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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:40 UTC

HMDB ID

HMDB0014564

Secondary Accession Numbers

HMDB14564

Metabolite Identification

Common Name

Promazine

Description

Promazine is only found in individuals that have used or taken this drug. It is a phenothiazine with actions similar to chlorpromazine but with less antipsychotic activity. It is primarily used in short-term treatment of disturbed behavior and as an antiemetic. [PubChem]Promazine is an antagonist at types 1, 2, and 4 dopamine receptors, 5-HT receptor types 2A and 2C, muscarinic receptors 1 through 5, alpha(1)-receptors, and histamine H1-receptors. Promazine's antipsychotic effect is due to antagonism at dopamine and serotonin type 2 receptors, with greater activity at serotonin 5-HT2 receptors than at dopamine type-2 receptors. This may explain the lack of extrapyramidal effects. Promazine does not appear to block dopamine within the tubero-infundibular tract, explaining the lower incidence of hyperprolactinemia than with typical antipsychotic agents or risperidone. Antagonism at muscarinic receptors, H1-receptors, and alpha(1)-receptors also occurs with promazine.

Structure

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

HMDB0014564
     RDKit          3D
Promazine
 40 42  0  0  0  0  0  0  0  0999 V2000
   -4.9618    0.0405   -0.0823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6743    0.1694    0.5756 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5556   -1.0057    1.4528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6635    0.0348   -0.4549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2576    0.1587    0.1526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3059    0.0054   -0.9919 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0951    0.1095   -0.6281 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6448    1.3890   -0.3442 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8112    2.5042   -0.4588 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2894    3.7906   -0.1981 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5933    4.0102    0.1795 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4053    2.9194    0.2901 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9184    1.6701    0.0309 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0920    0.3436    0.2025 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.2033   -1.1346   -0.1905 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9296   -2.3002   -0.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3283   -3.5032   -0.3840 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0009   -3.4741   -0.7375 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2786   -2.2756   -0.8166 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8815   -1.0591   -0.5387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7503   -0.3146    0.6171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8488   -0.7601   -0.8442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2568    0.9671   -0.6038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2048   -1.8741    0.8277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9194   -0.8150    2.3199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5629   -1.3080    1.8339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7992    0.7685   -1.2476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7138   -1.0056   -0.8460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2112   -0.7174    0.8568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1329    1.0336    0.7825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5737   -0.8723   -1.5936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5581    0.8627   -1.7068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2217    2.4798   -0.7507 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6514    4.6580   -0.2841 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9841    5.0049    0.3869 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4440    3.0942    0.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9709   -2.3273    0.1701 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8696   -4.4264   -0.3272 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5354   -4.4239   -0.9535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2450   -2.4169   -1.0969 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20  7  1  0
 13  8  1  0
 20 15  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 19 40  1  0
M  END

420
  Mrv0541 02231214402D          

 20 22  0  0  0  0            999 V2000
    3.6958   -2.3626    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.6958   -0.7784    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0678    1.5979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6958    0.0137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3819    0.4097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3819    1.2018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3819   -1.1744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0099   -1.1744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3819   -1.9665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0099   -1.9665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0899   -0.7508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3019   -0.7508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0899   -2.3899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3019   -2.3899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7537    1.2018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0678    2.3899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8076   -1.1579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5842   -1.1579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8076   -1.9830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5842   -1.9830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  1 10  1  0  0  0  0
  2  4  1  0  0  0  0
  2  7  1  0  0  0  0
  2  8  1  0  0  0  0
  3  6  1  0  0  0  0
  3 15  1  0  0  0  0
  3 16  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  9  1  0  0  0  0
  7 11  2  0  0  0  0
  8 10  1  0  0  0  0
  8 12  2  0  0  0  0
  9 13  2  0  0  0  0
 10 14  2  0  0  0  0
 11 17  1  0  0  0  0
 12 18  1  0  0  0  0
 13 19  1  0  0  0  0
 14 20  1  0  0  0  0
 17 19  2  0  0  0  0
 18 20  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014564

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)CCCN1C2=CC=CC=C2SC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C17H20N2S/c1-18(2)12-7-13-19-14-8-3-5-10-16(14)20-17-11-6-4-9-15(17)19/h3-6,8-11H,7,12-13H2,1-2H3

> <INCHI_KEY>
ZGUGWUXLJSTTMA-UHFFFAOYSA-N

> <FORMULA>
C17H20N2S

> <MOLECULAR_WEIGHT>
284.419

> <EXACT_MASS>
284.13471934

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
32.741980402245964

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
dimethyl[3-(10H-phenothiazin-10-yl)propyl]amine

> <ALOGPS_LOGP>
4.63

> <JCHEM_LOGP>
3.9309555659999997

> <ALOGPS_LOGS>
-4.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.19697678662742

> <JCHEM_POLAR_SURFACE_AREA>
6.48

> <JCHEM_REFRACTIVITY>
88.95150000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.07e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
promazine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0014564
     RDKit          3D
Promazine
 40 42  0  0  0  0  0  0  0  0999 V2000
   -4.9618    0.0405   -0.0823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6743    0.1694    0.5756 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5556   -1.0057    1.4528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6635    0.0348   -0.4549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2576    0.1587    0.1526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3059    0.0054   -0.9919 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0951    0.1095   -0.6281 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6448    1.3890   -0.3442 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8112    2.5042   -0.4588 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2894    3.7906   -0.1981 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5933    4.0102    0.1795 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4053    2.9194    0.2901 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9184    1.6701    0.0309 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0920    0.3436    0.2025 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.2033   -1.1346   -0.1905 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9296   -2.3002   -0.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3283   -3.5032   -0.3840 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0009   -3.4741   -0.7375 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2786   -2.2756   -0.8166 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8815   -1.0591   -0.5387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7503   -0.3146    0.6171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8488   -0.7601   -0.8442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2568    0.9671   -0.6038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2048   -1.8741    0.8277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9194   -0.8150    2.3199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5629   -1.3080    1.8339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7992    0.7685   -1.2476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7138   -1.0056   -0.8460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2112   -0.7174    0.8568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1329    1.0336    0.7825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5737   -0.8723   -1.5936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5581    0.8627   -1.7068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2217    2.4798   -0.7507 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6514    4.6580   -0.2841 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9841    5.0049    0.3869 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4440    3.0942    0.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9709   -2.3273    0.1701 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8696   -4.4264   -0.3272 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5354   -4.4239   -0.9535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2450   -2.4169   -1.0969 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20  7  1  0
 13  8  1  0
 20 15  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 19 40  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 420                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       6.899  -4.410   0.000  0.00  0.00           S+0
HETATM    2  N   UNK     0       6.899  -1.453   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       9.460   2.983   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       6.899   0.026   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.180   0.765   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.180   2.243   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.180  -2.192   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.618  -2.192   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.180  -3.671   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.618  -3.671   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.501  -1.401   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.297  -1.401   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.501  -4.461   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.297  -4.461   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.740   2.243   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.460   4.461   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.841  -2.161   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.957  -2.161   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.841  -3.702   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.957  -3.702   0.000  0.00  0.00           C+0
CONECT    1    9   10                                                       
CONECT    2    4    7    8                                                  
CONECT    3    6   15   16                                                  
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    3    5                                                       
CONECT    7    2    9   11                                                  
CONECT    8    2   10   12                                                  
CONECT    9    1    7   13                                                  
CONECT   10    1    8   14                                                  
CONECT   11    7   17                                                       
CONECT   12    8   18                                                       
CONECT   13    9   19                                                       
CONECT   14   10   20                                                       
CONECT   15    3                                                            
CONECT   16    3                                                            
CONECT   17   11   19                                                       
CONECT   18   12   20                                                       
CONECT   19   13   17                                                       
CONECT   20   14   18                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0014564
HETATM    1  C1  UNL     1      -4.962   0.040  -0.082  1.00  0.00           C  
HETATM    2  N1  UNL     1      -3.674   0.169   0.576  1.00  0.00           N  
HETATM    3  C2  UNL     1      -3.556  -1.006   1.453  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.664   0.035  -0.455  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.258   0.159   0.153  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.306   0.005  -0.992  1.00  0.00           C  
HETATM    7  N2  UNL     1       1.095   0.109  -0.628  1.00  0.00           N  
HETATM    8  C6  UNL     1       1.645   1.389  -0.344  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.811   2.504  -0.459  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.289   3.791  -0.198  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.593   4.010   0.180  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.405   2.919   0.290  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.918   1.670   0.031  1.00  0.00           C  
HETATM   14  S1  UNL     1       4.092   0.344   0.202  1.00  0.00           S  
HETATM   15  C12 UNL     1       3.203  -1.135  -0.191  1.00  0.00           C  
HETATM   16  C13 UNL     1       3.930  -2.300  -0.107  1.00  0.00           C  
HETATM   17  C14 UNL     1       3.328  -3.503  -0.384  1.00  0.00           C  
HETATM   18  C15 UNL     1       2.001  -3.474  -0.738  1.00  0.00           C  
HETATM   19  C16 UNL     1       1.279  -2.276  -0.817  1.00  0.00           C  
HETATM   20  C17 UNL     1       1.882  -1.059  -0.539  1.00  0.00           C  
HETATM   21  H1  UNL     1      -5.750  -0.315   0.617  1.00  0.00           H  
HETATM   22  H2  UNL     1      -4.849  -0.760  -0.844  1.00  0.00           H  
HETATM   23  H3  UNL     1      -5.257   0.967  -0.604  1.00  0.00           H  
HETATM   24  H4  UNL     1      -3.205  -1.874   0.828  1.00  0.00           H  
HETATM   25  H5  UNL     1      -2.919  -0.815   2.320  1.00  0.00           H  
HETATM   26  H6  UNL     1      -4.563  -1.308   1.834  1.00  0.00           H  
HETATM   27  H7  UNL     1      -2.799   0.768  -1.248  1.00  0.00           H  
HETATM   28  H8  UNL     1      -2.714  -1.006  -0.846  1.00  0.00           H  
HETATM   29  H9  UNL     1      -1.211  -0.717   0.857  1.00  0.00           H  
HETATM   30  H10 UNL     1      -1.133   1.034   0.783  1.00  0.00           H  
HETATM   31  H11 UNL     1      -0.574  -0.872  -1.594  1.00  0.00           H  
HETATM   32  H12 UNL     1      -0.558   0.863  -1.707  1.00  0.00           H  
HETATM   33  H13 UNL     1      -0.222   2.480  -0.751  1.00  0.00           H  
HETATM   34  H14 UNL     1       0.651   4.658  -0.284  1.00  0.00           H  
HETATM   35  H15 UNL     1       2.984   5.005   0.387  1.00  0.00           H  
HETATM   36  H16 UNL     1       4.444   3.094   0.591  1.00  0.00           H  
HETATM   37  H17 UNL     1       4.971  -2.327   0.170  1.00  0.00           H  
HETATM   38  H18 UNL     1       3.870  -4.426  -0.327  1.00  0.00           H  
HETATM   39  H19 UNL     1       1.535  -4.424  -0.953  1.00  0.00           H  
HETATM   40  H20 UNL     1       0.245  -2.417  -1.097  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3    4
CONECT    3   24   25   26
CONECT    4    5   27   28
CONECT    5    6   29   30
CONECT    6    7   31   32
CONECT    7    8   20
CONECT    8    9    9   13
CONECT    9   10   33
CONECT   10   11   11   34
CONECT   11   12   35
CONECT   12   13   13   36
CONECT   13   14
CONECT   14   15
CONECT   15   16   16   20
CONECT   16   17   37
CONECT   17   18   18   38
CONECT   18   19   39
CONECT   19   20   20   40
END

HMDB0014564
     RDKit          3D
Promazine
 40 42  0  0  0  0  0  0  0  0999 V2000
   -4.9618    0.0405   -0.0823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6743    0.1694    0.5756 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5556   -1.0057    1.4528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6635    0.0348   -0.4549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2576    0.1587    0.1526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3059    0.0054   -0.9919 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0951    0.1095   -0.6281 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6448    1.3890   -0.3442 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8112    2.5042   -0.4588 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2894    3.7906   -0.1981 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5933    4.0102    0.1795 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4053    2.9194    0.2901 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9184    1.6701    0.0309 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0920    0.3436    0.2025 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.2033   -1.1346   -0.1905 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9296   -2.3002   -0.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3283   -3.5032   -0.3840 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0009   -3.4741   -0.7375 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2786   -2.2756   -0.8166 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8815   -1.0591   -0.5387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7503   -0.3146    0.6171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8488   -0.7601   -0.8442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2568    0.9671   -0.6038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2048   -1.8741    0.8277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9194   -0.8150    2.3199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5629   -1.3080    1.8339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7992    0.7685   -1.2476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7138   -1.0056   -0.8460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2112   -0.7174    0.8568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1329    1.0336    0.7825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5737   -0.8723   -1.5936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5581    0.8627   -1.7068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2217    2.4798   -0.7507 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6514    4.6580   -0.2841 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9841    5.0049    0.3869 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4440    3.0942    0.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9709   -2.3273    0.1701 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8696   -4.4264   -0.3272 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5354   -4.4239   -0.9535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2450   -2.4169   -1.0969 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20  7  1  0
 13  8  1  0
 20 15  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 19 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
10-(3-(Dimethylamino)propyl)phenothiazine	ChEBI
N-(3-Dimethylaminopropyl)phenothiazine	ChEBI
N-Dimethylamino-1-methylethyl thiodiphenylamine	ChEBI
Promazina	ChEBI
Promazinum	ChEBI
Combelen	Kegg
Promazin	HMDB
Protactyl	HMDB
Promazine hydrochloride	HMDB
Hydrochloride, promazine	HMDB
Sinophenin	HMDB
Sparine	HMDB

Chemical Formula

C₁₇H₂₀N₂S

Average Molecular Weight

284.419

Monoisotopic Molecular Weight

284.13471934

IUPAC Name

dimethyl[3-(10H-phenothiazin-10-yl)propyl]amine

Traditional Name

promazine

CAS Registry Number

58-40-2

SMILES

CN(C)CCCN1C2=CC=CC=C2SC2=CC=CC=C12

InChI Identifier

InChI=1S/C17H20N2S/c1-18(2)12-7-13-19-14-8-3-5-10-16(14)20-17-11-6-4-9-15(17)19/h3-6,8-11H,7,12-13H2,1-2H3

InChI Key

ZGUGWUXLJSTTMA-UHFFFAOYSA-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
Tertiary aliphatic/aromatic amine
Para-thiazine
Benzenoid
Tertiary amine
Tertiary aliphatic amine
Thioether
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organonitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

phenothiazines (CHEBI:8459 )
tertiary amine (CHEBI:8459 )

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

Membrane (HMDB: HMDB0014564)

Source

Exogenous

Exogenous (HMDB: HMDB0014564)

Process

Not Available

Role

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	< 25 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.021 g/L	Not Available
LogP	4.3	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	161.5	30932474
[M+H]+	Not Available	161.363	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000985

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.021 g/L	ALOGPS
logP	4.63	ALOGPS
logP	3.93	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Basic)	9.2	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	6.48 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	88.95 m³·mol⁻¹	ChemAxon
Polarizability	32.74 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 Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	166.909	31661259
DarkChem	[M-H]-	163.441	31661259
DeepCCS	[M-2H]-	189.013	30932474
DeepCCS	[M+Na]+	164.578	30932474
AllCCS	[M+H]+	165.8	32859911
AllCCS	[M+H-H2O]+	162.5	32859911
AllCCS	[M+NH4]+	168.9	32859911
AllCCS	[M+Na]+	169.7	32859911
AllCCS	[M-H]-	169.7	32859911
AllCCS	[M+Na-2H]-	169.2	32859911
AllCCS	[M+HCOO]-	168.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.88 minutes	32390414
Predicted by Siyang on May 30, 2022	11.0563 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.42 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	43.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1141.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	262.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	159.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	185.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	109.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	356.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	430.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	694.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1013.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	285.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1076.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	224.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	345.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	408.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	388.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	9.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Promazine	CN(C)CCCN1C2=CC=CC=C2SC2=CC=CC=C12	3325.5	Standard polar	33892256
Promazine	CN(C)CCCN1C2=CC=CC=C2SC2=CC=CC=C12	2314.2	Standard non polar	33892256
Promazine	CN(C)CCCN1C2=CC=CC=C2SC2=CC=CC=C12	2308.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Promazine EI-B (Non-derivatized)	splash10-0a4r-9230000000-62cbfd979fa705bc6b5e	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Promazine EI-B (Non-derivatized)	splash10-053i-9470000000-c8ea76fcc1b124b82db0	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Promazine CI-B (Non-derivatized)	splash10-000i-2090000000-c38077fbc5880feb7eab	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Promazine EI-B (Non-derivatized)	splash10-0a4r-9230000000-62cbfd979fa705bc6b5e	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Promazine EI-B (Non-derivatized)	splash10-053i-9470000000-c8ea76fcc1b124b82db0	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Promazine CI-B (Non-derivatized)	splash10-000i-2090000000-c38077fbc5880feb7eab	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Promazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0bt9-9380000000-4268602a9238fb15661c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Promazine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Promazine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-9430000000-708a7cbef8d61ce76846	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Promazine 10V, Positive-QTOF	splash10-000i-1090000000-ae84d127d484047e5016	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Promazine 20V, Positive-QTOF	splash10-000l-5090000000-5d46ceef0ced8c3b4fd3	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Promazine 40V, Positive-QTOF	splash10-0006-9220000000-fb2bc50e3fc843771469	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Promazine 10V, Negative-QTOF	splash10-001i-0090000000-149bf8914d943f700602	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Promazine 20V, Negative-QTOF	splash10-00aj-0940000000-c0e629447aac15d08168	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Promazine 40V, Negative-QTOF	splash10-0002-2900000000-5d376e3b361f6d4469ce	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Promazine 10V, Positive-QTOF	splash10-000i-1090000000-eb710b269048129dc354	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Promazine 20V, Positive-QTOF	splash10-000i-9020000000-e2fb252f33540e1240df	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Promazine 40V, Positive-QTOF	splash10-0a4i-9100000000-7887c8f93cf8f9148ae9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Promazine 10V, Negative-QTOF	splash10-001i-0090000000-34b5b095a83ae223858e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Promazine 20V, Negative-QTOF	splash10-001i-0490000000-8b3f6932ff0b667dd708	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Promazine 40V, Negative-QTOF	splash10-0002-0910000000-8b82ae7472d26c1d3bdb	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00420	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00420	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

DB00420

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4757

KEGG Compound ID

C07379

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Promazine

METLIN ID

Not Available

PubChem Compound

4926

PDB ID

Not Available

ChEBI ID

8459

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

Showing metabocard for Promazine (HMDB0014564)

MOL for HMDB0014564 (Promazine)

3D MOL for HMDB0014564 (Promazine)

3D SDF for HMDB0014564 (Promazine)

3D-SDF for HMDB0014564 (Promazine)

PDB for HMDB0014564 (Promazine)

3D PDB for HMDB0014564 (Promazine)

SMILES for HMDB0014564 (Promazine)

INCHI for HMDB0014564 (Promazine)

Structure for HMDB0014564 (Promazine)

3D Structure for HMDB0014564 (Promazine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra