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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 02:51:51 UTC

HMDB ID

HMDB0015096

Secondary Accession Numbers

HMDB15096

Metabolite Identification

Common Name

Mepivacaine

Description

Mepivacaine, also known as carbocaine or carboplyin dental, belongs to the class of organic compounds known as piperidinecarboxamides. Piperidinecarboxamides are compounds containing a piperidine ring substituted with a carboxamide functional group. Mepivacaine is a drug which is used for production of local or regional analgesia and anesthesia by local infiltration, peripheral nerve block techniques, and central neural techniques including epidural and caudal blocks. In humans, mepivacaine is involved in the mepivacaine action pathway. Mepivacaine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Mepivacaine.

Structure

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

HMDB0015096
     RDKit          3D
Mepivacaine
 40 41  0  0  0  0  0  0  0  0999 V2000
   -1.8309   -2.3403   -1.0081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7090   -1.2724   -0.4791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0593   -1.3726   -0.6782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9618   -0.4308   -0.2250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4353    0.6583    0.4629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0745    0.7642    0.6664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5543    1.9514    1.4107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1811   -0.2061    0.1958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7872   -0.0822    0.4132 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0845    0.5820   -0.4932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3963    1.0864   -1.5399 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5196    0.6975   -0.2483 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3867    0.2163   -1.3832 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    0.6984   -1.1143 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9997    1.1928    0.2863 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2824    0.4229    1.3363 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9294    0.0662    0.9886 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8830   -1.3819    0.8970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0030   -2.5429   -0.3039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4837   -2.0235   -2.0065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3804   -3.3077   -1.1223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4450   -2.2228   -1.2126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0287   -0.5089   -0.3817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1390    1.4067    0.8244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6187    1.7661    2.5121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5111    2.1733    1.1324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2268    2.8224    1.2112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4157   -0.5128    1.2953 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7575    1.7935   -0.1221 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3498   -0.8895   -1.5026 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0046    0.6637   -2.3057 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0028    1.5494   -1.7947 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5450   -0.0834   -1.3753 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7928    2.2785    0.3862 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1051    1.0929    0.4972 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9027   -0.4377    1.6480 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2160    1.0866    2.2479 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2476   -1.7573    0.0953 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9038   -1.8117    0.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5354   -1.7848    1.8704 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
  8  2  1  0
 17 12  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
  9 28  1  0
 12 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 18 38  1  0
 18 39  1  0
 18 40  1  0
M  END

961
  Mrv0541 02231215082D          

 18 19  0  0  1  0            999 V2000
    4.5080   -0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.4438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.0313    0.0000 C   0  0  0  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
    4.5080    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  2  0  0  0  0
  2  4  1  0  0  0  0
  2  8  1  0  0  0  0
  2 10  1  0  0  0  0
  3  9  1  0  0  0  0
  3 11  1  0  0  0  0
  4  5  1  0  0  0  0
  4  9  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
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 16  1  0  0  0  0
 13 15  2  0  0  0  0
 13 17  1  0  0  0  0
 14 18  2  0  0  0  0
 15 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015096

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1CCCCC1C(=O)NC1=C(C)C=CC=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C15H22N2O/c1-11-7-6-8-12(2)14(11)16-15(18)13-9-4-5-10-17(13)3/h6-8,13H,4-5,9-10H2,1-3H3,(H,16,18)

> <INCHI_KEY>
INWLQCZOYSRPNW-UHFFFAOYSA-N

> <FORMULA>
C15H22N2O

> <MOLECULAR_WEIGHT>
246.348

> <EXACT_MASS>
246.173213336

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
28.607636461108108

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-(2,6-dimethylphenyl)-1-methylpiperidine-2-carboxamide

> <ALOGPS_LOGP>
2.16

> <JCHEM_LOGP>
3.191619869666667

> <ALOGPS_LOGS>
-2.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.623901615091178

> <JCHEM_PKA_STRONGEST_BASIC>
7.253864226422989

> <JCHEM_POLAR_SURFACE_AREA>
32.34

> <JCHEM_REFRACTIVITY>
76.31970000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.21e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
mepivacaine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0015096
     RDKit          3D
Mepivacaine
 40 41  0  0  0  0  0  0  0  0999 V2000
   -1.8309   -2.3403   -1.0081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7090   -1.2724   -0.4791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0593   -1.3726   -0.6782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9618   -0.4308   -0.2250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4353    0.6583    0.4629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0745    0.7642    0.6664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5543    1.9514    1.4107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1811   -0.2061    0.1958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7872   -0.0822    0.4132 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0845    0.5820   -0.4932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3963    1.0864   -1.5399 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5196    0.6975   -0.2483 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3867    0.2163   -1.3832 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    0.6984   -1.1143 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9997    1.1928    0.2863 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2824    0.4229    1.3363 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9294    0.0662    0.9886 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8830   -1.3819    0.8970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0030   -2.5429   -0.3039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4837   -2.0235   -2.0065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3804   -3.3077   -1.1223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4450   -2.2228   -1.2126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0287   -0.5089   -0.3817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1390    1.4067    0.8244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6187    1.7661    2.5121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5111    2.1733    1.1324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2268    2.8224    1.2112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4157   -0.5128    1.2953 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7575    1.7935   -0.1221 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3498   -0.8895   -1.5026 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0046    0.6637   -2.3057 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0028    1.5494   -1.7947 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5450   -0.0834   -1.3753 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7928    2.2785    0.3862 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1051    1.0929    0.4972 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9027   -0.4377    1.6480 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2160    1.0866    2.2479 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2476   -1.7573    0.0953 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9038   -1.8117    0.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5354   -1.7848    1.8704 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
  8  2  1  0
 17 12  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
  9 28  1  0
 12 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 18 38  1  0
 18 39  1  0
 18 40  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 961                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       8.415  -0.385   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       5.748   2.695   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       5.748  -0.385   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       7.081   1.925   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       8.415   4.235   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.081   5.005   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.748   4.235   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.081   0.385   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.414   1.925   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.748  -1.925   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.081  -2.695   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.414  -2.695   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.081  -4.235   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.414  -4.235   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.415  -1.925   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.080  -1.925   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.748  -5.005   0.000  0.00  0.00           C+0
CONECT    1    9                                                            
CONECT    2    4    8   10                                                  
CONECT    3    9   11                                                       
CONECT    4    2    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    2    7                                                       
CONECT    9    1    3    4                                                  
CONECT   10    2                                                            
CONECT   11    3   12   13                                                  
CONECT   12   11   14   16                                                  
CONECT   13   11   15   17                                                  
CONECT   14   12   18                                                       
CONECT   15   13   18                                                       
CONECT   16   12                                                            
CONECT   17   13                                                            
CONECT   18   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0250811
HETATM    1  C1  UNL     1      -2.475   1.804  -1.794  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.061   0.654  -1.079  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.312   0.120  -1.354  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.844  -0.957  -0.675  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.063  -1.506   0.322  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.814  -1.010   0.632  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.978  -1.600   1.702  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.327   0.065  -0.073  1.00  0.00           C  
HETATM    9  N1  UNL     1      -1.046   0.557   0.260  1.00  0.00           N  
HETATM   10  C9  UNL     1       0.131   0.055  -0.377  1.00  0.00           C  
HETATM   11  O1  UNL     1      -0.007  -0.842  -1.247  1.00  0.00           O  
HETATM   12  C10 UNL     1       1.481   0.521  -0.077  1.00  0.00           C  
HETATM   13  C11 UNL     1       1.862   0.438   1.379  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.142   1.207   1.529  1.00  0.00           C  
HETATM   15  C13 UNL     1       4.212   0.855   0.573  1.00  0.00           C  
HETATM   16  C14 UNL     1       3.793   0.323  -0.742  1.00  0.00           C  
HETATM   17  N2  UNL     1       2.453  -0.147  -0.847  1.00  0.00           N  
HETATM   18  C15 UNL     1       2.343  -1.588  -0.837  1.00  0.00           C  
HETATM   19  H1  UNL     1      -1.763   1.524  -2.585  1.00  0.00           H  
HETATM   20  H2  UNL     1      -3.323   2.348  -2.275  1.00  0.00           H  
HETATM   21  H3  UNL     1      -2.030   2.553  -1.081  1.00  0.00           H  
HETATM   22  H4  UNL     1      -4.893   0.577  -2.143  1.00  0.00           H  
HETATM   23  H5  UNL     1      -5.829  -1.359  -0.909  1.00  0.00           H  
HETATM   24  H6  UNL     1      -4.476  -2.365   0.872  1.00  0.00           H  
HETATM   25  H7  UNL     1      -1.580  -2.609   1.412  1.00  0.00           H  
HETATM   26  H8  UNL     1      -1.182  -0.932   2.014  1.00  0.00           H  
HETATM   27  H9  UNL     1      -2.669  -1.754   2.582  1.00  0.00           H  
HETATM   28  H10 UNL     1      -0.932   1.295   0.976  1.00  0.00           H  
HETATM   29  H11 UNL     1       1.528   1.617  -0.343  1.00  0.00           H  
HETATM   30  H12 UNL     1       2.051  -0.596   1.712  1.00  0.00           H  
HETATM   31  H13 UNL     1       1.109   0.899   2.052  1.00  0.00           H  
HETATM   32  H14 UNL     1       2.873   2.295   1.444  1.00  0.00           H  
HETATM   33  H15 UNL     1       3.464   1.071   2.603  1.00  0.00           H  
HETATM   34  H16 UNL     1       4.905   0.131   1.097  1.00  0.00           H  
HETATM   35  H17 UNL     1       4.855   1.768   0.419  1.00  0.00           H  
HETATM   36  H18 UNL     1       3.952   1.080  -1.542  1.00  0.00           H  
HETATM   37  H19 UNL     1       4.467  -0.533  -1.019  1.00  0.00           H  
HETATM   38  H20 UNL     1       1.662  -1.985  -0.081  1.00  0.00           H  
HETATM   39  H21 UNL     1       1.987  -1.905  -1.838  1.00  0.00           H  
HETATM   40  H22 UNL     1       3.334  -2.071  -0.659  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    3    8
CONECT    3    4   22
CONECT    4    5    5   23
CONECT    5    6   24
CONECT    6    7    8    8
CONECT    7   25   26   27
CONECT    8    9
CONECT    9   10   28
CONECT   10   11   11   12
CONECT   12   13   17   29
CONECT   13   14   30   31
CONECT   14   15   32   33
CONECT   15   16   34   35
CONECT   16   17   36   37
CONECT   17   18
CONECT   18   38   39   40
END

HMDB0015096
     RDKit          3D
Mepivacaine
 40 41  0  0  0  0  0  0  0  0999 V2000
   -1.8309   -2.3403   -1.0081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7090   -1.2724   -0.4791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0593   -1.3726   -0.6782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9618   -0.4308   -0.2250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4353    0.6583    0.4629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0745    0.7642    0.6664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5543    1.9514    1.4107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1811   -0.2061    0.1958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7872   -0.0822    0.4132 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0845    0.5820   -0.4932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3963    1.0864   -1.5399 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5196    0.6975   -0.2483 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3867    0.2163   -1.3832 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    0.6984   -1.1143 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9997    1.1928    0.2863 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2824    0.4229    1.3363 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9294    0.0662    0.9886 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8830   -1.3819    0.8970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0030   -2.5429   -0.3039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4837   -2.0235   -2.0065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3804   -3.3077   -1.1223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4450   -2.2228   -1.2126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0287   -0.5089   -0.3817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1390    1.4067    0.8244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6187    1.7661    2.5121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5111    2.1733    1.1324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2268    2.8224    1.2112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4157   -0.5128    1.2953 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7575    1.7935   -0.1221 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3498   -0.8895   -1.5026 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0046    0.6637   -2.3057 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0028    1.5494   -1.7947 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5450   -0.0834   -1.3753 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7928    2.2785    0.3862 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1051    1.0929    0.4972 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9027   -0.4377    1.6480 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2160    1.0866    2.2479 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2476   -1.7573    0.0953 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9038   -1.8117    0.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5354   -1.7848    1.8704 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
  8  2  1  0
 17 12  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
  9 28  1  0
 12 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 18 38  1  0
 18 39  1  0
 18 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+-)-1-Methyl-2',6'-pipecoloxylidide	ChEBI
1-Methyl-2',6'-pipecoloxylidide	ChEBI
Carbocaine	ChEBI
DL-Mepivacaine	ChEBI
Mepivacaina	ChEBI
Mepivacainum	ChEBI
N-(2,6-Dimethylphenyl)-1-methyl-2-piperidinecarboxamide	ChEBI
N-(2,6-Dimethylphenyl)-1-methylpiperidine-2-carboxamide	ChEBI
Carboplyin dental	Kegg
Mepivacaine HCL	HMDB
Mepivacaine hydrochloride	HMDB
Mepivicaine	HMDB
S-Ropivacaine mesylate	HMDB
3m Brand OF mepivacaine hydrochloride	HMDB
AstraZeneca brand OF mepivacaine hydrochloride	HMDB
Inibsa brand OF mepivacaine hydrochloride	HMDB
Isogaine	HMDB
Mepivacain injektopas	HMDB
Mepivacaina braun	HMDB
Monohydrochloride, mepivacaine	HMDB
Pascoe brand OF mepivacaine hydrochloride	HMDB
Scandicaine	HMDB
Astra brand OF mepivacaine hydrochloride	HMDB
Hexal brand OF mepivacaine hydrochloride	HMDB
Hydrochloride, mepivacaine	HMDB
Mepihexal	HMDB
Mepivastesin	HMDB
Novocol brand OF mepivacaine hydrochloride	HMDB
Polocaine	HMDB
Curasan brand OF mepivacaine hydrochloride	HMDB
Abbott brand OF mepivacaine hydrochloride	HMDB
Braun, mepivacaina	HMDB
Clarben brand OF mepivacaine hydrochloride	HMDB
Dentsply brand OF mepivacaine hydrochloride	HMDB
Meaverin	HMDB
Mecain	HMDB
Sanofi brand OF mepivacaine hydrochloride	HMDB
Scandinibsa	HMDB
Aventis brand OF mepivacaine hydrochloride	HMDB
Braun brand OF mepivicaine hydrochloride	HMDB
Carbocaïne	HMDB
Isocaine	HMDB
Mepivacain-injektopas	HMDB
Mepivacaine monohydrochloride	HMDB
Scandicain	HMDB
Scandonest	HMDB

Chemical Formula

C₁₅H₂₂N₂O

Average Molecular Weight

246.348

Monoisotopic Molecular Weight

246.173213336

IUPAC Name

N-(2,6-dimethylphenyl)-1-methylpiperidine-2-carboxamide

Traditional Name

mepivacaine

CAS Registry Number

96-88-8

SMILES

CN1CCCCC1C(=O)NC1=C(C)C=CC=C1C

InChI Identifier

InChI=1S/C15H22N2O/c1-11-7-6-8-12(2)14(11)16-15(18)13-9-4-5-10-17(13)3/h6-8,13H,4-5,9-10H2,1-3H3,(H,16,18)

InChI Key

INWLQCZOYSRPNW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as piperidinecarboxamides. Piperidinecarboxamides are compounds containing a piperidine ring substituted with a carboxamide functional group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Piperidines

Sub Class

Piperidinecarboxylic acids and derivatives

Direct Parent

Piperidinecarboxamides

Alternative Parents

Substituents

2-piperidinecarboxamide
Piperidinecarboxamide
M-xylene
Xylene
Monocyclic benzene moiety
Benzenoid
Tertiary aliphatic amine
Tertiary amine
Carboximidic acid
Carboximidic acid derivative
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Amine
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

piperidinecarboxamide (CHEBI:6759 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0015096)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Mepivacaine Pathway (HMDB: HMDB0015096)
Mepivacaine Action Pathway (PathBank: SMP0000399)

Role

Industrial application

Local anaesthetic (HMDB: HMDB0015096)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	150.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.62 g/L	Not Available
LogP	2.2	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	159.1	30932474
[M+H]+	Not Available	157.633	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000936

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.62 g/L	ALOGPS
logP	2.16	ALOGPS
logP	3.19	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	13.62	ChemAxon
pKa (Strongest Basic)	7.25	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	32.34 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	76.32 m³·mol⁻¹	ChemAxon
Polarizability	28.61 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]+	159.5	31661259
DarkChem	[M-H]-	158.071	31661259
DeepCCS	[M+H]+	161.749	30932474
DeepCCS	[M-H]-	159.391	30932474
DeepCCS	[M-2H]-	192.51	30932474
DeepCCS	[M+Na]+	167.842	30932474
AllCCS	[M+H]+	159.3	32859911
AllCCS	[M+H-H2O]+	155.5	32859911
AllCCS	[M+NH4]+	162.8	32859911
AllCCS	[M+Na]+	163.8	32859911
AllCCS	[M-H]-	164.3	32859911
AllCCS	[M+Na-2H]-	164.6	32859911
AllCCS	[M+HCOO]-	165.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Mepivacaine	CN1CCCCC1C(=O)NC1=C(C)C=CC=C1C	2365.1	Standard polar	33892256
Mepivacaine	CN1CCCCC1C(=O)NC1=C(C)C=CC=C1C	2045.8	Standard non polar	33892256
Mepivacaine	CN1CCCCC1C(=O)NC1=C(C)C=CC=C1C	2046.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Mepivacaine,1TMS,isomer #1	CC1=CC=CC(C)=C1N(C(=O)C1CCCCN1C)[Si](C)(C)C	1955.5	Semi standard non polar	33892256
Mepivacaine,1TMS,isomer #1	CC1=CC=CC(C)=C1N(C(=O)C1CCCCN1C)[Si](C)(C)C	1933.7	Standard non polar	33892256
Mepivacaine,1TMS,isomer #1	CC1=CC=CC(C)=C1N(C(=O)C1CCCCN1C)[Si](C)(C)C	2507.0	Standard polar	33892256
Mepivacaine,1TBDMS,isomer #1	CC1=CC=CC(C)=C1N(C(=O)C1CCCCN1C)[Si](C)(C)C(C)(C)C	2174.2	Semi standard non polar	33892256
Mepivacaine,1TBDMS,isomer #1	CC1=CC=CC(C)=C1N(C(=O)C1CCCCN1C)[Si](C)(C)C(C)(C)C	2149.2	Standard non polar	33892256
Mepivacaine,1TBDMS,isomer #1	CC1=CC=CC(C)=C1N(C(=O)C1CCCCN1C)[Si](C)(C)C(C)(C)C	2627.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Mepivacaine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0092-9200000000-a3a931af35da130669aa	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mepivacaine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mepivacaine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0002-9000000000-6a3d80d214452a24ab62	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mepivacaine LC-ESI-QFT , positive-QTOF	splash10-0002-9040000000-3c0a89a13f39484eef97	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mepivacaine LC-ESI-QFT , positive-QTOF	splash10-0002-9000000000-9073826aa2631981fe72	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mepivacaine LC-ESI-QFT , positive-QTOF	splash10-0002-9000000000-9b273b91b5148ef6a8fa	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mepivacaine LC-ESI-QFT , positive-QTOF	splash10-0002-9000000000-d541d397ca20f2f1a799	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mepivacaine LC-ESI-QFT , positive-QTOF	splash10-0002-9000000000-eda45d03ea77058a8429	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mepivacaine LC-ESI-QFT , positive-QTOF	splash10-006t-9000000000-f42a147676c3c718e38f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mepivacaine 30V, Positive-QTOF	splash10-0002-9000000000-9073826aa2631981fe72	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mepivacaine 45V, Positive-QTOF	splash10-0002-9000000000-9b273b91b5148ef6a8fa	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mepivacaine 15V, Positive-QTOF	splash10-0002-9040000000-3c0a89a13f39484eef97	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mepivacaine 60V, Positive-QTOF	splash10-0002-9000000000-d541d397ca20f2f1a799	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mepivacaine 75V, Positive-QTOF	splash10-0002-9000000000-4b9a3b3048a6c1bbd656	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mepivacaine 90V, Positive-QTOF	splash10-006t-9000000000-f42a147676c3c718e38f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Mepivacaine 35V, Positive-QTOF	splash10-0002-9000000000-e7a7508a46c81f01a0f6	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mepivacaine 10V, Positive-QTOF	splash10-006t-2890000000-4fd4344949c8e98d2d22	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mepivacaine 20V, Positive-QTOF	splash10-006t-9600000000-eccb3e339a3aafb57c83	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mepivacaine 40V, Positive-QTOF	splash10-00di-9100000000-923210fdcbf3093cec8c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mepivacaine 10V, Negative-QTOF	splash10-0002-0190000000-5c29854d995646f8e15f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mepivacaine 20V, Negative-QTOF	splash10-00fs-0960000000-75e4d525847b240eb8dd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mepivacaine 40V, Negative-QTOF	splash10-0g4i-6900000000-79da7c9893bedd422f3e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mepivacaine 10V, Positive-QTOF	splash10-0002-9380000000-6935f06f321d22f49f8f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mepivacaine 20V, Positive-QTOF	splash10-0002-9630000000-fc9251019b6aa4d95ac0	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mepivacaine 40V, Positive-QTOF	splash10-0002-9000000000-64648fb1fd5128b76827	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mepivacaine 10V, Negative-QTOF	splash10-0002-0090000000-4a0996a0879be85733ed	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mepivacaine 20V, Negative-QTOF	splash10-00dj-0950000000-7a84cb81cb305d4c644e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mepivacaine 40V, Negative-QTOF	splash10-00xr-1910000000-dcbc91df93a09683c261	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Mepivacaine Action Pathway		Not Available

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 DB00961	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00961	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

DB00961

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3922

KEGG Compound ID

C07528

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Mepivacaine

METLIN ID

Not Available

PubChem Compound

4062

PDB ID

Not Available

ChEBI ID

6759

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. Sodium channel protein type 10 subunit alpha

General function:: Involved in ion channel activity
Specific function:: This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which sodium ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant sodium channel isoform. Its electrophysiological properties vary depending on the type of the associated beta subunits (in vitro). Plays a role in neuropathic pain mechanisms
Gene Name:: SCN10A
Uniprot ID:: Q9Y5Y9
Molecular weight:: 220623.6

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Leffler A, Reckzeh J, Nau C: Block of sensory neuronal Na+ channels by the secreolytic ambroxol is associated with an interaction with local anesthetic binding sites. Eur J Pharmacol. 2010 Mar 25;630(1-3):19-28. doi: 10.1016/j.ejphar.2009.12.027. Epub 2010 Jan 4. [PubMed:20044988 ]

Showing metabocard for Mepivacaine (HMDB0015096)

MOL for HMDB0015096 (Mepivacaine)

3D MOL for HMDB0015096 (Mepivacaine)

3D SDF for HMDB0015096 (Mepivacaine)

3D-SDF for HMDB0015096 (Mepivacaine)

PDB for HMDB0015096 (Mepivacaine)

3D PDB for HMDB0015096 (Mepivacaine)

SMILES for HMDB0015096 (Mepivacaine)

INCHI for HMDB0015096 (Mepivacaine)

Structure for HMDB0015096 (Mepivacaine)

3D Structure for HMDB0015096 (Mepivacaine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References