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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:57 UTC

HMDB ID

HMDB0015352

Secondary Accession Numbers

HMDB15352

Metabolite Identification

Common Name

Ketamine

Description

Ketamine is only found in individuals that have used or taken this drug. It is a cyclohexanone derivative used for induction of anesthesia. Its mechanism of action is not well understood, but ketamine can block NMDA receptors (receptors, N-methyl-D-aspartate) and may interact with sigma receptors. [PubChem]Ketamine has several clinically useful properties, including analgesia and less cardiorespiratory depressant effects than other anaesthetic agents, it also causes some stimulation of the cardiocascular system. Ketamine has been reported to produce general as well as local anaesthesia. It interacts with N-methyl-D-aspartate (NMDA) receptors, opioid receptors, monoaminergic receptors, muscarinic receptors and voltage sensitive Ca ion channels. Unlike other general anaesthetic agents, ketamine does not interact with GABA receptors.

Structure

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

HMDB0243682
     RDKit          3D
(R)-Ketamine
 32 33  0  0  0  0  0  0  0  0999 V2000
   -0.1729    2.0771   -1.3449 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0453    0.7141   -1.4567 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1134   -0.1497   -0.2846 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2210   -0.4237    0.1974 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3140    0.1987   -0.4420 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6225    0.0367   -0.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9271   -0.7626    1.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9000   -1.3951    1.6755 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5654   -1.2185    1.2579 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3280   -2.0856    2.1135 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.0731   -1.2240   -0.5765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2246   -1.3292    0.3994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2146   -0.1929    0.0324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3389    1.0577    0.1878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9442    0.7689    0.6218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4626    1.2188    1.6270 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8929    2.5475   -2.0849 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7793    2.6325   -1.6828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4269    2.4800   -0.3547 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4589    0.2927   -2.2687 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1538    0.8275   -1.2904 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4475    0.5246   -0.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9645   -0.8873    1.3161 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0492   -2.0488    2.5233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5915   -0.9789   -1.5605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6267   -2.2163   -0.8117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9980   -0.9748    1.4349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7321   -2.2952    0.3741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6375   -0.3387   -0.9512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0341   -0.1440    0.7527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8246    1.7219    0.9504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4678    1.5665   -0.7670 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
  9 10  1  0
  3 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15  3  1  0
  9  4  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  5 21  1  0
  6 22  1  0
  7 23  1  0
  8 24  1  0
 11 25  1  0
 11 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
M  END

1221
  Mrv0541 02231215202D          

 16 17  0  0  1  0            999 V2000
    4.6295   -0.6759    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.1115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6665    0.6029    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.1115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.5240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.3491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -1.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.5240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.3491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7110    0.4188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4863    0.1366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5677    1.2312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8415    0.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1182    0.6669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1997    1.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9750    1.4794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  1  0  0  0  0
  2  8  2  0  0  0  0
  3  4  1  0  0  0  0
  3 13  1  0  0  0  0
  4  5  1  0  0  0  0
  4  8  1  0  0  0  0
  4 10  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  9  1  0  0  0  0
  8  9  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 11 14  2  0  0  0  0
 12 15  1  0  0  0  0
 14 16  1  0  0  0  0
 15 16  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015352

> <DATABASE_NAME>
hmdb

> <SMILES>
CNC1(CCCCC1=O)C1=CC=CC=C1Cl

> <INCHI_IDENTIFIER>
InChI=1S/C13H16ClNO/c1-15-13(9-5-4-8-12(13)16)10-6-2-3-7-11(10)14/h2-3,6-7,15H,4-5,8-9H2,1H3

> <INCHI_KEY>
YQEZLKZALYSWHR-UHFFFAOYSA-N

> <FORMULA>
C13H16ClNO

> <MOLECULAR_WEIGHT>
237.725

> <EXACT_MASS>
237.092041846

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
24.969862915889696

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(2-chlorophenyl)-2-(methylamino)cyclohexan-1-one

> <ALOGPS_LOGP>
2.69

> <JCHEM_LOGP>
3.347302666

> <ALOGPS_LOGS>
-3.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.78330470645551

> <JCHEM_PKA_STRONGEST_BASIC>
7.454261321661874

> <JCHEM_POLAR_SURFACE_AREA>
29.1

> <JCHEM_REFRACTIVITY>
65.55380000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.64e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ketamine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0243682
     RDKit          3D
(R)-Ketamine
 32 33  0  0  0  0  0  0  0  0999 V2000
   -0.1729    2.0771   -1.3449 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0453    0.7141   -1.4567 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1134   -0.1497   -0.2846 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2210   -0.4237    0.1974 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3140    0.1987   -0.4420 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6225    0.0367   -0.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9271   -0.7626    1.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9000   -1.3951    1.6755 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5654   -1.2185    1.2579 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3280   -2.0856    2.1135 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.0731   -1.2240   -0.5765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2246   -1.3292    0.3994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2146   -0.1929    0.0324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3389    1.0577    0.1878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9442    0.7689    0.6218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4626    1.2188    1.6270 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8929    2.5475   -2.0849 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7793    2.6325   -1.6828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4269    2.4800   -0.3547 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4589    0.2927   -2.2687 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1538    0.8275   -1.2904 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4475    0.5246   -0.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9645   -0.8873    1.3161 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0492   -2.0488    2.5233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5915   -0.9789   -1.5605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6267   -2.2163   -0.8117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9980   -0.9748    1.4349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7321   -2.2952    0.3741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6375   -0.3387   -0.9512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0341   -0.1440    0.7527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8246    1.7219    0.9504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4678    1.5665   -0.7670 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
  9 10  1  0
  3 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15  3  1  0
  9  4  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  5 21  1  0
  6 22  1  0
  7 23  1  0
  8 24  1  0
 11 25  1  0
 11 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1221                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       8.642  -1.262   0.000  0.00  0.00          Cl+0
HETATM    2  O   UNK     0       3.080  -0.208   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       4.977   1.125   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       5.747  -0.208   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.081  -0.978   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.081  -2.518   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.747  -3.288   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.414  -0.978   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.414  -2.518   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.927   0.782   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.374   0.255   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.660   2.298   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.437   1.125   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.554   1.245   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.839   3.288   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.287   2.762   0.000  0.00  0.00           C+0
CONECT    1   11                                                            
CONECT    2    8                                                            
CONECT    3    4   13                                                       
CONECT    4    3    5    8   10                                             
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    9                                                       
CONECT    8    2    4    9                                                  
CONECT    9    7    8                                                       
CONECT   10    4   11   12                                                  
CONECT   11    1   10   14                                                  
CONECT   12   10   15                                                       
CONECT   13    3                                                            
CONECT   14   11   16                                                       
CONECT   15   12   16                                                       
CONECT   16   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0015352
HETATM    1  C1  UNL     1      -1.787  -2.025   0.553  1.00  0.00           C  
HETATM    2  N1  UNL     1      -0.484  -1.616   0.263  1.00  0.00           N  
HETATM    3  C2  UNL     1      -0.196  -0.227   0.048  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.284  -0.236  -0.243  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.878   0.282  -1.335  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.288   0.245  -1.442  1.00  0.00           C  
HETATM    7  C6  UNL     1       4.007  -0.323  -0.418  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.384  -0.851   0.696  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.019  -0.820   0.808  1.00  0.00           C  
HETATM   10 CL1  UNL     1       1.284  -1.556   2.208  1.00  0.00          CL  
HETATM   11  C9  UNL     1      -0.957   0.214  -1.154  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.162   1.081  -0.886  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.980   2.098   0.196  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.757   1.240   1.467  1.00  0.00           C  
HETATM   15  C13 UNL     1      -0.401   0.667   1.202  1.00  0.00           C  
HETATM   16  O1  UNL     1       0.456   0.996   1.982  1.00  0.00           O  
HETATM   17  H1  UNL     1      -2.171  -1.794   1.564  1.00  0.00           H  
HETATM   18  H2  UNL     1      -2.491  -1.687  -0.231  1.00  0.00           H  
HETATM   19  H3  UNL     1      -1.852  -3.161   0.509  1.00  0.00           H  
HETATM   20  H4  UNL     1       0.096  -2.263  -0.277  1.00  0.00           H  
HETATM   21  H5  UNL     1       1.325   0.732  -2.149  1.00  0.00           H  
HETATM   22  H6  UNL     1       3.719   0.671  -2.334  1.00  0.00           H  
HETATM   23  H7  UNL     1       5.096  -0.353  -0.498  1.00  0.00           H  
HETATM   24  H8  UNL     1       4.025  -1.282   1.462  1.00  0.00           H  
HETATM   25  H9  UNL     1      -1.389  -0.684  -1.699  1.00  0.00           H  
HETATM   26  H10 UNL     1      -0.399   0.743  -1.930  1.00  0.00           H  
HETATM   27  H11 UNL     1      -2.398   1.661  -1.820  1.00  0.00           H  
HETATM   28  H12 UNL     1      -3.085   0.522  -0.662  1.00  0.00           H  
HETATM   29  H13 UNL     1      -2.898   2.691   0.274  1.00  0.00           H  
HETATM   30  H14 UNL     1      -1.069   2.678   0.032  1.00  0.00           H  
HETATM   31  H15 UNL     1      -1.807   1.842   2.379  1.00  0.00           H  
HETATM   32  H16 UNL     1      -2.576   0.518   1.435  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3   20
CONECT    3    4   11   15
CONECT    4    5    5    9
CONECT    5    6   21
CONECT    6    7    7   22
CONECT    7    8   23
CONECT    8    9    9   24
CONECT    9   10
CONECT   11   12   25   26
CONECT   12   13   27   28
CONECT   13   14   29   30
CONECT   14   15   31   32
CONECT   15   16   16
END

HMDB0243682
     RDKit          3D
(R)-Ketamine
 32 33  0  0  0  0  0  0  0  0999 V2000
   -0.1729    2.0771   -1.3449 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0453    0.7141   -1.4567 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1134   -0.1497   -0.2846 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2210   -0.4237    0.1974 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3140    0.1987   -0.4420 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6225    0.0367   -0.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9271   -0.7626    1.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9000   -1.3951    1.6755 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5654   -1.2185    1.2579 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3280   -2.0856    2.1135 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.0731   -1.2240   -0.5765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2246   -1.3292    0.3994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2146   -0.1929    0.0324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3389    1.0577    0.1878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9442    0.7689    0.6218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4626    1.2188    1.6270 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8929    2.5475   -2.0849 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7793    2.6325   -1.6828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4269    2.4800   -0.3547 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4589    0.2927   -2.2687 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1538    0.8275   -1.2904 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4475    0.5246   -0.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9645   -0.8873    1.3161 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0492   -2.0488    2.5233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5915   -0.9789   -1.5605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6267   -2.2163   -0.8117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9980   -0.9748    1.4349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7321   -2.2952    0.3741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6375   -0.3387   -0.9512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0341   -0.1440    0.7527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8246    1.7219    0.9504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4678    1.5665   -0.7670 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
  9 10  1  0
  3 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15  3  1  0
  9  4  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  5 21  1  0
  6 22  1  0
  7 23  1  0
  8 24  1  0
 11 25  1  0
 11 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+-)-Ketamine	ChEBI
2-(2-Chloro-phenyl)-2-methylamino-cyclohexanone	ChEBI
2-(Methylamino)-2-(2-chlorophenyl)cyclohexanone	ChEBI
2-(O-Chlorophenyl)-2-(methylamino)-cyclohexanone	ChEBI
DL-Ketamine	ChEBI
Ketamina	ChEBI
Ketaminum	ChEBI
NMDA	ChEBI
Special K	ChEBI
Tekam	Kegg
(-)-Ketamine	HMDB
(S)-(-)-Ketamine	HMDB
(S)-Ketamine	HMDB
CI 581 base	HMDB
Ketamine base	HMDB
Ketamine HCL	HMDB
L-Ketamine	HMDB
2-(2-Chlorophenyl)-2-(methylamino)cyclohexanone	HMDB
Calypsol	HMDB
Ketanest	HMDB
Calipsol	HMDB
Kalipsol	HMDB
Ketalar	HMDB
Ketamine hydrochloride	HMDB
Ketaset	HMDB

Chemical Formula

C₁₃H₁₆ClNO

Average Molecular Weight

237.725

Monoisotopic Molecular Weight

237.092041846

IUPAC Name

2-(2-chlorophenyl)-2-(methylamino)cyclohexan-1-one

Traditional Name

ketamine

CAS Registry Number

6740-88-1

SMILES

CNC1(CCCCC1=O)C1=CC=CC=C1Cl

InChI Identifier

InChI=1S/C13H16ClNO/c1-15-13(9-5-4-8-12(13)16)10-6-2-3-7-11(10)14/h2-3,6-7,15H,4-5,8-9H2,1H3

InChI Key

YQEZLKZALYSWHR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as chlorobenzenes. Chlorobenzenes are compounds containing one or more chlorine atoms attached to a benzene moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Halobenzenes

Direct Parent

Chlorobenzenes

Alternative Parents

Substituents

Chlorobenzene
Aralkylamine
Aryl chloride
Aryl halide
Ketone
Cyclic ketone
Secondary aliphatic amine
Secondary amine
Amine
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

secondary amino compound (CHEBI:6121 )
monochlorobenzenes (CHEBI:6121 )
cyclohexanones (CHEBI:6121 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	92.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.046 g/L	Not Available
LogP	2.9	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	149.2	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.046 g/L	ALOGPS
logP	2.69	ALOGPS
logP	3.35	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	18.78	ChemAxon
pKa (Strongest Basic)	7.45	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.1 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	65.55 m³·mol⁻¹	ChemAxon
Polarizability	24.97 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	152.143	30932474
DeepCCS	[M-H]-	149.785	30932474
DeepCCS	[M-2H]-	184.375	30932474
DeepCCS	[M+Na]+	159.285	30932474
AllCCS	[M+H]+	152.9	32859911
AllCCS	[M+H-H2O]+	148.9	32859911
AllCCS	[M+NH4]+	156.6	32859911
AllCCS	[M+Na]+	157.7	32859911
AllCCS	[M-H]-	156.5	32859911
AllCCS	[M+Na-2H]-	156.8	32859911
AllCCS	[M+HCOO]-	157.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ketamine	CNC1(CCCCC1=O)C1=CC=CC=C1Cl	2494.7	Standard polar	33892256
Ketamine	CNC1(CCCCC1=O)C1=CC=CC=C1Cl	1851.4	Standard non polar	33892256
Ketamine	CNC1(CCCCC1=O)C1=CC=CC=C1Cl	1836.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ketamine,1TMS,isomer #1	CNC1(C2=CC=CC=C2Cl)CCCC=C1O[Si](C)(C)C	1902.6	Semi standard non polar	33892256
Ketamine,1TMS,isomer #1	CNC1(C2=CC=CC=C2Cl)CCCC=C1O[Si](C)(C)C	1929.6	Standard non polar	33892256
Ketamine,1TMS,isomer #1	CNC1(C2=CC=CC=C2Cl)CCCC=C1O[Si](C)(C)C	2394.0	Standard polar	33892256
Ketamine,1TMS,isomer #2	CN(C1(C2=CC=CC=C2Cl)CCCCC1=O)[Si](C)(C)C	1921.1	Semi standard non polar	33892256
Ketamine,1TMS,isomer #2	CN(C1(C2=CC=CC=C2Cl)CCCCC1=O)[Si](C)(C)C	1981.4	Standard non polar	33892256
Ketamine,1TMS,isomer #2	CN(C1(C2=CC=CC=C2Cl)CCCCC1=O)[Si](C)(C)C	2413.3	Standard polar	33892256
Ketamine,2TMS,isomer #1	CN(C1(C2=CC=CC=C2Cl)CCCC=C1O[Si](C)(C)C)[Si](C)(C)C	1987.3	Semi standard non polar	33892256
Ketamine,2TMS,isomer #1	CN(C1(C2=CC=CC=C2Cl)CCCC=C1O[Si](C)(C)C)[Si](C)(C)C	1979.9	Standard non polar	33892256
Ketamine,2TMS,isomer #1	CN(C1(C2=CC=CC=C2Cl)CCCC=C1O[Si](C)(C)C)[Si](C)(C)C	2337.9	Standard polar	33892256
Ketamine,1TBDMS,isomer #1	CNC1(C2=CC=CC=C2Cl)CCCC=C1O[Si](C)(C)C(C)(C)C	2109.3	Semi standard non polar	33892256
Ketamine,1TBDMS,isomer #1	CNC1(C2=CC=CC=C2Cl)CCCC=C1O[Si](C)(C)C(C)(C)C	2099.0	Standard non polar	33892256
Ketamine,1TBDMS,isomer #1	CNC1(C2=CC=CC=C2Cl)CCCC=C1O[Si](C)(C)C(C)(C)C	2532.0	Standard polar	33892256
Ketamine,1TBDMS,isomer #2	CN(C1(C2=CC=CC=C2Cl)CCCCC1=O)[Si](C)(C)C(C)(C)C	2168.3	Semi standard non polar	33892256
Ketamine,1TBDMS,isomer #2	CN(C1(C2=CC=CC=C2Cl)CCCCC1=O)[Si](C)(C)C(C)(C)C	2239.4	Standard non polar	33892256
Ketamine,1TBDMS,isomer #2	CN(C1(C2=CC=CC=C2Cl)CCCCC1=O)[Si](C)(C)C(C)(C)C	2528.8	Standard polar	33892256
Ketamine,2TBDMS,isomer #1	CN(C1(C2=CC=CC=C2Cl)CCCC=C1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2443.8	Semi standard non polar	33892256
Ketamine,2TBDMS,isomer #1	CN(C1(C2=CC=CC=C2Cl)CCCC=C1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2321.5	Standard non polar	33892256
Ketamine,2TBDMS,isomer #1	CN(C1(C2=CC=CC=C2Cl)CCCC=C1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2546.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Ketamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ue9-1900000000-137b9855ffed670aa9f4	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ketamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ketamine 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 - Ketamine LC-ESI-QTOF , positive-QTOF	splash10-004i-0930000000-8216e02922628a5070cf	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ketamine LC-ESI-ITFT , positive-QTOF	splash10-00di-0090000000-7704dbbfa717abc4bab2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ketamine LC-ESI-ITFT , positive-QTOF	splash10-000i-0090000000-aff2b684d97275321043	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ketamine LC-ESI-ITFT , positive-QTOF	splash10-000i-0290000000-1707dec51cc3e89964c9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ketamine LC-ESI-ITFT , positive-QTOF	splash10-004i-0940000000-59871faec16835eb1b3a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ketamine LC-ESI-ITFT , positive-QTOF	splash10-004i-0900000000-ca62e82b4a1dfb81b3b0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ketamine LC-ESI-ITFT , positive-QTOF	splash10-004i-0900000000-6c243d7b1c2e8cf69efa	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ketamine LC-ESI-ITFT , positive-QTOF	splash10-004i-0900000000-441a423105753e2c8b9c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ketamine LC-ESI-ITFT , positive-QTOF	splash10-000i-0090000000-24585e7c2431b3b9319e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ketamine LC-ESI-ITFT , positive-QTOF	splash10-000i-0290000000-c9d734b085ec94dabd9a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ketamine LC-ESI-ITFT , positive-QTOF	splash10-004i-0940000000-054d77385726d4e35e20	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ketamine LC-ESI-ITFT , positive-QTOF	splash10-004i-0900000000-8c263bb521fb6ebe6cac	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ketamine LC-ESI-ITFT , positive-QTOF	splash10-004i-0900000000-702873d66ce0d419711d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ketamine LC-ESI-ITFT , positive-QTOF	splash10-004i-0900000000-e23ba411aa96df9b5d6f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ketamine LC-ESI-ITFT , positive-QTOF	splash10-00di-0090000000-5f14196db213c95f3e71	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ketamine LC-ESI-QQ , positive-QTOF	splash10-000i-0090000000-85385cf96aa2ac05921a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ketamine LC-ESI-QQ , positive-QTOF	splash10-05br-0390000000-9177663a5915fac51aa7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ketamine LC-ESI-QQ , positive-QTOF	splash10-004i-0910000000-d00d242dae695dc5aff9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ketamine LC-ESI-QQ , positive-QTOF	splash10-004i-0900000000-95c2a8805f1587266fea	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketamine 10V, Positive-QTOF	splash10-000i-0190000000-d3addd1c61dae1965d68	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketamine 20V, Positive-QTOF	splash10-000i-2490000000-4b32229520af03c01035	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketamine 40V, Positive-QTOF	splash10-0uy0-3900000000-f31baf727a934e3e0c6f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketamine 10V, Negative-QTOF	splash10-000i-0090000000-3166c540bb2a7f57489e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketamine 20V, Negative-QTOF	splash10-000i-0390000000-f6a156602d423ed34dc1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketamine 40V, Negative-QTOF	splash10-0229-8920000000-d5d51aef2ac12188e9e8	2016-08-03	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 DB01221	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01221	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

DB01221

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3689

KEGG Compound ID

C07525

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ketamine

METLIN ID

Not Available

PubChem Compound

3821

PDB ID

Not Available

ChEBI ID

6121

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

Harrison NL, Simmonds MA: Quantitative studies on some antagonists of N-methyl D-aspartate in slices of rat cerebral cortex. Br J Pharmacol. 1985 Feb;84(2):381-91. [PubMed:2858237 ]
Reboso Morales JA, Gonzalez Miranda F: [Ketamine]. Rev Esp Anestesiol Reanim. 1999 Mar;46(3):111-22. [PubMed:10228376 ]
Bergman SA: Ketamine: review of its pharmacology and its use in pediatric anesthesia. Anesth Prog. 1999 Winter;46(1):10-20. [PubMed:10551055 ]
Bonanno FG: Ketamine in war/tropical surgery (a final tribute to the racemic mixture). Injury. 2002 May;33(4):323-7. [PubMed:12091028 ]
Lankenau SE, Sanders B, Bloom JJ, Hathazi D, Alarcon E, Tortu S, Clatts MC: First injection of ketamine among young injection drug users (IDUs) in three U.S. cities. Drug Alcohol Depend. 2007 Mar 16;87(2-3):183-93. Epub 2006 Sep 18. [PubMed:16979848 ]

Showing metabocard for Ketamine (HMDB0015352)

MOL for HMDB0015352 (Ketamine)

3D MOL for HMDB0015352 (Ketamine)

3D SDF for HMDB0015352 (Ketamine)

3D-SDF for HMDB0015352 (Ketamine)

PDB for HMDB0015352 (Ketamine)

3D PDB for HMDB0015352 (Ketamine)

SMILES for HMDB0015352 (Ketamine)

INCHI for HMDB0015352 (Ketamine)

Structure for HMDB0015352 (Ketamine)

3D Structure for HMDB0015352 (Ketamine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra