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

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:49 UTC

HMDB ID

HMDB0015003

Secondary Accession Numbers

HMDB15003

Metabolite Identification

Common Name

Benzphetamine

Description

Benzphetamine is only found in individuals that have used or taken this drug. It is a sympathomimetic agent with properties similar to dextroamphetamine. It is used in the treatment of obesity. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1222)Although the mechanism of action of the sympathomimetic appetite suppressants in the treatment of obesity is not fully known, these medications have pharmacological effects similar to those of amphetamines. Amphetamine and related sympathomimetic medications (such as benzphetamine) are thought to stimulate the release of norepinephrine and/or dopamine from storage sites in nerve terminals in the lateral hypothalamic feeding center, thereby producing a decrease in appetite. This release is mediated by the binding of benzphetamine to centrally located adrenergic receptors.

Structure

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

HMDB0015003
     RDKit          3D
Benzphetamine
 39 40  0  0  0  0  0  0  0  0999 V2000
    1.0459    1.5941   -0.5354 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6730    0.1913   -0.1831 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5557   -0.4226    0.8676 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9598   -0.4575    0.4017 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4564   -1.5281   -0.3072 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7631   -1.5664   -0.7403 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6052   -0.5049   -0.4591 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1421    0.5668    0.2399 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8171    0.5803    0.6658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6839    0.0004    0.1953 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1177    0.6854    1.3599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5644    0.0392   -0.9257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9826   -0.1575   -0.5509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5878   -1.3924   -0.4843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9085   -1.5443   -0.1322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6701   -0.4265    0.1691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0632    0.7968    0.1012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7382    0.9512   -0.2521 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3579    2.2111    0.3531 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2002    2.1324   -1.0362 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8856    1.6319   -1.2585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8273   -0.4165   -1.1240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1988   -1.4654    1.0537 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4661    0.1050    1.8478 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8293   -2.3841   -0.5504 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1194   -2.4187   -1.2928 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6190   -0.5261   -0.7911 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7941    1.3937    0.4607 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4412    1.4244    1.2217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5271    0.3040    2.2361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0398    1.7725    1.3377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1667    0.3953    1.5645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4102    0.9636   -1.5264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2618   -0.8017   -1.6122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0161   -2.3006   -0.7168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3434   -2.5253   -0.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7136   -0.5388    0.4481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6320    1.6697    0.3297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3302    1.9685   -0.2828 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  2 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
  9  4  1  0
 18 13  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  6
  3 23  1  0
  3 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
 11 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
M  END


  Mrv1652303202019022D          

 18 19  0  0  0  0            999 V2000
    3.8484   -3.8637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5652   -3.4465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8484   -4.6910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1311   -3.4465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2790   -3.8603    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1311   -5.1047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4109   -3.8637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9959   -3.4465    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2824   -4.6841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4109   -4.6910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7095   -3.8568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9924   -2.6193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4232   -3.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1367   -3.8568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4196   -2.6193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8501   -3.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1332   -2.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8467   -2.6193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  2  5  1  0  0  0  0
  3  6  2  0  0  0  0
  4  7  1  0  0  0  0
  5  8  1  0  0  0  0
  5  9  1  1  0  0  0
  6 10  1  0  0  0  0
  8 11  1  0  0  0  0
  8 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
 15 17  2  0  0  0  0
 16 18  2  0  0  0  0
  7 10  2  0  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015003

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H21N/c1-15(13-16-9-5-3-6-10-16)18(2)14-17-11-7-4-8-12-17/h3-12,15H,13-14H2,1-2H3/t15-/m0/s1

> <INCHI_KEY>
YXKTVDFXDRQTKV-HNNXBMFYSA-N

> <FORMULA>
C17H21N

> <MOLECULAR_WEIGHT>
239.3553

> <EXACT_MASS>
239.167399677

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
29.02921849827269

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
benzyl(methyl)[(2S)-1-phenylpropan-2-yl]amine

> <ALOGPS_LOGP>
3.72

> <JCHEM_LOGP>
4.34435193

> <ALOGPS_LOGS>
-4.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.719455366577789

> <JCHEM_POLAR_SURFACE_AREA>
3.24

> <JCHEM_REFRACTIVITY>
78.38710000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.33e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
benzphetamine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0015003
     RDKit          3D
Benzphetamine
 39 40  0  0  0  0  0  0  0  0999 V2000
    1.0459    1.5941   -0.5354 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6730    0.1913   -0.1831 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5557   -0.4226    0.8676 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9598   -0.4575    0.4017 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4564   -1.5281   -0.3072 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7631   -1.5664   -0.7403 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6052   -0.5049   -0.4591 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1421    0.5668    0.2399 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8171    0.5803    0.6658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6839    0.0004    0.1953 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1177    0.6854    1.3599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5644    0.0392   -0.9257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9826   -0.1575   -0.5509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5878   -1.3924   -0.4843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9085   -1.5443   -0.1322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6701   -0.4265    0.1691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0632    0.7968    0.1012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7382    0.9512   -0.2521 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3579    2.2111    0.3531 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2002    2.1324   -1.0362 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8856    1.6319   -1.2585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8273   -0.4165   -1.1240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1988   -1.4654    1.0537 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4661    0.1050    1.8478 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8293   -2.3841   -0.5504 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1194   -2.4187   -1.2928 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6190   -0.5261   -0.7911 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7941    1.3937    0.4607 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4412    1.4244    1.2217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5271    0.3040    2.2361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0398    1.7725    1.3377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1667    0.3953    1.5645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4102    0.9636   -1.5264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2618   -0.8017   -1.6122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0161   -2.3006   -0.7168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3434   -2.5253   -0.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7136   -0.5388    0.4481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6320    1.6697    0.3297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3302    1.9685   -0.2828 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  2 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
  9  4  1  0
 18 13  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  6
  3 23  1  0
  3 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
 11 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
M  END

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0       7.184  -7.212   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.522  -6.433   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.184  -8.757   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.845  -6.433   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.854  -7.206   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.845  -9.529   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.500  -7.212   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      11.192  -6.433   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       9.860  -8.744   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.500  -8.757   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.524  -7.199   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.186  -4.889   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.857  -6.427   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.189  -7.199   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.850  -4.889   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.520  -6.427   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      15.182  -4.117   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.514  -4.889   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1    6                                                       
CONECT    4    1    7                                                       
CONECT    5    2    8    9                                                  
CONECT    6    3   10                                                       
CONECT    7    4   10                                                       
CONECT    8    5   11   12                                                  
CONECT    9    5                                                            
CONECT   10    6    7                                                       
CONECT   11    8   13                                                       
CONECT   12    8                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13   16                                                       
CONECT   15   13   17                                                       
CONECT   16   14   18                                                       
CONECT   17   15   18                                                       
CONECT   18   16   17                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0015003
HETATM    1  C1  UNL     1       1.046   1.594  -0.535  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.673   0.191  -0.183  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.556  -0.423   0.868  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.960  -0.458   0.402  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.456  -1.528  -0.307  1.00  0.00           C  
HETATM    6  C6  UNL     1       4.763  -1.566  -0.740  1.00  0.00           C  
HETATM    7  C7  UNL     1       5.605  -0.505  -0.459  1.00  0.00           C  
HETATM    8  C8  UNL     1       5.142   0.567   0.240  1.00  0.00           C  
HETATM    9  C9  UNL     1       3.817   0.580   0.666  1.00  0.00           C  
HETATM   10  N1  UNL     1      -0.684   0.000   0.195  1.00  0.00           N  
HETATM   11  C10 UNL     1      -1.118   0.685   1.360  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.564   0.039  -0.926  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.983  -0.158  -0.551  1.00  0.00           C  
HETATM   14  C13 UNL     1      -3.588  -1.392  -0.484  1.00  0.00           C  
HETATM   15  C14 UNL     1      -4.908  -1.544  -0.132  1.00  0.00           C  
HETATM   16  C15 UNL     1      -5.670  -0.426   0.169  1.00  0.00           C  
HETATM   17  C16 UNL     1      -5.063   0.797   0.101  1.00  0.00           C  
HETATM   18  C17 UNL     1      -3.738   0.951  -0.252  1.00  0.00           C  
HETATM   19  H1  UNL     1       1.358   2.211   0.353  1.00  0.00           H  
HETATM   20  H2  UNL     1       0.200   2.132  -1.036  1.00  0.00           H  
HETATM   21  H3  UNL     1       1.886   1.632  -1.258  1.00  0.00           H  
HETATM   22  H4  UNL     1       0.827  -0.416  -1.124  1.00  0.00           H  
HETATM   23  H5  UNL     1       1.199  -1.465   1.054  1.00  0.00           H  
HETATM   24  H6  UNL     1       1.466   0.105   1.848  1.00  0.00           H  
HETATM   25  H7  UNL     1       2.829  -2.384  -0.550  1.00  0.00           H  
HETATM   26  H8  UNL     1       5.119  -2.419  -1.293  1.00  0.00           H  
HETATM   27  H9  UNL     1       6.619  -0.526  -0.791  1.00  0.00           H  
HETATM   28  H10 UNL     1       5.794   1.394   0.461  1.00  0.00           H  
HETATM   29  H11 UNL     1       3.441   1.424   1.222  1.00  0.00           H  
HETATM   30  H12 UNL     1      -0.527   0.304   2.236  1.00  0.00           H  
HETATM   31  H13 UNL     1      -1.040   1.772   1.338  1.00  0.00           H  
HETATM   32  H14 UNL     1      -2.167   0.395   1.564  1.00  0.00           H  
HETATM   33  H15 UNL     1      -1.410   0.964  -1.526  1.00  0.00           H  
HETATM   34  H16 UNL     1      -1.262  -0.802  -1.612  1.00  0.00           H  
HETATM   35  H17 UNL     1      -3.016  -2.301  -0.717  1.00  0.00           H  
HETATM   36  H18 UNL     1      -5.343  -2.525  -0.092  1.00  0.00           H  
HETATM   37  H19 UNL     1      -6.714  -0.539   0.448  1.00  0.00           H  
HETATM   38  H20 UNL     1      -5.632   1.670   0.330  1.00  0.00           H  
HETATM   39  H21 UNL     1      -3.330   1.968  -0.283  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3   10   22
CONECT    3    4   23   24
CONECT    4    5    5    9
CONECT    5    6   25
CONECT    6    7    7   26
CONECT    7    8   27
CONECT    8    9    9   28
CONECT    9   29
CONECT   10   11   12
CONECT   11   30   31   32
CONECT   12   13   33   34
CONECT   13   14   14   18
CONECT   14   15   35
CONECT   15   16   16   36
CONECT   16   17   37
CONECT   17   18   18   38
CONECT   18   39
END

HMDB0015003
     RDKit          3D
Benzphetamine
 39 40  0  0  0  0  0  0  0  0999 V2000
    1.0459    1.5941   -0.5354 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6730    0.1913   -0.1831 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5557   -0.4226    0.8676 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9598   -0.4575    0.4017 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4564   -1.5281   -0.3072 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7631   -1.5664   -0.7403 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6052   -0.5049   -0.4591 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1421    0.5668    0.2399 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8171    0.5803    0.6658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6839    0.0004    0.1953 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1177    0.6854    1.3599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5644    0.0392   -0.9257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9826   -0.1575   -0.5509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5878   -1.3924   -0.4843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9085   -1.5443   -0.1322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6701   -0.4265    0.1691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0632    0.7968    0.1012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7382    0.9512   -0.2521 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3579    2.2111    0.3531 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2002    2.1324   -1.0362 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8856    1.6319   -1.2585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8273   -0.4165   -1.1240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1988   -1.4654    1.0537 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4661    0.1050    1.8478 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8293   -2.3841   -0.5504 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1194   -2.4187   -1.2928 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6190   -0.5261   -0.7911 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7941    1.3937    0.4607 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4412    1.4244    1.2217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5271    0.3040    2.2361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0398    1.7725    1.3377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1667    0.3953    1.5645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4102    0.9636   -1.5264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2618   -0.8017   -1.6122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0161   -2.3006   -0.7168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3434   -2.5253   -0.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7136   -0.5388    0.4481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6320    1.6697    0.3297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3302    1.9685   -0.2828 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  2 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
  9  4  1  0
 18 13  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  6
  3 23  1  0
  3 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
 11 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 14 35  1  0
 15 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-Benzphetamine	ChEBI
(+)-N,alpha-Dimethyl-N-(phenylmethyl)-benzeneethanamine	ChEBI
(+)-N-Benzyl-N,alpha-dimethylphenethylamine	ChEBI
(AlphaS)-N,alpha-dimethylphenethylamine	ChEBI
(S)-(+)-Benzphetamine	ChEBI
(S)-(+)-N-Benzyl-N,alpha-dimethylphenethylamine	ChEBI
(S)-Benzphetamine	ChEBI
Benzaphetamine	ChEBI
Benzfetamina	ChEBI
Benzfetamine	ChEBI
Benzfetaminum	ChEBI
Benzylamphetamine	ChEBI
D-N-Methyl-N-benzyl-beta-phenylisopropylamine	ChEBI
N-Methyl-1-phenyl-N-(phenylmethyl)propan-2-amine	ChEBI
(+)-N,a-Dimethyl-N-(phenylmethyl)-benzeneethanamine	Generator
(+)-N,Α-dimethyl-N-(phenylmethyl)-benzeneethanamine	Generator
(+)-N-Benzyl-N,a-dimethylphenethylamine	Generator
(+)-N-Benzyl-N,α-dimethylphenethylamine	Generator
(AlphaS)-N,a-dimethylphenethylamine	Generator
(AlphaS)-N,α-dimethylphenethylamine	Generator
(S)-(+)-N-Benzyl-N,a-dimethylphenethylamine	Generator
(S)-(+)-N-Benzyl-N,α-dimethylphenethylamine	Generator
D-N-Methyl-N-benzyl-b-phenylisopropylamine	Generator
D-N-Methyl-N-benzyl-β-phenylisopropylamine	Generator
Pfizer brand OF benzfetamine hydrochloride	HMDB
Didrex	HMDB

Chemical Formula

C₁₇H₂₁N

Average Molecular Weight

239.3553

Monoisotopic Molecular Weight

239.167399677

IUPAC Name

benzyl(methyl)[(2S)-1-phenylpropan-2-yl]amine

Traditional Name

benzphetamine

CAS Registry Number

156-08-1

SMILES

C[C@@H](CC1=CC=CC=C1)N(C)CC1=CC=CC=C1

InChI Identifier

InChI=1S/C17H21N/c1-15(13-16-9-5-3-6-10-16)18(2)14-17-11-7-4-8-12-17/h3-12,15H,13-14H2,1-2H3/t15-/m0/s1

InChI Key

YXKTVDFXDRQTKV-HNNXBMFYSA-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
Phenylpropane
Phenylmethylamine
Benzylamine
Aralkylamine
Tertiary aliphatic amine
Tertiary amine
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

tertiary amine (CHEBI:3044 )
amphetamines (CHEBI:3044 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015003)
Membrane (HMDB: HMDB0015003)

Not Available

adrenergic uptake inhibitor (HMDB: HMDB0015003)
dopamine uptake inhibitor (HMDB: HMDB0015003)

sympathomimetic agent (HMDB: HMDB0015003)

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

appetite depressant (HMDB: HMDB0015003)
sympathomimetic agent (HMDB: HMDB0015003)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	152 - 153 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.023 g/L	Not Available
LogP	4.1	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	154.8	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.023 g/L	ALOGPS
logP	3.72	ALOGPS
logP	4.34	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Basic)	9.72	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	3.24 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	78.39 m³·mol⁻¹	ChemAxon
Polarizability	29.03 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	158.495	31661259
DarkChem	[M-H]-	156.617	31661259
DeepCCS	[M+H]+	158.536	30932474
DeepCCS	[M-H]-	156.152	30932474
DeepCCS	[M-2H]-	189.062	30932474
DeepCCS	[M+Na]+	164.603	30932474
AllCCS	[M+H]+	157.9	32859911
AllCCS	[M+H-H2O]+	154.0	32859911
AllCCS	[M+NH4]+	161.7	32859911
AllCCS	[M+Na]+	162.7	32859911
AllCCS	[M-H]-	165.1	32859911
AllCCS	[M+Na-2H]-	165.0	32859911
AllCCS	[M+HCOO]-	165.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Benzphetamine	C[C@@H](CC1=CC=CC=C1)N(C)CC1=CC=CC=C1	2478.9	Standard polar	33892256
Benzphetamine	C[C@@H](CC1=CC=CC=C1)N(C)CC1=CC=CC=C1	1874.2	Standard non polar	33892256
Benzphetamine	C[C@@H](CC1=CC=CC=C1)N(C)CC1=CC=CC=C1	1908.5	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 - Benzphetamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dm-6920000000-7c83e10be43beca4a6db	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzphetamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Benzphetamine LC-ESI-QTOF 35V, positive-QTOF	splash10-0006-9120000000-500b274f6afef32ed4e1	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Benzphetamine 35V, Positive-QTOF	splash10-0006-9230000000-5fa8f51ec1e6f5ff1d31	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzphetamine 10V, Positive-QTOF	splash10-0006-0190000000-53abd8dba6ec13a440c6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzphetamine 20V, Positive-QTOF	splash10-00kg-3940000000-d297b9cbc93cf306977c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzphetamine 40V, Positive-QTOF	splash10-0006-9400000000-57e6a074201ba0c6f912	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzphetamine 10V, Negative-QTOF	splash10-000i-0190000000-6a88a2bf83016b16b90c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzphetamine 20V, Negative-QTOF	splash10-000i-0890000000-f2e83357a1507b2d57ea	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzphetamine 40V, Negative-QTOF	splash10-0arv-6900000000-c3eafb9fcd17634ca48e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzphetamine 10V, Positive-QTOF	splash10-0006-0090000000-256c7e14fc77a9080541	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzphetamine 20V, Positive-QTOF	splash10-0006-9560000000-cff805f0fb8a266e219b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzphetamine 40V, Positive-QTOF	splash10-0006-9100000000-bb878589696e5452d7fb	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzphetamine 10V, Negative-QTOF	splash10-000i-0090000000-a8c0494c6f42c28af745	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzphetamine 20V, Negative-QTOF	splash10-000i-2290000000-1cd11b6c14d9e0c19ff1	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzphetamine 40V, Negative-QTOF	splash10-00mo-9730000000-a6a72ee74a531f93fa40	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
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 DB00865	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00865	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

DB00865

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4470556

KEGG Compound ID

C07538

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Benzphetamine

METLIN ID

Not Available

PubChem Compound

5311017

PDB ID

Not Available

ChEBI ID

3044

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. NADPH--cytochrome P450 reductase

General function:: Involved in oxidoreductase activity
Specific function:: This enzyme is required for electron transfer from NADP to cytochrome P450 in microsomes. It can also provide electron transfer to heme oxygenase and cytochrome B5.
Gene Name:: POR
Uniprot ID:: P16435
Molecular weight:: 77047.575

References

Kanaeva IP, Nikityuk OV, Davydov DR, Dedinskii IR, Koen YM, Kuznetsova GP, Skotselyas ED, Bachmanova GI, Archakov AI: Comparative study of monomeric reconstituted and membrane microsomal monooxygenase systems of the rabbit liver. II. Kinetic parameters of reductase and monooxygenase reactions. Arch Biochem Biophys. 1992 Nov 1;298(2):403-12. [PubMed:1416971 ]
Matsumoto T, Emi Y, Kawabata S, Omura T: Purification and characterization of three male-specific and one female-specific forms of cytochrome P-450 from rat liver microsomes. J Biochem. 1986 Nov;100(5):1359-71. [PubMed:2434473 ]
Kojima H, Takahashi K, Sakane F, Koyama J: Purification and characterization of NADPH-cytochrome c reductase from porcine polymorphonuclear leukocytes. J Biochem. 1987 Nov;102(5):1083-8. [PubMed:3125159 ]
Dutton DR, McMillen SK, Parkinson A: Purification of rat liver microsomal cytochrome P-450b without the use of nonionic detergent. J Biochem Toxicol. 1988 Summer;3:131-45. [PubMed:3148724 ]
Halpert JR, Miller NE, Gorsky LD: On the mechanism of the inactivation of the major phenobarbital-inducible isozyme of rat liver cytochrome P-450 by chloramphenicol. J Biol Chem. 1985 Jul 15;260(14):8397-403. [PubMed:3924914 ]

Enzyme Details

2. Cytochrome P450 3A4

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 performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Seree EJ, Pisano PJ, Placidi M, Rahmani R, Barra YA: Identification of the human and animal hepatic cytochromes P450 involved in clonazepam metabolism. Fundam Clin Pharmacol. 1993;7(2):69-75. [PubMed:8486332 ]

Enzyme Details

3. Cytochrome P450 2B6

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. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:: CYP2B6
Uniprot ID:: P20813
Molecular weight:: 56277.81

References

Bumpus NN, Sridar C, Kent UM, Hollenberg PF: The naturally occurring cytochrome P450 (P450) 2B6 K262R mutant of P450 2B6 exhibits alterations in substrate metabolism and inactivation. Drug Metab Dispos. 2005 Jun;33(6):795-802. Epub 2005 Mar 15. [PubMed:15769884 ]
Shebley M, Kent UM, Ballou DP, Hollenberg PF: Mechanistic analysis of the inactivation of cytochrome P450 2B6 by phencyclidine: effects on substrate binding, electron transfer, and uncoupling. Drug Metab Dispos. 2009 Apr;37(4):745-52. doi: 10.1124/dmd.108.024661. Epub 2009 Jan 14. [PubMed:19144770 ]

Enzyme Details

4. Alpha-2A adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol
Gene Name:: ADRA2A
Uniprot ID:: P08913
Molecular weight:: 48956.3

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Enzyme Details

5. Synaptic vesicular amine transporter

General function:: Involved in transmembrane transport
Specific function:: Involved in the ATP-dependent vesicular transport of biogenic amine neurotransmitters. Pumps cytosolic monoamines including dopamine, norepinephrine, serotonin, and histamine into synaptic vesicles. Requisite for vesicular amine storage prior to secretion via exocytosis
Gene Name:: SLC18A2
Uniprot ID:: Q05940
Molecular weight:: 55712.1

References

Sulzer D, Chen TK, Lau YY, Kristensen H, Rayport S, Ewing A: Amphetamine redistributes dopamine from synaptic vesicles to the cytosol and promotes reverse transport. J Neurosci. 1995 May;15(5 Pt 2):4102-8. [PubMed:7751968 ]

Enzyme Details

6. Sodium-dependent dopamine transporter

General function:: Involved in neurotransmitter:sodium symporter activity
Specific function:: Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:: SLC6A3
Uniprot ID:: Q01959
Molecular weight:: 68494.255

References

Sulzer D, Sonders MS, Poulsen NW, Galli A: Mechanisms of neurotransmitter release by amphetamines: a review. Prog Neurobiol. 2005 Apr;75(6):406-33. [PubMed:15955613 ]
Kahlig KM, Binda F, Khoshbouei H, Blakely RD, McMahon DG, Javitch JA, Galli A: Amphetamine induces dopamine efflux through a dopamine transporter channel. Proc Natl Acad Sci U S A. 2005 Mar 1;102(9):3495-500. Epub 2005 Feb 22. [PubMed:15728379 ]

Enzyme Details

7. Alpha-1A adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins
Gene Name:: ADRA1A
Uniprot ID:: P35348
Molecular weight:: 51486.0

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Showing metabocard for Benzphetamine (HMDB0015003)

MOL for HMDB0015003 (Benzphetamine)

3D MOL for HMDB0015003 (Benzphetamine)

3D SDF for HMDB0015003 (Benzphetamine)

3D-SDF for HMDB0015003 (Benzphetamine)

PDB for HMDB0015003 (Benzphetamine)

3D PDB for HMDB0015003 (Benzphetamine)

SMILES for HMDB0015003 (Benzphetamine)

INCHI for HMDB0015003 (Benzphetamine)

Structure for HMDB0015003 (Benzphetamine)

3D Structure for HMDB0015003 (Benzphetamine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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