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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-13 02:05:27 UTC

Update Date

2023-02-21 17:16:45 UTC

HMDB ID

HMDB0003626

Secondary Accession Numbers

HMDB03626

Metabolite Identification

Common Name

(R)-N-Methylsalsolinol

Description

1(R),2(N)-dimethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline [N-methyl-(R)salsolinol, NM(R)Sal] is the most potent toxin among isoquinolines. Endogenous isoquinolines with and without catechol structure have been proposed to be neurotoxins specific for dopamine neurons. (PMID 9085193 ). (R)salsolinol N-methyltransferase synthesizes N-methyl(R)salsolinol, which is further oxidized into 1,2-dimethyl-6,7-dihydroxyisoquinolinium ion by non-enzymatic and enzymatic oxidation. (PMID 14697894 ). Dopamine-derived N-methyl(R)salsolinol is an endogenous MPTP-like neurotoxin to cause Parkinson's disease. 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. L-DOPA therapy did not seem to affect the level of this toxin. The results suggest that N-methyl(R)salsolinol level in the cerebrospinal fluid may indicate remaining dopamine neurons in the parkinsonian brain. (PMID 10076861 ). N-methyl(R)salsolinol (NM(R)Sal) induces apoptosis (but not necrosis) in SH-SY5Y cells, and the apoptotic cascade is initiated by mitochondrial permeability transition and activated by stepwise reactions. (PMID 12200198 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0003626
     RDKit          3D
(R)-N-Methylsalsolinol
 29 30  0  0  0  0  0  0  0  0999 V2000
   -1.2268    2.0536   -0.7116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0155    0.7885    0.0632 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4120    0.3938    0.0899 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4195    1.1479   -0.4327 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7136    0.6780   -0.3532 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7242    1.4531   -0.8872 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0313   -0.5269    0.2348 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3626   -0.9779    0.2995 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0072   -1.2844    0.7614 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6952   -0.8194    0.6869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4490   -1.5827    1.2358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6483   -1.4862    0.3675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7120   -0.3447   -0.5060 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0946   -0.0936   -0.7864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2689    2.2966   -0.8912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7211    2.0329   -1.7073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7795    2.8839   -0.1230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3766    0.9282    1.0931 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1442    2.0865   -0.8870 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5517    2.3412   -1.3285 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6016   -1.8572    0.7277 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1958   -2.2400    1.2359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7025   -1.0916    2.2189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1624   -2.6308    1.4590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5775   -1.5071    0.9796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6826   -2.4085   -0.2775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2590    0.5645   -1.6583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6170    0.2718    0.1268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5657   -1.0694   -1.0299 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13  2  1  0
 10  3  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  1
  4 19  1  0
  6 20  1  0
  8 21  1  0
  9 22  1  0
 11 23  1  0
 11 24  1  0
 12 25  1  0
 12 26  1  0
 14 27  1  0
 14 28  1  0
 14 29  1  0
M  END


  Mrv0541 02231219462D          

 14 15  0  0  1  0            999 V2000
   16.4736   -9.9550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4736  -10.7800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1880  -11.1926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9024  -10.7800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9024   -9.9550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1880   -9.5426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6170  -11.1926    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.3314  -10.7800    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.3314   -9.9550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6170   -9.5426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6170  -12.0176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0459  -11.1926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7591  -11.1926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7591   -9.5426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10  5  1  0  0  0  0
  7 11  1  6  0  0  0
  8 12  1  0  0  0  0
  2 13  1  0  0  0  0
  1 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0003626

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@H]1N(C)CCC2=CC(O)=C(O)C=C12

> <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

> <INCHI_KEY>
RKMGOUZXGHZLBJ-SSDOTTSWSA-N

> <FORMULA>
C11H15NO2

> <MOLECULAR_WEIGHT>
193.2423

> <EXACT_MASS>
193.110278729

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
21.35060997431016

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R)-1,2-dimethyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol

> <ALOGPS_LOGP>
1.23

> <JCHEM_LOGP>
1.58527630936146

> <ALOGPS_LOGS>
-0.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.824631679532871

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.9195382055972

> <JCHEM_PKA_STRONGEST_BASIC>
10.238325629387317

> <JCHEM_POLAR_SURFACE_AREA>
43.7

> <JCHEM_REFRACTIVITY>
56.2909

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.19e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-methyl-(R)-salsolinol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0003626
     RDKit          3D
(R)-N-Methylsalsolinol
 29 30  0  0  0  0  0  0  0  0999 V2000
   -1.2268    2.0536   -0.7116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0155    0.7885    0.0632 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4120    0.3938    0.0899 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4195    1.1479   -0.4327 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7136    0.6780   -0.3532 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7242    1.4531   -0.8872 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0313   -0.5269    0.2348 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3626   -0.9779    0.2995 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0072   -1.2844    0.7614 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6952   -0.8194    0.6869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4490   -1.5827    1.2358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6483   -1.4862    0.3675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7120   -0.3447   -0.5060 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0946   -0.0936   -0.7864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2689    2.2966   -0.8912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7211    2.0329   -1.7073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7795    2.8839   -0.1230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3766    0.9282    1.0931 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1442    2.0865   -0.8870 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5517    2.3412   -1.3285 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6016   -1.8572    0.7277 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1958   -2.2400    1.2359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7025   -1.0916    2.2189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1624   -2.6308    1.4590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5775   -1.5071    0.9796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6826   -2.4085   -0.2775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2590    0.5645   -1.6583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6170    0.2718    0.1268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5657   -1.0694   -1.0299 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13  2  1  0
 10  3  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  1
  4 19  1  0
  6 20  1  0
  8 21  1  0
  9 22  1  0
 11 23  1  0
 11 24  1  0
 12 25  1  0
 12 26  1  0
 14 27  1  0
 14 28  1  0
 14 29  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      30.751 -18.583   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      30.751 -20.123   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      32.084 -20.893   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      33.418 -20.123   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      33.418 -18.583   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      32.084 -17.813   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      34.752 -20.893   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      36.085 -20.123   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      36.085 -18.583   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      34.752 -17.813   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      34.752 -22.433   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      37.419 -20.893   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      29.417 -20.893   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      29.417 -17.813   0.000  0.00  0.00           O+0
CONECT    1    2    6   14                                                  
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    1                                                       
CONECT    7    4    8   11                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9    5                                                       
CONECT   11    7                                                            
CONECT   12    8                                                            
CONECT   13    2                                                            
CONECT   14    1                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

COMPND    HMDB0003626
HETATM    1  C1  UNL     1      -1.227   2.054  -0.712  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.016   0.789   0.063  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.412   0.394   0.090  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.420   1.148  -0.433  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.714   0.678  -0.353  1.00  0.00           C  
HETATM    6  O1  UNL     1       3.724   1.453  -0.887  1.00  0.00           O  
HETATM    7  C6  UNL     1       3.031  -0.527   0.235  1.00  0.00           C  
HETATM    8  O2  UNL     1       4.363  -0.978   0.300  1.00  0.00           O  
HETATM    9  C7  UNL     1       2.007  -1.284   0.761  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.695  -0.819   0.687  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.449  -1.583   1.236  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.648  -1.486   0.368  1.00  0.00           C  
HETATM   13  N1  UNL     1      -1.712  -0.345  -0.506  1.00  0.00           N  
HETATM   14  C11 UNL     1      -3.095  -0.094  -0.786  1.00  0.00           C  
HETATM   15  H1  UNL     1      -2.269   2.297  -0.891  1.00  0.00           H  
HETATM   16  H2  UNL     1      -0.721   2.033  -1.707  1.00  0.00           H  
HETATM   17  H3  UNL     1      -0.780   2.884  -0.123  1.00  0.00           H  
HETATM   18  H4  UNL     1      -1.377   0.928   1.093  1.00  0.00           H  
HETATM   19  H5  UNL     1       1.144   2.087  -0.887  1.00  0.00           H  
HETATM   20  H6  UNL     1       3.552   2.341  -1.329  1.00  0.00           H  
HETATM   21  H7  UNL     1       4.602  -1.857   0.728  1.00  0.00           H  
HETATM   22  H8  UNL     1       2.196  -2.240   1.236  1.00  0.00           H  
HETATM   23  H9  UNL     1      -0.702  -1.092   2.219  1.00  0.00           H  
HETATM   24  H10 UNL     1      -0.162  -2.631   1.459  1.00  0.00           H  
HETATM   25  H11 UNL     1      -2.578  -1.507   0.980  1.00  0.00           H  
HETATM   26  H12 UNL     1      -1.683  -2.408  -0.277  1.00  0.00           H  
HETATM   27  H13 UNL     1      -3.259   0.564  -1.658  1.00  0.00           H  
HETATM   28  H14 UNL     1      -3.617   0.272   0.127  1.00  0.00           H  
HETATM   29  H15 UNL     1      -3.566  -1.069  -1.030  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3   13   18
CONECT    3    4    4   10
CONECT    4    5   19
CONECT    5    6    7    7
CONECT    6   20
CONECT    7    8    9
CONECT    8   21
CONECT    9   10   10   22
CONECT   10   11
CONECT   11   12   23   24
CONECT   12   13   25   26
CONECT   13   14
CONECT   14   27   28   29
END

HMDB0003626
     RDKit          3D
(R)-N-Methylsalsolinol
 29 30  0  0  0  0  0  0  0  0999 V2000
   -1.2268    2.0536   -0.7116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0155    0.7885    0.0632 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4120    0.3938    0.0899 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4195    1.1479   -0.4327 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7136    0.6780   -0.3532 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7242    1.4531   -0.8872 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0313   -0.5269    0.2348 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3626   -0.9779    0.2995 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0072   -1.2844    0.7614 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6952   -0.8194    0.6869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4490   -1.5827    1.2358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6483   -1.4862    0.3675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7120   -0.3447   -0.5060 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0946   -0.0936   -0.7864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2689    2.2966   -0.8912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7211    2.0329   -1.7073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7795    2.8839   -0.1230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3766    0.9282    1.0931 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1442    2.0865   -0.8870 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5517    2.3412   -1.3285 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6016   -1.8572    0.7277 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1958   -2.2400    1.2359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7025   -1.0916    2.2189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1624   -2.6308    1.4590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5775   -1.5071    0.9796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6826   -2.4085   -0.2775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2590    0.5645   -1.6583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6170    0.2718    0.1268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5657   -1.0694   -1.0299 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13  2  1  0
 10  3  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  1
  4 19  1  0
  6 20  1  0
  8 21  1  0
  9 22  1  0
 11 23  1  0
 11 24  1  0
 12 25  1  0
 12 26  1  0
 14 27  1  0
 14 28  1  0
 14 29  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
N-Methyl-(R)-salsolinol	HMDB, MeSH
Salsoline hydrochloride, hydrate (4:4:1)	MeSH, HMDB
Salsoline	MeSH, HMDB
Salsoline hydrochloride	MeSH, HMDB
(+)-Salsoline	MeSH, HMDB
Salsoline (-)-form	MeSH, HMDB
D-Salosine	MeSH, HMDB
Salsoline hydrochloride, (R)-isomer	MeSH, HMDB
1(R),2(N)-Dimethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline	MeSH, HMDB
Salsoline hydrochloride, (S)-isomer	MeSH, HMDB
(S)-Salsoline	MeSH, HMDB
7-O-Methylsalsolinol	MeSH, HMDB
Methylsalsolinol	MeSH, HMDB
(-)-Salsoline	MeSH, HMDB

Chemical Formula

C₁₁H₁₅NO₂

Average Molecular Weight

193.2423

Monoisotopic Molecular Weight

193.110278729

IUPAC Name

(1R)-1,2-dimethyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol

Traditional Name

N-methyl-(R)-salsolinol

CAS Registry Number

53622-84-7

SMILES

C[C@H]1N(C)CCC2=CC(O)=C(O)C=C12

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

InChI Key

RKMGOUZXGHZLBJ-SSDOTTSWSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrahydroisoquinolines

Sub Class

Not Available

Direct Parent

Tetrahydroisoquinolines

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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	21.9 g/L	ALOGPS
logP	1.23	ALOGPS
logP	1.59	ChemAxon
logS	-0.94	ALOGPS
pKa (Strongest Acidic)	6.92	ChemAxon
pKa (Strongest Basic)	10.24	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	43.7 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	56.29 m³·mol⁻¹	ChemAxon
Polarizability	21.35 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	144.14	31661259
DarkChem	[M-H]-	142.566	31661259
DeepCCS	[M-2H]-	176.503	30932474
DeepCCS	[M+Na]+	151.086	30932474
AllCCS	[M+H]+	143.2	32859911
AllCCS	[M+H-H2O]+	138.9	32859911
AllCCS	[M+NH4]+	147.1	32859911
AllCCS	[M+Na]+	148.3	32859911
AllCCS	[M-H]-	145.9	32859911
AllCCS	[M+Na-2H]-	146.4	32859911
AllCCS	[M+HCOO]-	147.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.82 minutes	32390414
Predicted by Siyang on May 30, 2022	8.9495 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.37 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	137.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	427.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	243.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	93.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	151.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	40.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	279.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	270.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	687.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	602.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	51.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	684.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	161.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	193.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	631.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	513.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	189.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(R)-N-Methylsalsolinol	C[C@H]1N(C)CCC2=CC(O)=C(O)C=C12	2770.1	Standard polar	33892256
(R)-N-Methylsalsolinol	C[C@H]1N(C)CCC2=CC(O)=C(O)C=C12	1747.2	Standard non polar	33892256
(R)-N-Methylsalsolinol	C[C@H]1N(C)CCC2=CC(O)=C(O)C=C12	1889.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(R)-N-Methylsalsolinol,1TMS,isomer #1	C[C@@H]1C2=CC(O)=C(O[Si](C)(C)C)C=C2CCN1C	1841.7	Semi standard non polar	33892256
(R)-N-Methylsalsolinol,1TMS,isomer #2	C[C@@H]1C2=CC(O[Si](C)(C)C)=C(O)C=C2CCN1C	1831.1	Semi standard non polar	33892256
(R)-N-Methylsalsolinol,2TMS,isomer #1	C[C@@H]1C2=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C2CCN1C	1860.0	Semi standard non polar	33892256
(R)-N-Methylsalsolinol,1TBDMS,isomer #1	C[C@@H]1C2=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C2CCN1C	2114.7	Semi standard non polar	33892256
(R)-N-Methylsalsolinol,1TBDMS,isomer #2	C[C@@H]1C2=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C2CCN1C	2108.1	Semi standard non polar	33892256
(R)-N-Methylsalsolinol,2TBDMS,isomer #1	C[C@@H]1C2=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C2CCN1C	2338.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-N-Methylsalsolinol GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-0900000000-ce38275a97947ad0c207	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-N-Methylsalsolinol GC-MS (2 TMS) - 70eV, Positive	splash10-00di-2294000000-e81b4cd0f6a60cdbf289	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-N-Methylsalsolinol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-N-Methylsalsolinol 10V, Positive-QTOF	splash10-0006-0900000000-630f003fbd29862656db	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-N-Methylsalsolinol 20V, Positive-QTOF	splash10-0006-0900000000-2332ab63301661d2ad8b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-N-Methylsalsolinol 40V, Positive-QTOF	splash10-007a-3900000000-829765b96f19c1734e8f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-N-Methylsalsolinol 10V, Negative-QTOF	splash10-0006-0900000000-550798399b578a198d46	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-N-Methylsalsolinol 20V, Negative-QTOF	splash10-0006-0900000000-6c3f6aefc7671bf92e4b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-N-Methylsalsolinol 40V, Negative-QTOF	splash10-05di-3900000000-8e1121f2eeab5ab9b4ae	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-N-Methylsalsolinol 10V, Positive-QTOF	splash10-0006-0900000000-093c204a145d72b06e8c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-N-Methylsalsolinol 20V, Positive-QTOF	splash10-0006-0900000000-a5e47e491134faa38fe4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-N-Methylsalsolinol 40V, Positive-QTOF	splash10-0ab9-5900000000-23e7e3619291802dc08d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-N-Methylsalsolinol 10V, Negative-QTOF	splash10-0006-0900000000-5326ed117e0a68853a6c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-N-Methylsalsolinol 20V, Negative-QTOF	splash10-0006-0900000000-2db53ba347575442f27d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-N-Methylsalsolinol 40V, Negative-QTOF	splash10-001i-1900000000-79f2043772ff52170248	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Cerebrospinal Fluid (CSF)

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.005 +/- 0.002 (0.003 - 0.008) uM	Adult (>18 years old)	Not Specified	Normal	14978525	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.008 +/- 0.002 (0.006 - 0.01) uM	Adult (>18 years old)	Not Specified	Parkinson's disease	14978525	details

Associated Disorders and Diseases

Disease References

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

168600 (Parkinson's disease)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023207

KNApSAcK ID

Not Available

Chemspider ID

17216233

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12989303

PDB ID

Not Available

ChEBI ID

88955

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00000429

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Maruyama W, Akao Y, Carrillo MC, Kitani K, Youdium MB, Naoi M: Neuroprotection by propargylamines in Parkinson's disease: suppression of apoptosis and induction of prosurvival genes. Neurotoxicol Teratol. 2002 Sep-Oct;24(5):675-82. [PubMed:12200198 ]
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 ]
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 ]
Takahashi T, Maruyama W, Deng Y, Dostert P, Nakahara D, Niwa T, Ohta S, Naoi M: Cytotoxicity of endogenous isoquinolines to human dopaminergic neuroblastoma SH-SY5Y cells. J Neural Transm (Vienna). 1997;104(1):59-66. [PubMed:9085193 ]
Maruyama W, Abe T, Tohgi H, Naoi M: An endogenous MPTP-like dopaminergic neurotoxin, N-methyl(R)salsolinol, in the cerebrospinal fluid decreases with progression of Parkinson's disease. Neurosci Lett. 1999 Feb 26;262(1):13-6. [PubMed:10076861 ]

Showing metabocard for (R)-N-Methylsalsolinol (HMDB0003626)

MOL for HMDB0003626 ((R)-N-Methylsalsolinol)

3D MOL for HMDB0003626 ((R)-N-Methylsalsolinol)

3D SDF for HMDB0003626 ((R)-N-Methylsalsolinol)

3D-SDF for HMDB0003626 ((R)-N-Methylsalsolinol)

PDB for HMDB0003626 ((R)-N-Methylsalsolinol)

3D PDB for HMDB0003626 ((R)-N-Methylsalsolinol)

SMILES for HMDB0003626 ((R)-N-Methylsalsolinol)

INCHI for HMDB0003626 ((R)-N-Methylsalsolinol)

Structure for HMDB0003626 ((R)-N-Methylsalsolinol)

3D Structure for HMDB0003626 ((R)-N-Methylsalsolinol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra