| Record Information |
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| Version | 2.0 |
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| Created at | 2022-05-11 16:39:16 UTC |
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| Updated at | 2022-05-11 16:39:16 UTC |
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| NP-MRD ID | NP0087074 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | (R)-N-Methylsalsolinol |
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| Description | (R)-N-Methylsalsolinol, also known as salsoline or N-methyl-(R)-salsolinol, belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives (R)-N-Methylsalsolinol is a very strong basic compound (based on its pKa). The results suggest that N-methyl(R)salsolinol level in the cerebrospinal fluid may indicate remaining dopamine neurons in the parkinsonian brain. In the cerebrospinal fluid from newly diagnosed untreated patients with Parkinson's disease, the level of this toxin was found to increase significantly, compared to control and a disease control, multiple system atrophy. (R)-N-Methylsalsolinol was first documented in 2004 (PMID: 14978525). 1(R),2(N)-dimethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline is the most potent toxin among isoquinolines. |
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| Structure | C[C@H]1N(C)CCC2=CC(O)=C(O)C=C12 InChI=1S/C11H15NO2/c1-7-9-6-11(14)10(13)5-8(9)3-4-12(7)2/h5-7,13-14H,3-4H2,1-2H3/t7-/m1/s1 |
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| Synonyms | | Value | Source |
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| N-Methyl-(R)-salsolinol | HMDB | | Salsoline hydrochloride, hydrate (4:4:1) | HMDB | | Salsoline | HMDB | | Salsoline hydrochloride | HMDB | | (+)-Salsoline | HMDB | | Salsoline (-)-form | HMDB | | D-Salosine | HMDB | | Salsoline hydrochloride, (R)-isomer | HMDB | | 1(R),2(N)-Dimethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline | HMDB | | Salsoline hydrochloride, (S)-isomer | HMDB | | (S)-Salsoline | HMDB | | 7-O-Methylsalsolinol | HMDB | | Methylsalsolinol | HMDB | | (-)-Salsoline | HMDB |
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| Chemical Formula | C11H15NO2 |
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| Average Mass | 193.2423 Da |
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| Monoisotopic Mass | 193.11028 Da |
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| IUPAC Name | (1R)-1,2-dimethyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol |
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| Traditional Name | N-methyl-(R)-salsolinol |
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| CAS Registry Number | Not Available |
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| SMILES | C[C@H]1N(C)CCC2=CC(O)=C(O)C=C12 |
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| InChI Identifier | InChI=1S/C11H15NO2/c1-7-9-6-11(14)10(13)5-8(9)3-4-12(7)2/h5-7,13-14H,3-4H2,1-2H3/t7-/m1/s1 |
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| InChI Key | RKMGOUZXGHZLBJ-SSDOTTSWSA-N |
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| Experimental Spectra |
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| Not Available | | Predicted Spectra |
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| | Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 13C NMR Spectrum (1D, 25 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | Chemical Shift Submissions |
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| Not Available | | Species |
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| Species of Origin | |
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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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| Physical Properties |
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| State | Not Available |
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| Experimental 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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| Predicted Properties | |
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