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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (22) Show 22 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2021-09-14 14:59:19 UTC

HMDB ID

HMDB0015474

Secondary Accession Numbers

HMDB15474

Metabolite Identification

Common Name

Methotrimeprazine

Description

Methotrimeprazine, also known as levomepromazine or tisercin, belongs to the class of organic compounds known as phenothiazines. These are polycyclic aromatic compounds containing a phenothiazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a para-thiazine ring. As is typical of phenothiazine antipsychotics, levomepromazine is a "dirty drug", that is, it exerts its effects by blocking a variety of receptors, including adrenergic receptors, dopamine receptors, histamine receptors, muscarinic acetylcholine receptors and serotonin receptors. Methotrimeprazine is a drug which is used for the treatment of psychosis, particular those of schizophrenia, and manic phases of bipolar disorder. Levomepromazine is frequently prescribed and valued worldwide in palliative care medicine for its multimodal action, to treat intractable nausea or vomiting, and for severe delirium/agitation in the last days of life. Methotrimeprazine is a very strong basic compound (based on its pKa). Methotrimeprazine is a potentially toxic compound. Serious side effects include tardive dyskinesia, akathisia, abnormalities in the electrical cycle of the heart, low blood pressure and the potentially fatal neuroleptic malignant syndrome. Brand names include Nozinan, Levoprome, Detenler, Hirnamin, Levotomin and Neurocil. Palliative care physicians will commonly prescribe it orally or via subcutaneous syringe drivers in combination with opioid analgesics such as hydromorphone. A 2010 systematic review compared the efficacy of levomepromazine with atypical antipsychotic drugs:The most common side effect is akathisia. Levomepromazine is used for the treatment of psychosis, particularly those of schizophrenia, and manic phases of bipolar disorder. In any case, blood pressure and EKG should be monitored regularly. A rare but life-threatening side effect is neuroleptic malignant syndrome (NMS).

Structure

MOL SDF 3D SDF PDB 3D PDB SMILES InChI

1403
  Mrv0541 02231215282D          

 23 25  0  0  1  0            999 V2000
   12.2932  -12.4596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2932  -13.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0357  -13.6971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0357  -12.0472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7369  -12.4596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7369  -13.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4381  -13.6971    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.4381  -12.0472    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1806  -12.4596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1806  -13.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8406  -13.6971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5831  -13.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5831  -12.4596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8818  -12.0472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4381  -11.2221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1806  -10.8097    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.1806   -9.9847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8818  -11.2221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8818   -9.5722    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8818   -8.7472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6243   -9.9847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3030  -12.0479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0098  -12.4598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 14  9  1  0  0  0  0
  2  3  2  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  8 15  1  0  0  0  0
  7 10  1  0  0  0  0
 15 16  1  0  0  0  0
  9  8  1  0  0  0  0
 16 17  1  0  0  0  0
  8  5  1  0  0  0  0
 16 18  1  1  0  0  0
  3  6  1  0  0  0  0
 17 19  1  0  0  0  0
  5  4  1  0  0  0  0
 19 20  1  0  0  0  0
  4  1  2  0  0  0  0
 19 21  1  0  0  0  0
  1  2  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 22  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015474

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(SC3=C(C=CC=C3)N2C[C@H](C)CN(C)C)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H24N2OS/c1-14(12-20(2)3)13-21-16-7-5-6-8-18(16)23-19-10-9-15(22-4)11-17(19)21/h5-11,14H,12-13H2,1-4H3/t14-/m1/s1

> <INCHI_KEY>
VRQVVMDWGGWHTJ-CQSZACIVSA-N

> <FORMULA>
C19H24N2OS

> <MOLECULAR_WEIGHT>
328.472

> <EXACT_MASS>
328.16093409

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
36.765685745522234

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(2R)-3-(2-methoxy-10H-phenothiazin-10-yl)-2-methylpropyl]dimethylamine

> <ALOGPS_LOGP>
4.84

> <JCHEM_LOGP>
4.252607859666666

> <ALOGPS_LOGS>
-4.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.421368308045276

> <JCHEM_POLAR_SURFACE_AREA>
15.71

> <JCHEM_REFRACTIVITY>
99.83109999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.25e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methotrimeprazine

> <JCHEM_VEBER_RULE>
1

$$$$

https://cactus.nci.nih.gov/chemical/structure/COC1=CC2=C(SC3=C(C=CC=C3)N2C%5B...
 OpenBabel09142113233D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:46})
 47 49  0  0  0  0  0  0  0  0999 V2000
    4.9208   -3.0089   -0.5251 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5990   -2.6577   -0.9390 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0693   -1.5206   -0.4140 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7916   -1.1219   -0.7730 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2427    0.0395   -0.2398 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9882    0.7985    0.6569 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3274    2.2762    1.3495 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0083    2.6703    0.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5362    1.7100   -0.5850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5874    2.0534   -1.4287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1062    3.3342   -1.4120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5828    4.2845   -0.5559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5361    3.9547    0.2848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0463    0.4066   -0.6193 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9476   -0.6497   -1.0864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8236   -1.1231    0.0752 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3583   -0.2722    0.4974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9424   -1.7575    1.1531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8306   -2.1566   -0.4337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7700   -2.4965    0.6433 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7412   -1.4149    0.8555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4508   -3.7683    0.3662 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2677    0.3944    1.0134 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8058   -0.7639    0.4845 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6112   -2.2109   -0.7985 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9378   -3.1498    0.5556 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2218   -3.9340   -1.0169 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2194   -1.7157   -1.4705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0005    1.3152   -2.1001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9226    3.5932   -2.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9912    5.2843   -0.5438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1277    4.6983    0.9532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5806   -0.2608   -1.8839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3610   -1.4872   -1.4639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2996   -0.9946    1.5923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5730   -2.1919    1.9288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3267   -2.5380    0.7061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3808   -1.7424   -1.2785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3006   -3.0548   -0.7506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3062   -1.2488   -0.0617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4246   -1.6925    1.6580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2134   -0.5009    1.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7212   -4.5782    0.3648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1995   -3.9550    1.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9368   -3.7156   -0.6081 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8436    0.9853    1.7101 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8015   -1.0746    0.7644 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3 24  1  0  0  0  0
  4  5  1  0  0  0  0
  4 28  1  0  0  0  0
  5  6  2  0  0  0  0
  5 14  1  0  0  0  0
  6  7  1  0  0  0  0
  6 23  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 13  1  0  0  0  0
  9 10  1  0  0  0  0
  9 14  1  0  0  0  0
 10 11  2  0  0  0  0
 10 29  1  0  0  0  0
 11 12  1  0  0  0  0
 11 30  1  0  0  0  0
 12 13  2  0  0  0  0
 12 31  1  0  0  0  0
 13 32  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 33  1  0  0  0  0
 15 34  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 18 35  1  0  0  0  0
 18 36  1  0  0  0  0
 18 37  1  0  0  0  0
 19 20  1  0  0  0  0
 19 38  1  0  0  0  0
 19 39  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21 40  1  0  0  0  0
 21 41  1  0  0  0  0
 21 42  1  0  0  0  0
 22 43  1  0  0  0  0
 22 44  1  0  0  0  0
 22 45  1  0  0  0  0
 23 24  2  0  0  0  0
 23 46  1  0  0  0  0
 24 47  1  0  0  0  0
M  END
$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1403                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      22.947 -23.258   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      22.947 -24.798   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      24.333 -25.568   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      24.333 -22.488   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      25.642 -23.258   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      25.642 -24.798   0.000  0.00  0.00           C+0
HETATM    7  S   UNK     0      26.951 -25.568   0.000  0.00  0.00           S+0
HETATM    8  N   UNK     0      26.951 -22.488   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      28.337 -23.258   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      28.337 -24.798   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      29.569 -25.568   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      30.955 -24.798   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      30.955 -23.258   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      29.646 -22.488   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      26.951 -20.948   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      28.337 -20.178   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      28.337 -18.638   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      29.646 -20.948   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0      29.646 -17.868   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0      29.646 -16.328   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      31.032 -18.638   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      32.299 -22.489   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      33.618 -23.258   0.000  0.00  0.00           C+0
CONECT    1    4    2                                                       
CONECT    2    3    1                                                       
CONECT    3    2    6                                                       
CONECT    4    5    1                                                       
CONECT    5    6    8    4                                                  
CONECT    6    5    7    3                                                  
CONECT    7    6   10                                                       
CONECT    8   15    9    5                                                  
CONECT    9   14    8   10                                                  
CONECT   10    7    9   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   22                                                  
CONECT   14    9   13                                                       
CONECT   15    8   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16   19                                                       
CONECT   18   16                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   13   23                                                       
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    https://cactus.nci.nih.gov/chemical/structure/COC1=CC2=C(SC3=C(C=CC=C3)N2C%5B... 
AUTHOR    GENERATED BY OPEN BABEL 3.1.0
HETATM    1  C   UNL     1       4.921  -3.009  -0.525  1.00  0.00           C  
HETATM    2  O   UNL     1       3.599  -2.658  -0.939  1.00  0.00           O  
HETATM    3  C   UNL     1       3.069  -1.521  -0.414  1.00  0.00           C  
HETATM    4  C   UNL     1       1.792  -1.122  -0.773  1.00  0.00           C  
HETATM    5  C   UNL     1       1.243   0.040  -0.240  1.00  0.00           C  
HETATM    6  C   UNL     1       1.988   0.798   0.657  1.00  0.00           C  
HETATM    7  S   UNL     1       1.327   2.276   1.349  1.00  0.00           S  
HETATM    8  C   UNL     1      -0.008   2.670   0.273  1.00  0.00           C  
HETATM    9  C   UNL     1      -0.536   1.710  -0.585  1.00  0.00           C  
HETATM   10  C   UNL     1      -1.587   2.053  -1.429  1.00  0.00           C  
HETATM   11  C   UNL     1      -2.106   3.334  -1.412  1.00  0.00           C  
HETATM   12  C   UNL     1      -1.583   4.285  -0.556  1.00  0.00           C  
HETATM   13  C   UNL     1      -0.536   3.955   0.285  1.00  0.00           C  
HETATM   14  N   UNL     1      -0.046   0.407  -0.619  1.00  0.00           N  
HETATM   15  C   UNL     1      -0.948  -0.650  -1.086  1.00  0.00           C  
HETATM   16  C   UNL     1      -1.824  -1.123   0.075  1.00  0.00           C  
HETATM   17  H   UNL     1      -2.358  -0.272   0.497  1.00  0.00           H  
HETATM   18  C   UNL     1      -0.942  -1.758   1.153  1.00  0.00           C  
HETATM   19  C   UNL     1      -2.831  -2.157  -0.434  1.00  0.00           C  
HETATM   20  N   UNL     1      -3.770  -2.497   0.643  1.00  0.00           N  
HETATM   21  C   UNL     1      -4.741  -1.415   0.856  1.00  0.00           C  
HETATM   22  C   UNL     1      -4.451  -3.768   0.366  1.00  0.00           C  
HETATM   23  C   UNL     1       3.268   0.394   1.013  1.00  0.00           C  
HETATM   24  C   UNL     1       3.806  -0.764   0.484  1.00  0.00           C  
HETATM   25  H   UNL     1       5.611  -2.211  -0.798  1.00  0.00           H  
HETATM   26  H   UNL     1       4.938  -3.150   0.556  1.00  0.00           H  
HETATM   27  H   UNL     1       5.222  -3.934  -1.017  1.00  0.00           H  
HETATM   28  H   UNL     1       1.219  -1.716  -1.470  1.00  0.00           H  
HETATM   29  H   UNL     1      -2.001   1.315  -2.100  1.00  0.00           H  
HETATM   30  H   UNL     1      -2.923   3.593  -2.070  1.00  0.00           H  
HETATM   31  H   UNL     1      -1.991   5.284  -0.544  1.00  0.00           H  
HETATM   32  H   UNL     1      -0.128   4.698   0.953  1.00  0.00           H  
HETATM   33  H   UNL     1      -1.581  -0.261  -1.884  1.00  0.00           H  
HETATM   34  H   UNL     1      -0.361  -1.487  -1.464  1.00  0.00           H  
HETATM   35  H   UNL     1      -0.300  -0.995   1.592  1.00  0.00           H  
HETATM   36  H   UNL     1      -1.573  -2.192   1.929  1.00  0.00           H  
HETATM   37  H   UNL     1      -0.327  -2.538   0.706  1.00  0.00           H  
HETATM   38  H   UNL     1      -3.381  -1.742  -1.278  1.00  0.00           H  
HETATM   39  H   UNL     1      -2.301  -3.055  -0.751  1.00  0.00           H  
HETATM   40  H   UNL     1      -5.306  -1.249  -0.062  1.00  0.00           H  
HETATM   41  H   UNL     1      -5.425  -1.692   1.658  1.00  0.00           H  
HETATM   42  H   UNL     1      -4.213  -0.501   1.128  1.00  0.00           H  
HETATM   43  H   UNL     1      -3.721  -4.578   0.365  1.00  0.00           H  
HETATM   44  H   UNL     1      -5.199  -3.955   1.136  1.00  0.00           H  
HETATM   45  H   UNL     1      -4.937  -3.716  -0.608  1.00  0.00           H  
HETATM   46  H   UNL     1       3.844   0.985   1.710  1.00  0.00           H  
HETATM   47  H   UNL     1       4.801  -1.075   0.764  1.00  0.00           H  
CONECT    1    2   25   26   27                                       
CONECT    2    1    3                                                 
CONECT    3    2    4    4   24                                       
CONECT    4    3    3    5   28                                       
CONECT    5    4    6    6   14                                       
CONECT    6    5    5    7   23                                       
CONECT    7    6    8                                                 
CONECT    8    7    9    9   13                                       
CONECT    9    8    8   10   14                                       
CONECT   10    9   11   11   29                                       
CONECT   11   10   10   12   30                                       
CONECT   12   11   13   13   31                                       
CONECT   13   12   12    8   32                                       
CONECT   14    9    5   15                                            
CONECT   15   14   16   33   34                                       
CONECT   16   15   17   18   19                                       
CONECT   17   16                                                      
CONECT   18   16   35   36   37                                       
CONECT   19   16   20   38   39                                       
CONECT   20   19   21   22                                            
CONECT   21   20   40   41   42                                       
CONECT   22   20   43   44   45                                       
CONECT   23    6   24   24   46                                       
CONECT   24   23   23    3   47                                       
CONECT   25    1                                                      
CONECT   26    1                                                      
CONECT   27    1                                                      
CONECT   28    4                                                      
CONECT   29   10                                                      
CONECT   30   11                                                      
CONECT   31   12                                                      
CONECT   32   13                                                      
CONECT   33   15                                                      
CONECT   34   15                                                      
CONECT   35   18                                                      
CONECT   36   18                                                      
CONECT   37   18                                                      
CONECT   38   19                                                      
CONECT   39   19                                                      
CONECT   40   21                                                      
CONECT   41   21                                                      
CONECT   42   21                                                      
CONECT   43   22                                                      
CONECT   44   22                                                      
CONECT   45   22                                                      
CONECT   46   23                                                      
CONECT   47   24                                                      
MASTER        0    0    0    0    0    0    0    0   47    0   47    0
END

https://cactus.nci.nih.gov/chemical/structure/COC1=CC2=C(SC3=C(C=CC=C3)N2C%5B...
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M  END
$$$$

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-(2R)-3-(2-Methoxy-10H-phenothiazin-10-yl)-N,N,2-trimethylpropan-1-amine	ChEBI
(-)-10-(3-(Dimethylamino)-2-methylpropyl)-2-methoxyphenothiazine	ChEBI
2-Methoxytrimeprazine	ChEBI
Levomepromazina	ChEBI
Levomepromazine	ChEBI
Levomepromazinum	ChEBI
Levoprome	Kegg
Levopromazine	HMDB
Tisercin	HMDB
Levomeprazin	HMDB
Tizertsin	HMDB
Tizercine	HMDB

Chemical Formula

C₁₉H₂₄N₂OS

Average Molecular Weight

328.472

Monoisotopic Molecular Weight

328.16093409

IUPAC Name

[(2R)-3-(2-methoxy-10H-phenothiazin-10-yl)-2-methylpropyl]dimethylamine

Traditional Name

methotrimeprazine

CAS Registry Number

60-99-1

SMILES

COC1=CC2=C(SC3=C(C=CC=C3)N2C[C@H](C)CN(C)C)C=C1

InChI Identifier

InChI=1S/C19H24N2OS/c1-14(12-20(2)3)13-21-16-7-5-6-8-18(16)23-19-10-9-15(22-4)11-17(19)21/h5-11,14H,12-13H2,1-4H3/t14-/m1/s1

InChI Key

VRQVVMDWGGWHTJ-CQSZACIVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenothiazines. These are polycyclic aromatic compounds containing a phenothiazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a para-thiazine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzothiazines

Sub Class

Phenothiazines

Direct Parent

Phenothiazines

Alternative Parents

Substituents

Phenothiazine
Alkyldiarylamine
Diarylthioether
Aryl thioether
Anisole
Tertiary aliphatic/aromatic amine
Alkyl aryl ether
Para-thiazine
Benzenoid
Tertiary aliphatic amine
Tertiary amine
Ether
Azacycle
Thioether
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organic oxygen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

phenothiazines (CHEBI:6838 )
tertiary amine (CHEBI:6838 )

Ontology

Physiological effect

Health effect:

Health condition:

Coma

Disposition

Route of exposure:

Enteral:

Ingestion

Parenteral:

Intramuscular

Biological location:

Subcellular:

Biofluid and excreta:

Role

Industrial application:

Drug

Pharmaceutical industry:

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0052 g/L	Not Available
LogP	4.68	HANSCH,C ET AL. (1995)

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0052 g/L	ALOGPS
logP	4.84	ALOGPS
logP	4.25	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Basic)	9.42	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	15.71 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	99.83 m³·mol⁻¹	ChemAxon
Polarizability	36.77 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Spectral Properties

Collision Cross Sections

Name	Adduct	Type	Data Source	Value	Reference
DarkChem	[M+H]+	Predicted	Not Available	175.742	31661259
DarkChem	[M-H]-	Predicted	Not Available	176.93	31661259

Retention Indices

Underivatized

Not Available

Derivatized

Not Available

Spectra

GC-MS

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9272000000-663ed1e564555c7e8fae	2017-09-01	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-056r-9356000000-bb17e4980980d336d337	2014-09-20	View Spectrum

LC-MS/MS

Spectrum Type	Description	Splash Key	Deposition Date	View
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-004i-0009000000-292add600a1d733c3662	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-004i-0319000000-9bcdb870e16f29c42cc7	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0udi-2920000000-f73fff6b08acc61ea5b7	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0zfr-6920000000-dc5968beb0d112813d55	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a4i-9410000000-0d1f6734452bedc68d3f	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , positive	splash10-0udi-0910000000-10fe32fa41981fcda652	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0469000000-698db513d68f8238a284	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ue9-3983000000-0963d25ff0f442a1b819	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pc3-9420000000-45332e32eecba186d700	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0019000000-783dfd7af7ab08cc7337	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00p0-0494000000-78a58d14f5fb19218ba8	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-002b-3960000000-d1127cf211de0694b952	2016-08-03	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/Pathwhiz	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 DB01403	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01403	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

DB01403

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

65239

KEGG Compound ID

C07192

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Levomepromazine

METLIN ID

Not Available

PubChem Compound

72287

PDB ID

Not Available

ChEBI ID

6838

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Doctissimo [Link]

Only showing the first 10 proteins. There are 22 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Cytochrome P450 2E1

General function:: Involved in monooxygenase activity
Specific function:: Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:: CYP2E1
Uniprot ID:: P05181
Molecular weight:: 56848.42

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. 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

3. Cytochrome P450 1A2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

Green B, Pettit T, Faith L, Seaton K: Focus on levomepromazine. Curr Med Res Opin. 2004 Dec;20(12):1877-81. [PubMed:15701205 ]

Enzyme Details

4. Alpha-2A adrenergic receptor

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

References

Green B, Pettit T, Faith L, Seaton K: Focus on levomepromazine. Curr Med Res Opin. 2004 Dec;20(12):1877-81. [PubMed:15701205 ]
Dahl SG, Hough E, Hals PA: Phenothiazine drugs and metabolites: molecular conformation and dopaminergic, alpha adrenergic and muscarinic cholinergic receptor binding. Biochem Pharmacol. 1986 Apr 15;35(8):1263-9. [PubMed:2870716 ]
Tsukamoto T, Asakura M, Hirata N, Imafuku J, Matsui H, Hasegawa K: Interaction of neuroleptics and antidepressants with rat brain alpha 2-receptors: a possible relationship between alpha 2-receptor antagonism and antidepressant action. Biol Psychiatry. 1984 Sep;19(9):1283-91. [PubMed:6149771 ]

Enzyme Details

5. Alpha-2B adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine > norepinephrine > epinephrine = oxymetazoline > dopamine > p-tyramine = phenylephrine > serotonin > p-synephrine / p-octopamine. For antagonists, the rank order is yohimbine > chlorpromazine > phentolamine > mianserine > spiperone > prazosin > alprenolol > propanolol > pindolol
Gene Name:: ADRA2B
Uniprot ID:: P18089
Molecular weight:: 49953.1

References

Green B, Pettit T, Faith L, Seaton K: Focus on levomepromazine. Curr Med Res Opin. 2004 Dec;20(12):1877-81. [PubMed:15701205 ]
Dahl SG, Hough E, Hals PA: Phenothiazine drugs and metabolites: molecular conformation and dopaminergic, alpha adrenergic and muscarinic cholinergic receptor binding. Biochem Pharmacol. 1986 Apr 15;35(8):1263-9. [PubMed:2870716 ]
Tsukamoto T, Asakura M, Hirata N, Imafuku J, Matsui H, Hasegawa K: Interaction of neuroleptics and antidepressants with rat brain alpha 2-receptors: a possible relationship between alpha 2-receptor antagonism and antidepressant action. Biol Psychiatry. 1984 Sep;19(9):1283-91. [PubMed:6149771 ]

Enzyme Details

6. D(2) dopamine receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
Gene Name:: DRD2
Uniprot ID:: P14416
Molecular weight:: 50618.9

References

Green B, Pettit T, Faith L, Seaton K: Focus on levomepromazine. Curr Med Res Opin. 2004 Dec;20(12):1877-81. [PubMed:15701205 ]
Dahl SG, Hough E, Hals PA: Phenothiazine drugs and metabolites: molecular conformation and dopaminergic, alpha adrenergic and muscarinic cholinergic receptor binding. Biochem Pharmacol. 1986 Apr 15;35(8):1263-9. [PubMed:2870716 ]
Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]

Enzyme Details

7. D(4) dopamine receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
Gene Name:: DRD4
Uniprot ID:: P21917
Molecular weight:: 48359.9

References

Green B, Pettit T, Faith L, Seaton K: Focus on levomepromazine. Curr Med Res Opin. 2004 Dec;20(12):1877-81. [PubMed:15701205 ]

Enzyme Details

8. 5-hydroxytryptamine receptor 2A

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. This receptor is involved in tracheal smooth muscle contraction, bronchoconstriction, and control of aldosterone production
Gene Name:: HTR2A
Uniprot ID:: P28223
Molecular weight:: 52602.6

References

Green B, Pettit T, Faith L, Seaton K: Focus on levomepromazine. Curr Med Res Opin. 2004 Dec;20(12):1877-81. [PubMed:15701205 ]

Enzyme Details

9. 5-hydroxytryptamine receptor 2C

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system
Gene Name:: HTR2C
Uniprot ID:: P28335
Molecular weight:: 51820.7

References

Green B, Pettit T, Faith L, Seaton K: Focus on levomepromazine. Curr Med Res Opin. 2004 Dec;20(12):1877-81. [PubMed:15701205 ]

Enzyme Details

10. Histamine H1 receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system
Gene Name:: HRH1
Uniprot ID:: P35367
Molecular weight:: 55783.6

References

Hals PA, Hall H, Dahl SG: Muscarinic cholinergic and histamine H1 receptor binding of phenothiazine drug metabolites. Life Sci. 1988;43(5):405-12. [PubMed:2899826 ]

Only showing the first 10 proteins. There are 22 proteins in total.

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Showing metabocard for Methotrimeprazine (HMDB0015474)

MOL for HMDB0015474 (Methotrimeprazine)

3D MOL for HMDB0015474 (Methotrimeprazine)

3D SDF for HMDB0015474 (Methotrimeprazine)

3D-SDF for HMDB0015474 (Methotrimeprazine)

PDB for HMDB0015474 (Methotrimeprazine)

3D PDB for HMDB0015474 (Methotrimeprazine)

SMILES for HMDB0015474 (Methotrimeprazine)

INCHI for HMDB0015474 (Methotrimeprazine)

Structure for HMDB0015474 (Methotrimeprazine)

3D Structure for HMDB0015474 (Methotrimeprazine)

Collision Cross Sections

Retention Indices

Underivatized

Derivatized

GC-MS

LC-MS/MS

Enzymes

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