Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2013-07-04 18:58:09 UTC |
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Update Date | 2023-02-21 17:30:14 UTC |
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HMDB ID | HMDB0060765 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 4-Hydroxyamphetamine |
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Description | 4-Hydroxyamphetamine is a metabolite of methamphetamine. Methamphetamine, also known as methamfetamine, meth, N-methylamphetamine, methylamphetamine, and desoxyephedrine, is a psychostimulant of the phenethylamine and amphetamine class of psychoactive drugs. Methamphetamine increases alertness, concentration, energy, and in high doses, can induce euphoria, enhance self-esteem and increase libido. (Wikipedia ) |
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Structure | InChI=1S/C9H13NO/c1-7(10)6-8-2-4-9(11)5-3-8/h2-5,7,11H,6,10H2,1H3 |
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Synonyms | Value | Source |
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HYDROXYAMFETAMINE | HMDB | Hydrobromide, hydroxyamphetamine | HMDB | Hydroxyamphetamin | HMDB | Hydroxyamphetamine hydrobromide | HMDB | Norpholedrin | HMDB | Oxyamphetamine | HMDB | p-Hydroxyamphetamine | HMDB | Para hydroxyamphetamine | HMDB | Hydroxyphenylisopropylamine | HMDB | Paredrine | HMDB | p Hydroxyamphetamine | HMDB | Para-hydroxyamphetamine | HMDB | Methyltyramine | HMDB | Hydroxyamphetamine | HMDB |
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Chemical Formula | C9H13NO |
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Average Molecular Weight | 151.2056 |
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Monoisotopic Molecular Weight | 151.099714043 |
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IUPAC Name | 4-(2-aminopropyl)phenol |
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Traditional Name | p-hydroxyamphetamine |
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CAS Registry Number | Not Available |
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SMILES | CC(N)CC1=CC=C(O)C=C1 |
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InChI Identifier | InChI=1S/C9H13NO/c1-7(10)6-8-2-4-9(11)5-3-8/h2-5,7,11H,6,10H2,1H3 |
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InChI Key | GIKNHHRFLCDOEU-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-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 | Amphetamines and derivatives |
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Alternative Parents | |
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Substituents | - Amphetamine or derivatives
- Phenylpropane
- 1-hydroxy-2-unsubstituted benzenoid
- Aralkylamine
- Phenol
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Primary aliphatic amine
- Amine
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | Not Available |
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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 | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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4-Hydroxyamphetamine,1TMS,isomer #1 | CC(N)CC1=CC=C(O[Si](C)(C)C)C=C1 | 1500.5 | Semi standard non polar | 33892256 | 4-Hydroxyamphetamine,1TMS,isomer #2 | CC(CC1=CC=C(O)C=C1)N[Si](C)(C)C | 1665.3 | Semi standard non polar | 33892256 | 4-Hydroxyamphetamine,2TMS,isomer #1 | CC(CC1=CC=C(O[Si](C)(C)C)C=C1)N[Si](C)(C)C | 1629.4 | Semi standard non polar | 33892256 | 4-Hydroxyamphetamine,2TMS,isomer #1 | CC(CC1=CC=C(O[Si](C)(C)C)C=C1)N[Si](C)(C)C | 1629.4 | Standard non polar | 33892256 | 4-Hydroxyamphetamine,2TMS,isomer #1 | CC(CC1=CC=C(O[Si](C)(C)C)C=C1)N[Si](C)(C)C | 1768.6 | Standard polar | 33892256 | 4-Hydroxyamphetamine,2TMS,isomer #2 | CC(CC1=CC=C(O)C=C1)N([Si](C)(C)C)[Si](C)(C)C | 1817.4 | Semi standard non polar | 33892256 | 4-Hydroxyamphetamine,2TMS,isomer #2 | CC(CC1=CC=C(O)C=C1)N([Si](C)(C)C)[Si](C)(C)C | 1876.1 | Standard non polar | 33892256 | 4-Hydroxyamphetamine,2TMS,isomer #2 | CC(CC1=CC=C(O)C=C1)N([Si](C)(C)C)[Si](C)(C)C | 1972.4 | Standard polar | 33892256 | 4-Hydroxyamphetamine,3TMS,isomer #1 | CC(CC1=CC=C(O[Si](C)(C)C)C=C1)N([Si](C)(C)C)[Si](C)(C)C | 1867.0 | Semi standard non polar | 33892256 | 4-Hydroxyamphetamine,3TMS,isomer #1 | CC(CC1=CC=C(O[Si](C)(C)C)C=C1)N([Si](C)(C)C)[Si](C)(C)C | 1791.0 | Standard non polar | 33892256 | 4-Hydroxyamphetamine,3TMS,isomer #1 | CC(CC1=CC=C(O[Si](C)(C)C)C=C1)N([Si](C)(C)C)[Si](C)(C)C | 1786.5 | Standard polar | 33892256 | 4-Hydroxyamphetamine,1TBDMS,isomer #1 | CC(N)CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1 | 1723.5 | Semi standard non polar | 33892256 | 4-Hydroxyamphetamine,1TBDMS,isomer #2 | CC(CC1=CC=C(O)C=C1)N[Si](C)(C)C(C)(C)C | 1877.3 | Semi standard non polar | 33892256 | 4-Hydroxyamphetamine,2TBDMS,isomer #1 | CC(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)N[Si](C)(C)C(C)(C)C | 2127.5 | Semi standard non polar | 33892256 | 4-Hydroxyamphetamine,2TBDMS,isomer #1 | CC(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)N[Si](C)(C)C(C)(C)C | 2086.7 | Standard non polar | 33892256 | 4-Hydroxyamphetamine,2TBDMS,isomer #1 | CC(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)N[Si](C)(C)C(C)(C)C | 2058.7 | Standard polar | 33892256 | 4-Hydroxyamphetamine,2TBDMS,isomer #2 | CC(CC1=CC=C(O)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2250.8 | Semi standard non polar | 33892256 | 4-Hydroxyamphetamine,2TBDMS,isomer #2 | CC(CC1=CC=C(O)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2315.1 | Standard non polar | 33892256 | 4-Hydroxyamphetamine,2TBDMS,isomer #2 | CC(CC1=CC=C(O)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2135.8 | Standard polar | 33892256 | 4-Hydroxyamphetamine,3TBDMS,isomer #1 | CC(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2567.9 | Semi standard non polar | 33892256 | 4-Hydroxyamphetamine,3TBDMS,isomer #1 | CC(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2414.1 | Standard non polar | 33892256 | 4-Hydroxyamphetamine,3TBDMS,isomer #1 | CC(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2132.6 | Standard polar | 33892256 |
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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 - 4-Hydroxyamphetamine GC-MS (Non-derivatized) - 70eV, Positive | splash10-0006-9800000000-be314d40e4f3eec02c64 | 2017-08-28 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4-Hydroxyamphetamine GC-MS (1 TMS) - 70eV, Positive | splash10-0006-9520000000-27b26e501065c88f2e44 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4-Hydroxyamphetamine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4-Hydroxyamphetamine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4-Hydroxyamphetamine GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-11-03 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4-Hydroxyamphetamine GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-11-03 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4-Hydroxyamphetamine GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | 2021-11-03 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Hydroxyamphetamine 10V, Positive-QTOF | splash10-0udr-0900000000-ce983c3333043fa75138 | 2017-07-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Hydroxyamphetamine 20V, Positive-QTOF | splash10-0f79-1900000000-a25d07320a871a151c90 | 2017-07-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Hydroxyamphetamine 40V, Positive-QTOF | splash10-0670-8900000000-01eef85998096c783c89 | 2017-07-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Hydroxyamphetamine 10V, Negative-QTOF | splash10-0udi-0900000000-9127f6d37951111e3ca5 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Hydroxyamphetamine 20V, Negative-QTOF | splash10-0udi-0900000000-63b9d3f1a2d2019491a4 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Hydroxyamphetamine 40V, Negative-QTOF | splash10-001i-3900000000-82c27ad632334acd666f | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Hydroxyamphetamine 10V, Negative-QTOF | splash10-0zfr-0900000000-82f62a52cf320914dd1e | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Hydroxyamphetamine 20V, Negative-QTOF | splash10-0pb9-0900000000-a9f0104927f0505bdb7e | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Hydroxyamphetamine 40V, Negative-QTOF | splash10-0006-9400000000-c422ecbb2ca5cb2ab89d | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Hydroxyamphetamine 10V, Positive-QTOF | splash10-0f79-0900000000-1559527532c5eafbb7ee | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Hydroxyamphetamine 20V, Positive-QTOF | splash10-0a4i-3900000000-a43fa60f8dfe5ea4df1f | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Hydroxyamphetamine 40V, Positive-QTOF | splash10-004i-9100000000-5033c3c68adccf158b05 | 2021-10-12 | Wishart Lab | 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]-) | 2023-02-04 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-04 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-04 | FELIX lab | View Spectrum |
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