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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2006-05-18 09:00:56 UTC

Update Date

2022-09-22 18:34:16 UTC

HMDB ID

HMDB0001936

Secondary Accession Numbers

HMDB01936

Metabolite Identification

Common Name

Doxylamine

Description

Doxylamine is a sedating antihistamine that can be used by itself as a short-term sleep aid, in combination with other drugs as a night-time cold and allergy relief. It is a member of the ethanolamine class of antihistamines and has anti-allergy power superior to almost every other antihistamine on the market, with the exception of diphenhydramine (Benadryl). It is also the most effective over-the-counter sedative available in North America, and more sedating than some prescription hypnotics. In a study, it was found that doxylamine succinate is possibly more effective than the barbiturate, phenobarbital for use as a sedative. For this reason, doxylamine has sometimes been used off label in a manner similar to diphenhydramine for the reduction of anxiety symptoms; Doxylamine succinate is used by itself as a short-term sleep aid, in combination with other drugs as a night-time cold and allergy relief drug, and a preparation is prescribed in combination with Vitamin B6 (pyridoxine) to prevent morning sickness in pregnant women. In Commonwealth countries, doxylamine is available prepared with paracetamol/acetaminophen and codeine under the brand name Syndol or Mersyndol, as treatment for tension headache and other types of pain, or as a general OTC sleep-aid branded as Somnil, Donormyl, DSozile and Restavit containing Doxylamine Succinate only.

Structure

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

HMDB0001936
     RDKit          3D
Doxylamine
 42 43  0  0  0  0  0  0  0  0999 V2000
    4.7552    0.3217    1.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7470   -0.4151    0.6828 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2783   -0.7786   -0.5892 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5578    0.3594    0.6616 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4104   -0.2909   -0.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3462    0.5568   -0.0179 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8247    0.1326   -0.6298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5613   -0.0997   -2.1221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7751    1.2556   -0.4809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7333    2.0100    0.6600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6017    3.0605    0.8475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5267    3.3650   -0.1172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5968    2.6340   -1.2681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7016    1.5696   -1.4344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3418   -1.1253   -0.0626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6067   -1.2724    1.2833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0969   -2.4755    1.7937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3229   -3.5379    0.9479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0466   -3.3528   -0.3879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5789   -2.1901   -0.8418 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6607   -0.2794    1.6248 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0185    1.2787    0.9214 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2704    0.6096    2.4008 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2516   -1.3165   -0.3877 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6669   -1.4870   -1.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5235    0.0947   -1.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2436    0.5697    1.6890 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7718    1.3233    0.1371 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2416   -1.3200    0.2345 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7488   -0.3333   -1.1585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5270   -0.5307   -2.5208 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1542   -0.9534   -2.2273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2437    0.8136   -2.6228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9987    1.7948    1.4576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5283    3.6283    1.7691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2158    4.2037    0.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3331    2.8846   -2.0241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7994    1.0251   -2.3609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4526   -0.4838    1.9983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3021   -2.5765    2.8626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7071   -4.4876    1.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2235   -4.1852   -1.0512 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  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  7 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 14  9  1  0
 20 15  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  8 31  1  0
  8 32  1  0
  8 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 13 37  1  0
 14 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
M  END

3162
  Mrv1652305271900102D          

 20 21  0  0  1  0            999 V2000
    3.3001    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9501   -1.4289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7126   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5376   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7606    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7606   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7606    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7606   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751    2.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7751   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5376   -2.1435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751   -2.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  1  8  1  0  0  0  0
  2  9  1  0  0  0  0
  2 17  1  0  0  0  0
  2 18  1  0  0  0  0
  3  6  1  0  0  0  0
  3 19  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4  7  1  0  0  0  0
  5 10  2  0  0  0  0
  5 11  1  0  0  0  0
  6 12  2  0  0  0  0
  8  9  1  0  0  0  0
 10 13  1  0  0  0  0
 11 14  2  0  0  0  0
 12 15  1  0  0  0  0
 13 16  2  0  0  0  0
 14 16  1  0  0  0  0
 15 20  2  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001936

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H22N2O/c1-17(20-14-13-19(2)3,15-9-5-4-6-10-15)16-11-7-8-12-18-16/h4-12H,13-14H2,1-3H3

> <INCHI_KEY>
HCFDWZZGGLSKEP-UHFFFAOYSA-N

> <FORMULA>
C17H22N2O

> <MOLECULAR_WEIGHT>
270.3694

> <EXACT_MASS>
270.173213336

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
31.090987575298218

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
dimethyl({2-[1-phenyl-1-(pyridin-2-yl)ethoxy]ethyl})amine

> <ALOGPS_LOGP>
2.90

> <JCHEM_LOGP>
2.9619422236666666

> <ALOGPS_LOGS>
-2.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.866417098578472

> <JCHEM_POLAR_SURFACE_AREA>
25.36

> <JCHEM_REFRACTIVITY>
82.23730000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.41e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
doxylamine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0001936
     RDKit          3D
Doxylamine
 42 43  0  0  0  0  0  0  0  0999 V2000
    4.7552    0.3217    1.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7470   -0.4151    0.6828 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2783   -0.7786   -0.5892 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5578    0.3594    0.6616 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4104   -0.2909   -0.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3462    0.5568   -0.0179 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8247    0.1326   -0.6298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5613   -0.0997   -2.1221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7751    1.2556   -0.4809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7333    2.0100    0.6600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6017    3.0605    0.8475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5267    3.3650   -0.1172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5968    2.6340   -1.2681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7016    1.5696   -1.4344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3418   -1.1253   -0.0626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6067   -1.2724    1.2833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0969   -2.4755    1.7937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3229   -3.5379    0.9479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0466   -3.3528   -0.3879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5789   -2.1901   -0.8418 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6607   -0.2794    1.6248 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0185    1.2787    0.9214 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2704    0.6096    2.4008 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2516   -1.3165   -0.3877 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6669   -1.4870   -1.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5235    0.0947   -1.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2436    0.5697    1.6890 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7718    1.3233    0.1371 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2416   -1.3200    0.2345 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7488   -0.3333   -1.1585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5270   -0.5307   -2.5208 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1542   -0.9534   -2.2273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2437    0.8136   -2.6228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9987    1.7948    1.4576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5283    3.6283    1.7691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2158    4.2037    0.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3331    2.8846   -2.0241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7994    1.0251   -2.3609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4526   -0.4838    1.9983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3021   -2.5765    2.8626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7071   -4.4876    1.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2235   -4.1852   -1.0512 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  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  7 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 14  9  1  0
 20 15  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  8 31  1  0
  8 32  1  0
  8 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 13 37  1  0
 14 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 3162                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0       6.160   0.000   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       9.240  -2.667   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       5.954  -2.310   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       4.620   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.620   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.620  -1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.080   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.930  -1.334   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.470  -1.334   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.286   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.954   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.286  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.286   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.954   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.286  -3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.620   4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.780  -2.667   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.470  -4.001   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.954  -3.850   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.620  -4.620   0.000  0.00  0.00           C+0
CONECT    1    4    8                                                       
CONECT    2    9   17   18                                                  
CONECT    3    6   19                                                       
CONECT    4    1    5    6    7                                             
CONECT    5    4   10   11                                                  
CONECT    6    3    4   12                                                  
CONECT    7    4                                                            
CONECT    8    1    9                                                       
CONECT    9    2    8                                                       
CONECT   10    5   13                                                       
CONECT   11    5   14                                                       
CONECT   12    6   15                                                       
CONECT   13   10   16                                                       
CONECT   14   11   16                                                       
CONECT   15   12   20                                                       
CONECT   16   13   14                                                       
CONECT   17    2                                                            
CONECT   18    2                                                            
CONECT   19    3   20                                                       
CONECT   20   15   19                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0001936
HETATM    1  C1  UNL     1       4.755   0.322   1.422  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.747  -0.415   0.683  1.00  0.00           N  
HETATM    3  C2  UNL     1       4.278  -0.779  -0.589  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.558   0.359   0.662  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.410  -0.291  -0.080  1.00  0.00           C  
HETATM    6  O1  UNL     1       0.346   0.557  -0.018  1.00  0.00           O  
HETATM    7  C5  UNL     1      -0.825   0.133  -0.630  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.561  -0.100  -2.122  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.775   1.256  -0.481  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.733   2.010   0.660  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.602   3.061   0.847  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.527   3.365  -0.117  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.597   2.634  -1.268  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.702   1.570  -1.434  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.342  -1.125  -0.063  1.00  0.00           C  
HETATM   16  C14 UNL     1      -1.607  -1.272   1.283  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.097  -2.475   1.794  1.00  0.00           C  
HETATM   18  C16 UNL     1      -2.323  -3.538   0.948  1.00  0.00           C  
HETATM   19  C17 UNL     1      -2.047  -3.353  -0.388  1.00  0.00           C  
HETATM   20  N2  UNL     1      -1.579  -2.190  -0.842  1.00  0.00           N  
HETATM   21  H1  UNL     1       5.661  -0.279   1.625  1.00  0.00           H  
HETATM   22  H2  UNL     1       5.019   1.279   0.921  1.00  0.00           H  
HETATM   23  H3  UNL     1       4.270   0.610   2.401  1.00  0.00           H  
HETATM   24  H4  UNL     1       5.252  -1.317  -0.388  1.00  0.00           H  
HETATM   25  H5  UNL     1       3.667  -1.487  -1.159  1.00  0.00           H  
HETATM   26  H6  UNL     1       4.523   0.095  -1.222  1.00  0.00           H  
HETATM   27  H7  UNL     1       2.244   0.570   1.689  1.00  0.00           H  
HETATM   28  H8  UNL     1       2.772   1.323   0.137  1.00  0.00           H  
HETATM   29  H9  UNL     1       1.242  -1.320   0.235  1.00  0.00           H  
HETATM   30  H10 UNL     1       1.749  -0.333  -1.158  1.00  0.00           H  
HETATM   31  H11 UNL     1      -1.527  -0.531  -2.521  1.00  0.00           H  
HETATM   32  H12 UNL     1       0.154  -0.953  -2.227  1.00  0.00           H  
HETATM   33  H13 UNL     1      -0.244   0.814  -2.623  1.00  0.00           H  
HETATM   34  H14 UNL     1      -0.999   1.795   1.458  1.00  0.00           H  
HETATM   35  H15 UNL     1      -2.528   3.628   1.769  1.00  0.00           H  
HETATM   36  H16 UNL     1      -4.216   4.204   0.039  1.00  0.00           H  
HETATM   37  H17 UNL     1      -4.333   2.885  -2.024  1.00  0.00           H  
HETATM   38  H18 UNL     1      -2.799   1.025  -2.361  1.00  0.00           H  
HETATM   39  H19 UNL     1      -1.453  -0.484   1.998  1.00  0.00           H  
HETATM   40  H20 UNL     1      -2.302  -2.576   2.863  1.00  0.00           H  
HETATM   41  H21 UNL     1      -2.707  -4.488   1.333  1.00  0.00           H  
HETATM   42  H22 UNL     1      -2.224  -4.185  -1.051  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3    4
CONECT    3   24   25   26
CONECT    4    5   27   28
CONECT    5    6   29   30
CONECT    6    7
CONECT    7    8    9   15
CONECT    8   31   32   33
CONECT    9   10   10   14
CONECT   10   11   34
CONECT   11   12   12   35
CONECT   12   13   36
CONECT   13   14   14   37
CONECT   14   38
CONECT   15   16   16   20
CONECT   16   17   39
CONECT   17   18   18   40
CONECT   18   19   41
CONECT   19   20   20   42
END

HMDB0001936
     RDKit          3D
Doxylamine
 42 43  0  0  0  0  0  0  0  0999 V2000
    4.7552    0.3217    1.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7470   -0.4151    0.6828 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2783   -0.7786   -0.5892 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5578    0.3594    0.6616 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4104   -0.2909   -0.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3462    0.5568   -0.0179 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8247    0.1326   -0.6298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5613   -0.0997   -2.1221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7751    1.2556   -0.4809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7333    2.0100    0.6600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6017    3.0605    0.8475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5267    3.3650   -0.1172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5968    2.6340   -1.2681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7016    1.5696   -1.4344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3418   -1.1253   -0.0626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6067   -1.2724    1.2833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0969   -2.4755    1.7937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3229   -3.5379    0.9479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0466   -3.3528   -0.3879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5789   -2.1901   -0.8418 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6607   -0.2794    1.6248 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0185    1.2787    0.9214 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2704    0.6096    2.4008 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2516   -1.3165   -0.3877 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6669   -1.4870   -1.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5235    0.0947   -1.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2436    0.5697    1.6890 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7718    1.3233    0.1371 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2416   -1.3200    0.2345 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7488   -0.3333   -1.1585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5270   -0.5307   -2.5208 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1542   -0.9534   -2.2273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2437    0.8136   -2.6228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9987    1.7948    1.4576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5283    3.6283    1.7691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2158    4.2037    0.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3331    2.8846   -2.0241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7994    1.0251   -2.3609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4526   -0.4838    1.9983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3021   -2.5765    2.8626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7071   -4.4876    1.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2235   -4.1852   -1.0512 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  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  7 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 14  9  1  0
 20 15  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  8 31  1  0
  8 32  1  0
  8 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 13 37  1  0
 14 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(alpha-(2-(Dimethylamino)ethoxy)-alpha-methylbenzyl)pyridine	ChEBI
2-Dimethylaminoethoxyphenylmethyl-2-picoline	ChEBI
Dossilamina	ChEBI
Doxilamina	ChEBI
Doxilminio	ChEBI
Doxylaminum	ChEBI
N,N-Dimethyl-2-(1-phenyl-1-(2-pyridinyl)ethoxy)ethanamine	ChEBI
Phenyl-2-pyridylmethyl-beta-N,N-dimethylaminoethyl ether	ChEBI
2-(a-(2-(Dimethylamino)ethoxy)-a-methylbenzyl)pyridine	Generator
2-(Α-(2-(dimethylamino)ethoxy)-α-methylbenzyl)pyridine	Generator
Phenyl-2-pyridylmethyl-b-N,N-dimethylaminoethyl ether	Generator
Phenyl-2-pyridylmethyl-β-N,N-dimethylaminoethyl ether	Generator
Doxylamine hydrogen succinate	HMDB
Alsadorm	HMDB
Decapryn	HMDB
Decapryn succinate	HMDB
Doxylamine succinate	HMDB
Doxylamine succinate (1:1)	HMDB
Mereprine	HMDB

Chemical Formula

C₁₇H₂₂N₂O

Average Molecular Weight

270.3694

Monoisotopic Molecular Weight

270.173213336

IUPAC Name

dimethyl({2-[1-phenyl-1-(pyridin-2-yl)ethoxy]ethyl})amine

Traditional Name

doxylamine

CAS Registry Number

562-10-7

SMILES

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

InChI Identifier

InChI=1S/C17H22N2O/c1-17(20-14-13-19(2)3,15-9-5-4-6-10-15)16-11-7-8-12-18-16/h4-12H,13-14H2,1-3H3

InChI Key

HCFDWZZGGLSKEP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzylethers. These are aromatic ethers with the general formula ROCR' (R = alkyl, aryl; R'=benzene).

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzylethers

Direct Parent

Benzylethers

Alternative Parents

Substituents

Benzylether
Pyridine
Heteroaromatic compound
Tertiary amine
Tertiary aliphatic amine
Azacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Amine
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

tertiary amine (CHEBI:51380 )
pyridines (CHEBI:51380 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0001936)
Cell membrane (HMDB: HMDB0001936)

Source

Exogenous

Exogenous (HMDB: HMDB0001936)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Doxylamine H1-Antihistamine Action (HMDB: HMDB0001936)
Doxylamine H1-Antihistamine Action (PathBank: SMP0058803)

Role

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	2.151	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	161.9	30932474
[M+H]+	Not Available	162.643	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000821

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.54 g/L	ALOGPS
logP	2.9	ALOGPS
logP	2.96	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Basic)	8.87	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	25.36 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	82.24 m³·mol⁻¹	ChemAxon
Polarizability	31.09 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]+	164.096	31661259
DarkChem	[M-H]-	163.029	31661259
AllCCS	[M+H]+	162.138	32859911
AllCCS	[M-H]-	171.594	32859911
DeepCCS	[M+H]+	163.805	30932474
DeepCCS	[M-H]-	161.447	30932474
DeepCCS	[M-2H]-	194.333	30932474
DeepCCS	[M+Na]+	169.899	30932474
AllCCS	[M+H]+	162.1	32859911
AllCCS	[M+H-H2O]+	158.3	32859911
AllCCS	[M+NH4]+	165.7	32859911
AllCCS	[M+Na]+	166.7	32859911
AllCCS	[M-H]-	171.6	32859911
AllCCS	[M+Na-2H]-	171.7	32859911
AllCCS	[M+HCOO]-	171.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Doxylamine	CN(C)CCOC(C)(C1=CC=CC=C1)C1=CC=CC=N1	2473.0	Standard polar	33892256
Doxylamine	CN(C)CCOC(C)(C1=CC=CC=C1)C1=CC=CC=N1	1940.6	Standard non polar	33892256
Doxylamine	CN(C)CCOC(C)(C1=CC=CC=C1)C1=CC=CC=N1	1917.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Doxylamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a59-7900000000-24e4f3f90dbbb5862928	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Doxylamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0ab9-9200000000-5a71de62862f9881c2a1	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 - Doxylamine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-0040-0956300000-af11cf85a674e7db3735	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Doxylamine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-001i-0910000000-b3cb895f045d519f2bf3	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Doxylamine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-00kb-5597500000-8495062a84b32e776f33	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Doxylamine 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 - Doxylamine LC-ESI-QFT , positive-QTOF	splash10-001i-1920000000-07b98b36c7ef5d9ad048	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Doxylamine LC-ESI-QFT , positive-QTOF	splash10-001i-0900000000-1ae1143763892a7aac22	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Doxylamine LC-ESI-QFT , positive-QTOF	splash10-001i-0900000000-460d58a5bb6a5eb5f55b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Doxylamine LC-ESI-QFT , positive-QTOF	splash10-0159-0900000000-34dc5c06413efae437da	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Doxylamine LC-ESI-QFT , positive-QTOF	splash10-014i-0900000000-8a5f15b863b7129c1288	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Doxylamine LC-ESI-QFT , positive-QTOF	splash10-014i-0900000000-072ffba5139b7324d27a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Doxylamine , positive-QTOF	splash10-00lr-0900000000-fdf3fc57eff19bfe8fd8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Doxylamine 30V, Positive-QTOF	splash10-001i-0900000000-4bd3999ccd0a2246f1bf	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Doxylamine 15V, Positive-QTOF	splash10-001i-1920000000-1fbd7581ebf1730dac6d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Doxylamine 35V, Positive-QTOF	splash10-0159-1900000000-37f4e915e528d2466b80	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Doxylamine 45V, Positive-QTOF	splash10-001i-0900000000-a056c64c9344a9559905	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Doxylamine 60V, Positive-QTOF	splash10-0159-0900000000-0ab3cbbe5a34cba77313	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Doxylamine 90V, Positive-QTOF	splash10-014i-0900000000-1a3a34606ccd3aa3009c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Doxylamine 75V, Positive-QTOF	splash10-014i-0900000000-07c546b389aa80244f62	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Doxylamine 10V, Positive-QTOF	splash10-00di-1190000000-e7b1a3b0a0368fc310df	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Doxylamine 20V, Positive-QTOF	splash10-00e9-5790000000-7402b4fd77afe325c64b	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Doxylamine 40V, Positive-QTOF	splash10-00di-9510000000-b9439d5014a66b7857ec	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Doxylamine 10V, Negative-QTOF	splash10-014i-1290000000-1725573962a3041ca617	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Doxylamine 20V, Negative-QTOF	splash10-014j-1690000000-44de19831bffecc1c412	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Doxylamine 40V, Negative-QTOF	splash10-009t-5900000000-caa39da176327be2a9c2	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Doxylamine 10V, Negative-QTOF	splash10-00kb-0960000000-a2cc3fcbeb38ca35de58	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 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
Urine

Tissue Locations

Not Available

Pathways

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

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

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

DB00366

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022751

KNApSAcK ID

C00017814

Chemspider ID

3050

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Doxylamine

METLIN ID

4004

PubChem Compound

3162

PDB ID

Not Available

ChEBI ID

51380

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

Enzyme Details

2. Muscarinic acetylcholine receptor M1

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
Gene Name:: CHRM1
Uniprot ID:: P11229
Molecular weight:: 51420.4

Showing metabocard for Doxylamine (HMDB0001936)

MOL for HMDB0001936 (Doxylamine)

3D MOL for HMDB0001936 (Doxylamine)

3D SDF for HMDB0001936 (Doxylamine)

3D-SDF for HMDB0001936 (Doxylamine)

PDB for HMDB0001936 (Doxylamine)

3D PDB for HMDB0001936 (Doxylamine)

SMILES for HMDB0001936 (Doxylamine)

INCHI for HMDB0001936 (Doxylamine)

Structure for HMDB0001936 (Doxylamine)

3D Structure for HMDB0001936 (Doxylamine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes