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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-13 10:35:54 UTC

Update Date

2021-09-14 15:00:09 UTC

HMDB ID

HMDB0004087

Secondary Accession Numbers

HMDB04087

Metabolite Identification

Common Name

1-Benzyl-1,2,3,4-tetrahydroisoquinoline

Description

1-benzyl-1,2,3,4-tetrahydroisoquinoline (1BnTIQ) as a possible PD-eliciting neurotoxin and evaluated its characteristics relevant to Parkinson disease (PD). 1BnTIQ exist in mammals and is proposed as possible PD-eliciting neurotoxin. PD is believed to be induced by the interaction of genetic predisposition and environmental factors, and a type of neurotoxin is proposed to be one of the environmental factors. 1BnTIQ inhibits [3H] dopamine uptake in HEK293 cells which stably express dopamine transporter. 1BnTIQ also inhibits NADH-ubiquinone oxidoreductase (complex I) in the mitochondrial respiratory chain. 1BnTIQ decreases the dopamine content in the mesencephalon in both dose- and time-dependent manners and it irreversibly reduced the dopamine content. Furthermore, it causes morphological changes in tyrosine hydroxylase-positive cells in the mesencephalon and reduced the number of cells. (PMID 12440154 ).

Structure

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

HMDB0004087
     RDKit          3D
1-Benzyl-1,2,3,4-tetrahydroisoquinoline
 34 36  0  0  0  0  0  0  0  0999 V2000
   -4.7961   -0.3064   -0.1711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0309   -0.7921    0.8688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7091   -0.4062    1.0554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1444    0.4914    0.1720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7367    0.9159    0.3529 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2155   -0.0121   -0.4055 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0122   -1.3112    0.1369 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0371   -2.2684    0.0064 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4306   -1.7812    0.2447 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6034   -0.3352   -0.0325 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9048    0.1523    0.0321 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1862    1.4729   -0.2083 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1599    2.3199   -0.5170 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8503    1.8274   -0.5816 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837    0.5092   -0.3397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8819    1.0001   -0.8835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2004    0.5894   -1.0357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8310   -0.5985   -0.3304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5107   -1.4938    1.5392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1497   -0.8169    1.8887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4941    0.8028    1.4299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5842    1.9805    0.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0548   -0.0561   -1.4820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8691   -1.6995   -0.2684 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8485   -3.0853    0.7458 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9745   -2.7866   -0.9961 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7966   -1.9526    1.2784 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1245   -2.3145   -0.4384 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7312   -0.5012    0.2747 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2190    1.8498   -0.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3763    3.3522   -0.7053 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1102    2.5639   -0.8323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4066    1.7014   -1.5558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7651    0.9888   -1.8571 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  4 16  1  0
 16 17  2  0
 17  1  1  0
 15  6  1  0
 15 10  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  5 21  1  0
  5 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 16 33  1  0
 17 34  1  0
M  END


  Mrv0541 02231219522D          

 17 19  0  0  0  0            999 V2000
   15.0837  -11.7846    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7981  -12.1970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5126  -11.7846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7981  -10.5471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5126  -10.9595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0837  -10.9595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7981  -13.0219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2500  -12.2256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0837  -13.4345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2500  -10.5186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9975  -11.8017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9975  -10.9424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3693  -13.0219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0837  -14.2594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6548  -13.4345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3693  -14.6719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6548  -14.2594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2  7  1  0  0  0  0
  3  5  1  0  0  0  0
  3  8  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5 10  2  0  0  0  0
  7  9  1  0  0  0  0
  8 11  1  0  0  0  0
  9 13  2  0  0  0  0
  9 14  1  0  0  0  0
 10 12  1  0  0  0  0
 11 12  2  0  0  0  0
 13 15  1  0  0  0  0
 14 16  2  0  0  0  0
 15 17  2  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0004087

> <DATABASE_NAME>
hmdb

> <SMILES>
C(C1NCCC2=CC=CC=C12)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H17N/c1-2-6-13(7-3-1)12-16-15-9-5-4-8-14(15)10-11-17-16/h1-9,16-17H,10-12H2

> <INCHI_KEY>
YRYCIFUZSUMAAY-UHFFFAOYSA-N

> <FORMULA>
C16H17N

> <MOLECULAR_WEIGHT>
223.3129

> <EXACT_MASS>
223.136099549

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
26.19596972783652

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-benzyl-1,2,3,4-tetrahydroisoquinoline

> <ALOGPS_LOGP>
3.48

> <JCHEM_LOGP>
3.6443845443333327

> <ALOGPS_LOGS>
-4.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.53877413657242

> <JCHEM_POLAR_SURFACE_AREA>
12.03

> <JCHEM_REFRACTIVITY>
71.65340000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.52e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1BnTIQ

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0004087
     RDKit          3D
1-Benzyl-1,2,3,4-tetrahydroisoquinoline
 34 36  0  0  0  0  0  0  0  0999 V2000
   -4.7961   -0.3064   -0.1711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0309   -0.7921    0.8688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7091   -0.4062    1.0554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1444    0.4914    0.1720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7367    0.9159    0.3529 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2155   -0.0121   -0.4055 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0122   -1.3112    0.1369 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0371   -2.2684    0.0064 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4306   -1.7812    0.2447 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6034   -0.3352   -0.0325 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9048    0.1523    0.0321 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1862    1.4729   -0.2083 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1599    2.3199   -0.5170 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8503    1.8274   -0.5816 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837    0.5092   -0.3397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8819    1.0001   -0.8835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2004    0.5894   -1.0357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8310   -0.5985   -0.3304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5107   -1.4938    1.5392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1497   -0.8169    1.8887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4941    0.8028    1.4299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5842    1.9805    0.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0548   -0.0561   -1.4820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8691   -1.6995   -0.2684 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8485   -3.0853    0.7458 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9745   -2.7866   -0.9961 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7966   -1.9526    1.2784 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1245   -2.3145   -0.4384 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7312   -0.5012    0.2747 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2190    1.8498   -0.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3763    3.3522   -0.7053 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1102    2.5639   -0.8323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4066    1.7014   -1.5558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7651    0.9888   -1.8571 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  4 16  1  0
 16 17  2  0
 17  1  1  0
 15  6  1  0
 15 10  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  5 21  1  0
  5 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 16 33  1  0
 17 34  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  N   UNK     0      28.156 -21.998   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      29.490 -22.768   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      30.823 -21.998   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      29.490 -19.688   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      30.823 -20.458   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      28.156 -20.458   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      29.490 -24.308   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      32.200 -22.821   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      28.156 -25.078   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      32.200 -19.635   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      33.595 -22.030   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      33.595 -20.426   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      26.823 -24.308   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      28.156 -26.617   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      25.489 -25.078   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      26.823 -27.388   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      25.489 -26.617   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    5    8                                                  
CONECT    4    5    6                                                       
CONECT    5    3    4   10                                                  
CONECT    6    1    4                                                       
CONECT    7    2    9                                                       
CONECT    8    3   11                                                       
CONECT    9    7   13   14                                                  
CONECT   10    5   12                                                       
CONECT   11    8   12                                                       
CONECT   12   10   11                                                       
CONECT   13    9   15                                                       
CONECT   14    9   16                                                       
CONECT   15   13   17                                                       
CONECT   16   14   17                                                       
CONECT   17   15   16                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

COMPND    HMDB0004087
HETATM    1  C1  UNL     1      -4.796  -0.306  -0.171  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.031  -0.792   0.869  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.709  -0.406   1.055  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.144   0.491   0.172  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.737   0.916   0.353  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.216  -0.012  -0.406  1.00  0.00           C  
HETATM    7  N1  UNL     1       0.012  -1.311   0.137  1.00  0.00           N  
HETATM    8  C7  UNL     1       1.037  -2.268   0.006  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.431  -1.781   0.245  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.603  -0.335  -0.033  1.00  0.00           C  
HETATM   11  C10 UNL     1       3.905   0.152   0.032  1.00  0.00           C  
HETATM   12  C11 UNL     1       4.186   1.473  -0.208  1.00  0.00           C  
HETATM   13  C12 UNL     1       3.160   2.320  -0.517  1.00  0.00           C  
HETATM   14  C13 UNL     1       1.850   1.827  -0.582  1.00  0.00           C  
HETATM   15  C14 UNL     1       1.584   0.509  -0.340  1.00  0.00           C  
HETATM   16  C15 UNL     1      -2.882   1.000  -0.884  1.00  0.00           C  
HETATM   17  C16 UNL     1      -4.200   0.589  -1.036  1.00  0.00           C  
HETATM   18  H1  UNL     1      -5.831  -0.598  -0.330  1.00  0.00           H  
HETATM   19  H2  UNL     1      -4.511  -1.494   1.539  1.00  0.00           H  
HETATM   20  H3  UNL     1      -2.150  -0.817   1.889  1.00  0.00           H  
HETATM   21  H4  UNL     1      -0.494   0.803   1.430  1.00  0.00           H  
HETATM   22  H5  UNL     1      -0.584   1.981   0.105  1.00  0.00           H  
HETATM   23  H6  UNL     1      -0.055  -0.056  -1.482  1.00  0.00           H  
HETATM   24  H7  UNL     1      -0.869  -1.700  -0.268  1.00  0.00           H  
HETATM   25  H8  UNL     1       0.849  -3.085   0.746  1.00  0.00           H  
HETATM   26  H9  UNL     1       0.974  -2.787  -0.996  1.00  0.00           H  
HETATM   27  H10 UNL     1       2.797  -1.953   1.278  1.00  0.00           H  
HETATM   28  H11 UNL     1       3.125  -2.315  -0.438  1.00  0.00           H  
HETATM   29  H12 UNL     1       4.731  -0.501   0.275  1.00  0.00           H  
HETATM   30  H13 UNL     1       5.219   1.850  -0.155  1.00  0.00           H  
HETATM   31  H14 UNL     1       3.376   3.352  -0.705  1.00  0.00           H  
HETATM   32  H15 UNL     1       1.110   2.564  -0.832  1.00  0.00           H  
HETATM   33  H16 UNL     1      -2.407   1.701  -1.556  1.00  0.00           H  
HETATM   34  H17 UNL     1      -4.765   0.989  -1.857  1.00  0.00           H  
CONECT    1    2    2   17   18
CONECT    2    3   19
CONECT    3    4    4   20
CONECT    4    5   16
CONECT    5    6   21   22
CONECT    6    7   15   23
CONECT    7    8   24
CONECT    8    9   25   26
CONECT    9   10   27   28
CONECT   10   11   11   15
CONECT   11   12   29
CONECT   12   13   13   30
CONECT   13   14   31
CONECT   14   15   15   32
CONECT   16   17   17   33
CONECT   17   34
END

HMDB0004087
     RDKit          3D
1-Benzyl-1,2,3,4-tetrahydroisoquinoline
 34 36  0  0  0  0  0  0  0  0999 V2000
   -4.7961   -0.3064   -0.1711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0309   -0.7921    0.8688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7091   -0.4062    1.0554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1444    0.4914    0.1720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7367    0.9159    0.3529 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2155   -0.0121   -0.4055 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0122   -1.3112    0.1369 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0371   -2.2684    0.0064 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4306   -1.7812    0.2447 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6034   -0.3352   -0.0325 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9048    0.1523    0.0321 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1862    1.4729   -0.2083 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1599    2.3199   -0.5170 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8503    1.8274   -0.5816 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837    0.5092   -0.3397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8819    1.0001   -0.8835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2004    0.5894   -1.0357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8310   -0.5985   -0.3304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5107   -1.4938    1.5392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1497   -0.8169    1.8887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4941    0.8028    1.4299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5842    1.9805    0.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0548   -0.0561   -1.4820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8691   -1.6995   -0.2684 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8485   -3.0853    0.7458 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9745   -2.7866   -0.9961 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7966   -1.9526    1.2784 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1245   -2.3145   -0.4384 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7312   -0.5012    0.2747 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2190    1.8498   -0.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3763    3.3522   -0.7053 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1102    2.5639   -0.8323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4066    1.7014   -1.5558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7651    0.9888   -1.8571 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  4 16  1  0
 16 17  2  0
 17  1  1  0
 15  6  1  0
 15 10  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  5 21  1  0
  5 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 16 33  1  0
 17 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(R,S)-Tetrahydrobenzylisoquinoline	ChEBI
1,2,3,4-Tetrahydro-1-(phenylmethyl)isoquinoline	ChEBI
1BnTIQ	ChEBI
(RS)-1-Benzyl-1,2,3,4-tetrahydroisoquinoline	Kegg
1,2,3,4-tetrahydro-1-(Phenylmethyl)isoquinoline, (+-)-isomer	MeSH, HMDB
1,2,3,4-tetrahydro-1-(Phenylmethyl)isoquinoline, (R)-isomer	MeSH, HMDB
1,2,3,4-tetrahydro-1-(Phenylmethyl)isoquinoline, (S)-isomer	MeSH, HMDB
1,2,3,4-tetrahydro-1-(Phenylmethyl)isoquinoline hydrochloride	MeSH, HMDB
S49 Isoquinoline	MeSH, HMDB
1-Benzyl-1,2,3,4-tetrahydroisoquinoline	MeSH

Chemical Formula

C₁₆H₁₇N

Average Molecular Weight

223.3129

Monoisotopic Molecular Weight

223.136099549

IUPAC Name

1-benzyl-1,2,3,4-tetrahydroisoquinoline

Traditional Name

1BnTIQ

CAS Registry Number

19716-56-4

SMILES

C(C1NCCC2=CC=CC=C12)C1=CC=CC=C1

InChI Identifier

InChI=1S/C16H17N/c1-2-6-13(7-3-1)12-16-15-9-5-4-8-14(15)10-11-17-16/h1-9,16-17H,10-12H2

InChI Key

YRYCIFUZSUMAAY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoquinolines and derivatives

Sub Class

Benzylisoquinolines

Direct Parent

Benzylisoquinolines

Alternative Parents

Substituents

Benzylisoquinoline
Tetrahydroisoquinoline
Aralkylamine
Benzenoid
Monocyclic benzene moiety
Azacycle
Secondary amine
Secondary aliphatic amine
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

benzyltetrahydroisoquinoline (CHEBI:16804 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0004087)
Cell membrane (HMDB: HMDB0004087)

Non-excretory biofluid

Biofluid or Excreta

Cerebrospinal Fluid (CSF) (PMID: 7595560)
Cerebrospinal fluid (HMDB: HMDB0004087)

Source

Endogenous

Endogenous (HMDB: HMDB0004087)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Biomarker

Parkinson's disease (MarkerDB: MDB00000440)

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	0.0035 g/L	ALOGPS
logP	3.48	ALOGPS
logP	3.64	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Basic)	9.54	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	12.03 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	71.65 m³·mol⁻¹	ChemAxon
Polarizability	26.2 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	150.274	31661259
DarkChem	[M-H]-	151.27	31661259
DeepCCS	[M-2H]-	183.233	30932474
DeepCCS	[M+Na]+	158.547	30932474
AllCCS	[M+H]+	153.7	32859911
AllCCS	[M+H-H2O]+	149.6	32859911
AllCCS	[M+NH4]+	157.6	32859911
AllCCS	[M+Na]+	158.7	32859911
AllCCS	[M-H]-	159.5	32859911
AllCCS	[M+Na-2H]-	159.1	32859911
AllCCS	[M+HCOO]-	158.8	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.	5.95 minutes	32390414
Predicted by Siyang on May 30, 2022	12.2909 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.79 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	27.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1577.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	351.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	172.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	200.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	138.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	454.0 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	411.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	226.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1153.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	466.5 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	1191.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	293.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	318.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	312.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	238.8 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	7.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1-Benzyl-1,2,3,4-tetrahydroisoquinoline	C(C1NCCC2=CC=CC=C12)C1=CC=CC=C1	2741.7	Standard polar	33892256
1-Benzyl-1,2,3,4-tetrahydroisoquinoline	C(C1NCCC2=CC=CC=C12)C1=CC=CC=C1	1944.0	Standard non polar	33892256
1-Benzyl-1,2,3,4-tetrahydroisoquinoline	C(C1NCCC2=CC=CC=C12)C1=CC=CC=C1	1976.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1-Benzyl-1,2,3,4-tetrahydroisoquinoline,1TMS,isomer #1	C[Si](C)(C)N1CCC2=CC=CC=C2C1CC1=CC=CC=C1	2045.4	Semi standard non polar	33892256
1-Benzyl-1,2,3,4-tetrahydroisoquinoline,1TMS,isomer #1	C[Si](C)(C)N1CCC2=CC=CC=C2C1CC1=CC=CC=C1	2106.2	Standard non polar	33892256
1-Benzyl-1,2,3,4-tetrahydroisoquinoline,1TMS,isomer #1	C[Si](C)(C)N1CCC2=CC=CC=C2C1CC1=CC=CC=C1	2589.9	Standard polar	33892256
1-Benzyl-1,2,3,4-tetrahydroisoquinoline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCC2=CC=CC=C2C1CC1=CC=CC=C1	2264.9	Semi standard non polar	33892256
1-Benzyl-1,2,3,4-tetrahydroisoquinoline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCC2=CC=CC=C2C1CC1=CC=CC=C1	2359.7	Standard non polar	33892256
1-Benzyl-1,2,3,4-tetrahydroisoquinoline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCC2=CC=CC=C2C1CC1=CC=CC=C1	2743.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Benzyl-1,2,3,4-tetrahydroisoquinoline GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-2900000000-69767d6f6a91a5c24bd1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Benzyl-1,2,3,4-tetrahydroisoquinoline 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 - 1-Benzyl-1,2,3,4-tetrahydroisoquinoline 10V, Positive-QTOF	splash10-00di-0090000000-75679a6f444b9bd42db4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Benzyl-1,2,3,4-tetrahydroisoquinoline 20V, Positive-QTOF	splash10-05gl-3890000000-5df7dde54dbe0fe2b4fa	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Benzyl-1,2,3,4-tetrahydroisoquinoline 40V, Positive-QTOF	splash10-0006-9700000000-3f687e462c9cd0cc1ff2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Benzyl-1,2,3,4-tetrahydroisoquinoline 10V, Negative-QTOF	splash10-00di-0090000000-672b95459dab89c79e3c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Benzyl-1,2,3,4-tetrahydroisoquinoline 20V, Negative-QTOF	splash10-00di-0090000000-87a0dda1779b4676ba7c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Benzyl-1,2,3,4-tetrahydroisoquinoline 40V, Negative-QTOF	splash10-0059-1910000000-d2ecf13f470a7ba9cb0e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Benzyl-1,2,3,4-tetrahydroisoquinoline 10V, Negative-QTOF	splash10-00di-0090000000-279452a29859034561fa	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Benzyl-1,2,3,4-tetrahydroisoquinoline 20V, Negative-QTOF	splash10-00di-0090000000-939f38e3140d9ca30df6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Benzyl-1,2,3,4-tetrahydroisoquinoline 40V, Negative-QTOF	splash10-005c-2900000000-ed789626d72de391b664	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Benzyl-1,2,3,4-tetrahydroisoquinoline 10V, Positive-QTOF	splash10-00di-0090000000-0e93eae718d771100a69	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Benzyl-1,2,3,4-tetrahydroisoquinoline 20V, Positive-QTOF	splash10-05fr-2960000000-a0da7d0090f88d305999	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Benzyl-1,2,3,4-tetrahydroisoquinoline 40V, Positive-QTOF	splash10-0a4m-4900000000-148ae7c1169e2d0c08f0	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

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	0.0017 (0.0013 - 0.0022) uM	Adult (>18 years old)	Not Specified	Normal	7595560	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0052 (0.0036-0.0068) uM	Adult (>18 years old)	Not Specified	Parkinson's disease	7595560	details

Associated Disorders and Diseases

Disease References

Parkinson's disease
Kotake Y, Tasaki Y, Makino Y, Ohta S, Hirobe M: 1-Benzyl-1,2,3,4-tetrahydroisoquinoline as a parkinsonism-inducing agent: a novel endogenous amine in mouse brain and parkinsonian CSF. J Neurochem. 1995 Dec;65(6):2633-8. [PubMed:7595560 ]

Associated OMIM IDs

168600 (Parkinson's disease)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023308

KNApSAcK ID

Not Available

Chemspider ID

88923

KEGG Compound ID

C05201

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

98468

PDB ID

Not Available

ChEBI ID

16804

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00000440

Good Scents ID

Not Available

References

Synthesis Reference

Shinohara, Tatsumi; Takeda, Akira; Toda, Jun; Terasawa, Noriyo; Sano, Takehiro. A highly efficient synthesis of 1-methyl-, 1-benzyl-, and 1-phenyl-1,2,3,4-tetrahydroisoquinolines by a modified Pummerer reaction. Heterocycles (1997), 46 555-566.

Material Safety Data Sheet (MSDS)

Not Available

General References

Kotake Y, Tasaki Y, Makino Y, Ohta S, Hirobe M: 1-Benzyl-1,2,3,4-tetrahydroisoquinoline as a parkinsonism-inducing agent: a novel endogenous amine in mouse brain and parkinsonian CSF. J Neurochem. 1995 Dec;65(6):2633-8. [PubMed:7595560 ]
Kotake Y: [Tetrahydroisoquinoline derivatives as possible Parkinson's disease-inducing substances]. Yakugaku Zasshi. 2002 Nov;122(11):975-82. [PubMed:12440154 ]

Showing metabocard for 1-Benzyl-1,2,3,4-tetrahydroisoquinoline (HMDB0004087)

MOL for HMDB0004087 (1-Benzyl-1,2,3,4-tetrahydroisoquinoline)

3D MOL for HMDB0004087 (1-Benzyl-1,2,3,4-tetrahydroisoquinoline)

3D SDF for HMDB0004087 (1-Benzyl-1,2,3,4-tetrahydroisoquinoline)

3D-SDF for HMDB0004087 (1-Benzyl-1,2,3,4-tetrahydroisoquinoline)

PDB for HMDB0004087 (1-Benzyl-1,2,3,4-tetrahydroisoquinoline)

3D PDB for HMDB0004087 (1-Benzyl-1,2,3,4-tetrahydroisoquinoline)

SMILES for HMDB0004087 (1-Benzyl-1,2,3,4-tetrahydroisoquinoline)

INCHI for HMDB0004087 (1-Benzyl-1,2,3,4-tetrahydroisoquinoline)

Structure for HMDB0004087 (1-Benzyl-1,2,3,4-tetrahydroisoquinoline)

3D Structure for HMDB0004087 (1-Benzyl-1,2,3,4-tetrahydroisoquinoline)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra