Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:11:18 UTC |
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Update date | 2019-11-26 03:10:10 UTC |
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Primary ID | FDB014498 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | 3-(Dimethylaminomethyl)indole |
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Description | 3-(Dimethylaminomethyl)indole, also known as donaxin or (1H-indol-3-ylmethyl)dimethylamine, 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. 3-(Dimethylaminomethyl)indole has been detected, but not quantified in, several different foods, such as brassicas, barleys (Hordeum vulgare), common wheats (Triticum aestivum), breakfast cereal, and cereals and cereal products. This could make 3-(dimethylaminomethyl)indole a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 3-(Dimethylaminomethyl)indole. |
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CAS Number | 87-52-5 |
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Structure | |
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Synonyms | Synonym | Source |
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(1H-indol-3-Ylmethyl)dimethylamine | ChEBI | 3-(N,N-Dimethylaminomethyl)indole | ChEBI | 3-[(Dimethylamino)methyl]indole | ChEBI | beta-Dimethylaminomethylindole | ChEBI | Donaxin | ChEBI | Donaxine | ChEBI | Gramin | ChEBI | indol-3-Ylmethyldimethylamine | ChEBI | N,N-Dimethyl-1H-indole-3-methanamine | ChEBI | (1H-indol-3-yl)-N,N-Dimethylmethanamine | Kegg | b-Dimethylaminomethylindole | Generator | Β-dimethylaminomethylindole | Generator | (1H-indol-3-Ylmethyl)-dimethyl-amine | HMDB | (indol-3-Ylmethyl)dimethylamine | HMDB | 1-(1H-indol-3-yl)-N,N-Dimethylmethanamine | HMDB | 1H-indol-3-yl-N,N-Dimethylmethanamine | HMDB | 3-((dimethylamino)Methyl)-indole | HMDB | 3-Dimethylaminomethylindol (gramin) | HMDB | 3-[(dimethylamino)Methyl]-indole | HMDB | b-(Dimethylaminomethyl)indole | HMDB | beta -Dimethylaminomethylindole | HMDB | Doranine | HMDB | Indolalkylamine der. | HMDB | N,N-Dimethyl-1H-indole-3-methanamine, 9ci | HMDB | N,N-Dimethyl-1H-indole-3-methylamine | HMDB | 3-(Dimethylaminomethyl)indole | ChEBI | (1H-Indol-3-ylmethyl)-dimethyl-amine | biospider | (Indol-3-ylmethyl)dimethylamine | biospider | β-dimethylaminomethylindole | biospider | 1-(1H-indol-3-yl)-N,N-dimethylmethanamine | biospider | 1H-Indol-3-yl-N,N-dimethylmethanamine | biospider | 1H-Indole-3-methanamine, N,N-dimethyl- | biospider | B-(dimethylaminomethyl)indole | biospider | Beta-dimethylaminomethylindole | biospider | Gramine | db_source | Indol-3-ylmethyldimethylamine | biospider | Indole, 3-((dimethylamino)methyl)- | biospider | Indole, 3-[(dimethylamino)methyl]- | biospider | N,N-Dimethyl-1H-indole-3-methanamine, 9CI | db_source |
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Predicted Properties | |
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Chemical Formula | C11H14N2 |
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IUPAC name | [(1H-indol-3-yl)methyl]dimethylamine |
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InChI Identifier | InChI=1S/C11H14N2/c1-13(2)8-9-7-12-11-6-4-3-5-10(9)11/h3-7,12H,8H2,1-2H3 |
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InChI Key | OCDGBSUVYYVKQZ-UHFFFAOYSA-N |
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Isomeric SMILES | CN(C)CC1=CNC2=CC=CC=C12 |
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Average Molecular Weight | 174.2423 |
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Monoisotopic Molecular Weight | 174.115698458 |
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Classification |
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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. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Indoles and derivatives |
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Sub Class | Indoles |
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Direct Parent | 3-alkylindoles |
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Alternative Parents | |
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Substituents | - 3-alkylindole
- Aralkylamine
- Benzenoid
- Substituted pyrrole
- Heteroaromatic compound
- Pyrrole
- Tertiary aliphatic amine
- Tertiary amine
- Azacycle
- Organic nitrogen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Organonitrogen compound
- Amine
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Route of exposure: Source: Biological location: |
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Role | Biological role: |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Not Available | |
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Physical Description | Not Available | |
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Mass Composition | C 75.82%; H 8.10%; N 16.08% | DFC |
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Melting Point | Mp 138-139° | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | pKa 16 (25°,NH, aq. KOH) | DFC |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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EI-MS | Mass Spectrum (Electron Ionization) | splash10-001i-3900000000-d1d9e746dd89f8340e66 | Spectrum | Predicted GC-MS | 3-(Dimethylaminomethyl)indole, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-053r-2900000000-e16912ed7a8b64df55c8 | Spectrum | Predicted GC-MS | 3-(Dimethylaminomethyl)indole, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 3-(Dimethylaminomethyl)indole, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-0059-0900000000-46a2a8bc6df733c63b6e | Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-002b-0900000000-d62fe8bf9fe908b6c657 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-001i-0900000000-7ddf4cc8719b5bb02438 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-001i-0900000000-8a648696af7414a85f14 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-001i-0900000000-a15c86c98c024930425a | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-001i-1900000000-18494e76b11d09a6db0a | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-004i-9600000000-ad30c2cd79b87e7cf3d8 | Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-001i-0900000000-f9f2e8362c42c7d0ac11 | Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-004i-0900000000-d2c4aaf90ad86d48951e | Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-0002-0900000000-b9adc728e65f3947056c | Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-001i-0910000000-4d9be164e6468558ee0e | Spectrum | MS/MS | LC-MS/MS Spectrum - 30V, Positive | splash10-001i-2900000000-0b8ed5267aeded5f760a | Spectrum | MS/MS | LC-MS/MS Spectrum - 50V, Positive | splash10-001i-0900000000-b21eb9303021ba27c6a5 | Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0900000000-e913804323f598209148 | Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0900000000-cc77ee60897881ca3433 | Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0900000000-edce45bfa47c9f3c7cbe | Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0900000000-93027cb8819607deda32 | Spectrum | MS/MS | LC-MS/MS Spectrum - 30V, Positive | splash10-001i-0900000000-b734096fe5125e8b8158 | Spectrum | MS/MS | LC-MS/MS Spectrum - 50V, Positive | splash10-003r-6900000000-31b1a35b9a4b0478b41d | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004i-0900000000-67c885f9800d6d095f14 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-003r-0900000000-414a182f24f2887b5111 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-001i-0900000000-59033a77b0437b7c7b6a | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-0900000000-2f44253b46777aef2f62 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00di-0900000000-3b82d8097f71c789b8a5 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-06r6-7900000000-078092839a6793aa904f | Spectrum |
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NMR | |
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External Links |
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ChemSpider ID | 6625 |
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ChEMBL ID | CHEMBL254348 |
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KEGG Compound ID | C08304 |
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Pubchem Compound ID | 6890 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB35762 |
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CRC / DFC (Dictionary of Food Compounds) ID | JRK41-S:JRK41-S |
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EAFUS ID | Not Available |
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Dr. Duke ID | GRAMINE |
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BIGG ID | Not Available |
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KNApSAcK ID | C00001411 |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Not Available |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Descriptor | ID | Definition | Reference |
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anti arrhythmic | 38070 | A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres. | DUKE | anti feedant | | | DUKE | insecticide | 24852 | Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects. | 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 |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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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.
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