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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:04 UTC

HMDB ID

HMDB0015689

Secondary Accession Numbers

HMDB15689

Metabolite Identification

Common Name

Antazoline

Description

Antazoline is only found in individuals that have used or taken this drug. It is a 1st generation antihistamine that also anticholinergic properties used to relieve nasal congestion and in eye drops, usually in combination with naphazoline, to relieve the symptoms of allergic conjunctivitis.Antazoline binds to the histamine H1 receptor. This blocks the action of endogenous histamine, which subsequently leads to temporary relief of the negative symptoms brought on by histamine.

Structure

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

HMDB0015689
     RDKit          3D
Antazoline
 39 41  0  0  0  0  0  0  0  0999 V2000
    4.4380   -1.9412   -0.8888 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3372   -1.4099    0.3869 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1102   -1.0626    0.8867 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9051   -1.2141    0.1667 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6183   -0.8170    0.7787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1475    0.1386    0.0568 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1709   -0.1561   -0.9088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4482   -0.6426   -0.3556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5234    0.1086   -0.4842 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6442   -0.5271    0.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2330   -1.9769    0.1880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7760   -1.8245    0.3419 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0874    1.5368    0.3251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6724    2.5059   -0.2905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4533    3.8684   -0.0445 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5413    4.2185    0.8315 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3112    3.2703    1.4588 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0711    1.9273    1.1937 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0569   -1.7433   -1.0877 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2912   -2.1101   -1.6338 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3705   -2.2342   -1.3414 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2536   -1.2903    0.9404 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0811   -0.6565    1.8965 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0674   -1.8074    0.8743 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8349   -0.4301    1.7969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7804   -1.0349   -1.5228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3354    0.6401   -1.6262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5942   -0.3682   -0.4299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8477   -0.1816    1.1545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4563   -2.4327   -0.8108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6753   -2.5264    1.0303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1443   -2.4570    0.8543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4818    2.3208   -0.9817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0565    4.6133   -0.5370 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6776    5.2949    0.9964 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0836    3.5906    2.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7286    1.2529    1.7406 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2218   -1.9201   -1.7333 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3539   -2.5220   -2.6308 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  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  6 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
  4 19  1  0
 19 20  2  0
 20  1  1  0
 12  8  1  0
 18 13  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  5 24  1  0
  5 25  1  0
  7 26  1  0
  7 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
M  END

2200
  Mrv0541 02241214202D          

 20 22  0  0  1  0            999 V2000
    4.5080   -0.0160    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5550    1.7065    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8899    1.7065    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.3965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.2215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.3965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099    2.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.8410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6350    2.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.0160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.2535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.2535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.8410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.3965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -2.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.2535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.0160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -2.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.8410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  1  6  1  0  0  0  0
  1  8  1  0  0  0  0
  2  5  1  0  0  0  0
  2  7  1  0  0  0  0
  3  5  2  0  0  0  0
  3  9  1  0  0  0  0
  4  5  1  0  0  0  0
  6 10  1  0  0  0  0
  7  9  1  0  0  0  0
  8 11  2  0  0  0  0
  8 12  1  0  0  0  0
 10 13  2  0  0  0  0
 10 14  1  0  0  0  0
 11 15  1  0  0  0  0
 12 16  2  0  0  0  0
 13 17  1  0  0  0  0
 14 18  2  0  0  0  0
 15 19  2  0  0  0  0
 16 19  1  0  0  0  0
 17 20  2  0  0  0  0
 18 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015689

> <DATABASE_NAME>
hmdb

> <SMILES>
C(N(CC1=CC=CC=C1)C1=CC=CC=C1)C1=NCCN1

> <INCHI_IDENTIFIER>
InChI=1S/C17H19N3/c1-3-7-15(8-4-1)13-20(14-17-18-11-12-19-17)16-9-5-2-6-10-16/h1-10H,11-14H2,(H,18,19)

> <INCHI_KEY>
REYFJDPCWQRWAA-UHFFFAOYSA-N

> <FORMULA>
C17H19N3

> <MOLECULAR_WEIGHT>
265.3529

> <EXACT_MASS>
265.157897623

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
30.112006797685712

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-benzyl-N-(4,5-dihydro-1H-imidazol-2-ylmethyl)aniline

> <ALOGPS_LOGP>
3.22

> <JCHEM_LOGP>
2.8763921879999996

> <ALOGPS_LOGS>
-3.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.24373819787142

> <JCHEM_POLAR_SURFACE_AREA>
27.63

> <JCHEM_REFRACTIVITY>
82.88750000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.14e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
antazoline

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0015689
     RDKit          3D
Antazoline
 39 41  0  0  0  0  0  0  0  0999 V2000
    4.4380   -1.9412   -0.8888 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3372   -1.4099    0.3869 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1102   -1.0626    0.8867 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9051   -1.2141    0.1667 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6183   -0.8170    0.7787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1475    0.1386    0.0568 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1709   -0.1561   -0.9088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4482   -0.6426   -0.3556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5234    0.1086   -0.4842 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6442   -0.5271    0.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2330   -1.9769    0.1880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7760   -1.8245    0.3419 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0874    1.5368    0.3251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6724    2.5059   -0.2905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4533    3.8684   -0.0445 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5413    4.2185    0.8315 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3112    3.2703    1.4588 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0711    1.9273    1.1937 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0569   -1.7433   -1.0877 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2912   -2.1101   -1.6338 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3705   -2.2342   -1.3414 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2536   -1.2903    0.9404 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0811   -0.6565    1.8965 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0674   -1.8074    0.8743 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8349   -0.4301    1.7969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7804   -1.0349   -1.5228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3354    0.6401   -1.6262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5942   -0.3682   -0.4299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8477   -0.1816    1.1545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4563   -2.4327   -0.8108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6753   -2.5264    1.0303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1443   -2.4570    0.8543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4818    2.3208   -0.9817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0565    4.6133   -0.5370 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6776    5.2949    0.9964 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0836    3.5906    2.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7286    1.2529    1.7406 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2218   -1.9201   -1.7333 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3539   -2.5220   -2.6308 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  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  6 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
  4 19  1  0
 19 20  2  0
 20  1  1  0
 12  8  1  0
 18 13  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  5 24  1  0
  5 25  1  0
  7 26  1  0
  7 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 2200                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  N   UNK     0       8.415  -0.030   0.000  0.00  0.00           N+0
HETATM    2  N   UNK     0       8.503   3.185   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0      10.994   3.185   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       9.748   0.740   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.748   2.280   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.081   0.740   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.978   4.650   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.415  -1.570   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.519   4.650   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.747  -0.030   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.748  -2.340   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.081  -2.340   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.747  -1.570   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.414   0.740   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.748  -3.880   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.081  -3.880   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.414  -2.340   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.080  -0.030   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.415  -4.650   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.080  -1.570   0.000  0.00  0.00           C+0
CONECT    1    4    6    8                                                  
CONECT    2    5    7                                                       
CONECT    3    5    9                                                       
CONECT    4    1    5                                                       
CONECT    5    2    3    4                                                  
CONECT    6    1   10                                                       
CONECT    7    2    9                                                       
CONECT    8    1   11   12                                                  
CONECT    9    3    7                                                       
CONECT   10    6   13   14                                                  
CONECT   11    8   15                                                       
CONECT   12    8   16                                                       
CONECT   13   10   17                                                       
CONECT   14   10   18                                                       
CONECT   15   11   19                                                       
CONECT   16   12   19                                                       
CONECT   17   13   20                                                       
CONECT   18   14   20                                                       
CONECT   19   15   16                                                       
CONECT   20   17   18                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0015689
HETATM    1  C1  UNL     1       4.438  -1.941  -0.889  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.337  -1.410   0.387  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.110  -1.063   0.887  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.905  -1.214   0.167  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.618  -0.817   0.779  1.00  0.00           C  
HETATM    6  N1  UNL     1      -0.148   0.139   0.057  1.00  0.00           N  
HETATM    7  C6  UNL     1      -1.171  -0.156  -0.909  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.448  -0.643  -0.356  1.00  0.00           C  
HETATM    9  N2  UNL     1      -3.523   0.109  -0.484  1.00  0.00           N  
HETATM   10  C8  UNL     1      -4.644  -0.527   0.110  1.00  0.00           C  
HETATM   11  C9  UNL     1      -4.233  -1.977   0.188  1.00  0.00           C  
HETATM   12  N3  UNL     1      -2.776  -1.825   0.342  1.00  0.00           N  
HETATM   13  C10 UNL     1       0.087   1.537   0.325  1.00  0.00           C  
HETATM   14  C11 UNL     1      -0.672   2.506  -0.291  1.00  0.00           C  
HETATM   15  C12 UNL     1      -0.453   3.868  -0.045  1.00  0.00           C  
HETATM   16  C13 UNL     1       0.541   4.219   0.832  1.00  0.00           C  
HETATM   17  C14 UNL     1       1.311   3.270   1.459  1.00  0.00           C  
HETATM   18  C15 UNL     1       1.071   1.927   1.194  1.00  0.00           C  
HETATM   19  C16 UNL     1       2.057  -1.743  -1.088  1.00  0.00           C  
HETATM   20  C17 UNL     1       3.291  -2.110  -1.634  1.00  0.00           C  
HETATM   21  H1  UNL     1       5.370  -2.234  -1.341  1.00  0.00           H  
HETATM   22  H2  UNL     1       5.254  -1.290   0.940  1.00  0.00           H  
HETATM   23  H3  UNL     1       3.081  -0.656   1.896  1.00  0.00           H  
HETATM   24  H4  UNL     1       0.067  -1.807   0.874  1.00  0.00           H  
HETATM   25  H5  UNL     1       0.835  -0.430   1.797  1.00  0.00           H  
HETATM   26  H6  UNL     1      -0.780  -1.035  -1.523  1.00  0.00           H  
HETATM   27  H7  UNL     1      -1.335   0.640  -1.626  1.00  0.00           H  
HETATM   28  H8  UNL     1      -5.594  -0.368  -0.430  1.00  0.00           H  
HETATM   29  H9  UNL     1      -4.848  -0.182   1.155  1.00  0.00           H  
HETATM   30  H10 UNL     1      -4.456  -2.433  -0.811  1.00  0.00           H  
HETATM   31  H11 UNL     1      -4.675  -2.526   1.030  1.00  0.00           H  
HETATM   32  H12 UNL     1      -2.144  -2.457   0.854  1.00  0.00           H  
HETATM   33  H13 UNL     1      -1.482   2.321  -0.982  1.00  0.00           H  
HETATM   34  H14 UNL     1      -1.056   4.613  -0.537  1.00  0.00           H  
HETATM   35  H15 UNL     1       0.678   5.295   0.996  1.00  0.00           H  
HETATM   36  H16 UNL     1       2.084   3.591   2.141  1.00  0.00           H  
HETATM   37  H17 UNL     1       1.729   1.253   1.741  1.00  0.00           H  
HETATM   38  H18 UNL     1       1.222  -1.920  -1.733  1.00  0.00           H  
HETATM   39  H19 UNL     1       3.354  -2.522  -2.631  1.00  0.00           H  
CONECT    1    2    2   20   21
CONECT    2    3   22
CONECT    3    4    4   23
CONECT    4    5   19
CONECT    5    6   24   25
CONECT    6    7   13
CONECT    7    8   26   27
CONECT    8    9    9   12
CONECT    9   10
CONECT   10   11   28   29
CONECT   11   12   30   31
CONECT   12   32
CONECT   13   14   14   18
CONECT   14   15   33
CONECT   15   16   16   34
CONECT   16   17   35
CONECT   17   18   18   36
CONECT   18   37
CONECT   19   20   20   38
CONECT   20   39
END

HMDB0015689
     RDKit          3D
Antazoline
 39 41  0  0  0  0  0  0  0  0999 V2000
    4.4380   -1.9412   -0.8888 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3372   -1.4099    0.3869 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1102   -1.0626    0.8867 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9051   -1.2141    0.1667 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6183   -0.8170    0.7787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1475    0.1386    0.0568 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1709   -0.1561   -0.9088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4482   -0.6426   -0.3556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5234    0.1086   -0.4842 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6442   -0.5271    0.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2330   -1.9769    0.1880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7760   -1.8245    0.3419 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0874    1.5368    0.3251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6724    2.5059   -0.2905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4533    3.8684   -0.0445 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5413    4.2185    0.8315 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3112    3.2703    1.4588 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0711    1.9273    1.1937 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0569   -1.7433   -1.0877 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2912   -2.1101   -1.6338 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3705   -2.2342   -1.3414 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2536   -1.2903    0.9404 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0811   -0.6565    1.8965 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0674   -1.8074    0.8743 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8349   -0.4301    1.7969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7804   -1.0349   -1.5228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3354    0.6401   -1.6262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5942   -0.3682   -0.4299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8477   -0.1816    1.1545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4563   -2.4327   -0.8108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6753   -2.5264    1.0303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1443   -2.4570    0.8543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4818    2.3208   -0.9817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0565    4.6133   -0.5370 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6776    5.2949    0.9964 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0836    3.5906    2.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7286    1.2529    1.7406 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2218   -1.9201   -1.7333 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3539   -2.5220   -2.6308 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  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  6 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
  4 19  1  0
 19 20  2  0
 20  1  1  0
 12  8  1  0
 18 13  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  5 24  1  0
  5 25  1  0
  7 26  1  0
  7 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(N-Benzylanilinomethyl)-2-imidazoline	ChEBI
2-(N-Phenyl-N-benzylaminomethyl)imidazoline	ChEBI
4,5-Dihydro-N-phenyl-N-phenylmethyl-1H-imidazole-2-methanamine	ChEBI
Antazolina	ChEBI
Antazolinum	ChEBI
Phenazolin	HMDB
Phenazoline	HMDB
Antistine	HMDB
Arithmin	HMDB
Lannett brand OF antazoline phosphate	HMDB
Imidamine	HMDB
Antasten	HMDB
Antazoline hydrochloride	HMDB
Antazoline phosphate	HMDB
Analergine	HMDB
Antazoline phosphate (1:1)	HMDB
Hydrochloride, antazoline	HMDB
Phosphate, antazoline	HMDB

Chemical Formula

C₁₇H₁₉N₃

Average Molecular Weight

265.3529

Monoisotopic Molecular Weight

265.157897623

IUPAC Name

N-benzyl-N-(4,5-dihydro-1H-imidazol-2-ylmethyl)aniline

Traditional Name

antazoline

CAS Registry Number

91-75-8

SMILES

C(N(CC1=CC=CC=C1)C1=CC=CC=C1)C1=NCCN1

InChI Identifier

InChI=1S/C17H19N3/c1-3-7-15(8-4-1)13-20(14-17-18-11-12-19-17)16-9-5-2-6-10-16/h1-10H,11-14H2,(H,18,19)

InChI Key

REYFJDPCWQRWAA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylbenzamines. These are aromatic compounds consisting of a benzyl group that is N-linked to a benzamine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylmethylamines

Direct Parent

Phenylbenzamines

Alternative Parents

Substituents

Phenylbenzamine
Benzylamine
Tertiary aliphatic/aromatic amine
Aniline or substituted anilines
Dialkylarylamine
Aralkylamine
Imidolactam
2-imidazoline
Tertiary amine
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidamide
Amidine
Carboxylic acid amidine
Azacycle
Hydrocarbon derivative
Organopnictogen compound
Organonitrogen compound
Organic nitrogen compound
Amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

tertiary amino compound (CHEBI:84115 )
aromatic amine (CHEBI:84115 )
imidazolines (CHEBI:84115 )

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

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	162.225	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000746

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.11 g/L	ALOGPS
logP	3.22	ALOGPS
logP	2.88	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Basic)	9.24	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	27.63 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	82.89 m³·mol⁻¹	ChemAxon
Polarizability	30.11 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]+	160.398	31661259
DarkChem	[M-H]-	161.448	31661259
DeepCCS	[M+H]+	159.728	30932474
DeepCCS	[M-H]-	157.332	30932474
DeepCCS	[M-2H]-	190.216	30932474
DeepCCS	[M+Na]+	165.774	30932474
AllCCS	[M+H]+	163.2	32859911
AllCCS	[M+H-H2O]+	159.5	32859911
AllCCS	[M+NH4]+	166.6	32859911
AllCCS	[M+Na]+	167.6	32859911
AllCCS	[M-H]-	167.7	32859911
AllCCS	[M+Na-2H]-	167.2	32859911
AllCCS	[M+HCOO]-	166.9	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.	3.28 minutes	32390414
Predicted by Siyang on May 30, 2022	12.3102 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.59 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	29.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1518.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	304.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	167.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	184.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	97.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	464.8 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	387.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	76.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1036.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	417.2 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	1310.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	316.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	314.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	297.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	136.8 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
Antazoline	C(N(CC1=CC=CC=C1)C1=CC=CC=C1)C1=NCCN1	3155.6	Standard polar	33892256
Antazoline	C(N(CC1=CC=CC=C1)C1=CC=CC=C1)C1=NCCN1	2213.9	Standard non polar	33892256
Antazoline	C(N(CC1=CC=CC=C1)C1=CC=CC=C1)C1=NCCN1	2414.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Antazoline,1TMS,isomer #1	C[Si](C)(C)N1CCN=C1CN(CC1=CC=CC=C1)C1=CC=CC=C1	2573.0	Semi standard non polar	33892256
Antazoline,1TMS,isomer #1	C[Si](C)(C)N1CCN=C1CN(CC1=CC=CC=C1)C1=CC=CC=C1	2449.3	Standard non polar	33892256
Antazoline,1TMS,isomer #1	C[Si](C)(C)N1CCN=C1CN(CC1=CC=CC=C1)C1=CC=CC=C1	3445.5	Standard polar	33892256
Antazoline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCN=C1CN(CC1=CC=CC=C1)C1=CC=CC=C1	2783.8	Semi standard non polar	33892256
Antazoline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCN=C1CN(CC1=CC=CC=C1)C1=CC=CC=C1	2658.3	Standard non polar	33892256
Antazoline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCN=C1CN(CC1=CC=CC=C1)C1=CC=CC=C1	3529.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Antazoline EI-B (Non-derivatized)	splash10-001i-9000000000-1eb3fa441bd25a0e41a3	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Antazoline EI-B (Non-derivatized)	splash10-001i-9000000000-1eb3fa441bd25a0e41a3	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Antazoline GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9520000000-acee1c2b85e17e49b750	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Antazoline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Antazoline 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 - Antazoline 10V, Positive-QTOF	splash10-014i-4290000000-4ac08a84ab740fb2f33e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Antazoline 20V, Positive-QTOF	splash10-0006-9310000000-cdc9ceb7906b163a7989	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Antazoline 40V, Positive-QTOF	splash10-0006-9000000000-aeb9552d124a58684bc2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Antazoline 10V, Negative-QTOF	splash10-03di-0190000000-2a0590deb8d02d0510f6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Antazoline 20V, Negative-QTOF	splash10-03k9-2590000000-294ec8879dd0fa5e4b8f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Antazoline 40V, Negative-QTOF	splash10-0kcu-7900000000-a5218dce1e2e912dd19e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Antazoline 10V, Positive-QTOF	splash10-014i-0090000000-7e22bb674a6dd638c95f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Antazoline 20V, Positive-QTOF	splash10-014i-5190000000-02163279b08dfe80ac6e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Antazoline 40V, Positive-QTOF	splash10-0006-9000000000-5c02019daf74a4f6ece3	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Antazoline 10V, Negative-QTOF	splash10-03di-0090000000-eb9a3591bd2583334616	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Antazoline 20V, Negative-QTOF	splash10-001i-3930000000-07adc0d6c79a6a789cfa	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Antazoline 40V, Negative-QTOF	splash10-0059-8900000000-554f4ffa39078b568dc0	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Antazoline H1-Antihistamine Action		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB08799	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB08799	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB08799

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2115

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Antazoline

METLIN ID

Not Available

PubChem Compound

2200

PDB ID

Not Available

ChEBI ID

84115

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Figus M, Fogagnolo P, Lazzeri S, Capizzi F, Romagnoli M, Canovetti A, Iester M, Ferreras A, Rossetti L, Nardi M: Treatment of allergic conjunctivitis: results of a 1-month, single-masked randomized study. Eur J Ophthalmol. 2010 Sep-Oct;20(5):811-8. [PubMed:20383847 ]

Enzymes

Enzyme Details

1. Histamine H1 receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system
Gene Name:: HRH1
Uniprot ID:: P35367
Molecular weight:: 55783.6

References

Swiader MJ, Luszczki JJ, Wielosz M, Czuczwar SJ: Effect of histamine receptor antagonists on aminophylline-induced seizures and lethality in mice. Pharmacol Rep. 2005 Jul-Aug;57(4):531-5. [PubMed:16129921 ]

Showing metabocard for Antazoline (HMDB0015689)

MOL for HMDB0015689 (Antazoline)

3D MOL for HMDB0015689 (Antazoline)

3D SDF for HMDB0015689 (Antazoline)

3D-SDF for HMDB0015689 (Antazoline)

PDB for HMDB0015689 (Antazoline)

3D PDB for HMDB0015689 (Antazoline)

SMILES for HMDB0015689 (Antazoline)

INCHI for HMDB0015689 (Antazoline)

Structure for HMDB0015689 (Antazoline)

3D Structure for HMDB0015689 (Antazoline)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References