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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:39 UTC

HMDB ID

HMDB0014549

Secondary Accession Numbers

HMDB14549

Metabolite Identification

Common Name

Dexbrompheniramine

Description

Dexbrompheniramine, also known as parabromdylamine or disophrol, 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. Dexbrompheniramine is a histamine H1 antagonist (or more correctly, an inverse histamine agonist) of the alkylamine class. Signs of an overdose include fast or irregular heartbeat, mental or mood changes, tightness in the chest, and unusual tiredness or weakness. Dexbrompheniramine is a drug which is used for treatment and relief of symptoms of allergies, hay fever, and colds. Dexbrompheniramine is a very strong basic compound (based on its pKa). In humans, dexbrompheniramine is involved in brompheniramine h1-antihistamine action. In allergic reactions an allergen interacts with and cross-links surface IgE antibodies on mast cells and basophils. Once released, histamine can react with local or widespread tissues through histamine receptors. Histamine also increases vascular permeability and potentiates pain.

Structure

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

HMDB0014549
     RDKit          3D
Dexbrompheniramine
 38 39  0  0  0  0  0  0  0  0999 V2000
    4.2178    1.0960   -0.0970 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1468    0.4046    0.5491 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5947   -0.8007    1.1487 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9691    0.4253   -0.2110 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8792   -0.4887    0.3017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3491   -0.4073   -0.5599 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4277   -1.3140   -0.0676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2084   -2.0788   -0.9049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2079   -2.9294   -0.4782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4504   -3.0271    0.8634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8321   -4.2148    1.4285 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.6959   -2.2772    1.7708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6986   -1.4363    1.2788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8328    0.9825   -0.7393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8178    1.5335    0.0400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2130    2.8351   -0.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5880    3.5844   -1.1524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6086    3.0324   -1.9260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2721    1.7551   -1.6877 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5068    0.4844   -1.0135 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9391    2.0874   -0.4980 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1609    1.1299    0.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3627   -0.5543    1.9456 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1813   -1.4548    0.4442 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7883   -1.3661    1.6638 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1361    0.3661   -1.2846 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5164    1.4712   -0.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3172   -1.5301    0.2431 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6573   -0.2900    1.3665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0736   -0.7779   -1.5786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0131   -1.9989   -1.9716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7759   -3.5039   -1.2130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9181   -2.3839    2.8222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1376   -0.8729    2.0164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2767    0.9379    0.7919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9686    3.3142    0.4247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8685    4.6236   -1.3370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1394    3.6435   -2.6999 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  6
  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

405
  Mrv0541 02231214392D          

 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  1  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  6  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>
HMDB0014549

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)CC[C@@H](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/t15-/m0/s1

> <INCHI_KEY>
ZDIGNSYAACHWNL-HNNXBMFYSA-N

> <FORMULA>
C16H19BrN2

> <MOLECULAR_WEIGHT>
319.239

> <EXACT_MASS>
318.073161265

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
31.838223053041332

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(3S)-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>
dexbrompheniramine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0014549
     RDKit          3D
Dexbrompheniramine
 38 39  0  0  0  0  0  0  0  0999 V2000
    4.2178    1.0960   -0.0970 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1468    0.4046    0.5491 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5947   -0.8007    1.1487 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9691    0.4253   -0.2110 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8792   -0.4887    0.3017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3491   -0.4073   -0.5599 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4277   -1.3140   -0.0676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2084   -2.0788   -0.9049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2079   -2.9294   -0.4782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4504   -3.0271    0.8634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8321   -4.2148    1.4285 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.6959   -2.2772    1.7708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6986   -1.4363    1.2788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8328    0.9825   -0.7393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8178    1.5335    0.0400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2130    2.8351   -0.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5880    3.5844   -1.1524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6086    3.0324   -1.9260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2721    1.7551   -1.6877 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5068    0.4844   -1.0135 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9391    2.0874   -0.4980 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1609    1.1299    0.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3627   -0.5543    1.9456 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1813   -1.4548    0.4442 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7883   -1.3661    1.6638 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1361    0.3661   -1.2846 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5164    1.4712   -0.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3172   -1.5301    0.2431 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6573   -0.2900    1.3665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0736   -0.7779   -1.5786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0131   -1.9989   -1.9716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7759   -3.5039   -1.2130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9181   -2.3839    2.8222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1376   -0.8729    2.0164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2767    0.9379    0.7919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9686    3.3142    0.4247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8685    4.6236   -1.3370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1394    3.6435   -2.6999 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  6
  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                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 405                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         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    HMDB0014549
HETATM    1  C1  UNL     1       4.218   1.096  -0.097  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.147   0.405   0.549  1.00  0.00           N  
HETATM    3  C2  UNL     1       3.595  -0.801   1.149  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.969   0.425  -0.211  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.879  -0.489   0.302  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.349  -0.407  -0.560  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.428  -1.314  -0.068  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.208  -2.079  -0.905  1.00  0.00           C  
HETATM    9  C8  UNL     1      -3.208  -2.929  -0.478  1.00  0.00           C  
HETATM   10  C9  UNL     1      -3.450  -3.027   0.863  1.00  0.00           C  
HETATM   11 BR1  UNL     1      -4.832  -4.215   1.429  1.00  0.00          BR  
HETATM   12  C10 UNL     1      -2.696  -2.277   1.771  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.699  -1.436   1.279  1.00  0.00           C  
HETATM   14  C12 UNL     1      -0.833   0.982  -0.739  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.818   1.533   0.040  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.213   2.835  -0.148  1.00  0.00           C  
HETATM   17  C15 UNL     1      -1.588   3.584  -1.152  1.00  0.00           C  
HETATM   18  C16 UNL     1      -0.609   3.032  -1.926  1.00  0.00           C  
HETATM   19  N2  UNL     1      -0.272   1.755  -1.688  1.00  0.00           N  
HETATM   20  H1  UNL     1       4.507   0.484  -1.014  1.00  0.00           H  
HETATM   21  H2  UNL     1       3.939   2.087  -0.498  1.00  0.00           H  
HETATM   22  H3  UNL     1       5.161   1.130   0.516  1.00  0.00           H  
HETATM   23  H4  UNL     1       4.363  -0.554   1.946  1.00  0.00           H  
HETATM   24  H5  UNL     1       4.181  -1.455   0.444  1.00  0.00           H  
HETATM   25  H6  UNL     1       2.788  -1.366   1.664  1.00  0.00           H  
HETATM   26  H7  UNL     1       2.136   0.366  -1.285  1.00  0.00           H  
HETATM   27  H8  UNL     1       1.516   1.471  -0.048  1.00  0.00           H  
HETATM   28  H9  UNL     1       1.317  -1.530   0.243  1.00  0.00           H  
HETATM   29  H10 UNL     1       0.657  -0.290   1.366  1.00  0.00           H  
HETATM   30  H11 UNL     1      -0.074  -0.778  -1.579  1.00  0.00           H  
HETATM   31  H12 UNL     1      -2.013  -1.999  -1.972  1.00  0.00           H  
HETATM   32  H13 UNL     1      -3.776  -3.504  -1.213  1.00  0.00           H  
HETATM   33  H14 UNL     1      -2.918  -2.384   2.822  1.00  0.00           H  
HETATM   34  H15 UNL     1      -1.138  -0.873   2.016  1.00  0.00           H  
HETATM   35  H16 UNL     1      -2.277   0.938   0.792  1.00  0.00           H  
HETATM   36  H17 UNL     1      -2.969   3.314   0.425  1.00  0.00           H  
HETATM   37  H18 UNL     1      -1.868   4.624  -1.337  1.00  0.00           H  
HETATM   38  H19 UNL     1      -0.139   3.644  -2.700  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

HMDB0014549
     RDKit          3D
Dexbrompheniramine
 38 39  0  0  0  0  0  0  0  0999 V2000
    4.2178    1.0960   -0.0970 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1468    0.4046    0.5491 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5947   -0.8007    1.1487 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9691    0.4253   -0.2110 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8792   -0.4887    0.3017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3491   -0.4073   -0.5599 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4277   -1.3140   -0.0676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2084   -2.0788   -0.9049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2079   -2.9294   -0.4782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4504   -3.0271    0.8634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8321   -4.2148    1.4285 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.6959   -2.2772    1.7708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6986   -1.4363    1.2788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8328    0.9825   -0.7393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8178    1.5335    0.0400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2130    2.8351   -0.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5880    3.5844   -1.1524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6086    3.0324   -1.9260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2721    1.7551   -1.6877 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5068    0.4844   -1.0135 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9391    2.0874   -0.4980 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1609    1.1299    0.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3627   -0.5543    1.9456 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1813   -1.4548    0.4442 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7883   -1.3661    1.6638 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1361    0.3661   -1.2846 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5164    1.4712   -0.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3172   -1.5301    0.2431 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6573   -0.2900    1.3665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0736   -0.7779   -1.5786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0131   -1.9989   -1.9716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7759   -3.5039   -1.2130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9181   -2.3839    2.8222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1376   -0.8729    2.0164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2767    0.9379    0.7919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9686    3.3142    0.4247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8685    4.6236   -1.3370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1394    3.6435   -2.6999 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  6
  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
(+)-Brompheniraminum	ChEBI
(S)-(+)-Brompheniramine	ChEBI
(S)-Brompheniramine	ChEBI
D-Brompheniramine	ChEBI
Dexbromfeniramina	ChEBI
Dexbrompheniraminum	ChEBI
Parabromdylamine	HMDB
Parabromodylamine	HMDB
Disophrol	HMDB
Dexbrompheniramine maleate	HMDB

Chemical Formula

C₁₆H₁₉BrN₂

Average Molecular Weight

319.239

Monoisotopic Molecular Weight

318.073161265

IUPAC Name

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

Traditional Name

dexbrompheniramine

CAS Registry Number

132-21-8

SMILES

CN(C)CC[C@@H](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/t15-/m0/s1

InChI Key

ZDIGNSYAACHWNL-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
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

brompheniramine (CHEBI:59269 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014549)

Source

Exogenous

Exogenous (HMDB: HMDB0014549)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Dexbrompheniramine H1-Antihistamine Action (PathBank: SMP0057580)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.013 g/L	Not Available
LogP	3.4	Not Available

Experimental Chromatographic Properties

Not Available

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	31.84 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]+	167.222	30932474
DeepCCS	[M-H]-	164.864	30932474
DeepCCS	[M-2H]-	197.751	30932474
DeepCCS	[M+Na]+	173.316	30932474
AllCCS	[M+H]+	169.8	32859911
AllCCS	[M+H-H2O]+	166.2	32859911
AllCCS	[M+NH4]+	173.1	32859911
AllCCS	[M+Na]+	174.0	32859911
AllCCS	[M-H]-	171.0	32859911
AllCCS	[M+Na-2H]-	171.3	32859911
AllCCS	[M+HCOO]-	171.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dexbrompheniramine	CN(C)CC[C@@H](C1=CC=C(Br)C=C1)C1=CC=CC=N1	2993.0	Standard polar	33892256
Dexbrompheniramine	CN(C)CC[C@@H](C1=CC=C(Br)C=C1)C1=CC=CC=N1	2074.1	Standard non polar	33892256
Dexbrompheniramine	CN(C)CC[C@@H](C1=CC=C(Br)C=C1)C1=CC=CC=N1	2104.7	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 - Dexbrompheniramine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9050000000-d51445063b50de15bdcc	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dexbrompheniramine 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 - Dexbrompheniramine LC-ESI-qTof , Positive-QTOF	splash10-0292-0940000000-f369442eba5344b3ecb4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dexbrompheniramine , positive-QTOF	splash10-0292-0940000000-f369442eba5344b3ecb4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dexbrompheniramine 35V, Positive-QTOF	splash10-00di-0390000000-82ba7f6766f236ef3604	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexbrompheniramine 10V, Positive-QTOF	splash10-014i-0029000000-fa060b2610f05fd6963a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexbrompheniramine 20V, Positive-QTOF	splash10-01b9-0197000000-90a5b62f5a9e47f95802	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexbrompheniramine 40V, Positive-QTOF	splash10-0fef-3690000000-914dbc7e9fc6b1ce196a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexbrompheniramine 10V, Negative-QTOF	splash10-014i-0009000000-1bc9f3a3603646c31504	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexbrompheniramine 20V, Negative-QTOF	splash10-014i-1019000000-14a32020bd62ee6fb3b7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexbrompheniramine 40V, Negative-QTOF	splash10-0fi4-7591000000-cd391d2ec4970c9e8b8a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexbrompheniramine 10V, Negative-QTOF	splash10-014i-0009000000-615031c9863c28108e0f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexbrompheniramine 20V, Negative-QTOF	splash10-016r-6369000000-b40c997a38a0f9eb2fdb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexbrompheniramine 40V, Negative-QTOF	splash10-004j-9480000000-6c5bc7bd482fbd292a0c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexbrompheniramine 10V, Positive-QTOF	splash10-00di-0094000000-c8e61a4d45703ee2c906	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexbrompheniramine 20V, Positive-QTOF	splash10-00di-0090000000-363f1320fc00a31daef8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexbrompheniramine 40V, Positive-QTOF	splash10-006t-1290000000-3b9b35511af51a9e3bb5	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

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

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00405	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00405	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00405

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

16068

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dexbrompheniramine

METLIN ID

Not Available

PubChem Compound

16960

PDB ID

Not Available

ChEBI ID

59269

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

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

References

McLeod RL, Mingo G, O'Reilly S, Ruck LA, Bolser DC, Hey JA: Antitussive action of antihistamines is independent of sedative and ventilation activity in the guinea pig. Pharmacology. 1998 Aug;57(2):57-64. [PubMed:9691225 ]
Bokesoy TA, Onaran HO: Atypical Schild plots with histamine H1 receptor agonists and antagonists in the rabbit aorta. Eur J Pharmacol. 1991 May 2;197(1):49-56. [PubMed:1680053 ]
Onaran HO, Bokesoy TA: Kinetics of antagonism at histamine-H1 receptors in isolated rabbit arteries. Naunyn Schmiedebergs Arch Pharmacol. 1990 Apr;341(4):316-23. [PubMed:1970615 ]
Yanni JM, Stephens DJ, Parnell DW, Spellman JM: Preclinical efficacy of emedastine, a potent, selective histamine H1 antagonist for topical ocular use. J Ocul Pharmacol. 1994 Winter;10(4):665-75. [PubMed:7714410 ]
Sadofsky LR, Campi B, Trevisani M, Compton SJ, Morice AH: Transient receptor potential vanilloid-1-mediated calcium responses are inhibited by the alkylamine antihistamines dexbrompheniramine and chlorpheniramine. Exp Lung Res. 2008 Dec;34(10):681-93. doi: 10.1080/01902140802339623. [PubMed:19085565 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Showing metabocard for Dexbrompheniramine (HMDB0014549)

MOL for HMDB0014549 (Dexbrompheniramine)

3D MOL for HMDB0014549 (Dexbrompheniramine)

3D SDF for HMDB0014549 (Dexbrompheniramine)

3D-SDF for HMDB0014549 (Dexbrompheniramine)

PDB for HMDB0014549 (Dexbrompheniramine)

3D PDB for HMDB0014549 (Dexbrompheniramine)

SMILES for HMDB0014549 (Dexbrompheniramine)

INCHI for HMDB0014549 (Dexbrompheniramine)

Structure for HMDB0014549 (Dexbrompheniramine)

3D Structure for HMDB0014549 (Dexbrompheniramine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References