Hmdb loader
Survey
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:31 UTC
HMDB IDHMDB0001189
Secondary Accession Numbers
  • HMDB01189
Metabolite Identification
Common Name2(N)-Methyl-norsalsolinol
Description2(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 ).
Structure
Data?1676999731
Synonyms
ValueSource
1,2,3,4-tetrahydro-2-Methyl-6,7-isoquinolinediolHMDB
2-Methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinolineHMDB, MeSH
2-Methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrobromideMeSH, HMDB
NMNSALMeSH, HMDB
2-MDTIQMeSH, HMDB
2-Methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochlorideMeSH, HMDB
N-MethylnorsalsolinolMeSH, HMDB
Chemical FormulaC10H13NO2
Average Molecular Weight179.2157
Monoisotopic Molecular Weight179.094628665
IUPAC Name2-methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol
Traditional Name2(N)-methyl-norsalsolinol
CAS Registry Number63937-92-8
SMILES
CN1CCC2=CC(O)=C(O)C=C2C1
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
InChI KeyWETXYFNVBDLWIW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassTetrahydroisoquinolines
Sub ClassNot Available
Direct ParentTetrahydroisoquinolines
Alternative Parents
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
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility37.1 g/LALOGPS
logP0.59ALOGPS
logP1.35ChemAxon
logS-0.68ALOGPS
pKa (Strongest Acidic)9.43ChemAxon
pKa (Strongest Basic)7.47ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area43.7 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity51.87 m³·mol⁻¹ChemAxon
Polarizability19.56 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+140.33131661259
DarkChem[M-H]-136.70531661259
AllCCS[M+H]+138.15532859911
AllCCS[M-H]-140.89932859911
DeepCCS[M+H]+138.51730932474
DeepCCS[M-H]-135.96530932474
DeepCCS[M-2H]-172.04830932474
DeepCCS[M+Na]+147.41230932474
AllCCS[M+H]+138.232859911
AllCCS[M+H-H2O]+133.732859911
AllCCS[M+NH4]+142.332859911
AllCCS[M+Na]+143.532859911
AllCCS[M-H]-140.932859911
AllCCS[M+Na-2H]-141.532859911
AllCCS[M+HCOO]-142.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2(N)-Methyl-norsalsolinolCN1CCC2=CC(O)=C(O)C=C2C12552.3Standard polar33892256
2(N)-Methyl-norsalsolinolCN1CCC2=CC(O)=C(O)C=C2C11672.1Standard non polar33892256
2(N)-Methyl-norsalsolinolCN1CCC2=CC(O)=C(O)C=C2C11836.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2(N)-Methyl-norsalsolinol,1TMS,isomer #1CN1CCC2=CC(O[Si](C)(C)C)=C(O)C=C2C11807.5Semi standard non polar33892256
2(N)-Methyl-norsalsolinol,1TMS,isomer #2CN1CCC2=CC(O)=C(O[Si](C)(C)C)C=C2C11797.1Semi standard non polar33892256
2(N)-Methyl-norsalsolinol,2TMS,isomer #1CN1CCC2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C2C11812.6Semi standard non polar33892256
2(N)-Methyl-norsalsolinol,1TBDMS,isomer #1CN1CCC2=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C2C12076.1Semi standard non polar33892256
2(N)-Methyl-norsalsolinol,1TBDMS,isomer #2CN1CCC2=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C2C12057.4Semi standard non polar33892256
2(N)-Methyl-norsalsolinol,2TBDMS,isomer #1CN1CCC2=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C2C12281.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2(N)-Methyl-norsalsolinol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0h09-0900000000-bf4ec1062ac2b839282e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2(N)-Methyl-norsalsolinol GC-MS (2 TMS) - 70eV, Positivesplash10-05fr-1193000000-f8ec40086f347c196a772017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2(N)-Methyl-norsalsolinol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2(N)-Methyl-norsalsolinol 10V, Positive-QTOFsplash10-001i-0900000000-2d6d43a51cbdcaacb7912017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2(N)-Methyl-norsalsolinol 20V, Positive-QTOFsplash10-0f89-0900000000-9da5452488647aecc4ac2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2(N)-Methyl-norsalsolinol 40V, Positive-QTOFsplash10-0079-5900000000-b48adad337bbc3b4c3f22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2(N)-Methyl-norsalsolinol 10V, Negative-QTOFsplash10-004i-0900000000-59c2c966e5bb27fa34a42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2(N)-Methyl-norsalsolinol 20V, Negative-QTOFsplash10-004i-0900000000-4d8538c59706a2953c8b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2(N)-Methyl-norsalsolinol 40V, Negative-QTOFsplash10-074l-2900000000-f74a421baa4902e5b4f82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2(N)-Methyl-norsalsolinol 10V, Negative-QTOFsplash10-004i-0900000000-e9e4d0ba83478e578c422021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2(N)-Methyl-norsalsolinol 20V, Negative-QTOFsplash10-004i-0900000000-cab123cec057104fdf652021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2(N)-Methyl-norsalsolinol 40V, Negative-QTOFsplash10-00dr-1900000000-88f6a4deeb5a022ef56a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2(N)-Methyl-norsalsolinol 10V, Positive-QTOFsplash10-001i-0900000000-6326446584297a254a6a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2(N)-Methyl-norsalsolinol 20V, Positive-QTOFsplash10-001i-0900000000-d5a1eb90c086c04249432021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2(N)-Methyl-norsalsolinol 40V, Positive-QTOFsplash10-05mx-8900000000-66d4fc031f9937d4b4dd2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Cerebrospinal Fluid (CSF)
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedParkinson's disease details
Associated Disorders and Diseases
Disease References
Parkinson's disease
  1. 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 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022477
KNApSAcK IDNot Available
Chemspider ID34632
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound37764
PDB IDNot Available
ChEBI ID767276
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]