| Record Information |
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| Version | 1.0 |
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| Creation date | 2011-09-21 01:50:02 UTC |
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| Update date | 2017-10-04 21:24:47 UTC |
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| Primary ID | FDB029095 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | 1,2,3,4-Tetrahydro-beta-carboline |
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| Description | Tetrahydro-b-carbolines (THbCs)are potential neuroactive alkaloids found in chocolate and cocoa.
The formation of 1,2,3,4-tetrahydro-/3-carbolines (THBCs), via the Pictet-Spengler condensation of tryptamines with formaldehyde, has been demonstrated repeatedly in incubations of various mammalian tissues containing added indolethylamine substrate and the methyl donors .5-methyltetrahydrofolate (5-MTHF) or S-adenosylmethionine(SAM).
It is concluded that the formation of these THBCs is an artifact produced by the enzymatic liberation of formaldehyde from the methyl donors and the subsequent non-enzymatic condensation of this formaldehyde with the indole substrates. The formation of THBCs in vivo has thus remained a point of contention.
(PMID: 7213417) [HMDB]. 1,2,3,4-Tetrahydro-beta-carboline is a biomarker for the consumption of beer. |
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| CAS Number | Not Available |
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| Structure | |
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| Synonyms | |
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| Predicted Properties | |
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| Chemical Formula | C11H12N2 |
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| IUPAC name | 1H,2H,3H,4H,9H-pyrido[3,4-b]indole |
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| InChI Identifier | InChI=1S/C11H12N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-4,12-13H,5-7H2 |
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| InChI Key | CFTOTSJVQRFXOF-UHFFFAOYSA-N |
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| Isomeric SMILES | C1CC2=C(CN1)NC1=C2C=CC=C1 |
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| Average Molecular Weight | 172.2264 |
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| Monoisotopic Molecular Weight | 172.100048394 |
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| Classification |
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| Description | Belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety. |
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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 | Pyridoindoles |
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| Direct Parent | Beta carbolines |
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| Alternative Parents | |
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| Substituents | - Beta-carboline
- 3-alkylindole
- Indole
- Aralkylamine
- Benzenoid
- Heteroaromatic compound
- Pyrrole
- Azacycle
- Secondary amine
- Secondary aliphatic amine
- Organopnictogen compound
- Organonitrogen compound
- Amine
- Organic nitrogen compound
- Hydrocarbon derivative
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic heteropolycyclic compounds |
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| External Descriptors | Not Available |
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| Ontology |
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| Disposition | Source: |
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| Physico-Chemical Properties |
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| Physico-Chemical Properties - Experimental | |
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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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| Predicted GC-MS | 1,2,3,4-Tetrahydro-beta-carboline, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0596-0900000000-0c12ea5ede1ecce0b8a0 | Spectrum | | Predicted GC-MS | 1,2,3,4-Tetrahydro-beta-carboline, 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 - LC-ESI-qTof , Positive | splash10-0006-3900000000-59256f2013af0388b609 | 2017-09-14 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - , positive | splash10-0006-0900000000-298d086f2db7bfb96c7f | 2017-09-14 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - , positive | splash10-0006-3900000000-59256f2013af0388b609 | 2017-09-14 | View Spectrum | | MS/MS | LC-MS/MS Spectrum - 35V, Positive | splash10-0006-0900000000-0e95cd13061c8268d13d | 2021-09-20 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00di-0900000000-d1cf77f85d424207ea20 | 2017-09-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-006x-0900000000-fa3e868e9ca6a59d5b91 | 2017-09-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0560-0900000000-76a12e37b5faa4cbb856 | 2017-09-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-0900000000-2305b865b13eae850bbb | 2017-09-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00di-0900000000-d58681edbdcc31aced92 | 2017-09-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0596-0900000000-3e4b9943ce69d390f2aa | 2017-09-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00di-0900000000-ff5f70dda818b9673030 | 2021-09-22 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00di-0900000000-1b2e7c8ce9fa45740ef0 | 2021-09-22 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00bc-2900000000-f5466bd5eff0535cb5b2 | 2021-09-22 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-0900000000-84df739a23ca1993145c | 2021-09-23 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00di-0900000000-84df739a23ca1993145c | 2021-09-23 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-0900000000-234e77ff29e2c2061761 | 2021-09-23 | View Spectrum |
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| NMR | Not Available |
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| External Links |
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| ChemSpider ID | 96979 |
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| ChEMBL ID | CHEMBL269236 |
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| KEGG Compound ID | Not Available |
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| Pubchem Compound ID | 107838 |
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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 | HMDB12488 |
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| CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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| EAFUS ID | Not Available |
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| Dr. Duke ID | Not Available |
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| BIGG ID | Not Available |
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| KNApSAcK ID | Not Available |
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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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| Biological Effects and Interactions |
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| Health Effects / Bioactivities | Not Available |
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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 | |
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