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Showing metabocard for Propylhexedrine (HMDB0015659)

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enzymes (2)transporters (1) Show 3 proteins
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2023-02-21 17:18:33 UTC
HMDB IDHMDB0015659
Secondary Accession Numbers
  • HMDB15659
Metabolite Identification
Common NamePropylhexedrine
DescriptionPropylhexedrine is only found in individuals that have used or taken this drug. It is an alpha-adrenergic agonist often used in nasal decongestant inhalers. It is used to give temporary relief for nasal congestion from colds, allergic rhinitis, or allergies. Propylhexidrine causes the norepinephrine, dopamine, and serotonin (5HT) transporters to reverse their direction of flow. This inversion leads to a release of these transmitters from the vesicles to the cytoplasm and from the cytoplasm to the synapse. It also antagonizes the action of VMAT2, causing the release of more neurotransmitters.
Structure
Data?1676999913
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0015659 (Propylhexedrine)


  Mrv0541 02241212492D          

 11 11  0  0  0  0            999 V2000
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    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
    0.7145    1.2375    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    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
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3D MOL for HMDB0015659 (Propylhexedrine)

HMDB0015659
     RDKit          3D
Propylhexedrine
 32 32  0  0  0  0  0  0  0  0999 V2000
   -3.5444    0.2987   -0.5478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0683    0.5078    0.8034 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6988   -0.0076    0.8453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8235   -1.4842    0.5416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8674    0.7559   -0.1124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5608    0.4119   -0.2310 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3256    0.5612    1.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7603    0.8163    0.7136 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1220    0.3465   -0.6586 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4203   -0.8834   -1.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9331   -0.8983   -0.8114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2824   -0.6692   -0.9726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2735    1.1368   -1.2322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6742    0.3448   -0.5184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0329    1.5529    0.9370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3777    0.1590    1.8977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1766   -2.0954    1.2012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5917   -1.6925   -0.5110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8665   -1.8531    0.7131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9476    1.8455    0.0904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3307    0.6142   -1.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0065    1.2022   -0.9255 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2991   -0.4231    1.6118 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8855    1.3396    1.7306 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4696    0.4722    1.4967 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8836    1.9405    0.7046 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2234    0.0917   -0.6281 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0671    1.1717   -1.4220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9312   -1.8012   -0.7818 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5152   -0.8943   -2.2434 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3597   -1.1523   -1.7332 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7933   -1.7147   -0.0791 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
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11  6  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  4 19  1  0
  5 20  1  0
  5 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
M  END
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3D SDF for HMDB0015659 (Propylhexedrine)


  Mrv0541 02241212492D          

 11 11  0  0  0  0            999 V2000
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    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
    0.7145    1.2375    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    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015659

> <DATABASE_NAME>
hmdb

> <SMILES>
CNC(C)CC1CCCCC1

> <INCHI_IDENTIFIER>
InChI=1S/C10H21N/c1-9(11-2)8-10-6-4-3-5-7-10/h9-11H,3-8H2,1-2H3

> <INCHI_KEY>
JCRIVQIOJSSCQD-UHFFFAOYSA-N

> <FORMULA>
C10H21N

> <MOLECULAR_WEIGHT>
155.2804

> <EXACT_MASS>
155.167399677

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
20.265970560331418

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1-cyclohexylpropan-2-yl)(methyl)amine

> <ALOGPS_LOGP>
3.37

> <JCHEM_LOGP>
2.7045947563333326

> <ALOGPS_LOGS>
-3.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
10.614016211465927

> <JCHEM_POLAR_SURFACE_AREA>
12.03

> <JCHEM_REFRACTIVITY>
49.535199999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.04e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
propylhexedrine

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0015659 (Propylhexedrine)

HMDB0015659
     RDKit          3D
Propylhexedrine
 32 32  0  0  0  0  0  0  0  0999 V2000
   -3.5444    0.2987   -0.5478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0683    0.5078    0.8034 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6988   -0.0076    0.8453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8235   -1.4842    0.5416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8674    0.7559   -0.1124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5608    0.4119   -0.2310 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3256    0.5612    1.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7603    0.8163    0.7136 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1220    0.3465   -0.6586 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4203   -0.8834   -1.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9331   -0.8983   -0.8114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2824   -0.6692   -0.9726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2735    1.1368   -1.2322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6742    0.3448   -0.5184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0329    1.5529    0.9370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3777    0.1590    1.8977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1766   -2.0954    1.2012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5917   -1.6925   -0.5110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8665   -1.8531    0.7131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9476    1.8455    0.0904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3307    0.6142   -1.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0065    1.2022   -0.9255 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2991   -0.4231    1.6118 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8855    1.3396    1.7306 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4696    0.4722    1.4967 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8836    1.9405    0.7046 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2234    0.0917   -0.6281 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0671    1.1717   -1.4220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9312   -1.8012   -0.7818 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5152   -0.8943   -2.2434 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3597   -1.1523   -1.7332 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7933   -1.7147   -0.0791 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
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11  6  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  4 19  1  0
  5 20  1  0
  5 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
M  END
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PDB for HMDB0015659 (Propylhexedrine)

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       0.000   6.160   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    4                                                       
CONECT   10    2   11                                                       
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for HMDB0015659 (Propylhexedrine)

COMPND    HMDB0015659
HETATM    1  C1  UNL     1      -3.544   0.299  -0.548  1.00  0.00           C  
HETATM    2  N1  UNL     1      -3.068   0.508   0.803  1.00  0.00           N  
HETATM    3  C2  UNL     1      -1.699  -0.008   0.845  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.823  -1.484   0.542  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.867   0.756  -0.112  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.561   0.412  -0.231  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.326   0.561   1.080  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.760   0.816   0.714  1.00  0.00           C  
HETATM    9  C8  UNL     1       3.122   0.347  -0.659  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.420  -0.883  -1.117  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.933  -0.898  -0.811  1.00  0.00           C  
HETATM   12  H1  UNL     1      -3.282  -0.669  -0.973  1.00  0.00           H  
HETATM   13  H2  UNL     1      -3.273   1.137  -1.232  1.00  0.00           H  
HETATM   14  H3  UNL     1      -4.674   0.345  -0.518  1.00  0.00           H  
HETATM   15  H4  UNL     1      -3.033   1.553   0.937  1.00  0.00           H  
HETATM   16  H5  UNL     1      -1.378   0.159   1.898  1.00  0.00           H  
HETATM   17  H6  UNL     1      -1.177  -2.095   1.201  1.00  0.00           H  
HETATM   18  H7  UNL     1      -1.592  -1.693  -0.511  1.00  0.00           H  
HETATM   19  H8  UNL     1      -2.866  -1.853   0.713  1.00  0.00           H  
HETATM   20  H9  UNL     1      -0.948   1.846   0.090  1.00  0.00           H  
HETATM   21  H10 UNL     1      -1.331   0.614  -1.133  1.00  0.00           H  
HETATM   22  H11 UNL     1       1.007   1.202  -0.926  1.00  0.00           H  
HETATM   23  H12 UNL     1       1.299  -0.423   1.612  1.00  0.00           H  
HETATM   24  H13 UNL     1       0.885   1.340   1.731  1.00  0.00           H  
HETATM   25  H14 UNL     1       3.470   0.472   1.497  1.00  0.00           H  
HETATM   26  H15 UNL     1       2.884   1.940   0.705  1.00  0.00           H  
HETATM   27  H16 UNL     1       4.223   0.092  -0.628  1.00  0.00           H  
HETATM   28  H17 UNL     1       3.067   1.172  -1.422  1.00  0.00           H  
HETATM   29  H18 UNL     1       2.931  -1.801  -0.782  1.00  0.00           H  
HETATM   30  H19 UNL     1       2.515  -0.894  -2.243  1.00  0.00           H  
HETATM   31  H20 UNL     1       0.360  -1.152  -1.733  1.00  0.00           H  
HETATM   32  H21 UNL     1       0.793  -1.715  -0.079  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3   15
CONECT    3    4    5   16
CONECT    4   17   18   19
CONECT    5    6   20   21
CONECT    6    7   11   22
CONECT    7    8   23   24
CONECT    8    9   25   26
CONECT    9   10   27   28
CONECT   10   11   29   30
CONECT   11   31   32
END
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SMILES for HMDB0015659 (Propylhexedrine)

CNC(C)CC1CCCCC1
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INCHI for HMDB0015659 (Propylhexedrine)

InChI=1S/C10H21N/c1-9(11-2)8-10-6-4-3-5-7-10/h9-11H,3-8H2,1-2H3
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View in JSmolView Stereo Labels
Synonyms
ValueSource
Dristan inhalerKegg
Propylhexedrine hydrochlorideHMDB
Propylhexedrine hydrochloride, (S)-isomerHMDB
BenzedrexHMDB
PropylhexadrineHMDB
Chemical FormulaC10H21N
Average Molecular Weight155.2804
Monoisotopic Molecular Weight155.167399677
IUPAC Name(1-cyclohexylpropan-2-yl)(methyl)amine
Traditional Namepropylhexedrine
CAS Registry Number3595-11-7
SMILES
CNC(C)CC1CCCCC1
InChI Identifier
InChI=1S/C10H21N/c1-9(11-2)8-10-6-4-3-5-7-10/h9-11H,3-8H2,1-2H3
InChI KeyJCRIVQIOJSSCQD-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dialkylamines. These are organic compounds containing a dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct ParentDialkylamines
Alternative Parents
Substituents
  • Secondary aliphatic amine
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.09 g/LALOGPS
logP3.37ALOGPS
logP2.7ChemAxon
logS-3.2ALOGPS
pKa (Strongest Basic)10.61ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area12.03 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity49.54 m³·mol⁻¹ChemAxon
Polarizability20.27 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+136.81531661259
DarkChem[M-H]-133.73831661259
DeepCCS[M+H]+143.06430932474
DeepCCS[M-H]-140.49130932474
DeepCCS[M-2H]-176.86130932474
DeepCCS[M+Na]+152.12630932474
AllCCS[M+H]+138.132859911
AllCCS[M+H-H2O]+133.832859911
AllCCS[M+NH4]+142.132859911
AllCCS[M+Na]+143.332859911
AllCCS[M-H]-142.632859911
AllCCS[M+Na-2H]-144.332859911
AllCCS[M+HCOO]-146.332859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.3.6 minutes32390414
Predicted by Siyang on May 30, 202210.5863 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20224.37 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid55.7 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1389.5 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid274.9 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid139.7 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid174.0 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid228.8 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid331.9 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid368.7 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)347.8 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid954.9 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid318.8 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid936.2 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid225.8 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid291.3 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate410.0 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA206.5 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water58.0 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PropylhexedrineCNC(C)CC1CCCCC11413.1Standard polar33892256
PropylhexedrineCNC(C)CC1CCCCC11146.7Standard non polar33892256
PropylhexedrineCNC(C)CC1CCCCC11160.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Propylhexedrine,1TMS,isomer #1CC(CC1CCCCC1)N(C)[Si](C)(C)C1386.3Semi standard non polar33892256
Propylhexedrine,1TMS,isomer #1CC(CC1CCCCC1)N(C)[Si](C)(C)C1399.2Standard non polar33892256
Propylhexedrine,1TMS,isomer #1CC(CC1CCCCC1)N(C)[Si](C)(C)C1591.6Standard polar33892256
Propylhexedrine,1TBDMS,isomer #1CC(CC1CCCCC1)N(C)[Si](C)(C)C(C)(C)C1611.6Semi standard non polar33892256
Propylhexedrine,1TBDMS,isomer #1CC(CC1CCCCC1)N(C)[Si](C)(C)C(C)(C)C1670.4Standard non polar33892256
Propylhexedrine,1TBDMS,isomer #1CC(CC1CCCCC1)N(C)[Si](C)(C)C(C)(C)C1755.1Standard polar33892256
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB06714 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB06714 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB06714
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID7277
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPropylhexedrine
METLIN IDNot Available
PubChem Compound7558
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. 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
  1. Nakahara Y, Hanajiri R: Hair analysis for drugs of abuse XXI. Effect of para-substituents on benzene ring of methamphetamine on drug incorporation into rat hair. Life Sci. 2000;66(7):563-74. [PubMed:10794512 ]
  2. Wesson DR: Propylhexdrine. Drug Alcohol Depend. 1986 Jun;17(2-3):273-8. [PubMed:2874970 ]
  3. 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 ]
  4. 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
2. Trace amine-associated receptor 1
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Receptor for trace amines, including beta- phenylethylamine (b-PEA), p-tyramine (p-TYR), octopamine and tryptamine, with highest affinity for b-PEA and p-TYR. Unresponsive to classical biogenic amines, such as epinephrine and histamine and only partially activated by dopamine and serotonine. Trace amines are biogenic amines present in very low levels in mammalian tissues. Although some trace amines have clearly defined roles as neurotransmitters in invertebrates, the extent to which they function as true neurotransmitters in vertebrates has remained speculative. Trace amines are likely to be involved in a variety of physiological functions that have yet to be fully understood. The signal transduced by this receptor is mediated by the G(s)-class of G-proteins which activate adenylate cyclase
Gene Name:
TAAR1
Uniprot ID:
Q96RJ0
Molecular weight:
39091.3
References
  1. Reese EA, Bunzow JR, Arttamangkul S, Sonders MS, Grandy DK: Trace amine-associated receptor 1 displays species-dependent stereoselectivity for isomers of methamphetamine, amphetamine, and para-hydroxyamphetamine. J Pharmacol Exp Ther. 2007 Apr;321(1):178-86. Epub 2007 Jan 11. [PubMed:17218486 ]
  2. Xie Z, Westmoreland SV, Bahn ME, Chen GL, Yang H, Vallender EJ, Yao WD, Madras BK, Miller GM: Rhesus monkey trace amine-associated receptor 1 signaling: enhancement by monoamine transporters and attenuation by the D2 autoreceptor in vitro. J Pharmacol Exp Ther. 2007 Apr;321(1):116-27. Epub 2007 Jan 18. [PubMed:17234900 ]
  3. Wolinsky TD, Swanson CJ, Smith KE, Zhong H, Borowsky B, Seeman P, Branchek T, Gerald CP: The Trace Amine 1 receptor knockout mouse: an animal model with relevance to schizophrenia. Genes Brain Behav. 2007 Oct;6(7):628-39. Epub 2006 Dec 21. [PubMed:17212650 ]
  4. Xie Z, Miller GM: Trace amine-associated receptor 1 is a modulator of the dopamine transporter. J Pharmacol Exp Ther. 2007 Apr;321(1):128-36. Epub 2007 Jan 18. [PubMed:17234899 ]
  5. Miller GM, Verrico CD, Jassen A, Konar M, Yang H, Panas H, Bahn M, Johnson R, Madras BK: Primate trace amine receptor 1 modulation by the dopamine transporter. J Pharmacol Exp Ther. 2005 Jun;313(3):983-94. Epub 2005 Mar 11. [PubMed:15764732 ]

Transporters

Enzyme Details
1. Solute carrier family 22 member 3
General function:
Involved in transmembrane transport
Specific function:
Mediates potential-dependent transport of a variety of organic cations. May play a significant role in the disposition of cationic neurotoxins and neurotransmitters in the brain
Gene Name:
SLC22A3
Uniprot ID:
O75751
Molecular weight:
61279.5
References
  1. Wu X, Kekuda R, Huang W, Fei YJ, Leibach FH, Chen J, Conway SJ, Ganapathy V: Identity of the organic cation transporter OCT3 as the extraneuronal monoamine transporter (uptake2) and evidence for the expression of the transporter in the brain. J Biol Chem. 1998 Dec 4;273(49):32776-86. [PubMed:9830022 ]