)(C)C	2650.3	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Indole-3-methanamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00ls-2900000000-4c29488a2b5c9c8815e1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Indole-3-methanamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Indole-3-methanamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-methanamine 10V, Positive-QTOF	splash10-000t-0900000000-ce8e5fc9a3b6d67ac28b	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-methanamine 20V, Positive-QTOF	splash10-001i-0900000000-b9af0590d6f8cb9dd7bc	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-methanamine 40V, Positive-QTOF	splash10-001i-1900000000-8ab90fc4051045e54cfa	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-methanamine 10V, Negative-QTOF	splash10-0002-0900000000-db45f60da0f460059712	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-methanamine 20V, Negative-QTOF	splash10-00kb-0900000000-2beec07e88df365da4bb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-methanamine 40V, Negative-QTOF	splash10-014i-2900000000-34e01321d03753a2d2af	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-methanamine 10V, Positive-QTOF	splash10-000t-0900000000-60044d8faa947e8dbc25	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-methanamine 20V, Positive-QTOF	splash10-001i-0900000000-1672aeb600ec9946fee3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-methanamine 40V, Positive-QTOF	splash10-0fvl-9500000000-de4afc5833eeabb66e59	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-methanamine 10V, Negative-QTOF	splash10-0002-0900000000-84eb1fba9fbf46f85dd1	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-methanamine 20V, Negative-QTOF	splash10-014i-0900000000-31bf9a9ecd1d0ceb261a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-methanamine 40V, Negative-QTOF	splash10-014i-0900000000-2c585ff1d4f9fb03226d	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB000940

KNApSAcK ID

C00055141

Chemspider ID

414602

KEGG Compound ID

Not Available

BioCyc ID

CPD-8913

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

472107

PDB ID

Not Available

ChEBI ID

65009

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Indole-3-methanamine (HMDB0029740)

MOL for HMDB0029740 (Indole-3-methanamine)

3D MOL for HMDB0029740 (Indole-3-methanamine)

3D SDF for HMDB0029740 (Indole-3-methanamine)

3D-SDF for HMDB0029740 (Indole-3-methanamine)

PDB for HMDB0029740 (Indole-3-methanamine)

3D PDB for HMDB0029740 (Indole-3-methanamine)

SMILES for HMDB0029740 (Indole-3-methanamine)

INCHI for HMDB0029740 (Indole-3-methanamine)

Structure for HMDB0029740 (Indole-3-methanamine)

3D Structure for HMDB0029740 (Indole-3-methanamine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra