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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-05-18 09:20:41 UTC

Update Date

2022-03-07 02:49:11 UTC

HMDB ID

HMDB0001944

Secondary Accession Numbers

HMDB0004994
HMDB01944
HMDB04994

Metabolite Identification

Common Name

Chlorpheniramine

Description

Chlorpheniramine is a histamine H1 antagonist used in allergic reactions, hay fever, rhinitis, urticaria, and asthma. It has also been used in veterinary applications. One of the most widely used of the classical antihistaminics, it generally causes less drowsiness and sedation than Promethazine. -- Pubchem; Chlorphenamine or chlorpheniramine, commonly marketed as its salt chlorphenamine maleate (Chlor- Trimeton, Piriton, Chlor- Tripolon), is a first generation antihistamine used in the prevention of the symptoms of allergic conditions such as rhinitis and urticaria.- wikipedia.

Structure

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

HMDB0001944
     RDKit          3D
Chlorpheniramine
 38 39  0  0  0  0  0  0  0  0999 V2000
   -2.0853    1.9354    0.5997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5653    0.8799   -0.1726 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4669    1.2358   -1.2371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4391   -0.4418    0.1402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1362   -1.1111   -0.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0716   -0.6680    0.6755 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6501    0.6297    0.3943 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7858    1.0940   -0.9236 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3518    2.2990   -1.2236 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8179    3.1157   -0.2278 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5337    4.6446   -0.6439 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.7034    2.6955    1.0841 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1343    1.4859    1.3735 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0982   -1.7757    0.6088 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3558   -2.3673   -0.5972 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3112   -3.3887   -0.6230 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9470   -3.7574    0.5385 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6610   -3.1374    1.7371 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7416   -2.1659    1.7202 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7221    1.6139    1.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9979    2.6138    0.8010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3702    2.6167    0.1388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5044    0.9236   -0.9903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1343    0.7416   -2.1663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4607    2.3367   -1.3179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8497   -0.6366    1.2119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2537   -1.0144   -0.4517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8777   -1.2130   -1.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3359   -2.2288    0.2237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2269   -0.6294    1.8007 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4329    0.4813   -1.7232 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4264    2.5989   -2.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0832    3.3722    1.8520 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0591    1.1870    2.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8722   -2.0982   -1.5399 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5133   -3.8542   -1.5900 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6857   -4.5540    0.5031 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1899   -3.4594    2.6286 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
  6 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 13  7  1  0
 19 14  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  8 31  1  0
  9 32  1  0
 12 33  1  0
 13 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
M  END

1114
  Mrv1652305271900052D          

 19 20  0  0  1  0            999 V2000
    3.7935   -2.8876    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    2.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 17  1  0  0  0  0
  2  6  1  0  0  0  0
  2 12  1  0  0  0  0
  2 13  1  0  0  0  0
  3  8  1  0  0  0  0
  3 18  2  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5  6  1  0  0  0  0
  7  9  2  0  0  0  0
  7 10  1  0  0  0  0
  8 11  2  0  0  0  0
  9 14  1  0  0  0  0
 10 15  2  0  0  0  0
 11 16  1  0  0  0  0
 14 17  2  0  0  0  0
 15 17  1  0  0  0  0
 16 19  2  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001944

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)CCC(C1=CC=C(Cl)C=C1)C1=CC=CC=N1

> <INCHI_IDENTIFIER>
InChI=1S/C16H19ClN2/c1-19(2)12-10-15(16-5-3-4-11-18-16)13-6-8-14(17)9-7-13/h3-9,11,15H,10,12H2,1-2H3

> <INCHI_KEY>
SOYKEARSMXGVTM-UHFFFAOYSA-N

> <FORMULA>
C16H19ClN2

> <MOLECULAR_WEIGHT>
274.788

> <EXACT_MASS>
274.123676325

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
30.821200958347674

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[3-(4-chlorophenyl)-3-(pyridin-2-yl)propyl]dimethylamine

> <ALOGPS_LOGP>
3.74

> <JCHEM_LOGP>
3.5849509150000003

> <ALOGPS_LOGS>
-3.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.474711663883962

> <JCHEM_POLAR_SURFACE_AREA>
16.130000000000003

> <JCHEM_REFRACTIVITY>
80.8503

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.19e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
chlorpheniramine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0001944
     RDKit          3D
Chlorpheniramine
 38 39  0  0  0  0  0  0  0  0999 V2000
   -2.0853    1.9354    0.5997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5653    0.8799   -0.1726 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4669    1.2358   -1.2371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4391   -0.4418    0.1402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1362   -1.1111   -0.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0716   -0.6680    0.6755 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6501    0.6297    0.3943 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7858    1.0940   -0.9236 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3518    2.2990   -1.2236 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8179    3.1157   -0.2278 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5337    4.6446   -0.6439 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.7034    2.6955    1.0841 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1343    1.4859    1.3735 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0982   -1.7757    0.6088 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3558   -2.3673   -0.5972 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3112   -3.3887   -0.6230 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9470   -3.7574    0.5385 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6610   -3.1374    1.7371 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7416   -2.1659    1.7202 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7221    1.6139    1.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9979    2.6138    0.8010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3702    2.6167    0.1388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5044    0.9236   -0.9903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1343    0.7416   -2.1663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4607    2.3367   -1.3179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8497   -0.6366    1.2119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2537   -1.0144   -0.4517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8777   -1.2130   -1.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3359   -2.2288    0.2237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2269   -0.6294    1.8007 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4329    0.4813   -1.7232 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4264    2.5989   -2.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0832    3.3722    1.8520 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0591    1.1870    2.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8722   -2.0982   -1.5399 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5133   -3.8542   -1.5900 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6857   -4.5540    0.5031 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1899   -3.4594    2.6286 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
  6 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 13  7  1  0
 19 14  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  8 31  1  0
  9 32  1  0
 12 33  1  0
 13 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1114                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1 Cl   UNK     0       7.081  -5.390   0.000  0.00  0.00          Cl+0
HETATM    2  N   UNK     0       4.414   3.850   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       8.415   3.080   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       7.081   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.748   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.748   3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.081  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.415   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.415  -1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.748  -1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.748   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.080   3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.414   5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.415  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.748  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.082   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.081  -3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.748   3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.082   3.080   0.000  0.00  0.00           C+0
CONECT    1   17                                                            
CONECT    2    6   12   13                                                  
CONECT    3    8   18                                                       
CONECT    4    5    7    8                                                  
CONECT    5    4    6                                                       
CONECT    6    2    5                                                       
CONECT    7    4    9   10                                                  
CONECT    8    3    4   11                                                  
CONECT    9    7   14                                                       
CONECT   10    7   15                                                       
CONECT   11    8   16                                                       
CONECT   12    2                                                            
CONECT   13    2                                                            
CONECT   14    9   17                                                       
CONECT   15   10   17                                                       
CONECT   16   11   19                                                       
CONECT   17    1   14   15                                                  
CONECT   18    3   19                                                       
CONECT   19   16   18                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0242205
HETATM    1  C1  UNL     1       4.025  -0.532  -0.597  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.050  -1.211   0.195  1.00  0.00           N  
HETATM    3  C2  UNL     1       3.142  -1.076   1.596  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.718  -1.153  -0.281  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.111   0.237  -0.215  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.297   0.139  -0.760  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.039   1.401  -0.768  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.991   2.325   0.260  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.707   3.496   0.210  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.510   3.812  -0.870  1.00  0.00           C  
HETATM   11 CL1  UNL     1      -3.413   5.326  -0.900  1.00  0.00          CL  
HETATM   12  C10 UNL     1      -2.578   2.912  -1.909  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.860   1.741  -1.853  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.070  -0.934  -0.085  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.024  -1.122   1.285  1.00  0.00           C  
HETATM   16  C14 UNL     1      -1.750  -2.130   1.860  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.538  -2.977   1.112  1.00  0.00           C  
HETATM   18  C16 UNL     1      -2.569  -2.770  -0.252  1.00  0.00           C  
HETATM   19  N2  UNL     1      -1.848  -1.775  -0.796  1.00  0.00           N  
HETATM   20  H1  UNL     1       3.937  -0.764  -1.683  1.00  0.00           H  
HETATM   21  H2  UNL     1       3.828   0.566  -0.520  1.00  0.00           H  
HETATM   22  H3  UNL     1       5.058  -0.704  -0.277  1.00  0.00           H  
HETATM   23  H4  UNL     1       2.241  -0.578   2.007  1.00  0.00           H  
HETATM   24  H5  UNL     1       3.134  -2.116   2.044  1.00  0.00           H  
HETATM   25  H6  UNL     1       4.058  -0.537   1.936  1.00  0.00           H  
HETATM   26  H7  UNL     1       1.752  -1.498  -1.360  1.00  0.00           H  
HETATM   27  H8  UNL     1       1.058  -1.906   0.206  1.00  0.00           H  
HETATM   28  H9  UNL     1       1.076   0.560   0.841  1.00  0.00           H  
HETATM   29  H10 UNL     1       1.725   0.959  -0.754  1.00  0.00           H  
HETATM   30  H11 UNL     1      -0.177  -0.186  -1.833  1.00  0.00           H  
HETATM   31  H12 UNL     1      -0.363   2.082   1.110  1.00  0.00           H  
HETATM   32  H13 UNL     1      -1.665   4.215   1.018  1.00  0.00           H  
HETATM   33  H14 UNL     1      -3.195   3.121  -2.774  1.00  0.00           H  
HETATM   34  H15 UNL     1      -1.900   1.007  -2.676  1.00  0.00           H  
HETATM   35  H16 UNL     1      -0.406  -0.458   1.876  1.00  0.00           H  
HETATM   36  H17 UNL     1      -1.735  -2.303   2.931  1.00  0.00           H  
HETATM   37  H18 UNL     1      -3.120  -3.782   1.572  1.00  0.00           H  
HETATM   38  H19 UNL     1      -3.157  -3.385  -0.900  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    4
CONECT    3   23   24   25
CONECT    4    5   26   27
CONECT    5    6   28   29
CONECT    6    7   14   30
CONECT    7    8    8   13
CONECT    8    9   31
CONECT    9   10   10   32
CONECT   10   11   12
CONECT   12   13   13   33
CONECT   13   34
CONECT   14   15   15   19
CONECT   15   16   35
CONECT   16   17   17   36
CONECT   17   18   37
CONECT   18   19   19   38
END

HMDB0001944
     RDKit          3D
Chlorpheniramine
 38 39  0  0  0  0  0  0  0  0999 V2000
   -2.0853    1.9354    0.5997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5653    0.8799   -0.1726 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4669    1.2358   -1.2371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4391   -0.4418    0.1402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1362   -1.1111   -0.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0716   -0.6680    0.6755 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6501    0.6297    0.3943 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7858    1.0940   -0.9236 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3518    2.2990   -1.2236 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8179    3.1157   -0.2278 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5337    4.6446   -0.6439 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.7034    2.6955    1.0841 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1343    1.4859    1.3735 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0982   -1.7757    0.6088 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3558   -2.3673   -0.5972 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3112   -3.3887   -0.6230 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9470   -3.7574    0.5385 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6610   -3.1374    1.7371 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7416   -2.1659    1.7202 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7221    1.6139    1.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9979    2.6138    0.8010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3702    2.6167    0.1388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5044    0.9236   -0.9903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1343    0.7416   -2.1663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4607    2.3367   -1.3179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8497   -0.6366    1.2119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2537   -1.0144   -0.4517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8777   -1.2130   -1.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3359   -2.2288    0.2237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2269   -0.6294    1.8007 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4329    0.4813   -1.7232 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4264    2.5989   -2.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0832    3.3722    1.8520 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0591    1.1870    2.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8722   -2.0982   -1.5399 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5133   -3.8542   -1.5900 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6857   -4.5540    0.5031 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1899   -3.4594    2.6286 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
  6 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 13  7  1  0
 19 14  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  8 31  1  0
  9 32  1  0
 12 33  1  0
 13 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-(p-Chlorophenyl)-1-(2-pyridyl)-3-dimethylaminopropane	ChEBI
1-(p-Chlorophenyl)-1-(2-pyridyl)-3-N,N-dimethylpropylamine	ChEBI
2-[p-Chloro-alpha-[2-(dimethylamino)ethyl]benzyl]pyridine	ChEBI
3-(p-Chlorophenyl)-3-(2-pyridyl)-N,N-dimethylpropylamine	ChEBI
Chlorophenylpyridamine	ChEBI
Chlorphenamin	ChEBI
Chlorphenaminum	ChEBI
Chlorpheniraminum	ChEBI
Clofeniramina	ChEBI
Clorfenamina	ChEBI
Clorfeniramina	ChEBI
gamma-(4-Chlorophenyl)-gamma-(2-pyridyl)propyldimethylamine	ChEBI
gamma-(4-Chlorophenyl)-N,N-dimethyl-2-pyridinepropanamine	ChEBI
Haynon	ChEBI
Chlorphenamine	Kegg
2-[p-Chloro-a-[2-(dimethylamino)ethyl]benzyl]pyridine	Generator
2-[p-Chloro-α-[2-(dimethylamino)ethyl]benzyl]pyridine	Generator
g-(4-Chlorophenyl)-g-(2-pyridyl)propyldimethylamine	Generator
Γ-(4-chlorophenyl)-γ-(2-pyridyl)propyldimethylamine	Generator
g-(4-Chlorophenyl)-N,N-dimethyl-2-pyridinepropanamine	Generator
Γ-(4-chlorophenyl)-N,N-dimethyl-2-pyridinepropanamine	Generator
Chlor-trimeton	HMDB
Chloropheniramine maleate	HMDB
Chlorphenamine hydrogen maleate	HMDB
Chlorphenamine maleate	HMDB
Chlorpheniaramine maleate	HMDB
Chlorpheniramine maleate	HMDB
Teldrin	HMDB
Aller-chlor	HMDB
Chlor-tripolon	HMDB
Chlorpro	HMDB
Cloro-trimeton	HMDB
Kloromin	HMDB
Maleate, chlorpheniramine	HMDB
Piriton	HMDB
Rugby brand OF chlorpheniramine maleate	HMDB
Schering-plough brand OF chlorpheniramine maleate	HMDB
Tannate, chlorpheniramine	HMDB
Bayer brand OF chlorpheniramine maleate	HMDB
Chlo-amine	HMDB
Hogil brand 1 OF chlorpheniramine maleate	HMDB
Llorens brand OF chlorpheniramine maleate	HMDB
Schering brand OF chlorpheniramine maleate	HMDB
Vortech brand 1 OF chlorpheniramine maleate	HMDB
Antihistaminico llorens	HMDB
Chlorprophenpyridamine	HMDB
Chlorspan 12	HMDB
Chlortab-4	HMDB
Halsey drug brand OF chlorpheniramine maleate	HMDB
Stafford-miller brand OF chlorpheniramine maleate	HMDB
Vortech brand 3 OF chlorpheniramine maleate	HMDB
Chlor-100	HMDB
Chlorpheniramine tannate	HMDB
Efidac 24	HMDB
Hogil brand 2 OF chlorpheniramine maleate	HMDB
Intra brand OF chlorpheniramine maleate	HMDB
Schein brand OF chlorpheniramine maleate	HMDB
Vortech brand 2 OF chlorpheniramine maleate	HMDB

Chemical Formula

C₁₆H₁₉ClN₂

Average Molecular Weight

274.788

Monoisotopic Molecular Weight

274.123676325

IUPAC Name

[3-(4-chlorophenyl)-3-(pyridin-2-yl)propyl]dimethylamine

Traditional Name

chlorpheniramine

CAS Registry Number

113-92-8

SMILES

CN(C)CCC(C1=CC=C(Cl)C=C1)C1=CC=CC=N1

InChI Identifier

InChI=1S/C16H19ClN2/c1-19(2)12-10-15(16-5-3-4-11-18-16)13-6-8-14(17)9-7-13/h3-9,11,15H,10,12H2,1-2H3

InChI Key

SOYKEARSMXGVTM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pheniramines. Pheniramines are compounds containing a pheniramine moiety, which is structurally characterized by the presence of a 2-benzylpyridine linked to an dimethyl(propyl)amine to form a dimethyl[3-phenyl-3-(pyridin-2-yl)propyl]amine skeleton.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Pheniramines

Direct Parent

Pheniramines

Alternative Parents

Substituents

Pheniramine
Chlorobenzene
Halobenzene
Aralkylamine
Aryl chloride
Benzenoid
Monocyclic benzene moiety
Aryl halide
Heteroaromatic compound
Tertiary aliphatic amine
Tertiary amine
Azacycle
Organic nitrogen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Amine
Hydrocarbon derivative
Organopnictogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

tertiary amino compound (CHEBI:52010 )
pyridines (CHEBI:52010 )
monochlorobenzenes (CHEBI:52010 )

Ontology

Physiological effect

Organoleptic effect

Taste

Bitter

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0001944)
Cell membrane (HMDB: HMDB0001944)

Tissue

Epithelium

Epidermis (HMDB: HMDB0001944)

Organ

Skin (HMDB: HMDB0001944)

Route of exposure

Enteral

Gastrointestinal (HMDB: HMDB0001944)

Source

Exogenous

Exogenous (HMDB: HMDB0001944)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Chlorphenamine H1-Antihistamine Action (HMDB: HMDB0001944)
Chlorphenamine H1-Antihistamine Action (PathBank: SMP0056661)

Role

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	130 - 135 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	160 mg/mL at 25 °C	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	163.461	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000970

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.052 g/L	ALOGPS
logP	3.74	ALOGPS
logP	3.58	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Basic)	9.47	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	16.13 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	80.85 m³·mol⁻¹	ChemAxon
Polarizability	30.82 Å³	ChemAxon
Number of Rings	2	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
AllCCS	[M+H]+	162.044	32859911
AllCCS	[M-H]-	168.092	32859911
DeepCCS	[M+H]+	160.784	30932474
DeepCCS	[M-H]-	158.426	30932474
DeepCCS	[M-2H]-	191.312	30932474
DeepCCS	[M+Na]+	166.877	30932474
AllCCS	[M+H]+	162.0	32859911
AllCCS	[M+H-H2O]+	158.3	32859911
AllCCS	[M+NH4]+	165.6	32859911
AllCCS	[M+Na]+	166.6	32859911
AllCCS	[M-H]-	168.1	32859911
AllCCS	[M+Na-2H]-	168.2	32859911
AllCCS	[M+HCOO]-	168.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Chlorpheniramine	CN(C)CCC(C1=CC=C(Cl)C=C1)C1=CC=CC=N1	2892.2	Standard polar	33892256
Chlorpheniramine	CN(C)CCC(C1=CC=C(Cl)C=C1)C1=CC=CC=N1	2036.8	Standard non polar	33892256
Chlorpheniramine	CN(C)CCC(C1=CC=C(Cl)C=C1)C1=CC=CC=N1	1978.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Chlorpheniramine EI-B (Non-derivatized)	splash10-0zfr-6290000000-2ca3230cde716588805e	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Chlorpheniramine EI-B (Non-derivatized)	splash10-0zfr-6290000000-2ca3230cde716588805e	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chlorpheniramine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9380000000-f4a0f7b13adeafb1762d	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chlorpheniramine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chlorpheniramine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chlorpheniramine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0zfr-6490000000-8e58cd1c686f23a7dac6	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpheniramine Quattro_QQQ 10V, N/A-QTOF (Annotated)	splash10-01b9-3900000000-ea4ccfd2afe05f49fc7a	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpheniramine Quattro_QQQ 25V, N/A-QTOF (Annotated)	splash10-004i-0090000000-9e46eb080de95d4f8f8e	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpheniramine Quattro_QQQ 40V, N/A-QTOF (Annotated)	splash10-014i-1920000000-d2d2acf559d9070a1d47	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpheniramine EI-B (Unknown) , Positive-QTOF	splash10-0zfr-6190000000-2ca3230cde716588805e	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpheniramine LC-ESI-qTof , Positive-QTOF	splash10-0uy0-0960000000-1f750af75fe542c6c06f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpheniramine , positive-QTOF	splash10-001i-0290000000-03651b7b90a1745fdf23	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpheniramine , positive-QTOF	splash10-0uy0-0960000000-1f750af75fe542c6c06f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpheniramine 35V, Positive-QTOF	splash10-001i-0490000000-3d28aeb0e77391e8e9b2	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorpheniramine 10V, Positive-QTOF	splash10-004i-0090000000-9b4d486e9c2c7712ca4d	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorpheniramine 20V, Positive-QTOF	splash10-0059-0190000000-2c96b165338a445b284d	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorpheniramine 40V, Positive-QTOF	splash10-0ue9-3960000000-73025748bd5a00459938	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorpheniramine 10V, Negative-QTOF	splash10-00di-0090000000-90a6e640c735788d17ca	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorpheniramine 20V, Negative-QTOF	splash10-00di-1090000000-89ac3cf688134ba8a50b	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorpheniramine 40V, Negative-QTOF	splash10-01tc-6490000000-4242ef7cec7b0b0a7393	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorpheniramine 10V, Positive-QTOF	splash10-001i-0090000000-c38223f80e776a39c840	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorpheniramine 20V, Positive-QTOF	splash10-001i-0090000000-5c9ac02f7374772460c8	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorpheniramine 40V, Positive-QTOF	splash10-0ue9-1290000000-cc70655f6b19de3dc41d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorpheniramine 10V, Negative-QTOF	splash10-00di-0090000000-df52e539d08e1efa7d95	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorpheniramine 20V, Negative-QTOF	splash10-00di-4390000000-4b1316bcb291af4998c9	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorpheniramine 40V, Negative-QTOF	splash10-0ue9-8490000000-4bf6d67eb7d38a21b96b	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Epidermis

Pathways

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

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01114

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022759

KNApSAcK ID

Not Available

Chemspider ID

2624

KEGG Compound ID

C06905

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Chlorpheniramine

METLIN ID

1734

PubChem Compound

2725

PDB ID

Not Available

ChEBI ID

52010

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

Bantz EW, Dolen WK, Chadwick EW, Nelson HS: Chronic chlorpheniramine therapy: subsensitivity, drug metabolism, and compliance. Ann Allergy. 1987 Nov;59(5):341-6. [PubMed:3688558 ]
Simons FE, Silver NA, Gu X, Simons KJ: Clinical pharmacology of H1-antihistamines in the skin. J Allergy Clin Immunol. 2002 Nov;110(5):777-83. [PubMed:12417888 ]
MSDS [Link]

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

Enzyme Details

2. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

Enzyme Details

3. Serum albumin

General function:: Involved in transport
Specific function:: Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloidal osmotic pressure of blood. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc
Gene Name:: ALB
Uniprot ID:: P02768
Molecular weight:: 69365.9

Enzyme Details

4. 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

Enzyme Details

5. Histamine H4 receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: The H4 subclass of histamine receptors could mediate the histamine signals in peripheral tissues. Displays a significant level of constitutive activity (spontaneous activity in the absence of agonist)
Gene Name:: HRH4
Uniprot ID:: Q9H3N8
Molecular weight:: 44495.4

Showing metabocard for Chlorpheniramine (HMDB0001944)

MOL for HMDB0001944 (Chlorpheniramine)

3D MOL for HMDB0001944 (Chlorpheniramine)

3D SDF for HMDB0001944 (Chlorpheniramine)

3D-SDF for HMDB0001944 (Chlorpheniramine)

PDB for HMDB0001944 (Chlorpheniramine)

3D PDB for HMDB0001944 (Chlorpheniramine)

SMILES for HMDB0001944 (Chlorpheniramine)

INCHI for HMDB0001944 (Chlorpheniramine)

Structure for HMDB0001944 (Chlorpheniramine)

3D Structure for HMDB0001944 (Chlorpheniramine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes