Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2006-08-13 17:39:03 UTC |
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Update Date | 2023-02-21 17:17:01 UTC |
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HMDB ID | HMDB0004366 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Hordenine |
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Description | Hordenine, also known as anhalin or cactine, belongs to the class of organic compounds known as phenethylamines. Phenethylamines are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine. Hordenine is a very strong basic compound (based on its pKa). Hordenine exists in all living organisms, ranging from bacteria to humans. Outside of the human body, Hordenine is found, on average, in the highest concentration within barley. Hordenine has also been detected, but not quantified in, several different foods, such as cereals and cereal products, corns, oats, sweet oranges, and tamarinds. This could make hordenine a potential biomarker for the consumption of these foods. In a subsequent paper, Camus reported that the intravenous (IV) administration of some hundreds of mg of hordenine sulfate to dogs or rabbits caused an increase in blood pressure and changes in the rhythm and force of contraction of the heart, noting also that the drug was not orally active. Common salts are hordenine hydrochloride, R-NH3+Cl−, m.p. 178 °C, and hordenine sulfate, (R-NH3+)2SO42−, m.p. 211 °C.The "methyl hordenine HCl" which is listed as an ingredient on the labels of some nutritional supplements is in all likelihood simply hordenine hydrochloride, since the "description" of "methyl hordenine HCl" given by virtually all bulk suppliers of this substance corresponds to that for hordenine hydrochloride (or possibly just hordenine). The hordenine content of various malts and malt fractions was extensively studied by Poocharoen himself, who also provided a good coverage of related literature up to 1983. |
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Structure | InChI=1S/C10H15NO/c1-11(2)8-7-9-3-5-10(12)6-4-9/h3-6,12H,7-8H2,1-2H3 |
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Synonyms | Value | Source |
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4-[2-(Dimethylamino)ethyl]phenol | ChEBI | N,N-Dimethyl-2-(4-hydroxyphenyl)ethylamine | ChEBI | N,N-Dimethyl-4-hydroxy-beta-phenethylamine | ChEBI | N,N-Dimethyltyramine | ChEBI | p-(2-Dimethylaminoethyl)phenol | ChEBI | N,N-Dimethyl-4-hydroxy-b-phenethylamine | Generator | N,N-Dimethyl-4-hydroxy-β-phenethylamine | Generator | Hordenine hydrochloride | HMDB | Hordenine sulfate (2:1) | HMDB | Hordenine sulfate (1:1) | HMDB | 4-(2-Dimethylaminoethyl)phenol | HMDB | Anhalin | HMDB | Anhaline | HMDB | Cactine | HMDB | Eremursine | HMDB | Hordenin | HMDB | Hordetin | HMDB | N,N-Dimethyl-p-hydroxyphenethylamine | HMDB | Ordenina | HMDB | Ordenine | HMDB | p-Hydroxy-N,N-dimethylphenethylamine | HMDB | p-[2-(Dimethylamino)ethyl]phenol | HMDB | Peyocactine | HMDB |
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Chemical Formula | C10H15NO |
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Average Molecular Weight | 165.2322 |
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Monoisotopic Molecular Weight | 165.115364107 |
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IUPAC Name | 4-[2-(dimethylamino)ethyl]phenol |
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Traditional Name | hordenine |
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CAS Registry Number | 539-15-1 |
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SMILES | CN(C)CCC1=CC=C(O)C=C1 |
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InChI Identifier | InChI=1S/C10H15NO/c1-11(2)8-7-9-3-5-10(12)6-4-9/h3-6,12H,7-8H2,1-2H3 |
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InChI Key | KUBCEEMXQZUPDQ-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as phenethylamines. Phenethylamines are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Benzene and substituted derivatives |
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Sub Class | Phenethylamines |
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Direct Parent | Phenethylamines |
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Alternative Parents | |
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Substituents | - Phenethylamine
- 1-hydroxy-2-unsubstituted benzenoid
- Aralkylamine
- Phenol
- Tertiary aliphatic amine
- Tertiary amine
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Amine
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 117.5 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 7 mg/mL | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Experimental Collision Cross Sections |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatized |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Hordenine GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a4i-9500000000-acdc91b4203b177fc754 | 2017-07-27 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Hordenine GC-MS (1 TMS) - 70eV, Positive | splash10-0a4i-9310000000-734c4e2c455b97372774 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Hordenine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Hordenine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - Hordenine n/a 11V, negative-QTOF | splash10-0a4i-0900000000-a2d459701f761877da82 | 2020-07-21 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hordenine 10V, Negative-QTOF | splash10-08fr-0900000000-31d50de8a8a2bed634a1 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hordenine 20V, Negative-QTOF | splash10-0a4i-0900000000-a31932c1e05061756730 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hordenine 40V, Negative-QTOF | splash10-014i-0900000000-7837d9fdc06599e5e477 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hordenine QqQ , positive-QTOF | splash10-0uvo-9900000000-130b6ae804451c70f74f | 2020-07-21 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hordenine LC-ESI-QTOF 10V, positive-QTOF | splash10-00xr-0900000000-25885270de2c1836c33b | 2020-07-21 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hordenine LC-ESI-QTOF 30V, positive-QTOF | splash10-0096-9500000000-8b84d5e79a70fa3d426a | 2020-07-21 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hordenine LC-ESI-QTOF 50V, positive-QTOF | splash10-00dl-8900000000-31b039648b094d1219b1 | 2020-07-21 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hordenine LC-ESI-QTOF 6V, positive-QTOF | splash10-00xr-0900000000-25885270de2c1836c33b | 2020-07-21 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hordenine LC-ESI-ITFT 3V, positive-QTOF | splash10-014i-0900000000-af85ba014415bf9af025 | 2020-07-21 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hordenine LC-ESI-ITFT 4V, positive-QTOF | splash10-014i-0900000000-35709636b966d858c147 | 2020-07-21 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hordenine LC-ESI-ITFT 6V, positive-QTOF | splash10-014i-0900000000-cb918f599a55448f67b1 | 2020-07-21 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hordenine LC-ESI-ITFT 8V, positive-QTOF | splash10-014i-0900000000-2c71ef92063a1e597ef9 | 2020-07-21 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hordenine LC-ESI-ITFT 9V, positive-QTOF | splash10-01b9-0900000000-4a5dab8033ea67d49fed | 2020-07-21 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hordenine LC-ESI-ITFT 11V, positive-QTOF | splash10-00xr-0900000000-ceea75c15d32fbdad6b1 | 2020-07-21 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hordenine LC-ESI-ITFT 13V, positive-QTOF | splash10-00di-0900000000-0786df40672ae99b4702 | 2020-07-21 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hordenine LC-ESI-ITFT 14V, positive-QTOF | splash10-00di-0900000000-739407a14a5e392c93bb | 2020-07-21 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hordenine LC-ESI-ITFT 16V, positive-QTOF | splash10-00di-0900000000-ea6d249aa8c9a2734603 | 2020-07-21 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hordenine LC-ESI-ITFT 18V, positive-QTOF | splash10-00di-0900000000-95ea20554b9c70cfdb04 | 2020-07-21 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hordenine LC-ESI-ITFT 19V, positive-QTOF | splash10-00di-0900000000-840ccb1e804c5f2bd859 | 2020-07-21 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hordenine LC-ESI-ITFT 21V, positive-QTOF | splash10-00di-1900000000-b5bd97221f7577432dff | 2020-07-21 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hordenine LC-ESI-ITFT 23V, positive-QTOF | splash10-00di-1900000000-4e1722b74214bbe8fb5d | 2020-07-21 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hordenine LC-ESI-ITFT 24V, positive-QTOF | splash10-00di-2900000000-ace89f936dcba1a15015 | 2020-07-21 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hordenine LC-ESI-ITFT 26V, positive-QTOF | splash10-00di-3900000000-1c1e33c685a2bab4ba2e | 2020-07-21 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hordenine LC-ESI-ITFT 28V, positive-QTOF | splash10-00dl-4900000000-77c74c5dbd9c018c64f5 | 2020-07-21 | HMDB team, MONA | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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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 |
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