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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

enzymes (1) Show 1 protein

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:01 UTC

HMDB ID

HMDB0015557

Secondary Accession Numbers

HMDB15557

Metabolite Identification

Common Name

Pheniramine

Description

Pheniramine is only found in individuals that have used or taken this drug. It is one of the histamine H1 antagonists with little sedative action. It is used in treatment of hay fever, rhinitis, allergic dermatoses, and pruritus. [PubChem]Antihistamines such as pheniramine appear to compete with histamine for histamine H1- receptor sites on effector cells. The antihistamines antagonize those pharmacological effects of histamine which are mediated through activation of H1- receptor sites and thereby reduce the intensity of allergic reactions and tissue injury response involving histamine release. Antihistamines suppress the histamine-induced wheal (swelling) and flare (vasodilation) response by blocking the binding of histamine to its receptors on nerves, vascular smooth muscle, glandular cells, endothelium, and mast cells. They effectively exert competitive antagonism of histamine for H1-receptors.

Structure

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

HMDB0015557
     RDKit          3D
Pheniramine
 38 39  0  0  0  0  0  0  0  0999 V2000
    2.9880   -2.8530    1.2518 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4802   -1.5343    1.2965 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3949   -0.5037    1.6045 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4944   -1.2187    0.3117 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9845    0.1928    0.3982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0548    0.3966   -0.7015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2049   -0.5332   -0.5656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7450   -0.8765    0.6393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8263   -1.7545    0.7132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3489   -2.2759   -0.4426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8286   -1.9505   -1.6694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7556   -1.0761   -1.7036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4911    1.8002   -0.8284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6881    2.5584    0.2938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0936    3.8695    0.2078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3034    4.4225   -1.0344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1020    3.6504   -2.1465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7023    2.3622   -2.0263 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9346   -2.9385    1.8039 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2566   -3.6402    1.5479 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2449   -3.0861    0.1776 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2680   -0.9504    2.1383 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0114    0.2924    2.2693 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8120   -0.0910    0.6536 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6151   -1.8910    0.3834 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9564   -1.3652   -0.6867 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4624    0.3820    1.3562 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7577    0.9497    0.2552 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4807    0.1124   -1.6629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3588   -0.4843    1.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2276   -2.0033    1.6858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1973   -2.9680   -0.4247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2038   -2.3338   -2.6092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3391   -0.8154   -2.6841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5292    2.1440    1.3023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2555    4.4880    1.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6292    5.4725   -1.1337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2569    4.0502   -3.1452 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
 11 12  2  0
  6 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 12  7  1  0
 18 13  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 12 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
M  END

1620
  Mrv0541 02231215362D          

 18 19  0  0  1  0            999 V2000
    2.3645    1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    2.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  1 11  1  0  0  0  0
  1 12  1  0  0  0  0
  2  7  1  0  0  0  0
  2 17  2  0  0  0  0
  3  4  1  0  0  0  0
  3  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  5  1  0  0  0  0
  6  8  2  0  0  0  0
  6  9  1  0  0  0  0
  7 10  2  0  0  0  0
  8 13  1  0  0  0  0
  9 14  2  0  0  0  0
 10 15  1  0  0  0  0
 13 16  2  0  0  0  0
 14 16  1  0  0  0  0
 15 18  2  0  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015557

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H20N2/c1-18(2)13-11-15(14-8-4-3-5-9-14)16-10-6-7-12-17-16/h3-10,12,15H,11,13H2,1-2H3

> <INCHI_KEY>
IJHNSHDBIRRJRN-UHFFFAOYSA-N

> <FORMULA>
C16H20N2

> <MOLECULAR_WEIGHT>
240.3434

> <EXACT_MASS>
240.16264865

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
28.409848442993137

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
dimethyl[3-phenyl-3-(pyridin-2-yl)propyl]amine

> <ALOGPS_LOGP>
2.85

> <JCHEM_LOGP>
2.9809062386666665

> <ALOGPS_LOGS>
-2.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.484963287532704

> <JCHEM_POLAR_SURFACE_AREA>
16.130000000000003

> <JCHEM_REFRACTIVITY>
76.04550000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.77e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pheniramine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0015557
     RDKit          3D
Pheniramine
 38 39  0  0  0  0  0  0  0  0999 V2000
    2.9880   -2.8530    1.2518 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4802   -1.5343    1.2965 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3949   -0.5037    1.6045 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4944   -1.2187    0.3117 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9845    0.1928    0.3982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0548    0.3966   -0.7015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2049   -0.5332   -0.5656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7450   -0.8765    0.6393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8263   -1.7545    0.7132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3489   -2.2759   -0.4426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8286   -1.9505   -1.6694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7556   -1.0761   -1.7036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4911    1.8002   -0.8284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6881    2.5584    0.2938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0936    3.8695    0.2078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3034    4.4225   -1.0344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1020    3.6504   -2.1465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7023    2.3622   -2.0263 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9346   -2.9385    1.8039 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2566   -3.6402    1.5479 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2449   -3.0861    0.1776 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2680   -0.9504    2.1383 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0114    0.2924    2.2693 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8120   -0.0910    0.6536 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6151   -1.8910    0.3834 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9564   -1.3652   -0.6867 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4624    0.3820    1.3562 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7577    0.9497    0.2552 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4807    0.1124   -1.6629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3588   -0.4843    1.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2276   -2.0033    1.6858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1973   -2.9680   -0.4247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2038   -2.3338   -2.6092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3391   -0.8154   -2.6841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5292    2.1440    1.3023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2555    4.4880    1.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6292    5.4725   -1.1337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2569    4.0502   -3.1452 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
 11 12  2  0
  6 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 12  7  1  0
 18 13  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 12 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1620                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0       4.414   3.080   0.000  0.00  0.00           N+0
HETATM    2  N   UNK     0       9.748   0.000   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       7.081   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.748   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.748   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.081  -1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.415   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.415  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.748  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.415   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.080   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.415  -3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.748  -3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.748   3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.081  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.082   0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.082   2.310   0.000  0.00  0.00           C+0
CONECT    1    5   11   12                                                  
CONECT    2    7   17                                                       
CONECT    3    4    6    7                                                  
CONECT    4    3    5                                                       
CONECT    5    1    4                                                       
CONECT    6    3    8    9                                                  
CONECT    7    2    3   10                                                  
CONECT    8    6   13                                                       
CONECT    9    6   14                                                       
CONECT   10    7   15                                                       
CONECT   11    1                                                            
CONECT   12    1                                                            
CONECT   13    8   16                                                       
CONECT   14    9   16                                                       
CONECT   15   10   18                                                       
CONECT   16   13   14                                                       
CONECT   17    2   18                                                       
CONECT   18   15   17                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0015557
HETATM    1  C1  UNL     1       2.988  -2.853   1.252  1.00  0.00           C  
HETATM    2  N1  UNL     1       2.480  -1.534   1.297  1.00  0.00           N  
HETATM    3  C2  UNL     1       3.395  -0.504   1.605  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.494  -1.219   0.312  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.985   0.193   0.398  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.055   0.397  -0.701  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.205  -0.533  -0.566  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.745  -0.876   0.639  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.826  -1.754   0.713  1.00  0.00           C  
HETATM   10  C9  UNL     1      -3.349  -2.276  -0.443  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.829  -1.950  -1.669  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.756  -1.076  -1.704  1.00  0.00           C  
HETATM   13  C12 UNL     1      -0.491   1.800  -0.828  1.00  0.00           C  
HETATM   14  C13 UNL     1      -0.688   2.558   0.294  1.00  0.00           C  
HETATM   15  C14 UNL     1      -1.094   3.869   0.208  1.00  0.00           C  
HETATM   16  C15 UNL     1      -1.303   4.422  -1.034  1.00  0.00           C  
HETATM   17  C16 UNL     1      -1.102   3.650  -2.147  1.00  0.00           C  
HETATM   18  N2  UNL     1      -0.702   2.362  -2.026  1.00  0.00           N  
HETATM   19  H1  UNL     1       3.935  -2.939   1.804  1.00  0.00           H  
HETATM   20  H2  UNL     1       2.257  -3.640   1.548  1.00  0.00           H  
HETATM   21  H3  UNL     1       3.245  -3.086   0.178  1.00  0.00           H  
HETATM   22  H4  UNL     1       4.268  -0.950   2.138  1.00  0.00           H  
HETATM   23  H5  UNL     1       3.011   0.292   2.269  1.00  0.00           H  
HETATM   24  H6  UNL     1       3.812  -0.091   0.654  1.00  0.00           H  
HETATM   25  H7  UNL     1       0.615  -1.891   0.383  1.00  0.00           H  
HETATM   26  H8  UNL     1       1.956  -1.365  -0.687  1.00  0.00           H  
HETATM   27  H9  UNL     1       0.462   0.382   1.356  1.00  0.00           H  
HETATM   28  H10 UNL     1       1.758   0.950   0.255  1.00  0.00           H  
HETATM   29  H11 UNL     1       0.481   0.112  -1.663  1.00  0.00           H  
HETATM   30  H12 UNL     1      -1.359  -0.484   1.569  1.00  0.00           H  
HETATM   31  H13 UNL     1      -3.228  -2.003   1.686  1.00  0.00           H  
HETATM   32  H14 UNL     1      -4.197  -2.968  -0.425  1.00  0.00           H  
HETATM   33  H15 UNL     1      -3.204  -2.334  -2.609  1.00  0.00           H  
HETATM   34  H16 UNL     1      -1.339  -0.815  -2.684  1.00  0.00           H  
HETATM   35  H17 UNL     1      -0.529   2.144   1.302  1.00  0.00           H  
HETATM   36  H18 UNL     1      -1.255   4.488   1.083  1.00  0.00           H  
HETATM   37  H19 UNL     1      -1.629   5.473  -1.134  1.00  0.00           H  
HETATM   38  H20 UNL     1      -1.257   4.050  -3.145  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    4
CONECT    3   22   23   24
CONECT    4    5   25   26
CONECT    5    6   27   28
CONECT    6    7   13   29
CONECT    7    8    8   12
CONECT    8    9   30
CONECT    9   10   10   31
CONECT   10   11   32
CONECT   11   12   12   33
CONECT   12   34
CONECT   13   14   14   18
CONECT   14   15   35
CONECT   15   16   16   36
CONECT   16   17   37
CONECT   17   18   18   38
END

HMDB0015557
     RDKit          3D
Pheniramine
 38 39  0  0  0  0  0  0  0  0999 V2000
    2.9880   -2.8530    1.2518 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4802   -1.5343    1.2965 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3949   -0.5037    1.6045 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4944   -1.2187    0.3117 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9845    0.1928    0.3982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0548    0.3966   -0.7015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2049   -0.5332   -0.5656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7450   -0.8765    0.6393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8263   -1.7545    0.7132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3489   -2.2759   -0.4426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8286   -1.9505   -1.6694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7556   -1.0761   -1.7036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4911    1.8002   -0.8284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6881    2.5584    0.2938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0936    3.8695    0.2078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3034    4.4225   -1.0344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1020    3.6504   -2.1465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7023    2.3622   -2.0263 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9346   -2.9385    1.8039 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2566   -3.6402    1.5479 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2449   -3.0861    0.1776 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2680   -0.9504    2.1383 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0114    0.2924    2.2693 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8120   -0.0910    0.6536 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6151   -1.8910    0.3834 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9564   -1.3652   -0.6867 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4624    0.3820    1.3562 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7577    0.9497    0.2552 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4807    0.1124   -1.6629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3588   -0.4843    1.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2276   -2.0033    1.6858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1973   -2.9680   -0.4247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2038   -2.3338   -2.6092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3391   -0.8154   -2.6841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5292    2.1440    1.3023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2555    4.4880    1.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6292    5.4725   -1.1337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2569    4.0502   -3.1452 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
 11 12  2  0
  6 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 12  7  1  0
 18 13  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 12 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Feniramine	HMDB
Propheniramine	HMDB
Prophenpyridamine	HMDB
Histapyridamine	HMDB
Pheniramine bimaleate	HMDB
Aventis brand OF pheniramine maleate	HMDB
Avil	HMDB
Maleate, pheniramine	HMDB
Pheniramine maleate	HMDB
Bimaleate, pheniramine	HMDB
Daneral	HMDB

Chemical Formula

C₁₆H₂₀N₂

Average Molecular Weight

240.3434

Monoisotopic Molecular Weight

240.16264865

IUPAC Name

dimethyl[3-phenyl-3-(pyridin-2-yl)propyl]amine

Traditional Name

pheniramine

CAS Registry Number

86-21-5

SMILES

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

InChI Identifier

InChI=1S/C16H20N2/c1-18(2)13-11-15(14-8-4-3-5-9-14)16-10-6-7-12-17-16/h3-10,12,15H,11,13H2,1-2H3

InChI Key

IJHNSHDBIRRJRN-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
Aralkylamine
Benzenoid
Monocyclic benzene moiety
Heteroaromatic compound
Tertiary aliphatic amine
Tertiary amine
Azacycle
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015557)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Pheniramine H1-Antihistamine Action (PathBank: SMP0056662)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	< 25 °C	Not Available
Boiling Point	175.00 °C. @ 25.00 mm Hg	The Good Scents Company Information System
Water Solubility	0.38 g/L	Not Available
LogP	1.110 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	155.057	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000951

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.38 g/L	ALOGPS
logP	2.85	ALOGPS
logP	2.98	ChemAxon
logS	-2.8	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	76.05 m³·mol⁻¹	ChemAxon
Polarizability	28.41 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
DarkChem	[M+H]+	158.326	31661259
DarkChem	[M-H]-	158.151	31661259
DeepCCS	[M+H]+	152.224	30932474
DeepCCS	[M-H]-	149.866	30932474
DeepCCS	[M-2H]-	182.972	30932474
DeepCCS	[M+Na]+	158.317	30932474
AllCCS	[M+H]+	155.0	32859911
AllCCS	[M+H-H2O]+	151.0	32859911
AllCCS	[M+NH4]+	158.8	32859911
AllCCS	[M+Na]+	159.9	32859911
AllCCS	[M-H]-	163.6	32859911
AllCCS	[M+Na-2H]-	163.7	32859911
AllCCS	[M+HCOO]-	163.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Pheniramine	CN(C)CCC(C1=CC=CC=C1)C1=CC=CC=N1	2588.7	Standard polar	33892256
Pheniramine	CN(C)CCC(C1=CC=CC=C1)C1=CC=CC=N1	1843.7	Standard non polar	33892256
Pheniramine	CN(C)CCC(C1=CC=CC=C1)C1=CC=CC=N1	1796.7	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 - Pheniramine GC-MS (Non-derivatized) - 70eV, Positive	splash10-066r-7910000000-96eb6f4bb716d4764770	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pheniramine 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 - Pheniramine LC-ESI-QFT , positive-QTOF	splash10-0002-0920000000-fd728bb396d025cac3f0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pheniramine LC-ESI-QFT , positive-QTOF	splash10-0002-0900000000-7af6ac1b513c7f2f33a9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pheniramine LC-ESI-QFT , positive-QTOF	splash10-0002-0900000000-ea7e67a76460b33d8306	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pheniramine LC-ESI-QFT , positive-QTOF	splash10-0002-0900000000-f5daabe4b8aedf8605e6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pheniramine LC-ESI-QFT , positive-QTOF	splash10-014j-0900000000-4ccd8055b59ae6eabc90	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pheniramine LC-ESI-QFT , positive-QTOF	splash10-014i-1900000000-deb31ec7e47ca6a0e3ff	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pheniramine LC-ESI-QFT , positive-QTOF	splash10-014i-1900000000-add8b8849c3db116e181	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pheniramine LC-ESI-QFT , positive-QTOF	splash10-014i-2900000000-c38a45f14fb4ab5b1687	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pheniramine LC-ESI-QFT , positive-QTOF	splash10-014r-3900000000-1f2c04e07e8c46a0c722	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pheniramine LC-ESI-QFT , positive-QTOF	splash10-0002-0910000000-549410c48d9c44650beb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pheniramine LC-ESI-QFT , positive-QTOF	splash10-0002-0900000000-669fdf1a00514df13bf2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pheniramine LC-ESI-QFT , positive-QTOF	splash10-0002-0900000000-59e6f9e272a364ed620a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pheniramine LC-ESI-QFT , positive-QTOF	splash10-0002-0900000000-a9b1b534a7a36bdaf014	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pheniramine LC-ESI-QFT , positive-QTOF	splash10-014i-0900000000-0d3c0ba161b03c4cc7d5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pheniramine 60V, Positive-QTOF	splash10-0002-0900000000-b8fac5c4ad178dbca8f1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pheniramine 75V, Positive-QTOF	splash10-014j-0900000000-8c102cbdd49b481d0627	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pheniramine 30V, Positive-QTOF	splash10-0002-0900000000-7af6ac1b513c7f2f33a9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pheniramine 45V, Positive-QTOF	splash10-0002-0900000000-af33f4c17bcc16d14b33	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pheniramine 15V, Positive-QTOF	splash10-0002-0920000000-fd728bb396d025cac3f0	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pheniramine 10V, Positive-QTOF	splash10-0006-0190000000-7366bfe1512ab11f5f47	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pheniramine 20V, Positive-QTOF	splash10-0007-0980000000-33028cde378f5ae398e2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pheniramine 40V, Positive-QTOF	splash10-01ba-3910000000-38e90d8ee368fe03cf5d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pheniramine 10V, Negative-QTOF	splash10-000i-0090000000-3a929a14b25a39d76c95	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pheniramine 20V, Negative-QTOF	splash10-000i-1090000000-f70051070830e7002817	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pheniramine 40V, Negative-QTOF	splash10-004i-8920000000-20990e9f1eda4700b6ce	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Pheniramine 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 DB01620	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01620	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01620

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4597

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Pheniramine

METLIN ID

Not Available

PubChem Compound

4761

PDB ID

Not Available

ChEBI ID

308661

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1584301

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

Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Leurs R, Bast A, Timmerman H: High affinity, saturable [3H]mepyramine binding sites on rat liver plasma membrane do not represent histamine H1-receptors. A warning. Biochem Pharmacol. 1989 Jul 1;38(13):2175-80. [PubMed:2567596 ]
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 ]
Nath C, Gupta MB: Role of central histaminergic system in lorazepam withdrawal syndrome in rats. Pharmacol Biochem Behav. 2001 Apr;68(4):777-82. [PubMed:11526976 ]
Karadag CH, Ulugol A, Dokmeci D, Dokmeci I: The role of histamine H1-receptors in the anticonvulsive effect of morphine against maximal electroconvulsive shock in mice. Jpn J Pharmacol. 1996 Jun;71(2):109-12. [PubMed:8835636 ]
Nosal R, Drabikova K, Jancinova V, Moravcova J, Lojek A, Ciz M, Macickova T, Pecivova J: H1-antihistamines and oxidative burst of professional phagocytes. Neuro Endocrinol Lett. 2009;30 Suppl 1:133-6. [PubMed:20027159 ]
Gepdiremen A, Buyukokuroglu ME, Hacimuftuoglu A, Suleyman H: Contribution of the histaminergic receptor subtypes to histamine-induced cerebellar granular neurotoxicity. Pol J Pharmacol. 2003 May-Jun;55(3):383-8. [PubMed:14506317 ]
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 Pheniramine (HMDB0015557)

MOL for HMDB0015557 (Pheniramine)

3D MOL for HMDB0015557 (Pheniramine)

3D SDF for HMDB0015557 (Pheniramine)

3D-SDF for HMDB0015557 (Pheniramine)

PDB for HMDB0015557 (Pheniramine)

3D PDB for HMDB0015557 (Pheniramine)

SMILES for HMDB0015557 (Pheniramine)

INCHI for HMDB0015557 (Pheniramine)

Structure for HMDB0015557 (Pheniramine)

3D Structure for HMDB0015557 (Pheniramine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References