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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-18 09:07:14 UTC

Update Date

2022-03-07 02:49:11 UTC

HMDB ID

HMDB0001941

Secondary Accession Numbers

HMDB01941

Metabolite Identification

Common Name

Brompheniramine

Description

Brompheniramine (also known as Bromfed, Bromfenex, and Dimetane) is an antihistamine drug of the propylamine class. It is commonly available over the counter and is indicated for the treatment of the symptoms of the common cold and allergic rhinitis, such as runny nose, itchy eyes, watery eyes, and sneezing. It is a first-generation antihistamine; Brompheniramine (also known as Bromfed, Bromfenex, and Dimetane) is an antihistamine drug of the propylamine class. It is commonly available over the counter and is indicated for the treatment of the symptoms of the common cold and allergic rhinitis, such as runny nose, itchy eyes, watery eyes, and sneezing. It is a first-generation antihistamine. -- Wikipedia ; Histamine H1 antagonist used in treatment of allergies, rhinitis, and urticaria.

Structure

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

HMDB0001941
     RDKit          3D
Brompheniramine
 38 39  0  0  0  0  0  0  0  0999 V2000
    3.7423    0.3487    0.7427 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8201   -0.7123    1.1696 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5706   -1.9532    1.0386 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7296   -0.7917    0.1915 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8701    0.4736    0.2723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2395    0.3651   -0.7398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1107   -0.8084   -0.4948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6820   -1.4877   -1.5500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5001   -2.5850   -1.3808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7371   -2.9965   -0.0714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8630   -4.5120    0.2333 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.1713   -2.3254    0.9922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3481   -1.2194    0.7994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9773    1.6442   -0.7957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2525    2.3196    0.3619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9394    3.5086    0.2784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3142    3.9563   -0.9671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0192    3.2461   -2.1253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3562    2.1060   -2.0010 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7037    0.3533   -0.3680 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4271    1.3253    1.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7769    0.1427    1.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4996   -1.9335    1.6439 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8994   -2.0294   -0.0252 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9487   -2.8474    1.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0757   -1.6416    0.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1633   -0.8432   -0.8252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5338    0.6170    1.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5594    1.3093    0.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2477    0.1662   -1.7467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5125   -1.1860   -2.5921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9542   -3.1267   -2.1997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3543   -2.6449    2.0177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9374   -0.7395    1.6766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9570    1.9607    1.3330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1725    4.0645    1.1564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8652    4.8966   -1.1134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3043    3.5799   -3.1108 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

835
  Mrv1652305271900042D          

 19 20  0  0  1  0            999 V2000
    3.7935   -2.8876    0.0000 Br  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>
HMDB0001941

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H19BrN2/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>
ZDIGNSYAACHWNL-UHFFFAOYSA-N

> <FORMULA>
C16H19BrN2

> <MOLECULAR_WEIGHT>
319.239

> <EXACT_MASS>
318.073161265

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
32.075815760458504

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.63

> <JCHEM_LOGP>
3.749658864

> <ALOGPS_LOGS>
-4.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.478390040370506

> <JCHEM_POLAR_SURFACE_AREA>
16.130000000000003

> <JCHEM_REFRACTIVITY>
83.66830000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.27e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
brompheniramine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0001941
     RDKit          3D
Brompheniramine
 38 39  0  0  0  0  0  0  0  0999 V2000
    3.7423    0.3487    0.7427 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8201   -0.7123    1.1696 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5706   -1.9532    1.0386 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7296   -0.7917    0.1915 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8701    0.4736    0.2723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2395    0.3651   -0.7398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1107   -0.8084   -0.4948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6820   -1.4877   -1.5500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5001   -2.5850   -1.3808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7371   -2.9965   -0.0714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8630   -4.5120    0.2333 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.1713   -2.3254    0.9922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3481   -1.2194    0.7994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9773    1.6442   -0.7957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2525    2.3196    0.3619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9394    3.5086    0.2784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3142    3.9563   -0.9671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0192    3.2461   -2.1253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3562    2.1060   -2.0010 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7037    0.3533   -0.3680 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4271    1.3253    1.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7769    0.1427    1.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4996   -1.9335    1.6439 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8994   -2.0294   -0.0252 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9487   -2.8474    1.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0757   -1.6416    0.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1633   -0.8432   -0.8252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5338    0.6170    1.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5594    1.3093    0.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2477    0.1662   -1.7467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5125   -1.1860   -2.5921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9542   -3.1267   -2.1997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3543   -2.6449    2.0177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9374   -0.7395    1.6766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9570    1.9607    1.3330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1725    4.0645    1.1564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8652    4.8966   -1.1134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3043    3.5799   -3.1108 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: 835                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1 Br   UNK     0       7.081  -5.390   0.000  0.00  0.00          Br+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    HMDB0001941
HETATM    1  C1  UNL     1       3.742   0.349   0.743  1.00  0.00           C  
HETATM    2  N1  UNL     1       2.820  -0.712   1.170  1.00  0.00           N  
HETATM    3  C2  UNL     1       3.571  -1.953   1.039  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.730  -0.792   0.191  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.870   0.474   0.272  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.239   0.365  -0.740  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.111  -0.808  -0.495  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.682  -1.488  -1.550  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.500  -2.585  -1.381  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.737  -2.996  -0.071  1.00  0.00           C  
HETATM   11 BR1  UNL     1      -3.863  -4.512   0.233  1.00  0.00          BR  
HETATM   12  C10 UNL     1      -2.171  -2.325   0.992  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.348  -1.219   0.799  1.00  0.00           C  
HETATM   14  C12 UNL     1      -0.977   1.644  -0.796  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.252   2.320   0.362  1.00  0.00           C  
HETATM   16  C14 UNL     1      -1.939   3.509   0.278  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.314   3.956  -0.967  1.00  0.00           C  
HETATM   18  C16 UNL     1      -2.019   3.246  -2.125  1.00  0.00           C  
HETATM   19  N2  UNL     1      -1.356   2.106  -2.001  1.00  0.00           N  
HETATM   20  H1  UNL     1       3.704   0.353  -0.368  1.00  0.00           H  
HETATM   21  H2  UNL     1       3.427   1.325   1.172  1.00  0.00           H  
HETATM   22  H3  UNL     1       4.777   0.143   1.046  1.00  0.00           H  
HETATM   23  H4  UNL     1       4.500  -1.934   1.644  1.00  0.00           H  
HETATM   24  H5  UNL     1       3.899  -2.029  -0.025  1.00  0.00           H  
HETATM   25  H6  UNL     1       2.949  -2.847   1.242  1.00  0.00           H  
HETATM   26  H7  UNL     1       1.076  -1.642   0.373  1.00  0.00           H  
HETATM   27  H8  UNL     1       2.163  -0.843  -0.825  1.00  0.00           H  
HETATM   28  H9  UNL     1       0.534   0.617   1.305  1.00  0.00           H  
HETATM   29  H10 UNL     1       1.559   1.309   0.038  1.00  0.00           H  
HETATM   30  H11 UNL     1       0.248   0.166  -1.747  1.00  0.00           H  
HETATM   31  H12 UNL     1      -1.512  -1.186  -2.592  1.00  0.00           H  
HETATM   32  H13 UNL     1      -2.954  -3.127  -2.200  1.00  0.00           H  
HETATM   33  H14 UNL     1      -2.354  -2.645   2.018  1.00  0.00           H  
HETATM   34  H15 UNL     1      -0.937  -0.739   1.677  1.00  0.00           H  
HETATM   35  H16 UNL     1      -0.957   1.961   1.333  1.00  0.00           H  
HETATM   36  H17 UNL     1      -2.173   4.064   1.156  1.00  0.00           H  
HETATM   37  H18 UNL     1      -2.865   4.897  -1.113  1.00  0.00           H  
HETATM   38  H19 UNL     1      -2.304   3.580  -3.111  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

HMDB0001941
     RDKit          3D
Brompheniramine
 38 39  0  0  0  0  0  0  0  0999 V2000
    3.7423    0.3487    0.7427 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8201   -0.7123    1.1696 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5706   -1.9532    1.0386 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7296   -0.7917    0.1915 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8701    0.4736    0.2723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2395    0.3651   -0.7398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1107   -0.8084   -0.4948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6820   -1.4877   -1.5500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5001   -2.5850   -1.3808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7371   -2.9965   -0.0714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8630   -4.5120    0.2333 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.1713   -2.3254    0.9922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3481   -1.2194    0.7994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9773    1.6442   -0.7957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2525    2.3196    0.3619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9394    3.5086    0.2784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3142    3.9563   -0.9671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0192    3.2461   -2.1253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3562    2.1060   -2.0010 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7037    0.3533   -0.3680 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4271    1.3253    1.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7769    0.1427    1.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4996   -1.9335    1.6439 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8994   -2.0294   -0.0252 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9487   -2.8474    1.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0757   -1.6416    0.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1633   -0.8432   -0.8252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5338    0.6170    1.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5594    1.3093    0.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2477    0.1662   -1.7467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5125   -1.1860   -2.5921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9542   -3.1267   -2.1997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3543   -2.6449    2.0177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9374   -0.7395    1.6766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9570    1.9607    1.3330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1725    4.0645    1.1564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8652    4.8966   -1.1134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3043    3.5799   -3.1108 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-Bromophenyl)-1-(2-pyridyl)-3-dimethylaminopropane	ChEBI
2-(p-Bromo-alpha-(2-dimethylaminoethyl)benzyl)pyridine	ChEBI
3-(4-Bromophenyl)-N,N-dimethyl-3-(2-pyridinyl)-1-propanamine	ChEBI
3-(p-Bromophenyl)-3-(2-pyridyl)-N,N-dimethylpropylamine	ChEBI
[3-(4-Bromo-phenyl)-3-pyridin-2-yl-propyl]-dimethyl-amine	ChEBI
Bromfeniramina	ChEBI
Brompheniraminum	ChEBI
Brotane	Kegg
2-(p-Bromo-a-(2-dimethylaminoethyl)benzyl)pyridine	Generator
2-(p-Bromo-α-(2-dimethylaminoethyl)benzyl)pyridine	Generator
Antihistamine compound	HMDB
Brompheniramine maleate	HMDB, MeSH
D-Brompheniramine	HMDB
Dexbromfeniramina	HMDB
Dexbrompheniramine	HMDB
Dexbrompheniramine brompheniramine	HMDB
Dexbrompheniramine maleate	HMDB
Dexbrompheniramine maleate salt	HMDB
Dexbrompheniraminum	HMDB
Dimetane	HMDB, MeSH
Dimetane-ten	HMDB, MeSH
Dimetapp allergy	HMDB, MeSH
Ilvin	HMDB
Parabromdylamine	HMDB
Parabromodylamine	HMDB
Veltane	HMDB
Dimetane ten	MeSH, HMDB
Maleate, brompheniramine	MeSH, HMDB
Whitehall-robins brand OF brompheniramine maleate	MeSH, HMDB
Para bromdylamine	MeSH, HMDB
Chlorphed	MeSH, HMDB
Brompheniramine maleate (1:1)	MeSH, HMDB
Oraminic 2	MeSH, HMDB
Oraminic-2	MeSH, HMDB
Roberts brand OF brompheniramine maleate	MeSH, HMDB
Robins brand OF brompheniramine maleate	MeSH, HMDB
P Bromdylamine	MeSH, HMDB
P-Bromdylamine	MeSH, HMDB
Vortech brand OF brompheniramine maleate	MeSH, HMDB
Para-bromdylamine	MeSH, HMDB

Chemical Formula

C₁₆H₁₉BrN₂

Average Molecular Weight

319.239

Monoisotopic Molecular Weight

318.073161265

IUPAC Name

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

Traditional Name

brompheniramine

CAS Registry Number

86-22-6

SMILES

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

InChI Identifier

InChI=1S/C16H19BrN2/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

ZDIGNSYAACHWNL-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
Bromobenzene
Halobenzene
Aralkylamine
Aryl bromide
Benzenoid
Monocyclic benzene moiety
Aryl halide
Heteroaromatic compound
Tertiary aliphatic amine
Tertiary amine
Azacycle
Organic nitrogen compound
Organonitrogen compound
Organobromide
Organohalogen compound
Amine
Hydrocarbon derivative
Organopnictogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

organobromine compound (CHEBI:3183 )
pyridines (CHEBI:3183 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 9949311)

Cellular substructure

Membrane (HMDB: HMDB0001941)
Cell membrane (HMDB: HMDB0001941)

Source

Exogenous

Exogenous (HMDB: HMDB0001941)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Brompheniramine H1-Antihistamine Action (HMDB: HMDB0001941)
Brompheniramine H1-Antihistamine Action (PathBank: SMP0057579)

Role

Industrial application

H1-receptor antagonist (HMDB: HMDB0001941)
Anti-allergic agent (HMDB: HMDB0001941)

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0001941)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	< 25 °C	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	166.3	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001064

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.013 g/L	ALOGPS
logP	3.63	ALOGPS
logP	3.75	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Basic)	9.48	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	83.67 m³·mol⁻¹	ChemAxon
Polarizability	32.08 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]+	169.854	32859911
AllCCS	[M-H]-	171.19	32859911
DeepCCS	[M+H]+	160.932	30932474
DeepCCS	[M-H]-	158.574	30932474
DeepCCS	[M-2H]-	191.46	30932474
DeepCCS	[M+Na]+	167.025	30932474
AllCCS	[M+H]+	169.9	32859911
AllCCS	[M+H-H2O]+	166.3	32859911
AllCCS	[M+NH4]+	173.1	32859911
AllCCS	[M+Na]+	174.1	32859911
AllCCS	[M-H]-	171.2	32859911
AllCCS	[M+Na-2H]-	171.5	32859911
AllCCS	[M+HCOO]-	172.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Brompheniramine	CN(C)CCC(C1=CC=C(Br)C=C1)C1=CC=CC=N1	2982.4	Standard polar	33892256
Brompheniramine	CN(C)CCC(C1=CC=C(Br)C=C1)C1=CC=CC=N1	1991.3	Standard non polar	33892256
Brompheniramine	CN(C)CCC(C1=CC=C(Br)C=C1)C1=CC=CC=N1	2084.0	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 - Brompheniramine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-9081000000-bc4d350922643027fea6	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Brompheniramine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Brompheniramine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0002-5490000000-9c3b804de0b552198b85	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 - Brompheniramine Quattro_QQQ 10V, N/A-QTOF (Annotated)	splash10-014i-4954000000-f0a4889ab8cd0d5dcacc	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Brompheniramine Quattro_QQQ 25V, N/A-QTOF (Annotated)	splash10-00di-0090000000-02a74d4d4927d8e443aa	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Brompheniramine Quattro_QQQ 40V, N/A-QTOF (Annotated)	splash10-014i-0920000000-ad3d20cb0f1b7362fbc3	2012-07-25	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brompheniramine 10V, Positive-QTOF	splash10-014i-0029000000-fa060b2610f05fd6963a	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brompheniramine 20V, Positive-QTOF	splash10-01b9-0197000000-90a5b62f5a9e47f95802	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brompheniramine 40V, Positive-QTOF	splash10-0fef-3690000000-914dbc7e9fc6b1ce196a	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brompheniramine 10V, Negative-QTOF	splash10-014i-0009000000-1bc9f3a3603646c31504	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brompheniramine 20V, Negative-QTOF	splash10-014i-1019000000-14a32020bd62ee6fb3b7	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brompheniramine 40V, Negative-QTOF	splash10-0fi4-7591000000-cd391d2ec4970c9e8b8a	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brompheniramine 10V, Negative-QTOF	splash10-014i-0009000000-615031c9863c28108e0f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brompheniramine 20V, Negative-QTOF	splash10-016r-6369000000-b40c997a38a0f9eb2fdb	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brompheniramine 40V, Negative-QTOF	splash10-004j-9480000000-6c5bc7bd482fbd292a0c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brompheniramine 10V, Positive-QTOF	splash10-00di-0094000000-c8e61a4d45703ee2c906	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brompheniramine 20V, Positive-QTOF	splash10-00di-0090000000-363f1320fc00a31daef8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brompheniramine 40V, Positive-QTOF	splash10-006t-1290000000-3b9b35511af51a9e3bb5	2021-09-24	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

Blood

Tissue Locations

Not Available

Pathways

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

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.024 +/- 0.0021 uM	Adult (>18 years old)	Both	Normal	9949311	details

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

DB00835

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022756

KNApSAcK ID

Not Available

Chemspider ID

6573

KEGG Compound ID

C06857

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Brompheniramine

METLIN ID

1383

PubChem Compound

6834

PDB ID

Not Available

ChEBI ID

3183

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)

Download (PDF)

General References

Not Available

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

Showing metabocard for Brompheniramine (HMDB0001941)

MOL for HMDB0001941 (Brompheniramine)

3D MOL for HMDB0001941 (Brompheniramine)

3D SDF for HMDB0001941 (Brompheniramine)

3D-SDF for HMDB0001941 (Brompheniramine)

PDB for HMDB0001941 (Brompheniramine)

3D PDB for HMDB0001941 (Brompheniramine)

SMILES for HMDB0001941 (Brompheniramine)

INCHI for HMDB0001941 (Brompheniramine)

Structure for HMDB0001941 (Brompheniramine)

3D Structure for HMDB0001941 (Brompheniramine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes