Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 13:41:06 UTC

Update Date

2021-09-26 23:08:22 UTC

HMDB ID

HMDB0254404

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Medifoxamine

Description

Medifoxamine belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring. Medifoxamine is a very strong basic compound (based on its pKa). It was withdrawn from the market in 1999 (Morocco) and 2000 (France) following incidences of hepatotoxicity. Effectiveness and tolerability Unlike many tricyclic antidepressants, medifoxamine lacks anticholinergic and alpha blocker properties (very low affinity for the muscarinic acetylcholine receptors and 10-fold lower affinity for the α1-adrenergic receptor relative to 5-HT2 binding sites), and is also apparently inactive as a norepinephrine reuptake inhibitor (although the same source stating this also states that it is inactive as a serotonin reuptake inhibitor, which was subsequently found not to be the case). Medifoxamine, previously sold under the brand names Clédial and Gerdaxyl, is an atypical antidepressant with additional anxiolytic properties acting via dopaminergic and serotonergic mechanisms which was formerly marketed in France and Spain, as well as Morocco. Double-blind controlled clinical studies have found it to have similar effectiveness to imipramine, clomipramine, and maprotiline in the treatment of depression. Medifoxamine has been found to act preferentially as a relatively weak dopamine reuptake inhibitor, but also as an even weaker serotonin reuptake inhibitor (IC50 1,500 nM) and as a weak antagonist of the 5-HT2A and 5-HT2C receptors (IC50 950 and 980, respectively; notably greater affinity relative to amitriptyline and imipramine). It is known to produce two active metabolites during first-pass metabolism in the liver, CRE-10086 (N-methyl-2,2-diphenoxyethylamine) and CRE-10357 (N,N-dimethyl-2-hydroxyphenoxy-2-phenoxyethylamine). The IC50 values of CRE-10086 for serotonin transporter, 5-HT2A, and 5-HT2C binding are 450 nM, 330 nM, and 700 nM, respectively, while those of CRE-10357 are 660 nM, 1,600 nM, and 6,300 M. Medifoxamine and its metabolites lack affinity for other serotonin receptors including 5-HT1A, 5-HT1B, 5-HT1D, and 5-HT3 (>10,000 nM). Studies in mice revealed that the drug does not possess any sedative or locomotor stimulant effects. This compound has been identified in human blood as reported by (PMID: 31557052 ). Medifoxamine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Medifoxamine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0254404
     RDKit          3D
Medifoxamine
 38 39  0  0  0  0  0  0  0  0999 V2000
    0.1723   -3.3392   -1.3424 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9175   -2.8157   -0.2572 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8339   -3.7671    0.2944 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3005   -2.0498    0.6888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1622   -0.6468    0.4249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1387   -0.3580   -0.5440 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2693    0.3869   -0.3460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8441    0.6492    0.8595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0088    1.4248    1.0351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6172    1.9489   -0.0787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0796    1.7095   -1.3292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9086    0.9433   -1.4700 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8172    0.2679    0.3079 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7376    1.1217    0.2033 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5218    2.2589   -0.6482 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4089    3.2723   -0.8571 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6368    3.2118   -0.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8921    2.1453    0.6281 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9544    1.1327    0.8135 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4909   -2.8351   -2.3020 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3539   -4.4489   -1.4932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9270   -3.2132   -1.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1360   -4.5809   -0.4094 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3721   -4.2977    1.1797 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7921   -3.3162    0.6315 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9985   -1.9226    1.5959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5402   -2.6904    1.1670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6304   -0.3903    1.4551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4016    0.2477    1.7930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4483    1.6212    1.9944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5236    2.5578   -0.0231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5519    2.1720   -2.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4559    0.7304   -2.3980 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5940    2.2677   -1.1847 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1956    4.1147   -1.5070 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3241    4.0103   -0.3577 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8543    2.1553    1.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2030    0.3215    1.4735 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
  5 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 12  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
  8 29  1  0
  9 30  1  0
 10 31  1  0
 11 32  1  0
 12 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
M  END


  Mrv1652306031609492D          

 19 20  0  0  0  0            999 V2000
    4.2868    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  2  0  0  0  0
  6  3  1  0  0  0  0
  7  4  2  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 11  7  1  0  0  0  0
 12  8  2  0  0  0  0
 14  9  2  0  0  0  0
 14 10  1  0  0  0  0
 15 11  2  0  0  0  0
 15 12  1  0  0  0  0
 16 13  1  0  0  0  0
 17  1  1  0  0  0  0
 17  2  1  0  0  0  0
 17 13  1  0  0  0  0
 18 14  1  0  0  0  0
 18 16  1  0  0  0  0
 19 15  1  0  0  0  0
 19 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254404

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)CC(OC1=CC=CC=C1)OC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H19NO2/c1-17(2)13-16(18-14-9-5-3-6-10-14)19-15-11-7-4-8-12-15/h3-12,16H,13H2,1-2H3

> <INCHI_KEY>
QNMGHBMGNRQPNL-UHFFFAOYSA-N

> <FORMULA>
C16H19NO2

> <MOLECULAR_WEIGHT>
257.333

> <EXACT_MASS>
257.141578856

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
28.206375504362207

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2,2-diphenoxyethyl)dimethylamine

> <ALOGPS_LOGP>
3.05

> <JCHEM_LOGP>
3.8041467499999992

> <ALOGPS_LOGS>
-2.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.179909710038109

> <JCHEM_POLAR_SURFACE_AREA>
21.700000000000003

> <JCHEM_REFRACTIVITY>
75.83010000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.27e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
medifoxamine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0254404
     RDKit          3D
Medifoxamine
 38 39  0  0  0  0  0  0  0  0999 V2000
    0.1723   -3.3392   -1.3424 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9175   -2.8157   -0.2572 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8339   -3.7671    0.2944 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3005   -2.0498    0.6888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1622   -0.6468    0.4249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1387   -0.3580   -0.5440 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2693    0.3869   -0.3460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8441    0.6492    0.8595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0088    1.4248    1.0351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6172    1.9489   -0.0787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0796    1.7095   -1.3292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9086    0.9433   -1.4700 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8172    0.2679    0.3079 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7376    1.1217    0.2033 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5218    2.2589   -0.6482 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4089    3.2723   -0.8571 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6368    3.2118   -0.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8921    2.1453    0.6281 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9544    1.1327    0.8135 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4909   -2.8351   -2.3020 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3539   -4.4489   -1.4932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9270   -3.2132   -1.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1360   -4.5809   -0.4094 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3721   -4.2977    1.1797 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7921   -3.3162    0.6315 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9985   -1.9226    1.5959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5402   -2.6904    1.1670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6304   -0.3903    1.4551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4016    0.2477    1.7930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4483    1.6212    1.9944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5236    2.5578   -0.0231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5519    2.1720   -2.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4559    0.7304   -2.3980 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5940    2.2677   -1.1847 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1956    4.1147   -1.5070 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3241    4.0103   -0.3577 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8543    2.1553    1.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2030    0.3215    1.4735 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
  5 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 12  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
  8 29  1  0
  9 30  1  0
 10 31  1  0
 11 32  1  0
 12 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
M  END

HEADER    PROTEIN                                 03-JUN-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-JUN-16         0                                  
HETATM    1  C   UNK     0       8.002   3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   5.390   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668   0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       8.002   1.540   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0       4.001   0.770   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.335   3.080   0.000  0.00  0.00           O+0
CONECT    1   17                                                            
CONECT    2   17                                                            
CONECT    3    5    6                                                       
CONECT    4    7    8                                                       
CONECT    5    3    9                                                       
CONECT    6    3   10                                                       
CONECT    7    4   11                                                       
CONECT    8    4   12                                                       
CONECT    9    5   14                                                       
CONECT   10    6   14                                                       
CONECT   11    7   15                                                       
CONECT   12    8   15                                                       
CONECT   13   16   17                                                       
CONECT   14    9   10   18                                                  
CONECT   15   11   12   19                                                  
CONECT   16   13   18   19                                                  
CONECT   17    1    2   13                                                  
CONECT   18   14   16                                                       
CONECT   19   15   16                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0254404
HETATM    1  C1  UNL     1       0.172  -3.339  -1.342  1.00  0.00           C  
HETATM    2  N1  UNL     1       0.918  -2.816  -0.257  1.00  0.00           N  
HETATM    3  C2  UNL     1       1.834  -3.767   0.294  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.300  -2.050   0.689  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.162  -0.647   0.425  1.00  0.00           C  
HETATM    6  O1  UNL     1      -1.139  -0.358  -0.544  1.00  0.00           O  
HETATM    7  C5  UNL     1      -2.269   0.387  -0.346  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.844   0.649   0.859  1.00  0.00           C  
HETATM    9  C7  UNL     1      -4.009   1.425   1.035  1.00  0.00           C  
HETATM   10  C8  UNL     1      -4.617   1.949  -0.079  1.00  0.00           C  
HETATM   11  C9  UNL     1      -4.080   1.709  -1.329  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.909   0.943  -1.470  1.00  0.00           C  
HETATM   13  O2  UNL     1       0.817   0.268   0.308  1.00  0.00           O  
HETATM   14  C11 UNL     1       1.738   1.122   0.203  1.00  0.00           C  
HETATM   15  C12 UNL     1       1.522   2.259  -0.648  1.00  0.00           C  
HETATM   16  C13 UNL     1       2.409   3.272  -0.857  1.00  0.00           C  
HETATM   17  C14 UNL     1       3.637   3.212  -0.202  1.00  0.00           C  
HETATM   18  C15 UNL     1       3.892   2.145   0.628  1.00  0.00           C  
HETATM   19  C16 UNL     1       2.954   1.133   0.814  1.00  0.00           C  
HETATM   20  H1  UNL     1       0.491  -2.835  -2.302  1.00  0.00           H  
HETATM   21  H2  UNL     1       0.354  -4.449  -1.493  1.00  0.00           H  
HETATM   22  H3  UNL     1      -0.927  -3.213  -1.230  1.00  0.00           H  
HETATM   23  H4  UNL     1       2.136  -4.581  -0.409  1.00  0.00           H  
HETATM   24  H5  UNL     1       1.372  -4.298   1.180  1.00  0.00           H  
HETATM   25  H6  UNL     1       2.792  -3.316   0.631  1.00  0.00           H  
HETATM   26  H7  UNL     1       0.999  -1.923   1.596  1.00  0.00           H  
HETATM   27  H8  UNL     1      -0.540  -2.690   1.167  1.00  0.00           H  
HETATM   28  H9  UNL     1      -0.630  -0.390   1.455  1.00  0.00           H  
HETATM   29  H10 UNL     1      -2.402   0.248   1.793  1.00  0.00           H  
HETATM   30  H11 UNL     1      -4.448   1.621   1.994  1.00  0.00           H  
HETATM   31  H12 UNL     1      -5.524   2.558  -0.023  1.00  0.00           H  
HETATM   32  H13 UNL     1      -4.552   2.172  -2.203  1.00  0.00           H  
HETATM   33  H14 UNL     1      -2.456   0.730  -2.398  1.00  0.00           H  
HETATM   34  H15 UNL     1       0.594   2.268  -1.185  1.00  0.00           H  
HETATM   35  H16 UNL     1       2.196   4.115  -1.507  1.00  0.00           H  
HETATM   36  H17 UNL     1       4.324   4.010  -0.358  1.00  0.00           H  
HETATM   37  H18 UNL     1       4.854   2.155   1.123  1.00  0.00           H  
HETATM   38  H19 UNL     1       3.203   0.322   1.474  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   13   28
CONECT    6    7
CONECT    7    8    8   12
CONECT    8    9   29
CONECT    9   10   10   30
CONECT   10   11   31
CONECT   11   12   12   32
CONECT   12   33
CONECT   13   14
CONECT   14   15   15   19
CONECT   15   16   34
CONECT   16   17   17   35
CONECT   17   18   36
CONECT   18   19   19   37
CONECT   19   38
END

HMDB0254404
     RDKit          3D
Medifoxamine
 38 39  0  0  0  0  0  0  0  0999 V2000
    0.1723   -3.3392   -1.3424 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9175   -2.8157   -0.2572 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8339   -3.7671    0.2944 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3005   -2.0498    0.6888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1622   -0.6468    0.4249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1387   -0.3580   -0.5440 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2693    0.3869   -0.3460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8441    0.6492    0.8595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0088    1.4248    1.0351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6172    1.9489   -0.0787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0796    1.7095   -1.3292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9086    0.9433   -1.4700 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8172    0.2679    0.3079 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7376    1.1217    0.2033 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5218    2.2589   -0.6482 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4089    3.2723   -0.8571 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6368    3.2118   -0.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8921    2.1453    0.6281 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9544    1.1327    0.8135 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4909   -2.8351   -2.3020 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3539   -4.4489   -1.4932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9270   -3.2132   -1.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1360   -4.5809   -0.4094 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3721   -4.2977    1.1797 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7921   -3.3162    0.6315 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9985   -1.9226    1.5959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5402   -2.6904    1.1670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6304   -0.3903    1.4551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4016    0.2477    1.7930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4483    1.6212    1.9944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5236    2.5578   -0.0231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5519    2.1720   -2.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4559    0.7304   -2.3980 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5940    2.2677   -1.1847 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1956    4.1147   -1.5070 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3241    4.0103   -0.3577 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8543    2.1553    1.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2030    0.3215    1.4735 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
  5 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 12  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
  8 29  1  0
  9 30  1  0
 10 31  1  0
 11 32  1  0
 12 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Medifoxamine fumarate	MeSH

Chemical Formula

C₁₆H₁₉NO₂

Average Molecular Weight

257.333

Monoisotopic Molecular Weight

257.141578856

IUPAC Name

(2,2-diphenoxyethyl)dimethylamine

Traditional Name

medifoxamine

CAS Registry Number

Not Available

SMILES

CN(C)CC(OC1=CC=CC=C1)OC1=CC=CC=C1

InChI Identifier

InChI=1S/C16H19NO2/c1-17(2)13-16(18-14-9-5-3-6-10-14)19-15-11-7-4-8-12-15/h3-12,16H,13H2,1-2H3

InChI Key

QNMGHBMGNRQPNL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenol ethers

Sub Class

Not Available

Direct Parent

Phenol ethers

Alternative Parents

Substituents

Phenoxy compound
Phenol ether
Monocyclic benzene moiety
Tertiary aliphatic amine
Tertiary amine
Acetal
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	3.05	ALOGPS
logP	3.8	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Basic)	8.18	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	21.7 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	75.83 m³·mol⁻¹	ChemAxon
Polarizability	28.21 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]+	158.206	30932474
DeepCCS	[M-H]-	155.848	30932474
DeepCCS	[M-2H]-	188.734	30932474
DeepCCS	[M+Na]+	164.3	30932474
AllCCS	[M+H]+	160.0	32859911
AllCCS	[M+H-H2O]+	156.2	32859911
AllCCS	[M+NH4]+	163.5	32859911
AllCCS	[M+Na]+	164.6	32859911
AllCCS	[M-H]-	165.3	32859911
AllCCS	[M+Na-2H]-	164.9	32859911
AllCCS	[M+HCOO]-	164.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Medifoxamine	CN(C)CC(OC1=CC=CC=C1)OC1=CC=CC=C1	2555.8	Standard polar	33892256
Medifoxamine	CN(C)CC(OC1=CC=CC=C1)OC1=CC=CC=C1	1929.3	Standard non polar	33892256
Medifoxamine	CN(C)CC(OC1=CC=CC=C1)OC1=CC=CC=C1	1816.6	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 - Medifoxamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9000000000-2cff45972d505cf1d074	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Medifoxamine 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Medifoxamine 10V, Positive-QTOF	splash10-0a4i-1090000000-2b6d2983f83b79f3892a	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Medifoxamine 20V, Positive-QTOF	splash10-0002-9120000000-11c385664b0ce2fba334	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Medifoxamine 40V, Positive-QTOF	splash10-0fdk-9100000000-9c389879aa6a074f3c89	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Medifoxamine 10V, Negative-QTOF	splash10-0a4i-3090000000-9baabb46637e76ff7df8	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Medifoxamine 20V, Negative-QTOF	splash10-052f-9060000000-9158a6841cd6749ab738	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Medifoxamine 40V, Negative-QTOF	splash10-0006-9100000000-9c90cd24d0fd19038e05	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Medifoxamine 10V, Positive-QTOF	splash10-0a4i-0090000000-a2d06cd81bcf7aaafc39	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Medifoxamine 20V, Positive-QTOF	splash10-0300-6900000000-910b50c4cda6b1bb046b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Medifoxamine 40V, Positive-QTOF	splash10-05dj-9100000000-2d1989e6123260342e01	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Medifoxamine 10V, Negative-QTOF	splash10-0a4l-7190000000-f88d8e46cf394071fe8e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Medifoxamine 20V, Negative-QTOF	splash10-0006-9000000000-bc1c51385c4ba2ad6f4c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Medifoxamine 40V, Negative-QTOF	splash10-0006-9000000000-08485aaf085c13d5129a	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB13219

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Medifoxamine

METLIN ID

Not Available

PubChem Compound

36109

PDB ID

Not Available

ChEBI ID

Not Available

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Medifoxamine (HMDB0254404)

MOL for HMDB0254404 (Medifoxamine)

3D MOL for HMDB0254404 (Medifoxamine)

3D SDF for HMDB0254404 (Medifoxamine)

3D-SDF for HMDB0254404 (Medifoxamine)

PDB for HMDB0254404 (Medifoxamine)

3D PDB for HMDB0254404 (Medifoxamine)

SMILES for HMDB0254404 (Medifoxamine)

INCHI for HMDB0254404 (Medifoxamine)

Structure for HMDB0254404 (Medifoxamine)

3D Structure for HMDB0254404 (Medifoxamine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra