Record Information
Version3.6
Creation Date2006-12-06 15:50:25 UTC
Update Date2013-05-29 19:41:55 UTC
HMDB IDHMDB05199
Secondary Accession NumbersNone
Metabolite Identification
Common Name(R)-Salsolinol
DescriptionSalsolinol is an endogenous catechol isoquinoline detected in humans. Salsolinol was detected in urine of parkinsonian patients administered with L-DOPA. This finding stimulated the studies on Salsolinol derivatives in the brain, and gave new aspects of the endogenous alkaloids, which had been considered to occur only in plants. In normal non-alcoholic subjects and alcoholics, Salsolinol and O-methylated Salsolinol were found in urine, cerebrospinal fluid and brains. Salsolinol has an asymmetric center at first position and exists as (R)- and (S)enantiomer. The (R)enantiomer of Salsolinol is predominant in urine from healthy volunteers. Only the (R)enantiomers of Salsolinol and N-methylated Salsolinol occur in the human brain, cerebrospinal fluid (CSF) and intraventricular fluid (IVF), and the (S)enantiomers were not detected. (R)salsolinol synthase catalyzes the enantio-selective synthesis of (R)Salsolinol and 1-carboxyl(R)Salsolinol from dopamine with acetaldehyde or pyruvic acid. The N-methylation of (R)salsolinol into N-methylsalsolinol (NMSal) is catalyzed by two N-methyltransferases with different optimum pH, at pH 7.0 and 8.4. NM(R)Salsolinol is enzymatically oxidized into 1,2-dimethyl-6,7-dihydroxyisoquinolinium ion (DMDHIQ+) by an oxidase sensitive to semicarbaside and also non-enzymatically by autoxidation. NM(R)Salsolinol and its precursor, dopamine, were found to occur selectively in the nigro-striatum, whereas (R)Salsolinol distributes uniformly among the brain regions. (PMID 14697894 ).
Structure
Thumb
Synonyms
  1. (+)-(R)-Salsolinol
  2. (+)-Salsolinol
  3. (R)-(+)-Salsolinol
  4. (R)-Salsolinol
  5. 1-Methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline
Chemical FormulaC10H13NO2
Average Molecular Weight179.2157
Monoisotopic Molecular Weight179.094628665
IUPAC Name1-methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol
Traditional IUPAC Name1-methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol
CAS Registry Number525-72-4
SMILES
CC1NCCC2=C1C=C(O)C(O)=C2
InChI Identifier
InChI=1S/C10H13NO2/c1-6-8-5-10(13)9(12)4-7(8)2-3-11-6/h4-6,11-13H,2-3H2,1H3
InChI KeyIBRKLUSXDYATLG-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Heteropolycyclic Compounds
ClassIsoquinolines
Sub ClassN/A
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
Substituents
  • 1,2 Diphenol
  • Phenol
  • Phenol Derivative
  • Secondary Aliphatic Amine (Dialkylamine)
Direct ParentIsoquinolines
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility6.71 g/LALOGPS
logP0.16ALOGPS
logP0.96ChemAxon
logS-1.4ALOGPS
pKa (strongest acidic)9.61ChemAxon
pKa (strongest basic)8.7ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count3ChemAxon
hydrogen donor count3ChemAxon
polar surface area52.49ChemAxon
rotatable bond count0ChemAxon
refractivity51ChemAxon
polarizability19.24ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified0.0022 +/- 0.0015 uMAdult (>18 years old)BothNormal
BloodDetected and Quantified0.00042 +/- 0.000094 uMAdult (>18 years old)BothNormal
Cerebrospinal Fluid (CSF)Detected and Quantified0.005 +/- 0.002 uMAdult (>18 years old)Not SpecifiedNormal
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified0.0019 +/- 0.00078 uMAdult (>18 years old)BothAfter alcohol intake
BloodDetected and Quantified0.0010 +/- 0.00043 uMAdult (>18 years old)BothHypertension
Cerebrospinal Fluid (CSF)Detected and Quantified0.005 +/- 0.001 uMAdult (>18 years old)Not SpecifiedParkinson's disease
Cerebrospinal Fluid (CSF)Detected and Quantified0.004 +/- 0.001 uMAdult (>18 years old)Not SpecifiedMultiple System Atrophy (MSA)
Associated Disorders and Diseases
Disease References
Hypertension
  • Andrew R, Best SA, Watson DG, Midgley JM, Reid JL, Squire IB: Analysis of biogenic amines in plasma of hypertensive patients and a control group. Neurochem Res. 1993 Nov;18(11):1179-82. Pubmed: 8255371
Multiple system atrophy
  • Naoi M, Maruyama W: Cell death of dopamine neurons in aging and Parkinson's disease. Mech Ageing Dev. 1999 Nov;111(2-3):175-88. Pubmed: 10656535
Parkinson's disease
  • Zhang W, Xie Y, Gu J, Ai S, Wang J, Yamamoto K, Jin L: Liquid chromatography with amperometric detection at a nano crystalline Ce-doped lead dioxide film modified electrode for determination of (R)-Salsolinol, (R)-N-methylsalsolinol and monoamine neurotransmitters in Parkinsonian patients' cerebrospinal fluid. Analyst. 2004 Mar;129(3):229-34. Epub 2004 Feb 6. Pubmed: 14978525
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB000429
KNApSAcK IDNot Available
Chemspider ID49181
KEGG Compound IDC09642
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB05199
Metagene LinkHMDB05199
METLIN IDNot Available
PubChem Compound54456
PDB IDNot Available
ChEBI ID123715
References
Synthesis ReferenceKovacs, Odon; Fodor, Gabor. The synthesis of tetrahydroisoquinoline alkaloids under physiological conditions. Chemische Berichte (1951), 84 795-801.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Zhang W, Xie Y, Gu J, Ai S, Wang J, Yamamoto K, Jin L: Liquid chromatography with amperometric detection at a nano crystalline Ce-doped lead dioxide film modified electrode for determination of (R)-Salsolinol, (R)-N-methylsalsolinol and monoamine neurotransmitters in Parkinsonian patients' cerebrospinal fluid. Analyst. 2004 Mar;129(3):229-34. Epub 2004 Feb 6. Pubmed: 14978525
  2. Naoi M, Maruyama W: Cell death of dopamine neurons in aging and Parkinson's disease. Mech Ageing Dev. 1999 Nov;111(2-3):175-88. Pubmed: 10656535
  3. Naoi M, Maruyama W, Nagy GM: Dopamine-derived salsolinol derivatives as endogenous monoamine oxidase inhibitors: occurrence, metabolism and function in human brains. Neurotoxicology. 2004 Jan;25(1-2):193-204. Pubmed: 14697894