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Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2023-02-21 17:15:31 UTC |
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HMDB ID | HMDB0001189 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 2(N)-Methyl-norsalsolinol |
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Description | 2(N)-methyl-norsalsolinol (NMNorsal) is a dihydroxylated tetrahydroisoquinoline derivative 2(N)-analogue of salsolinol, identified as a putative endogenous neurotoxin in patients with Parkinson's disease. A prominent blood-brain barrier (BBB) is described to exist for salsolinol, but penetration of NMNorsal occurs through the BBB into the caudate nucleus of the rat brain. There was no alteration in extracellular dopamine or 3,4-dihydroxyphenylacetic acid levels. (PMID 11924888 ). 2(N)-methyl-norsalsolinol was identified in L-DOPA-treated patients with Parkinson's disease and proposed to be responsible for behavioral changes. Atypical heterocyclic L-DOPA/dopamine metabolite NMNorsal is able to modify long-term regulation of serotonin and opioid receptor expression in striatum. Since the occurrence of hallucinosis or psychosis following L-DOPA treatment is related to the serotonergic system, these results probably reflect a link between NMNorsal and L-DOPA side effects in Parkinson's disease. (PMID 14607311 ). |
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Structure | InChI=1S/C10H13NO2/c1-11-3-2-7-4-9(12)10(13)5-8(7)6-11/h4-5,12-13H,2-3,6H2,1H3 |
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Synonyms | Value | Source |
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1,2,3,4-tetrahydro-2-Methyl-6,7-isoquinolinediol | HMDB | 2-Methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline | HMDB, MeSH | 2-Methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrobromide | MeSH, HMDB | NMNSAL | MeSH, HMDB | 2-MDTIQ | MeSH, HMDB | 2-Methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride | MeSH, HMDB | N-Methylnorsalsolinol | MeSH, HMDB |
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Chemical Formula | C10H13NO2 |
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Average Molecular Weight | 179.2157 |
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Monoisotopic Molecular Weight | 179.094628665 |
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IUPAC Name | 2-methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol |
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Traditional Name | 2(N)-methyl-norsalsolinol |
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CAS Registry Number | 63937-92-8 |
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SMILES | CN1CCC2=CC(O)=C(O)C=C2C1 |
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InChI Identifier | InChI=1S/C10H13NO2/c1-11-3-2-7-4-9(12)10(13)5-8(7)6-11/h4-5,12-13H,2-3,6H2,1H3 |
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InChI Key | WETXYFNVBDLWIW-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Tetrahydroisoquinolines |
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Sub Class | Not Available |
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Direct Parent | Tetrahydroisoquinolines |
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Alternative Parents | |
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Substituents | - Tetrahydroisoquinoline
- 1-hydroxy-2-unsubstituted benzenoid
- Aralkylamine
- Benzenoid
- Tertiary aliphatic amine
- Tertiary amine
- Azacycle
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Amine
- 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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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 | Solid |
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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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2(N)-Methyl-norsalsolinol,1TMS,isomer #1 | CN1CCC2=CC(O[Si](C)(C)C)=C(O)C=C2C1 | 1807.5 | Semi standard non polar | 33892256 | 2(N)-Methyl-norsalsolinol,1TMS,isomer #2 | CN1CCC2=CC(O)=C(O[Si](C)(C)C)C=C2C1 | 1797.1 | Semi standard non polar | 33892256 | 2(N)-Methyl-norsalsolinol,2TMS,isomer #1 | CN1CCC2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C2C1 | 1812.6 | Semi standard non polar | 33892256 | 2(N)-Methyl-norsalsolinol,1TBDMS,isomer #1 | CN1CCC2=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C2C1 | 2076.1 | Semi standard non polar | 33892256 | 2(N)-Methyl-norsalsolinol,1TBDMS,isomer #2 | CN1CCC2=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C2C1 | 2057.4 | Semi standard non polar | 33892256 | 2(N)-Methyl-norsalsolinol,2TBDMS,isomer #1 | CN1CCC2=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C2C1 | 2281.3 | Semi standard non polar | 33892256 |
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Spectra |
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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 - 2(N)-Methyl-norsalsolinol GC-MS (Non-derivatized) - 70eV, Positive | splash10-0h09-0900000000-bf4ec1062ac2b839282e | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 2(N)-Methyl-norsalsolinol GC-MS (2 TMS) - 70eV, Positive | splash10-05fr-1193000000-f8ec40086f347c196a77 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 2(N)-Methyl-norsalsolinol 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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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2(N)-Methyl-norsalsolinol 10V, Positive-QTOF | splash10-001i-0900000000-2d6d43a51cbdcaacb791 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2(N)-Methyl-norsalsolinol 20V, Positive-QTOF | splash10-0f89-0900000000-9da5452488647aecc4ac | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2(N)-Methyl-norsalsolinol 40V, Positive-QTOF | splash10-0079-5900000000-b48adad337bbc3b4c3f2 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2(N)-Methyl-norsalsolinol 10V, Negative-QTOF | splash10-004i-0900000000-59c2c966e5bb27fa34a4 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2(N)-Methyl-norsalsolinol 20V, Negative-QTOF | splash10-004i-0900000000-4d8538c59706a2953c8b | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2(N)-Methyl-norsalsolinol 40V, Negative-QTOF | splash10-074l-2900000000-f74a421baa4902e5b4f8 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2(N)-Methyl-norsalsolinol 10V, Negative-QTOF | splash10-004i-0900000000-e9e4d0ba83478e578c42 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2(N)-Methyl-norsalsolinol 20V, Negative-QTOF | splash10-004i-0900000000-cab123cec057104fdf65 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2(N)-Methyl-norsalsolinol 40V, Negative-QTOF | splash10-00dr-1900000000-88f6a4deeb5a022ef56a | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2(N)-Methyl-norsalsolinol 10V, Positive-QTOF | splash10-001i-0900000000-6326446584297a254a6a | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2(N)-Methyl-norsalsolinol 20V, Positive-QTOF | splash10-001i-0900000000-d5a1eb90c086c0424943 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2(N)-Methyl-norsalsolinol 40V, Positive-QTOF | splash10-05mx-8900000000-66d4fc031f9937d4b4dd | 2021-09-22 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-29 | 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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Biological Properties |
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Cellular Locations | Not Available |
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Biospecimen Locations | - Cerebrospinal Fluid (CSF)
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Abnormal Concentrations |
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Cerebrospinal Fluid (CSF) | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Not Specified | Parkinson's disease | | details |
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Associated Disorders and Diseases |
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Disease References | Parkinson's disease |
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- Moser A, Scholz J, Nobbe F, Vieregge P, Bohme V, Bamberg H: Presence of N-methyl-norsalsolinol in the CSF: correlations with dopamine metabolites of patients with Parkinson's disease. J Neurol Sci. 1995 Aug;131(2):183-9. [PubMed:7595645 ]
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Associated OMIM IDs | |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB022477 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 34632 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 37764 |
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PDB ID | Not Available |
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ChEBI ID | 767276 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Moser A, Scholz J, Nobbe F, Vieregge P, Bohme V, Bamberg H: Presence of N-methyl-norsalsolinol in the CSF: correlations with dopamine metabolites of patients with Parkinson's disease. J Neurol Sci. 1995 Aug;131(2):183-9. [PubMed:7595645 ]
- Thumen A, Behnecke A, Qadri F, Bauml E, Thumen A, Behnecke CA, Qadri F, Bauml E, Moser A: N-methyl-norsalsolinol, a putative dopaminergic neurotoxin, passes through the blood-brain barrier in vivo. Neuroreport. 2002 Jan 21;13(1):25-8. [PubMed:11924888 ]
- Moser A, Thumen A, Qadri F: Modulation of striatal serotonin and opioid receptor mRNA expression following systemic N-methyl-norsalsolinol administration. J Neurol Sci. 2003 Dec 15;216(1):109-12. [PubMed:14607311 ]
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