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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2)transporters (2) Show 4 proteins XML

enzymes (2)transporters (2) Show 4 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:03 UTC

HMDB ID

HMDB0015647

Secondary Accession Numbers

HMDB15647

Metabolite Identification

Common Name

Dexmethylphenidate

Description

Dexmethylphenidate is only found in individuals that have used or taken this drug. It is the dextrorotary form of methylphenidate. It is used for treatment of Attention Deficit Hyperactivity Disorder (ADHD). Methylphenidate blocks dopamine uptake in central adrenergic neurons by blocking dopamine transport or carrier proteins. Methylphenidate acts at the brain stem arousal system and the cerebral cortex and causes increased sympathomimetic activity in the central nervous system.Methylphenidate is a catecholamine reuptake inhibitor that indirectly increases catecholaminergic neurotransmission by inhibiting the dopamine transporter (DAT) and norepinephrine transporter (NET), which are responsible for clearing catecholamines from the synapse, particularly in the striatum and meso-limbic system.

Structure

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

HMDB0015647
     RDKit          3D
Dexmethylphenidate
 36 37  0  0  0  0  0  0  0  0999 V2000
   -3.0420    2.6839    1.3843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3654    1.8630    0.4757 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0563    1.4460    0.6172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4098    1.8159    1.6212 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4946    0.5902   -0.4199 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2476   -0.6776   -0.5637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3385   -1.5751    0.4877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0427   -2.7412    0.3229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6817   -3.0843   -0.8533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5826   -2.1786   -1.8952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8876   -1.0189   -1.7452 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9751    0.3065   -0.2710 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8225    1.5305   -0.2984 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2766    1.1431   -0.4703 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4564   -0.3518   -0.3372 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7016   -0.8040    0.8731 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3106   -0.4777    0.8744 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9631    2.1207    1.7038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3619    3.6515    0.9845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4348    2.7906    2.3153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5934    1.1434   -1.4005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8425   -1.3208    1.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0944   -3.4315    1.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2261   -4.0140   -0.9400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0796   -2.4215   -2.8442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8259   -0.3185   -2.5900 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2577   -0.3074   -1.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5585    2.2186   -1.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7307    2.0259    0.7056 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6810    1.4849   -1.4618 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9170    1.6336    0.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2044   -0.9041   -1.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5366   -0.5754   -0.1450 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7962   -1.9146    0.9927 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2402   -0.3753    1.7669 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1057    0.0439    1.7544 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  5 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 11  6  1  0
 17 12  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  5 21  1  6
  7 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  6
 13 28  1  0
 13 29  1  0
 14 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  0
M  END

154101
  Mrv0541 02241212462D          

 17 18  0  0  1  0            999 V2000
    3.0791   -1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.6188    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5080    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.2063    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2224    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  1  0  0  0  0
  1 17  1  0  0  0  0
  2 11  2  0  0  0  0
  3  4  1  0  0  0  0
  3  9  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  1  0  0  0
  5  7  1  0  0  0  0
  6 10  1  0  0  0  0
  6 11  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10 12  2  0  0  0  0
 10 13  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  2  0  0  0  0
 14 16  2  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015647

> <DATABASE_NAME>
hmdb

> <SMILES>
COC(=O)[C@@H]([C@H]1CCCCN1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H19NO2/c1-17-14(16)13(11-7-3-2-4-8-11)12-9-5-6-10-15-12/h2-4,7-8,12-13,15H,5-6,9-10H2,1H3/t12-,13-/m1/s1

> <INCHI_KEY>
DUGOZIWVEXMGBE-CHWSQXEVSA-N

> <FORMULA>
C14H19NO2

> <MOLECULAR_WEIGHT>
233.3062

> <EXACT_MASS>
233.141578857

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
26.226923219726338

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2R)-2-phenyl-2-[(2R)-piperidin-2-yl]acetate

> <ALOGPS_LOGP>
1.47

> <JCHEM_LOGP>
2.254935081666666

> <ALOGPS_LOGS>
-3.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.088826845099911

> <JCHEM_POLAR_SURFACE_AREA>
38.33

> <JCHEM_REFRACTIVITY>
66.72820000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.82e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dexmethylphenidate

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0015647
     RDKit          3D
Dexmethylphenidate
 36 37  0  0  0  0  0  0  0  0999 V2000
   -3.0420    2.6839    1.3843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3654    1.8630    0.4757 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0563    1.4460    0.6172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4098    1.8159    1.6212 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4946    0.5902   -0.4199 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2476   -0.6776   -0.5637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3385   -1.5751    0.4877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0427   -2.7412    0.3229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6817   -3.0843   -0.8533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5826   -2.1786   -1.8952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8876   -1.0189   -1.7452 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9751    0.3065   -0.2710 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8225    1.5305   -0.2984 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2766    1.1431   -0.4703 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4564   -0.3518   -0.3372 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7016   -0.8040    0.8731 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3106   -0.4777    0.8744 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9631    2.1207    1.7038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3619    3.6515    0.9845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4348    2.7906    2.3153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5934    1.1434   -1.4005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8425   -1.3208    1.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0944   -3.4315    1.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2261   -4.0140   -0.9400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0796   -2.4215   -2.8442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8259   -0.3185   -2.5900 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2577   -0.3074   -1.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5585    2.2186   -1.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7307    2.0259    0.7056 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6810    1.4849   -1.4618 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9170    1.6336    0.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2044   -0.9041   -1.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5366   -0.5754   -0.1450 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7962   -1.9146    0.9927 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2402   -0.3753    1.7669 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1057    0.0439    1.7544 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  5 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 11  6  1  0
 17 12  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  5 21  1  6
  7 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  6
 13 28  1  0
 13 29  1  0
 14 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 154101                                            
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       5.748  -1.925   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       8.415  -1.925   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       9.748   0.385   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       8.415   1.155   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.415   2.695   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.081   0.385   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.748   3.465   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.082   2.695   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.082   1.155   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.748   1.155   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.081  -1.155   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.414   0.385   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.748   2.695   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.080   1.155   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.414   3.465   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.080   2.695   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.748  -3.465   0.000  0.00  0.00           C+0
CONECT    1   11   17                                                       
CONECT    2   11                                                            
CONECT    3    4    9                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4    7                                                       
CONECT    6    4   10   11                                                  
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    3    8                                                       
CONECT   10    6   12   13                                                  
CONECT   11    1    2    6                                                  
CONECT   12   10   14                                                       
CONECT   13   10   15                                                       
CONECT   14   12   16                                                       
CONECT   15   13   16                                                       
CONECT   16   14   15                                                       
CONECT   17    1                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0015647
HETATM    1  C1  UNL     1      -3.042   2.684   1.384  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.365   1.863   0.476  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.056   1.446   0.617  1.00  0.00           C  
HETATM    4  O2  UNL     1      -0.410   1.816   1.621  1.00  0.00           O  
HETATM    5  C3  UNL     1      -0.495   0.590  -0.420  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.248  -0.678  -0.564  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.339  -1.575   0.488  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.043  -2.741   0.323  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.682  -3.084  -0.853  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.583  -2.179  -1.895  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.888  -1.019  -1.745  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.975   0.306  -0.271  1.00  0.00           C  
HETATM   13  C11 UNL     1       1.822   1.531  -0.298  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.277   1.143  -0.470  1.00  0.00           C  
HETATM   15  C13 UNL     1       3.456  -0.352  -0.337  1.00  0.00           C  
HETATM   16  C14 UNL     1       2.702  -0.804   0.873  1.00  0.00           C  
HETATM   17  N1  UNL     1       1.311  -0.478   0.874  1.00  0.00           N  
HETATM   18  H1  UNL     1      -3.963   2.121   1.704  1.00  0.00           H  
HETATM   19  H2  UNL     1      -3.362   3.652   0.985  1.00  0.00           H  
HETATM   20  H3  UNL     1      -2.435   2.791   2.315  1.00  0.00           H  
HETATM   21  H4  UNL     1      -0.593   1.143  -1.400  1.00  0.00           H  
HETATM   22  H5  UNL     1      -0.843  -1.321   1.420  1.00  0.00           H  
HETATM   23  H6  UNL     1      -2.094  -3.431   1.179  1.00  0.00           H  
HETATM   24  H7  UNL     1      -3.226  -4.014  -0.940  1.00  0.00           H  
HETATM   25  H8  UNL     1      -3.080  -2.422  -2.844  1.00  0.00           H  
HETATM   26  H9  UNL     1      -1.826  -0.318  -2.590  1.00  0.00           H  
HETATM   27  H10 UNL     1       1.258  -0.307  -1.177  1.00  0.00           H  
HETATM   28  H11 UNL     1       1.559   2.219  -1.121  1.00  0.00           H  
HETATM   29  H12 UNL     1       1.731   2.026   0.706  1.00  0.00           H  
HETATM   30  H13 UNL     1       3.681   1.485  -1.462  1.00  0.00           H  
HETATM   31  H14 UNL     1       3.917   1.634   0.317  1.00  0.00           H  
HETATM   32  H15 UNL     1       3.204  -0.904  -1.262  1.00  0.00           H  
HETATM   33  H16 UNL     1       4.537  -0.575  -0.145  1.00  0.00           H  
HETATM   34  H17 UNL     1       2.796  -1.915   0.993  1.00  0.00           H  
HETATM   35  H18 UNL     1       3.240  -0.375   1.767  1.00  0.00           H  
HETATM   36  H19 UNL     1       1.106   0.044   1.754  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6   12   21
CONECT    6    7    7   11
CONECT    7    8   22
CONECT    8    9    9   23
CONECT    9   10   24
CONECT   10   11   11   25
CONECT   11   26
CONECT   12   13   17   27
CONECT   13   14   28   29
CONECT   14   15   30   31
CONECT   15   16   32   33
CONECT   16   17   34   35
CONECT   17   36
END

HMDB0015647
     RDKit          3D
Dexmethylphenidate
 36 37  0  0  0  0  0  0  0  0999 V2000
   -3.0420    2.6839    1.3843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3654    1.8630    0.4757 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0563    1.4460    0.6172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4098    1.8159    1.6212 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4946    0.5902   -0.4199 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2476   -0.6776   -0.5637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3385   -1.5751    0.4877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0427   -2.7412    0.3229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6817   -3.0843   -0.8533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5826   -2.1786   -1.8952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8876   -1.0189   -1.7452 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9751    0.3065   -0.2710 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8225    1.5305   -0.2984 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2766    1.1431   -0.4703 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4564   -0.3518   -0.3372 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7016   -0.8040    0.8731 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3106   -0.4777    0.8744 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9631    2.1207    1.7038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3619    3.6515    0.9845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4348    2.7906    2.3153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5934    1.1434   -1.4005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8425   -1.3208    1.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0944   -3.4315    1.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2261   -4.0140   -0.9400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0796   -2.4215   -2.8442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8259   -0.3185   -2.5900 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2577   -0.3074   -1.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5585    2.2186   -1.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7307    2.0259    0.7056 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6810    1.4849   -1.4618 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9170    1.6336    0.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2044   -0.9041   -1.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5366   -0.5754   -0.1450 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7962   -1.9146    0.9927 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2402   -0.3753    1.7669 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1057    0.0439    1.7544 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  5 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 11  6  1  0
 17 12  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  5 21  1  6
  7 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  6
 13 28  1  0
 13 29  1  0
 14 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-Threo-methylphenidate	ChEBI
D-Threo-methylphenidate	ChEBI
Dexmethylphenidatum	ChEBI
Dexmetilfenidato	ChEBI
Methyl (R)-phenyl[(R)-piperidin-2-yl]acetate	ChEBI
(+)-Threo-methylphenidic acid	Generator
D-Threo-methylphenidic acid	Generator
Methyl (R)-phenyl[(R)-piperidin-2-yl]acetic acid	Generator
Dexmethylphenidic acid	Generator
Dexmethylphenidate hydrochloride	HMDB
Focalin XR	HMDB
Hydrochloride, dexmethylphenidate	HMDB
XR, Focalin	HMDB
Focalin	HMDB

Chemical Formula

C₁₄H₁₉NO₂

Average Molecular Weight

233.3062

Monoisotopic Molecular Weight

233.141578857

IUPAC Name

methyl (2R)-2-phenyl-2-[(2R)-piperidin-2-yl]acetate

Traditional Name

dexmethylphenidate

CAS Registry Number

40431-64-9

SMILES

COC(=O)[C@@H]([C@H]1CCCCN1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C14H19NO2/c1-17-14(16)13(11-7-3-2-4-8-11)12-9-5-6-10-15-12/h2-4,7-8,12-13,15H,5-6,9-10H2,1H3/t12-,13-/m1/s1

InChI Key

DUGOZIWVEXMGBE-CHWSQXEVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

Aralkylamines

Alternative Parents

Substituents

Aralkylamine
Monocyclic benzene moiety
Piperidine
Benzenoid
Methyl ester
Amino acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Secondary aliphatic amine
Monocarboxylic acid or derivatives
Secondary amine
Azacycle
Organoheterocyclic compound
Organopnictogen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

methyl phenyl(piperidin-2-yl)acetate (CHEBI:51860 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.18 g/L	ALOGPS
logP	1.47	ALOGPS
logP	2.25	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Basic)	9.09	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.33 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	66.73 m³·mol⁻¹	ChemAxon
Polarizability	26.23 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]+	154.905	31661259
DarkChem	[M-H]-	153.083	31661259
DeepCCS	[M+H]+	156.94	30932474
DeepCCS	[M-H]-	154.582	30932474
DeepCCS	[M-2H]-	187.468	30932474
DeepCCS	[M+Na]+	163.033	30932474
AllCCS	[M+H]+	154.7	32859911
AllCCS	[M+H-H2O]+	150.6	32859911
AllCCS	[M+NH4]+	158.5	32859911
AllCCS	[M+Na]+	159.6	32859911
AllCCS	[M-H]-	160.1	32859911
AllCCS	[M+Na-2H]-	160.3	32859911
AllCCS	[M+HCOO]-	160.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dexmethylphenidate	COC(=O)[C@@H]([C@H]1CCCCN1)C1=CC=CC=C1	2319.0	Standard polar	33892256
Dexmethylphenidate	COC(=O)[C@@H]([C@H]1CCCCN1)C1=CC=CC=C1	1740.5	Standard non polar	33892256
Dexmethylphenidate	COC(=O)[C@@H]([C@H]1CCCCN1)C1=CC=CC=C1	1768.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dexmethylphenidate,1TMS,isomer #1	COC(=O)[C@H](C1=CC=CC=C1)[C@H]1CCCCN1[Si](C)(C)C	1815.0	Semi standard non polar	33892256
Dexmethylphenidate,1TMS,isomer #1	COC(=O)[C@H](C1=CC=CC=C1)[C@H]1CCCCN1[Si](C)(C)C	1858.8	Standard non polar	33892256
Dexmethylphenidate,1TMS,isomer #1	COC(=O)[C@H](C1=CC=CC=C1)[C@H]1CCCCN1[Si](C)(C)C	2559.4	Standard polar	33892256
Dexmethylphenidate,1TBDMS,isomer #1	COC(=O)[C@H](C1=CC=CC=C1)[C@H]1CCCCN1[Si](C)(C)C(C)(C)C	2016.7	Semi standard non polar	33892256
Dexmethylphenidate,1TBDMS,isomer #1	COC(=O)[C@H](C1=CC=CC=C1)[C@H]1CCCCN1[Si](C)(C)C(C)(C)C	2043.2	Standard non polar	33892256
Dexmethylphenidate,1TBDMS,isomer #1	COC(=O)[C@H](C1=CC=CC=C1)[C@H]1CCCCN1[Si](C)(C)C(C)(C)C	2685.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dexmethylphenidate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0089-9610000000-8e4c1241e36274356032	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dexmethylphenidate 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 - Dexmethylphenidate 10V, Positive-QTOF	splash10-001i-1190000000-8803b6fb1d54baf20a6f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexmethylphenidate 20V, Positive-QTOF	splash10-001i-6390000000-63f6ddbd32540d6c0e4e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexmethylphenidate 40V, Positive-QTOF	splash10-001i-9500000000-dab6b5667313005cbcd2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexmethylphenidate 10V, Negative-QTOF	splash10-001i-0090000000-dbf1d73eb0c9410efbf6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexmethylphenidate 20V, Negative-QTOF	splash10-001i-2290000000-4a7ee5089439605a9759	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexmethylphenidate 40V, Negative-QTOF	splash10-00w9-9520000000-aa484f1df63a11905d5a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexmethylphenidate 10V, Positive-QTOF	splash10-001i-2190000000-aa6695fd8b35db2e4b41	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexmethylphenidate 20V, Positive-QTOF	splash10-001i-9440000000-3e2430ca32eb71f561e4	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexmethylphenidate 40V, Positive-QTOF	splash10-001i-9300000000-2d49d7918e562aad8156	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexmethylphenidate 10V, Negative-QTOF	splash10-001i-0090000000-96a8c87419b47af6da2a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexmethylphenidate 20V, Negative-QTOF	splash10-00lr-4790000000-8bbed2d476f383bd9813	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexmethylphenidate 40V, Negative-QTOF	splash10-0006-9400000000-dabf09c5d3b6f3c788fe	2021-10-12	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 DB06701	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB06701	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

DB06701

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

135807

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dexmethylphenidate

METLIN ID

Not Available

PubChem Compound

154101

PDB ID

Not Available

ChEBI ID

51860

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. 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

2. 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

Markowitz JS, Patrick KS: Differential pharmacokinetics and pharmacodynamics of methylphenidate enantiomers: does chirality matter? J Clin Psychopharmacol. 2008 Jun;28(3 Suppl 2):S54-61. doi: 10.1097/JCP.0b013e3181733560. [PubMed:18480678 ]
Ding YS, Fowler JS, Volkow ND, Dewey SL, Wang GJ, Logan J, Gatley SJ, Pappas N: Chiral drugs: comparison of the pharmacokinetics of [11C]d-threo and L-threo-methylphenidate in the human and baboon brain. Psychopharmacology (Berl). 1997 May;131(1):71-8. [PubMed:9181638 ]
Davids E, Zhang K, Tarazi FI, Baldessarini RJ: Stereoselective effects of methylphenidate on motor hyperactivity in juvenile rats induced by neonatal 6-hydroxydopamine lesioning. Psychopharmacology (Berl). 2002 Feb;160(1):92-8. Epub 2001 Dec 18. [PubMed:11862378 ]
Volkow ND, Fowler JS, Gatley SJ, Dewey SL, Wang GJ, Logan J, Ding YS, Franceschi D, Gifford A, Morgan A, Pappas N, King P: Comparable changes in synaptic dopamine induced by methylphenidate and by cocaine in the baboon brain. Synapse. 1999 Jan;31(1):59-66. [PubMed:10025684 ]
Wayment HK, Deutsch H, Schweri MM, Schenk JO: Effects of methylphenidate analogues on phenethylamine substrates for the striatal dopamine transporter: potential as amphetamine antagonists? J Neurochem. 1999 Mar;72(3):1266-74. [PubMed:10037500 ]
Dresel SH, Kung MP, Huang X, Plossl K, Hou C, Shiue CY, Karp J, Kung HF: In vivo imaging of serotonin transporters with [99mTc]TRODAT-1 in nonhuman primates. Eur J Nucl Med. 1999 Apr;26(4):342-7. [PubMed:10199939 ]
Volkow ND, Wang GJ, Fowler JS, Fischman M, Foltin R, Abumrad NN, Gatley SJ, Logan J, Wong C, Gifford A, Ding YS, Hitzemann R, Pappas N: Methylphenidate and cocaine have a similar in vivo potency to block dopamine transporters in the human brain. Life Sci. 1999;65(1):PL7-12. [PubMed:10403500 ]
Izenwasser S, Coy AE, Ladenheim B, Loeloff RJ, Cadet JL, French D: Chronic methylphenidate alters locomotor activity and dopamine transporters differently from cocaine. Eur J Pharmacol. 1999 Jun 4;373(2-3):187-93. [PubMed:10414438 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [PubMed:9537821 ]
Viggiano D, Vallone D, Sadile A: Dysfunctions in dopamine systems and ADHD: evidence from animals and modeling. Neural Plast. 2004;11(1-2):97-114. [PubMed:15303308 ]
Tilley MR, Gu HH: The effects of methylphenidate on knockin mice with a methylphenidate-resistant dopamine transporter. J Pharmacol Exp Ther. 2008 Nov;327(2):554-60. doi: 10.1124/jpet.108.141713. Epub 2008 Aug 12. [PubMed:18698001 ]

Transporters

Enzyme Details

1. Sodium-dependent noradrenaline transporter

General function:: Involved in neurotransmitter:sodium symporter activity
Specific function:: Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:: SLC6A2
Uniprot ID:: P23975
Molecular weight:: 69331.42

References

Markowitz JS, Patrick KS: Differential pharmacokinetics and pharmacodynamics of methylphenidate enantiomers: does chirality matter? J Clin Psychopharmacol. 2008 Jun;28(3 Suppl 2):S54-61. doi: 10.1097/JCP.0b013e3181733560. [PubMed:18480678 ]
Ding YS, Fowler JS, Volkow ND, Dewey SL, Wang GJ, Logan J, Gatley SJ, Pappas N: Chiral drugs: comparison of the pharmacokinetics of [11C]d-threo and L-threo-methylphenidate in the human and baboon brain. Psychopharmacology (Berl). 1997 May;131(1):71-8. [PubMed:9181638 ]
Davids E, Zhang K, Tarazi FI, Baldessarini RJ: Stereoselective effects of methylphenidate on motor hyperactivity in juvenile rats induced by neonatal 6-hydroxydopamine lesioning. Psychopharmacology (Berl). 2002 Feb;160(1):92-8. Epub 2001 Dec 18. [PubMed:11862378 ]
Yang L, Wang YF, Li J, Faraone SV: Association of norepinephrine transporter gene with methylphenidate response. J Am Acad Child Adolesc Psychiatry. 2004 Sep;43(9):1154-8. [PubMed:15322419 ]
Williard RL, Middaugh LD, Zhu HJ, Patrick KS: Methylphenidate and its ethanol transesterification metabolite ethylphenidate: brain disposition, monoamine transporters and motor activity. Behav Pharmacol. 2007 Feb;18(1):39-51. [PubMed:17218796 ]
Chuhan YS, Taukulis HK: Impairment of single-trial memory formation by oral methylphenidate in the rat. Neurobiol Learn Mem. 2006 Mar;85(2):125-31. Epub 2005 Oct 24. [PubMed:16246598 ]
Gray JD, Punsoni M, Tabori NE, Melton JT, Fanslow V, Ward MJ, Zupan B, Menzer D, Rice J, Drake CT, Romeo RD, Brake WG, Torres-Reveron A, Milner TA: Methylphenidate administration to juvenile rats alters brain areas involved in cognition, motivated behaviors, appetite, and stress. J Neurosci. 2007 Jul 4;27(27):7196-207. [PubMed:17611273 ]
Sandoval V, Riddle EL, Ugarte YV, Hanson GR, Fleckenstein AE: Methamphetamine-induced rapid and reversible changes in dopamine transporter function: an in vitro model. J Neurosci. 2001 Feb 15;21(4):1413-9. [PubMed:11160413 ]
Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [PubMed:9537821 ]
Tilley MR, Gu HH: The effects of methylphenidate on knockin mice with a methylphenidate-resistant dopamine transporter. J Pharmacol Exp Ther. 2008 Nov;327(2):554-60. doi: 10.1124/jpet.108.141713. Epub 2008 Aug 12. [PubMed:18698001 ]

Enzyme Details

2. 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

Dresel SH, Kung MP, Huang X, Plossl K, Hou C, Shiue CY, Karp J, Kung HF: In vivo imaging of serotonin transporters with [99mTc]TRODAT-1 in nonhuman primates. Eur J Nucl Med. 1999 Apr;26(4):342-7. [PubMed:10199939 ]
Izenwasser S, Coy AE, Ladenheim B, Loeloff RJ, Cadet JL, French D: Chronic methylphenidate alters locomotor activity and dopamine transporters differently from cocaine. Eur J Pharmacol. 1999 Jun 4;373(2-3):187-93. [PubMed:10414438 ]
Stehouwer JS, Jarkas N, Zeng F, Voll RJ, Williams L, Owens MJ, Votaw JR, Goodman MM: Synthesis, radiosynthesis, and biological evaluation of carbon-11 labeled 2beta-carbomethoxy-3beta-(3'-((Z)-2-haloethenyl)phenyl)nortropanes: candidate radioligands for in vivo imaging of the serotonin transporter with positron emission tomography. J Med Chem. 2006 Nov 16;49(23):6760-7. [PubMed:17154506 ]

Showing metabocard for Dexmethylphenidate (HMDB0015647)

MOL for HMDB0015647 (Dexmethylphenidate)

3D MOL for HMDB0015647 (Dexmethylphenidate)

3D SDF for HMDB0015647 (Dexmethylphenidate)

3D-SDF for HMDB0015647 (Dexmethylphenidate)

PDB for HMDB0015647 (Dexmethylphenidate)

3D PDB for HMDB0015647 (Dexmethylphenidate)

SMILES for HMDB0015647 (Dexmethylphenidate)

INCHI for HMDB0015647 (Dexmethylphenidate)

Structure for HMDB0015647 (Dexmethylphenidate)

3D Structure for HMDB0015647 (Dexmethylphenidate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

Transporters

References

References