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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-11-16 23:09:02 UTC

Update Date

2022-03-07 03:18:13 UTC

HMDB ID

HMDB0240218

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Dexchlorpheniramine

Description

Dexchlorpheniramine, also known as dapriton or polaramin, 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. In humans, dexchlorpheniramine is involved in the dexchlorpheniramine h1-antihistamine action pathway. Based on a literature review a significant number of articles have been published on Dexchlorpheniramine.

Structure

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

HMDB0240218
     RDKit          3D
Dexchlorpheniramine
 38 39  0  0  0  0  0  0  0  0999 V2000
   -3.5849   -0.0410    0.4732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5765   -0.9695    0.0634 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1714   -2.2613   -0.2172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8131   -0.5637   -1.0750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9223    0.6235   -0.7961 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0707    0.3669    0.2854 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0060   -0.7389    0.0310 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4122   -1.5683    1.0592 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2926   -2.5895    0.7702 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7917   -2.8257   -0.5041 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9158   -4.1512   -0.8024 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.3804   -1.9900   -1.5326 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4930   -0.9598   -1.2438 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8036    1.6536    0.5467 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1029    2.0799    1.8092 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7776    3.2628    2.0115 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1641    4.0400    0.9453 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8543    3.5945   -0.3104 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1983    2.4423   -0.4852 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4463   -0.6292    0.8994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9891    0.5724   -0.3446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2200    0.5804    1.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2571   -2.3569   -1.3170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1708   -2.3720    0.2500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4565   -3.0398    0.1437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1385   -1.4219   -1.3370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4358   -0.3913   -1.9758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3791    0.9030   -1.7201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5258    1.5096   -0.4970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4947    0.1282    1.2332 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0588   -1.4438    2.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6041   -3.2370    1.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7677   -2.1686   -2.5343 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1974   -0.3309   -2.0786 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8139    1.4957    2.6678 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0189    3.6109    3.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6978    4.9787    1.0724 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1601    4.2078   -1.1604 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  1
  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

      
  Mrv1652311211717282D          

 19 20  0  0  1  0            999 V2000
    1.5325   -5.3934    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.8217   -3.7368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1061   -1.6848    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4004   -3.7368    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6747   -4.1571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1111   -4.1472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9590   -3.7468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6747   -4.9830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4004   -2.9210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1111   -4.9830    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2483   -4.9830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2483   -4.1571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9590   -5.3934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1061   -2.5106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5375   -4.1472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8217   -5.3934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5375   -4.9830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3804   -1.2644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8067   -1.2794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  1  0  0  0  0
  3 14  1  0  0  0  0
  3 18  1  0  0  0  0
  3 19  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4  9  1  6  0  0  0
  5  7  2  0  0  0  0
  5  8  1  0  0  0  0
  7 12  1  0  0  0  0
  8 13  2  0  0  0  0
  9 14  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 15 17  1  0  0  0  0
 16 17  2  0  0  0  0
  2  6  1  0  0  0  0
  2 15  2  0  0  0  0
  6 10  2  0  0  0  0
 10 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0240218

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)CC[C@@H](C1=CC=C(Cl)C=C1)C1=NC=CC=C1

> <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/t15-/m0/s1

> <INCHI_KEY>
SOYKEARSMXGVTM-HNNXBMFYSA-N

> <FORMULA>
C16H19ClN2

> <MOLECULAR_WEIGHT>
274.79

> <EXACT_MASS>
274.1236763

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
30.8205314118093

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(3S)-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

$$$$

HMDB0240218
     RDKit          3D
Dexchlorpheniramine
 38 39  0  0  0  0  0  0  0  0999 V2000
   -3.5849   -0.0410    0.4732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5765   -0.9695    0.0634 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1714   -2.2613   -0.2172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8131   -0.5637   -1.0750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9223    0.6235   -0.7961 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0707    0.3669    0.2854 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0060   -0.7389    0.0310 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4122   -1.5683    1.0592 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2926   -2.5895    0.7702 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7917   -2.8257   -0.5041 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9158   -4.1512   -0.8024 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.3804   -1.9900   -1.5326 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4930   -0.9598   -1.2438 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8036    1.6536    0.5467 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1029    2.0799    1.8092 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7776    3.2628    2.0115 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1641    4.0400    0.9453 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8543    3.5945   -0.3104 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1983    2.4423   -0.4852 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4463   -0.6292    0.8994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9891    0.5724   -0.3446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2200    0.5804    1.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2571   -2.3569   -1.3170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1708   -2.3720    0.2500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4565   -3.0398    0.1437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1385   -1.4219   -1.3370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4358   -0.3913   -1.9758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3791    0.9030   -1.7201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5258    1.5096   -0.4970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4947    0.1282    1.2332 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0588   -1.4438    2.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6041   -3.2370    1.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7677   -2.1686   -2.5343 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1974   -0.3309   -2.0786 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8139    1.4957    2.6678 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0189    3.6109    3.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6978    4.9787    1.0724 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1601    4.2078   -1.1604 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  1
  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                                 21-NOV-17   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-NOV-17         0                                  
HETATM    1 Cl   UNK     0       2.861 -10.068   0.000  0.00  0.00          Cl+0
HETATM    2  C   UNK     0      10.867  -6.975   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       9.531  -3.145   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       8.214  -6.975   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.859  -7.760   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.541  -7.741   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.523  -6.994   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.859  -9.302   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.214  -5.453   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       9.541  -9.302   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       4.197  -9.302   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.197  -7.760   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.523 -10.068   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.531  -4.686   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.203  -7.741   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.867 -10.068   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.203  -9.302   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.177  -2.360   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.839  -2.388   0.000  0.00  0.00           C+0
CONECT    1   11                                                            
CONECT    2    6   15                                                       
CONECT    3   14   18   19                                                  
CONECT    4    5    6    9                                                  
CONECT    5    4    7    8                                                  
CONECT    6    4    2   10                                                  
CONECT    7    5   12                                                       
CONECT    8    5   13                                                       
CONECT    9    4   14                                                       
CONECT   10    6   16                                                       
CONECT   11    1   12   13                                                  
CONECT   12    7   11                                                       
CONECT   13    8   11                                                       
CONECT   14    3    9                                                       
CONECT   15   17    2                                                       
CONECT   16   17   10                                                       
CONECT   17   15   16                                                       
CONECT   18    3                                                            
CONECT   19    3                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0240218
HETATM    1  C1  UNL     1      -3.585  -0.041   0.473  1.00  0.00           C  
HETATM    2  N1  UNL     1      -2.576  -0.970   0.063  1.00  0.00           N  
HETATM    3  C2  UNL     1      -3.171  -2.261  -0.217  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.813  -0.564  -1.075  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.922   0.624  -0.796  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.071   0.367   0.285  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.006  -0.739   0.031  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.412  -1.568   1.059  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.293  -2.589   0.770  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.792  -2.826  -0.504  1.00  0.00           C  
HETATM   11 CL1  UNL     1       3.916  -4.151  -0.802  1.00  0.00          CL  
HETATM   12  C10 UNL     1       2.380  -1.990  -1.533  1.00  0.00           C  
HETATM   13  C11 UNL     1       1.493  -0.960  -1.244  1.00  0.00           C  
HETATM   14  C12 UNL     1       0.804   1.654   0.547  1.00  0.00           C  
HETATM   15  C13 UNL     1       1.103   2.080   1.809  1.00  0.00           C  
HETATM   16  C14 UNL     1       1.778   3.263   2.011  1.00  0.00           C  
HETATM   17  C15 UNL     1       2.164   4.040   0.945  1.00  0.00           C  
HETATM   18  C16 UNL     1       1.854   3.594  -0.310  1.00  0.00           C  
HETATM   19  N2  UNL     1       1.198   2.442  -0.485  1.00  0.00           N  
HETATM   20  H1  UNL     1      -4.446  -0.629   0.899  1.00  0.00           H  
HETATM   21  H2  UNL     1      -3.989   0.572  -0.345  1.00  0.00           H  
HETATM   22  H3  UNL     1      -3.220   0.580   1.324  1.00  0.00           H  
HETATM   23  H4  UNL     1      -3.257  -2.357  -1.317  1.00  0.00           H  
HETATM   24  H5  UNL     1      -4.171  -2.372   0.250  1.00  0.00           H  
HETATM   25  H6  UNL     1      -2.456  -3.040   0.144  1.00  0.00           H  
HETATM   26  H7  UNL     1      -1.139  -1.422  -1.337  1.00  0.00           H  
HETATM   27  H8  UNL     1      -2.436  -0.391  -1.976  1.00  0.00           H  
HETATM   28  H9  UNL     1      -0.379   0.903  -1.720  1.00  0.00           H  
HETATM   29  H10 UNL     1      -1.526   1.510  -0.497  1.00  0.00           H  
HETATM   30  H11 UNL     1      -0.495   0.128   1.233  1.00  0.00           H  
HETATM   31  H12 UNL     1       1.059  -1.444   2.094  1.00  0.00           H  
HETATM   32  H13 UNL     1       2.604  -3.237   1.598  1.00  0.00           H  
HETATM   33  H14 UNL     1       2.768  -2.169  -2.534  1.00  0.00           H  
HETATM   34  H15 UNL     1       1.197  -0.331  -2.079  1.00  0.00           H  
HETATM   35  H16 UNL     1       0.814   1.496   2.668  1.00  0.00           H  
HETATM   36  H17 UNL     1       2.019   3.611   3.005  1.00  0.00           H  
HETATM   37  H18 UNL     1       2.698   4.979   1.072  1.00  0.00           H  
HETATM   38  H19 UNL     1       2.160   4.208  -1.160  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

HMDB0240218
     RDKit          3D
Dexchlorpheniramine
 38 39  0  0  0  0  0  0  0  0999 V2000
   -3.5849   -0.0410    0.4732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5765   -0.9695    0.0634 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1714   -2.2613   -0.2172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8131   -0.5637   -1.0750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9223    0.6235   -0.7961 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0707    0.3669    0.2854 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0060   -0.7389    0.0310 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4122   -1.5683    1.0592 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2926   -2.5895    0.7702 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7917   -2.8257   -0.5041 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9158   -4.1512   -0.8024 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.3804   -1.9900   -1.5326 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4930   -0.9598   -1.2438 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8036    1.6536    0.5467 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1029    2.0799    1.8092 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7776    3.2628    2.0115 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1641    4.0400    0.9453 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8543    3.5945   -0.3104 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1983    2.4423   -0.4852 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4463   -0.6292    0.8994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9891    0.5724   -0.3446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2200    0.5804    1.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2571   -2.3569   -1.3170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1708   -2.3720    0.2500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4565   -3.0398    0.1437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1385   -1.4219   -1.3370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4358   -0.3913   -1.9758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3791    0.9030   -1.7201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5258    1.5096   -0.4970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4947    0.1282    1.2332 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0588   -1.4438    2.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6041   -3.2370    1.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7677   -2.1686   -2.5343 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1974   -0.3309   -2.0786 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8139    1.4957    2.6678 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0189    3.6109    3.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6978    4.9787    1.0724 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1601    4.2078   -1.1604 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  1
  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
(+)-Chlorpheniramine	ChEBI
(S)-(+)-2-[p-Chloro-alpha-[2-(dimethylamino)ethyl]benzyl]pyridine	ChEBI
(S)-gamma-(4-Chlorophenyl)-N,N-dimethyl-2-pyridinepropanamine	ChEBI
D-Chlorpheniramine	ChEBI
Dapriton	ChEBI
Dexchlorpheniraminum	ChEBI
Dexclorfeniramina	ChEBI
D-Chloropheniramine	Kegg
(S)-(+)-2-[p-Chloro-a-[2-(dimethylamino)ethyl]benzyl]pyridine	Generator
(S)-(+)-2-[p-Chloro-α-[2-(dimethylamino)ethyl]benzyl]pyridine	Generator
(S)-g-(4-Chlorophenyl)-N,N-dimethyl-2-pyridinepropanamine	Generator
(S)-Γ-(4-chlorophenyl)-N,N-dimethyl-2-pyridinepropanamine	Generator
Dexclor	HMDB
Dexchlorpheniramine maleate (1:1), (R)-isomer	HMDB
Dexchlorpheniramine, (+-)-isomer	HMDB
Dexclorfeniramine	HMDB
Polaramin	HMDB
Polargen TD	HMDB
Dexchlorpheniramine maleate (1:1), (+-)-isomer	HMDB
Dexchlorpheniramine, (R)-isomer	HMDB
Dextrochlorpheniramine maleate	HMDB
Polaronil	HMDB
Polaramine	HMDB
Dexchlorpheniramine maleate	HMDB
Dexchlorpheniramine maleate (1:1), (S)-isomer	HMDB
Dexchlorpheniramine monohydrochloride	HMDB
Dexchlorpheniramine sodium maleate (1:1)	HMDB
Dexchlorpheniramine, monohydrochloride, (S)-isomer	HMDB

Chemical Formula

C₁₆H₁₉ClN₂

Average Molecular Weight

274.79

Monoisotopic Molecular Weight

274.1236763

IUPAC Name

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

Traditional Name

(+)-chlorpheniramine

CAS Registry Number

25523-97-1

SMILES

CN(C)CC[C@@H](C1=CC=C(Cl)C=C1)C1=NC=CC=C1

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/t15-/m0/s1

InChI Key

SOYKEARSMXGVTM-HNNXBMFYSA-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

chlorphenamine (CHEBI:4464 )

Ontology

Not Available

Exogenous (HMDB: HMDB0240218)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Dexchlorpheniramine H1-Antihistamine Action (PathBank: SMP0056811)

Role

Not Available

Physical Properties

State

Not Available

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
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
DeepCCS	[M+H]+	167.86	30932474
DeepCCS	[M-H]-	165.502	30932474
DeepCCS	[M-2H]-	198.388	30932474
DeepCCS	[M+Na]+	173.953	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 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.	5.76 minutes	32390414
Predicted by Siyang on May 30, 2022	9.9383 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.8 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	799.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	233.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	138.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	176.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	90.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	313.7 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	323.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	535.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	733.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	52.9 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	921.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	182.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	273.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	462.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	201.6 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	17.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dexchlorpheniramine	CN(C)CC[C@@H](C1=CC=C(Cl)C=C1)C1=NC=CC=C1	2913.1	Standard polar	33892256
Dexchlorpheniramine	CN(C)CC[C@@H](C1=CC=C(Cl)C=C1)C1=NC=CC=C1	2016.3	Standard non polar	33892256
Dexchlorpheniramine	CN(C)CC[C@@H](C1=CC=C(Cl)C=C1)C1=NC=CC=C1	2001.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dexchlorpheniramine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9380000000-f4a0f7b13adeafb1762d	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dexchlorpheniramine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dexchlorpheniramine 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dexchlorpheniramine LC-ESI-qTof , Positive-QTOF	splash10-0uy0-0960000000-24a36e80af50293ed70d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dexchlorpheniramine , positive-QTOF	splash10-001i-0190000000-f6ef5e736260c9c22a16	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dexchlorpheniramine , positive-QTOF	splash10-0uy0-0960000000-24a36e80af50293ed70d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dexchlorpheniramine 40V, Negative-QTOF	splash10-0006-9350000000-9779048010f442953f05	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dexchlorpheniramine 20V, Negative-QTOF	splash10-020v-9760000000-7a2dde5051e33fb99e9b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dexchlorpheniramine 10V, Negative-QTOF	splash10-00di-1290000000-781890d92c473a549bee	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dexchlorpheniramine 35V, Positive-QTOF	splash10-001i-0490000000-bd5f7072acbea14ac94b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dexchlorpheniramine 20V, Positive-QTOF	splash10-001i-0090000000-7bdad05e8a60c7e72e2a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dexchlorpheniramine 40V, Positive-QTOF	splash10-014i-0930000000-737ef0ba4ac30a71f3df	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dexchlorpheniramine 10V, Positive-QTOF	splash10-001i-0090000000-29b571daf91aa7b99143	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexchlorpheniramine 10V, Positive-QTOF	splash10-004i-0090000000-9b4d486e9c2c7712ca4d	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexchlorpheniramine 20V, Positive-QTOF	splash10-0059-0190000000-2c96b165338a445b284d	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexchlorpheniramine 40V, Positive-QTOF	splash10-0ue9-3960000000-73025748bd5a00459938	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexchlorpheniramine 10V, Negative-QTOF	splash10-00di-0090000000-90a6e640c735788d17ca	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexchlorpheniramine 20V, Negative-QTOF	splash10-00di-1090000000-89ac3cf688134ba8a50b	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexchlorpheniramine 40V, Negative-QTOF	splash10-01tc-6490000000-4242ef7cec7b0b0a7393	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexchlorpheniramine 10V, Negative-QTOF	splash10-00di-0090000000-df52e539d08e1efa7d95	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexchlorpheniramine 20V, Negative-QTOF	splash10-00di-4190000000-96b9d2a99d0b21099662	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexchlorpheniramine 40V, Negative-QTOF	splash10-0ue9-7290000000-01c0916a8749a49cbb87	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexchlorpheniramine 10V, Positive-QTOF	splash10-003r-0090000000-5f85b20ee35517cd8192	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexchlorpheniramine 20V, Positive-QTOF	splash10-001i-0090000000-2b9a28bfe8944378684a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexchlorpheniramine 40V, Positive-QTOF	splash10-0fsi-1590000000-38bfc333cd948f84c929	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

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

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB13679

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

30576

KEGG Compound ID

C06946

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dexchlorpheniramine

METLIN ID

Not Available

PubChem Compound

33036

PDB ID

Not Available

ChEBI ID

4464

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

Theunissen EL, Vermeeren A, Ramaekers JG: Repeated-dose effects of mequitazine, cetirizine and dexchlorpheniramine on driving and psychomotor performance. Br J Clin Pharmacol. 2006 Jan;61(1):79-86. [PubMed:16390354 ]

Showing metabocard for Dexchlorpheniramine (HMDB0240218)

MOL for HMDB0240218 (Dexchlorpheniramine)

3D MOL for HMDB0240218 (Dexchlorpheniramine)

3D SDF for HMDB0240218 (Dexchlorpheniramine)

3D-SDF for HMDB0240218 (Dexchlorpheniramine)

PDB for HMDB0240218 (Dexchlorpheniramine)

3D PDB for HMDB0240218 (Dexchlorpheniramine)

SMILES for HMDB0240218 (Dexchlorpheniramine)

INCHI for HMDB0240218 (Dexchlorpheniramine)

Structure for HMDB0240218 (Dexchlorpheniramine)

3D Structure for HMDB0240218 (Dexchlorpheniramine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra