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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (7)transporters (1) Show 8 proteins XML

enzymes (7)transporters (1) Show 8 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:56 UTC

HMDB ID

HMDB0015322

Secondary Accession Numbers

HMDB15322

Metabolite Identification

Common Name

Dexfenfluramine

Description

Dexfenfluramine, also known as redux, belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine. Dexfenfluramine is a drug which is used for the management of obesity including weight loss and maintenance of weight loss in patients on a reduced calorie diet. Dexfenfluramine is a very strong basic compound (based on its pKa). Dexfenfluramine is a potentially toxic compound. The S-enantiomer of fenfluramine. It stimulates the release of serotonin and selectively inhibits its reuptake, but unlike fenfluramine it does not possess catecholamine agonist activity. It was formerly given by mouth as the hydrochloride in the treatment of obesity, but, like fenfluramine, was withdrawn wolrdwide following reports of valvular heart defects.

Structure

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

HMDB0015322
     RDKit          3D
Dexfenfluramine
 32 32  0  0  0  0  0  0  0  0999 V2000
    4.2548   -0.1313    0.6702 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5297   -1.1957   -0.0924 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4361   -0.7271   -0.8312 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2564   -0.2871   -0.1840 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3998    0.9242    0.6497 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1920   -0.1993   -1.2682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1217    0.2563   -0.7797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4864    1.5780   -0.7947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7279    2.0077   -0.3248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6528    1.1147    0.1817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3021   -0.2224    0.2033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2677   -1.2256    0.7333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8081   -2.5081    0.4959 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5194   -1.0223    0.2088 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2632   -1.0524    2.1030 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0669   -0.6306   -0.2658 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3658    0.7751    0.0426 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7507    0.0644    1.6161 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2946   -0.5088    0.8673 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2587   -1.6529   -0.8351 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2123   -2.0297    0.5628 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6316   -0.2900   -1.7348 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9124   -1.1421    0.5022 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4617    1.5511    0.6667 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2319    1.6064    0.3802 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5062    0.6297    1.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1170   -1.2475   -1.6931 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6073    0.4078   -2.0732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7977    2.3166   -1.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9871    3.0608   -0.3548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6190    1.4650    0.5430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7990   -1.6848   -0.2417 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  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  1  0
 12 13  1  0
 12 14  1  0
 12 15  1  0
 11 16  2  0
 16  7  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  4 23  1  1
  5 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 16 32  1  0
M  END


  Mrv0541 04191212172D          

 16 16  0  0  1  0            999 V2000
    4.1890   -6.4628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9035   -6.0503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6179   -6.4628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3324   -6.0503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1890   -7.2879    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.4745   -6.0503    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.0469   -6.4628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7614   -5.2253    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9035   -5.2253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7614   -6.0503    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6179   -4.8128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3324   -5.2253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4759   -6.4628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4690   -6.8822    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.0469   -4.8128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0469   -3.9878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  5  1  1  0  0  0  0
  6  1  1  0  0  0  0
  3  2  2  0  0  0  0
  9  2  1  0  0  0  0
  4  3  1  0  0  0  0
  7  4  1  0  0  0  0
 12  4  2  0  0  0  0
 10  7  1  0  0  0  0
 10  8  1  1  0  0  0
 11  9  2  0  0  0  0
 13 10  1  0  0  0  0
 12 11  1  0  0  0  0
  1 14  1  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015322

> <DATABASE_NAME>
hmdb

> <SMILES>
CCN[C@@H](C)CC1=CC=CC(=C1)C(F)(F)F

> <INCHI_IDENTIFIER>
InChI=1S/C12H16F3N/c1-3-16-9(2)7-10-5-4-6-11(8-10)12(13,14)15/h4-6,8-9,16H,3,7H2,1-2H3/t9-/m0/s1

> <INCHI_KEY>
DBGIVFWFUFKIQN-VIFPVBQESA-N

> <FORMULA>
C12H16F3N

> <MOLECULAR_WEIGHT>
231.2573

> <EXACT_MASS>
231.123484132

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
22.68515765531197

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
ethyl[(2S)-1-[3-(trifluoromethyl)phenyl]propan-2-yl]amine

> <ALOGPS_LOGP>
3.30

> <JCHEM_LOGP>
3.4714873116666665

> <ALOGPS_LOGS>
-4.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
10.215413995825989

> <JCHEM_POLAR_SURFACE_AREA>
12.03

> <JCHEM_REFRACTIVITY>
59.2021

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.15e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dexfenfluramine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0015322
     RDKit          3D
Dexfenfluramine
 32 32  0  0  0  0  0  0  0  0999 V2000
    4.2548   -0.1313    0.6702 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5297   -1.1957   -0.0924 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4361   -0.7271   -0.8312 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2564   -0.2871   -0.1840 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3998    0.9242    0.6497 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1920   -0.1993   -1.2682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1217    0.2563   -0.7797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4864    1.5780   -0.7947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7279    2.0077   -0.3248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6528    1.1147    0.1817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3021   -0.2224    0.2033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2677   -1.2256    0.7333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8081   -2.5081    0.4959 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5194   -1.0223    0.2088 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2632   -1.0524    2.1030 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0669   -0.6306   -0.2658 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3658    0.7751    0.0426 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7507    0.0644    1.6161 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2946   -0.5088    0.8673 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2587   -1.6529   -0.8351 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2123   -2.0297    0.5628 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6316   -0.2900   -1.7348 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9124   -1.1421    0.5022 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4617    1.5511    0.6667 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2319    1.6064    0.3802 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5062    0.6297    1.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1170   -1.2475   -1.6931 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6073    0.4078   -2.0732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7977    2.3166   -1.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9871    3.0608   -0.3548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6190    1.4650    0.5430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7990   -1.6848   -0.2417 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  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  1  0
 12 13  1  0
 12 14  1  0
 12 15  1  0
 11 16  2  0
 16  7  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  4 23  1  1
  5 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 16 32  1  0
M  END

HEADER    PROTEIN                                 19-APR-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-12         0                                  
HETATM    1  C   UNK     0       7.819 -12.064   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.153 -11.294   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.487 -12.064   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.820 -11.294   0.000  0.00  0.00           C+0
HETATM    5  F   UNK     0       7.819 -13.604   0.000  0.00  0.00           F+0
HETATM    6  F   UNK     0       6.486 -11.294   0.000  0.00  0.00           F+0
HETATM    7  C   UNK     0      13.154 -12.064   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      14.488  -9.754   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       9.153  -9.754   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.488 -11.294   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.487  -8.984   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.820  -9.754   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.822 -12.064   0.000  0.00  0.00           C+0
HETATM   14  F   UNK     0       6.475 -12.847   0.000  0.00  0.00           F+0
HETATM   15  C   UNK     0      13.154  -8.984   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.154  -7.444   0.000  0.00  0.00           C+0
CONECT    1    2    5    6   14                                             
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    7   12                                                  
CONECT    5    1                                                            
CONECT    6    1                                                            
CONECT    7    4   10                                                       
CONECT    8   10   15                                                       
CONECT    9    2   11                                                       
CONECT   10    7    8   13                                                  
CONECT   11    9   12                                                       
CONECT   12    4   11                                                       
CONECT   13   10                                                            
CONECT   14    1                                                            
CONECT   15    8   16                                                       
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0015322
HETATM    1  C1  UNL     1       4.255  -0.131   0.670  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.530  -1.196  -0.092  1.00  0.00           C  
HETATM    3  N1  UNL     1       2.436  -0.727  -0.831  1.00  0.00           N  
HETATM    4  C3  UNL     1       1.256  -0.287  -0.184  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.400   0.924   0.650  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.192  -0.199  -1.268  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.122   0.256  -0.780  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.486   1.578  -0.795  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.728   2.008  -0.325  1.00  0.00           C  
HETATM   10  C9  UNL     1      -3.653   1.115   0.182  1.00  0.00           C  
HETATM   11  C10 UNL     1      -3.302  -0.222   0.203  1.00  0.00           C  
HETATM   12  C11 UNL     1      -4.268  -1.226   0.733  1.00  0.00           C  
HETATM   13  F1  UNL     1      -3.808  -2.508   0.496  1.00  0.00           F  
HETATM   14  F2  UNL     1      -5.519  -1.022   0.209  1.00  0.00           F  
HETATM   15  F3  UNL     1      -4.263  -1.052   2.103  1.00  0.00           F  
HETATM   16  C12 UNL     1      -2.067  -0.631  -0.266  1.00  0.00           C  
HETATM   17  H1  UNL     1       4.366   0.775   0.043  1.00  0.00           H  
HETATM   18  H2  UNL     1       3.751   0.064   1.616  1.00  0.00           H  
HETATM   19  H3  UNL     1       5.295  -0.509   0.867  1.00  0.00           H  
HETATM   20  H4  UNL     1       4.259  -1.653  -0.835  1.00  0.00           H  
HETATM   21  H5  UNL     1       3.212  -2.030   0.563  1.00  0.00           H  
HETATM   22  H6  UNL     1       2.632  -0.290  -1.735  1.00  0.00           H  
HETATM   23  H7  UNL     1       0.912  -1.142   0.502  1.00  0.00           H  
HETATM   24  H8  UNL     1       0.462   1.551   0.667  1.00  0.00           H  
HETATM   25  H9  UNL     1       2.232   1.606   0.380  1.00  0.00           H  
HETATM   26  H10 UNL     1       1.506   0.630   1.729  1.00  0.00           H  
HETATM   27  H11 UNL     1       0.117  -1.248  -1.693  1.00  0.00           H  
HETATM   28  H12 UNL     1       0.607   0.408  -2.073  1.00  0.00           H  
HETATM   29  H13 UNL     1      -0.798   2.317  -1.186  1.00  0.00           H  
HETATM   30  H14 UNL     1      -2.987   3.061  -0.355  1.00  0.00           H  
HETATM   31  H15 UNL     1      -4.619   1.465   0.543  1.00  0.00           H  
HETATM   32  H16 UNL     1      -1.799  -1.685  -0.242  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3   20   21
CONECT    3    4   22
CONECT    4    5    6   23
CONECT    5   24   25   26
CONECT    6    7   27   28
CONECT    7    8    8   16
CONECT    8    9   29
CONECT    9   10   10   30
CONECT   10   11   31
CONECT   11   12   16   16
CONECT   12   13   14   15
CONECT   16   32
END

HMDB0015322
     RDKit          3D
Dexfenfluramine
 32 32  0  0  0  0  0  0  0  0999 V2000
    4.2548   -0.1313    0.6702 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5297   -1.1957   -0.0924 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4361   -0.7271   -0.8312 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2564   -0.2871   -0.1840 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3998    0.9242    0.6497 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1920   -0.1993   -1.2682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1217    0.2563   -0.7797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4864    1.5780   -0.7947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7279    2.0077   -0.3248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6528    1.1147    0.1817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3021   -0.2224    0.2033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2677   -1.2256    0.7333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8081   -2.5081    0.4959 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5194   -1.0223    0.2088 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2632   -1.0524    2.1030 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0669   -0.6306   -0.2658 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3658    0.7751    0.0426 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7507    0.0644    1.6161 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2946   -0.5088    0.8673 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2587   -1.6529   -0.8351 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2123   -2.0297    0.5628 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6316   -0.2900   -1.7348 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9124   -1.1421    0.5022 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4617    1.5511    0.6667 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2319    1.6064    0.3802 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5062    0.6297    1.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1170   -1.2475   -1.6931 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6073    0.4078   -2.0732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7977    2.3166   -1.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9871    3.0608   -0.3548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6190    1.4650    0.5430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7990   -1.6848   -0.2417 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  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  1  0
 12 13  1  0
 12 14  1  0
 12 15  1  0
 11 16  2  0
 16  7  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  4 23  1  1
  5 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 16 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-Fenfluramine	ChEBI
(S)-N-Ethyl-1-[3-(trifluoromethyl)phenyl]propan-2-amine	ChEBI
D-N-Ethyl-alpha-methyl-m-trifluoromethylphenethylamine	ChEBI
Dexfenfluramina	ChEBI
Dexfenfluraminum	ChEBI
Dextrofenfluramine	ChEBI
D-N-Ethyl-a-methyl-m-trifluoromethylphenethylamine	Generator
D-N-Ethyl-α-methyl-m-trifluoromethylphenethylamine	Generator
(S)-Fenfluramine	HMDB
Dexfenfluramine hydrochloride	HMDB
Redux	HMDB
Wyeth brand OF dexfenfluramine hydrochloride	HMDB
Hydrochloride, dexfenfluramine	HMDB
Dexfenfluramine	ChEBI

Chemical Formula

C₁₂H₁₆F₃N

Average Molecular Weight

231.2573

Monoisotopic Molecular Weight

231.123484132

IUPAC Name

ethyl[(2S)-1-[3-(trifluoromethyl)phenyl]propan-2-yl]amine

Traditional Name

dexfenfluramine

CAS Registry Number

3239-44-9

SMILES

CCN[C@@H](C)CC1=CC=CC(=C1)C(F)(F)F

InChI Identifier

InChI=1S/C12H16F3N/c1-3-16-9(2)7-10-5-4-6-11(8-10)12(13,14)15/h4-6,8-9,16H,3,7H2,1-2H3/t9-/m0/s1

InChI Key

DBGIVFWFUFKIQN-VIFPVBQESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenethylamines

Direct Parent

Amphetamines and derivatives

Alternative Parents

Substituents

Amphetamine or derivatives
Trifluoromethylbenzene
Phenylpropane
Aralkylamine
Secondary aliphatic amine
Secondary amine
Alkyl fluoride
Hydrocarbon derivative
Organonitrogen compound
Organofluoride
Organohalogen compound
Organopnictogen compound
Organic nitrogen compound
Amine
Alkyl halide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

fenfluramine (CHEBI:439329 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015322)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

appetite depressant (HMDB: HMDB0015322)
serotonergic agonist (HMDB: HMDB0015322)

Biological role

serotonergic agonist (HMDB: HMDB0015322)

Modulator

Inhibitor

Enzyme inhibitor

serotonin uptake inhibitor (HMDB: HMDB0015322)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.022 g/L	Not Available
LogP	3.5	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.022 g/L	ALOGPS
logP	3.3	ALOGPS
logP	3.47	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Basic)	10.22	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	12.03 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	59.2 m³·mol⁻¹	ChemAxon
Polarizability	22.69 Å³	ChemAxon
Number of Rings	1	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]+	156.909	30932474
DeepCCS	[M-H]-	154.551	30932474
DeepCCS	[M-2H]-	188.002	30932474
DeepCCS	[M+Na]+	163.005	30932474
AllCCS	[M+H]+	152.3	32859911
AllCCS	[M+H-H2O]+	148.5	32859911
AllCCS	[M+NH4]+	155.9	32859911
AllCCS	[M+Na]+	156.9	32859911
AllCCS	[M-H]-	152.5	32859911
AllCCS	[M+Na-2H]-	152.9	32859911
AllCCS	[M+HCOO]-	153.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dexfenfluramine	CCN[C@@H](C)CC1=CC=CC(=C1)C(F)(F)F	1712.5	Standard polar	33892256
Dexfenfluramine	CCN[C@@H](C)CC1=CC=CC(=C1)C(F)(F)F	1276.3	Standard non polar	33892256
Dexfenfluramine	CCN[C@@H](C)CC1=CC=CC(=C1)C(F)(F)F	1248.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dexfenfluramine,1TMS,isomer #1	CCN([C@@H](C)CC1=CC=CC(C(F)(F)F)=C1)[Si](C)(C)C	1472.6	Semi standard non polar	33892256
Dexfenfluramine,1TMS,isomer #1	CCN([C@@H](C)CC1=CC=CC(C(F)(F)F)=C1)[Si](C)(C)C	1532.8	Standard non polar	33892256
Dexfenfluramine,1TMS,isomer #1	CCN([C@@H](C)CC1=CC=CC(C(F)(F)F)=C1)[Si](C)(C)C	1476.0	Standard polar	33892256
Dexfenfluramine,1TBDMS,isomer #1	CCN([C@@H](C)CC1=CC=CC(C(F)(F)F)=C1)[Si](C)(C)C(C)(C)C	1698.3	Semi standard non polar	33892256
Dexfenfluramine,1TBDMS,isomer #1	CCN([C@@H](C)CC1=CC=CC(C(F)(F)F)=C1)[Si](C)(C)C(C)(C)C	1731.4	Standard non polar	33892256
Dexfenfluramine,1TBDMS,isomer #1	CCN([C@@H](C)CC1=CC=CC(C(F)(F)F)=C1)[Si](C)(C)C(C)(C)C	1618.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dexfenfluramine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-9110000000-1bb444f1022b28d94dc0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dexfenfluramine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dexfenfluramine 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 - Dexfenfluramine 10V, Positive-QTOF	splash10-001i-1190000000-7fbe4443e51aea6826c3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexfenfluramine 20V, Positive-QTOF	splash10-001r-8890000000-5cd73b17e1103d99e7fb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexfenfluramine 40V, Positive-QTOF	splash10-00ov-9610000000-58d820854fe8992bc6a3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexfenfluramine 10V, Negative-QTOF	splash10-001i-0090000000-96055c6c721aecfc76f8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexfenfluramine 20V, Negative-QTOF	splash10-001i-2190000000-2f8c88fb4bc53943412f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexfenfluramine 40V, Negative-QTOF	splash10-0006-9410000000-a342d0ae14c5230c00a4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexfenfluramine 10V, Positive-QTOF	splash10-001i-0290000000-ac3db862ce9c06ed67f5	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexfenfluramine 20V, Positive-QTOF	splash10-0a4i-0910000000-6cb4ba049f7be32b0f1c	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexfenfluramine 40V, Positive-QTOF	splash10-0a4i-1900000000-43131e1ffc852067efa9	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexfenfluramine 10V, Negative-QTOF	splash10-001i-0090000000-8ae4a9b01f14913328e8	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexfenfluramine 20V, Negative-QTOF	splash10-0a5i-0930000000-c301feb5a0d5278285b2	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexfenfluramine 40V, Negative-QTOF	splash10-0a4i-0900000000-30767724225603e597e1	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

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 DB01191	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01191	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01191

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

59646

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dexfenfluramine

METLIN ID

Not Available

PubChem Compound

66265

PDB ID

Not Available

ChEBI ID

439329

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

Kalia M: Reversible, short-lasting, and dose-dependent effect of (+)-fenfluramine on neocortical serotonergic axons. Brain Res. 1991 May 10;548(1-2):111-25. [PubMed:1868326 ]

Enzymes

Enzyme Details

1. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

3. Cytochrome P450 2E1

General function:: Involved in monooxygenase activity
Specific function:: Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:: CYP2E1
Uniprot ID:: P05181
Molecular weight:: 56848.42

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

4. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

5. Cytochrome P450 1A2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

6. Cytochrome P450 2A6

General function:: Involved in monooxygenase activity
Specific function:: Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity.
Gene Name:: CYP2A6
Uniprot ID:: P11509
Molecular weight:: 56517.005

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

7. 5-hydroxytryptamine receptor 2C

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system
Gene Name:: HTR2C
Uniprot ID:: P28335
Molecular weight:: 51820.7

References

Vickers SP, Clifton PG, Dourish CT, Tecott LH: Reduced satiating effect of d-fenfluramine in serotonin 5-HT(2C) receptor mutant mice. Psychopharmacology (Berl). 1999 Apr;143(3):309-14. [PubMed:10353435 ]
Wilson AW, Costall B, Neill JC: Manipulation of operant responding for an ethanol-paired conditioned stimulus in the rat by pharmacological alteration of the serotonergic system. J Psychopharmacol. 2000;14(4):340-6. [PubMed:11198050 ]
Vickers SP, Dourish CT, Kennett GA: Evidence that hypophagia induced by d-fenfluramine and d-norfenfluramine in the rat is mediated by 5-HT2C receptors. Neuropharmacology. 2001 Aug;41(2):200-9. [PubMed:11489456 ]
Tomkins DM, Joharchi N, Tampakeras M, Martin JR, Wichmann J, Higgins GA: An investigation of the role of 5-HT(2C) receptors in modifying ethanol self-administration behaviour. Pharmacol Biochem Behav. 2002 Apr;71(4):735-44. [PubMed:11888565 ]
Bickerdike MJ: 5-HT2C receptor agonists as potential drugs for the treatment of obesity. Curr Top Med Chem. 2003;3(8):885-97. [PubMed:12678838 ]

Transporters

Enzyme Details

1. Sodium-dependent serotonin transporter

General function:: Involved in neurotransmitter:sodium symporter activity
Specific function:: Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into the pre-synaptic terminal for re-utilization. Plays a key role in mediating regulation of the availability of serotonin to other receptors of serotonergic systems. Terminates the action of serotonin and recycles it in a sodium-dependent manner.
Gene Name:: SLC6A4
Uniprot ID:: P31645
Molecular weight:: 70324.165

References

Eddahibi S, Adnot S, Frisdal E, Levame M, Hamon M, Raffestin B: Dexfenfluramine-associated changes in 5-hydroxytryptamine transporter expression and development of hypoxic pulmonary hypertension in rats. J Pharmacol Exp Ther. 2001 Apr;297(1):148-54. [PubMed:11259539 ]
Russell BR, Laverty R: The effect of (R)-HA966 or ACEA 1021 on dexfenfluramine or (S)-MDMA-induced changes in temperature, activity, and neurotoxicity. Pharmacol Biochem Behav. 2001 Mar;68(3):565-74. [PubMed:11325413 ]
Rothman RB, Jayanthi S, Wang X, Dersch CM, Cadet JL, Prisinzano T, Rice KC, Baumann MH: High-dose fenfluramine administration decreases serotonin transporter binding, but not serotonin transporter protein levels, in rat forebrain. Synapse. 2003 Dec 1;50(3):233-9. [PubMed:14515341 ]
Johnson GJ, Leis LA, Dunlop PC, Weir EK: The effect of the anorectic agent, d-fenfluramine, and its primary metabolite, d-norfenfluramine, on intact human platelet serotonin uptake and efflux. J Thromb Haemost. 2003 Dec;1(12):2663-8. [PubMed:14675103 ]
Wang X, Baumann MH, Xu H, Rothman RB: 3,4-methylenedioxymethamphetamine (MDMA) administration to rats decreases brain tissue serotonin but not serotonin transporter protein and glial fibrillary acidic protein. Synapse. 2004 Sep 15;53(4):240-8. [PubMed:15266556 ]

Showing metabocard for Dexfenfluramine (HMDB0015322)

MOL for HMDB0015322 (Dexfenfluramine)

3D MOL for HMDB0015322 (Dexfenfluramine)

3D SDF for HMDB0015322 (Dexfenfluramine)

3D-SDF for HMDB0015322 (Dexfenfluramine)

PDB for HMDB0015322 (Dexfenfluramine)

3D PDB for HMDB0015322 (Dexfenfluramine)

SMILES for HMDB0015322 (Dexfenfluramine)

INCHI for HMDB0015322 (Dexfenfluramine)

Structure for HMDB0015322 (Dexfenfluramine)

3D Structure for HMDB0015322 (Dexfenfluramine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References

References

References

Transporters

References