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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (7)transporters (2) Show 9 proteins XML

enzymes (7)transporters (2) Show 9 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:42 UTC

HMDB ID

HMDB0014683

Secondary Accession Numbers

HMDB14683

Metabolite Identification

Common Name

Amoxapine

Description

Amoxapine, the N-demethylated derivative of the antipsychotic agent loxapine, is a dibenzoxazepine-derivative tricyclic antidepressant (TCA). TCAs are structurally similar to phenothiazines. They contain a tricyclic ring system with an alkyl amine substituent on the central ring. In non-depressed individuals, amoxapine does not affect mood or arousal, but may cause sedation. In depressed individuals, amoxapine exerts a positive effect on mood. TCAs are potent inhibitors of serotonin and norepinephrine reuptake. In addition, TCAs down-regulate cerebral cortical β-adrenergic receptors and sensitize post-synaptic serotonergic receptors with chronic use. The antidepressant effects of TCAs are thought to be due to an overall increase in serotonergic neurotransmission. TCAs also block histamine H₁ receptors, α₁-adrenergic receptors and muscarinic receptors, which accounts for their sedative, hypotensive and anticholinergic effects (e.g. blurred vision, dry mouth, constipation, urinary retention), respectively. See toxicity section below for a complete listing of side effects. Amoxapine may be used to treat neurotic and reactive depressive disorders, endogenous and psychotic depression, and mixed symptoms of depression and anxiety or agitation.

Structure

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

HMDB0014683
     RDKit          3D
Amoxapine
 38 41  0  0  0  0  0  0  0  0999 V2000
    0.6463    4.8550   -1.3277 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.3150    3.5356   -0.7149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6399    3.7594   -0.3605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4166    2.7364    0.1243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8610    1.4899    0.2523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5456    1.2737   -0.1010 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2515    2.2796   -0.5880 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2074    0.0270   -0.0324 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6091    0.1496   -0.0658 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3198   -0.3296   -1.2266 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7672   -0.6002   -0.8590 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7426   -1.2451    0.4570 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3153   -0.3681    1.4982 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3841    0.7265    1.0043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3129   -1.1618    0.0578 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6523   -1.6098    0.1147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8020   -2.9421   -0.1770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0726   -3.4885   -0.1501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1891   -2.7380    0.1597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9928   -1.3995    0.4472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7440   -0.8145    0.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7584    0.5567    0.7524 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1110    4.7337   -0.4492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4527    2.8747    0.4103 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2796    2.0799   -0.8579 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2292    0.2835   -2.1203 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8815   -1.3478   -1.4492 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1727   -1.2822   -1.6232 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2763    0.3750   -0.7991 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1862   -2.1188    0.4183 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1845    0.1212    1.9694 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7283   -0.9568    2.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0661    1.5395    0.6308 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7615    1.0653    1.8565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9226   -3.5433   -0.4233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1733   -4.5503   -0.3848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1820   -3.1675    0.1801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8653   -0.7983    0.6927 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  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
  8 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
  7  2  1  0
 14  9  1  0
 21 16  1  0
 22  5  1  0
  3 23  1  0
  4 24  1  0
  7 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
M  END

543
  Mrv0541 02231214452D          

 22 25  0  0  0  0            999 V2000
    1.5842   -0.9947    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.6236   -2.0459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8840    0.4029    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1967    1.8302    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0197   -0.3107    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3302    1.0573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0942    0.4621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9866    1.7710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7505    1.1757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2277   -0.3107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7338   -0.9300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9100   -1.7022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5136   -0.9300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9492   -0.6747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3373   -1.7023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3140   -2.2726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3401   -1.2311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5237   -2.0355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2982   -0.6747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9334   -2.2726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9073   -1.2312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7236   -2.0355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 17  1  0  0  0  0
  2 12  1  0  0  0  0
  2 15  1  0  0  0  0
  3  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3 10  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  0  0  0  0
  5 10  2  0  0  0  0
  5 13  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 14  1  0  0  0  0
 12 16  1  0  0  0  0
 13 15  1  0  0  0  0
 13 19  2  0  0  0  0
 14 17  2  0  0  0  0
 15 20  2  0  0  0  0
 16 18  2  0  0  0  0
 17 18  1  0  0  0  0
 19 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21 22  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014683

> <DATABASE_NAME>
hmdb

> <SMILES>
ClC1=CC2=C(OC3=CC=CC=C3N=C2N2CCNCC2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H16ClN3O/c18-12-5-6-15-13(11-12)17(21-9-7-19-8-10-21)20-14-3-1-2-4-16(14)22-15/h1-6,11,19H,7-10H2

> <INCHI_KEY>
QWGDMFLQWFTERH-UHFFFAOYSA-N

> <FORMULA>
C17H16ClN3O

> <MOLECULAR_WEIGHT>
313.781

> <EXACT_MASS>
313.098189856

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
32.81716403494525

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
13-chloro-10-(piperazin-1-yl)-2-oxa-9-azatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,9,12,14-heptaene

> <ALOGPS_LOGP>
2.82

> <JCHEM_LOGP>
3.077554494666667

> <ALOGPS_LOGS>
-3.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.825946769984718

> <JCHEM_POLAR_SURFACE_AREA>
36.86

> <JCHEM_REFRACTIVITY>
89.81640000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.71e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
amoxapine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0014683
     RDKit          3D
Amoxapine
 38 41  0  0  0  0  0  0  0  0999 V2000
    0.6463    4.8550   -1.3277 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.3150    3.5356   -0.7149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6399    3.7594   -0.3605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4166    2.7364    0.1243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8610    1.4899    0.2523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5456    1.2737   -0.1010 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2515    2.2796   -0.5880 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2074    0.0270   -0.0324 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6091    0.1496   -0.0658 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3198   -0.3296   -1.2266 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7672   -0.6002   -0.8590 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7426   -1.2451    0.4570 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3153   -0.3681    1.4982 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3841    0.7265    1.0043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3129   -1.1618    0.0578 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6523   -1.6098    0.1147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8020   -2.9421   -0.1770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0726   -3.4885   -0.1501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1891   -2.7380    0.1597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9928   -1.3995    0.4472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7440   -0.8145    0.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7584    0.5567    0.7524 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1110    4.7337   -0.4492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4527    2.8747    0.4103 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2796    2.0799   -0.8579 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2292    0.2835   -2.1203 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8815   -1.3478   -1.4492 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1727   -1.2822   -1.6232 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2763    0.3750   -0.7991 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1862   -2.1188    0.4183 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1845    0.1212    1.9694 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7283   -0.9568    2.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0661    1.5395    0.6308 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7615    1.0653    1.8565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9226   -3.5433   -0.4233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1733   -4.5503   -0.3848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1820   -3.1675    0.1801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8653   -0.7983    0.6927 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  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
  8 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
  7  2  1  0
 14  9  1  0
 21 16  1  0
 22  5  1  0
  3 23  1  0
  4 24  1  0
  7 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 543                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       2.957  -1.857   0.000  0.00  0.00          Cl+0
HETATM    2  O   UNK     0       8.631  -3.819   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       7.250   0.752   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       5.967   3.416   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       9.370  -0.580   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       8.083   1.974   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.776   0.863   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.442   3.306   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.134   2.195   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.892  -0.580   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.970  -1.736   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.299  -3.177   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.292  -1.736   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.505  -1.259   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.963  -3.178   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.186  -4.242   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.368  -2.298   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.711  -3.800   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.757  -1.259   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.076  -4.242   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.894  -2.298   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.551  -3.800   0.000  0.00  0.00           C+0
CONECT    1   17                                                            
CONECT    2   12   15                                                       
CONECT    3    6    7   10                                                  
CONECT    4    8    9                                                       
CONECT    5   10   13                                                       
CONECT    6    3    8                                                       
CONECT    7    3    9                                                       
CONECT    8    4    6                                                       
CONECT    9    4    7                                                       
CONECT   10    3    5   11                                                  
CONECT   11   10   12   14                                                  
CONECT   12    2   11   16                                                  
CONECT   13    5   15   19                                                  
CONECT   14   11   17                                                       
CONECT   15    2   13   20                                                  
CONECT   16   12   18                                                       
CONECT   17    1   14   18                                                  
CONECT   18   16   17                                                       
CONECT   19   13   21                                                       
CONECT   20   15   22                                                       
CONECT   21   19   22                                                       
CONECT   22   20   21                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0014683
HETATM    1 CL1  UNL     1       0.646   4.855  -1.328  1.00  0.00          CL  
HETATM    2  C1  UNL     1      -0.315   3.536  -0.715  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.640   3.759  -0.360  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.417   2.736   0.124  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.861   1.490   0.252  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.546   1.274  -0.101  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.252   2.280  -0.588  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.207   0.027  -0.032  1.00  0.00           C  
HETATM    9  N1  UNL     1       1.609   0.150  -0.066  1.00  0.00           N  
HETATM   10  C8  UNL     1       2.320  -0.330  -1.227  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.767  -0.600  -0.859  1.00  0.00           C  
HETATM   12  N2  UNL     1       3.743  -1.245   0.457  1.00  0.00           N  
HETATM   13  C10 UNL     1       3.315  -0.368   1.498  1.00  0.00           C  
HETATM   14  C11 UNL     1       2.384   0.726   1.004  1.00  0.00           C  
HETATM   15  N3  UNL     1      -0.313  -1.162   0.058  1.00  0.00           N  
HETATM   16  C12 UNL     1      -1.652  -1.610   0.115  1.00  0.00           C  
HETATM   17  C13 UNL     1      -1.802  -2.942  -0.177  1.00  0.00           C  
HETATM   18  C14 UNL     1      -3.073  -3.488  -0.150  1.00  0.00           C  
HETATM   19  C15 UNL     1      -4.189  -2.738   0.160  1.00  0.00           C  
HETATM   20  C16 UNL     1      -3.993  -1.399   0.447  1.00  0.00           C  
HETATM   21  C17 UNL     1      -2.744  -0.814   0.432  1.00  0.00           C  
HETATM   22  O1  UNL     1      -2.758   0.557   0.752  1.00  0.00           O  
HETATM   23  H1  UNL     1      -2.111   4.734  -0.449  1.00  0.00           H  
HETATM   24  H2  UNL     1      -3.453   2.875   0.410  1.00  0.00           H  
HETATM   25  H3  UNL     1       1.280   2.080  -0.858  1.00  0.00           H  
HETATM   26  H4  UNL     1       2.229   0.283  -2.120  1.00  0.00           H  
HETATM   27  H5  UNL     1       1.881  -1.348  -1.449  1.00  0.00           H  
HETATM   28  H6  UNL     1       4.173  -1.282  -1.623  1.00  0.00           H  
HETATM   29  H7  UNL     1       4.276   0.375  -0.799  1.00  0.00           H  
HETATM   30  H8  UNL     1       3.186  -2.119   0.418  1.00  0.00           H  
HETATM   31  H9  UNL     1       4.184   0.121   1.969  1.00  0.00           H  
HETATM   32  H10 UNL     1       2.728  -0.957   2.252  1.00  0.00           H  
HETATM   33  H11 UNL     1       3.066   1.540   0.631  1.00  0.00           H  
HETATM   34  H12 UNL     1       1.762   1.065   1.857  1.00  0.00           H  
HETATM   35  H13 UNL     1      -0.923  -3.543  -0.423  1.00  0.00           H  
HETATM   36  H14 UNL     1      -3.173  -4.550  -0.385  1.00  0.00           H  
HETATM   37  H15 UNL     1      -5.182  -3.168   0.180  1.00  0.00           H  
HETATM   38  H16 UNL     1      -4.865  -0.798   0.693  1.00  0.00           H  
CONECT    1    2
CONECT    2    3    3    7
CONECT    3    4   23
CONECT    4    5    5   24
CONECT    5    6   22
CONECT    6    7    7    8
CONECT    7   25
CONECT    8    9   15   15
CONECT    9   10   14
CONECT   10   11   26   27
CONECT   11   12   28   29
CONECT   12   13   30
CONECT   13   14   31   32
CONECT   14   33   34
CONECT   15   16
CONECT   16   17   17   21
CONECT   17   18   35
CONECT   18   19   19   36
CONECT   19   20   37
CONECT   20   21   21   38
CONECT   21   22
END

HMDB0014683
     RDKit          3D
Amoxapine
 38 41  0  0  0  0  0  0  0  0999 V2000
    0.6463    4.8550   -1.3277 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.3150    3.5356   -0.7149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6399    3.7594   -0.3605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4166    2.7364    0.1243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8610    1.4899    0.2523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5456    1.2737   -0.1010 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2515    2.2796   -0.5880 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2074    0.0270   -0.0324 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6091    0.1496   -0.0658 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3198   -0.3296   -1.2266 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7672   -0.6002   -0.8590 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7426   -1.2451    0.4570 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3153   -0.3681    1.4982 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3841    0.7265    1.0043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3129   -1.1618    0.0578 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6523   -1.6098    0.1147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8020   -2.9421   -0.1770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0726   -3.4885   -0.1501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1891   -2.7380    0.1597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9928   -1.3995    0.4472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7440   -0.8145    0.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7584    0.5567    0.7524 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1110    4.7337   -0.4492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4527    2.8747    0.4103 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2796    2.0799   -0.8579 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2292    0.2835   -2.1203 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8815   -1.3478   -1.4492 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1727   -1.2822   -1.6232 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2763    0.3750   -0.7991 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1862   -2.1188    0.4183 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1845    0.1212    1.9694 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7283   -0.9568    2.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0661    1.5395    0.6308 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7615    1.0653    1.8565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9226   -3.5433   -0.4233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1733   -4.5503   -0.3848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1820   -3.1675    0.1801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8653   -0.7983    0.6927 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  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
  8 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
  7  2  1  0
 14  9  1  0
 21 16  1  0
 22  5  1  0
  3 23  1  0
  4 24  1  0
  7 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Chloro-11-(1-piperazinyl)dibenz(b,F)(1,4)oxazepine	ChEBI
Amoxapina	ChEBI
Amoxapinum	ChEBI
Desmethylloxapin	ChEBI
Asendin	Kegg
Amoxepine	HMDB
Amoxapine lederle brand	HMDB
Défanyl	HMDB
Cyanamid brand OF amoxapine	HMDB
Amoxapine wyeth brand	HMDB
Asendis	HMDB
Desmethylloxapine	HMDB
Amoxapine cyanamid brand	HMDB
Demolox	HMDB
Lederle brand OF amoxapine	HMDB
Wyeth brand OF amoxapine	HMDB

Chemical Formula

C₁₇H₁₆ClN₃O

Average Molecular Weight

313.781

Monoisotopic Molecular Weight

313.098189856

IUPAC Name

13-chloro-10-(piperazin-1-yl)-2-oxa-9-azatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,9,12,14-heptaene

Traditional Name

amoxapine

CAS Registry Number

14028-44-5

SMILES

ClC1=CC2=C(OC3=CC=CC=C3N=C2N2CCNCC2)C=C1

InChI Identifier

InChI=1S/C17H16ClN3O/c18-12-5-6-15-13(11-12)17(21-9-7-19-8-10-21)20-14-3-1-2-4-16(14)22-15/h1-6,11,19H,7-10H2

InChI Key

QWGDMFLQWFTERH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzoxazepines. Dibenzoxazepines are compounds containing a dibenzoxazepine moiety, which consists of two benzene connected by an oxazepine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzoxazepines

Sub Class

Dibenzoxazepines

Direct Parent

Dibenzoxazepines

Alternative Parents

Substituents

Dibenzoxazepine
Diaryl ether
Aryl chloride
Aryl halide
1,4-diazinane
Piperazine
Imidolactam
Benzenoid
Amidine
Carboxylic acid amidine
Secondary aliphatic amine
Oxacycle
Ether
Azacycle
Secondary amine
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Organic oxygen compound
Organohalogen compound
Organochloride
Organonitrogen compound
Organooxygen compound
Amine
Organopnictogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dibenzooxazepine (CHEBI:2675 )

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

Extracellular (HMDB: HMDB0014683)
Membrane (HMDB: HMDB0014683)

Source

Exogenous

Exogenous (HMDB: HMDB0014683)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Antidepressant (HMDB: HMDB0014683)

Biological role

Modulator

Adrenergic uptake inhibitor (HMDB: HMDB0014683)

Inhibitor

Enzyme inhibitor

Dopamine uptake inhibitor (HMDB: HMDB0014683)

Serotonin uptake inhibitor (HMDB: HMDB0014683)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	175.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.17 g/L	Not Available
LogP	3.4	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	170.2	30932474
[M+H]+	Not Available	171.19	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001109

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.17 g/L	ALOGPS
logP	2.82	ALOGPS
logP	3.08	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Basic)	8.83	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	36.86 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	89.82 m³·mol⁻¹	ChemAxon
Polarizability	32.82 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	173.399	30932474
DeepCCS	[M-H]-	171.041	30932474
DeepCCS	[M-2H]-	203.927	30932474
DeepCCS	[M+Na]+	179.492	30932474
AllCCS	[M+H]+	171.3	32859911
AllCCS	[M+H-H2O]+	167.9	32859911
AllCCS	[M+NH4]+	174.4	32859911
AllCCS	[M+Na]+	175.2	32859911
AllCCS	[M-H]-	173.0	32859911
AllCCS	[M+Na-2H]-	172.2	32859911
AllCCS	[M+HCOO]-	171.6	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.	2.67 minutes	32390414
Predicted by Siyang on May 30, 2022	10.3105 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.91 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	131.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	925.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	247.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	135.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	183.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	99.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	325.6 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	361.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	499.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	772.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	301.3 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	822.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	211.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	291.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	372.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	284.6 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	23.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Amoxapine	ClC1=CC2=C(OC3=CC=CC=C3N=C2N2CCNCC2)C=C1	3987.0	Standard polar	33892256
Amoxapine	ClC1=CC2=C(OC3=CC=CC=C3N=C2N2CCNCC2)C=C1	2671.8	Standard non polar	33892256
Amoxapine	ClC1=CC2=C(OC3=CC=CC=C3N=C2N2CCNCC2)C=C1	2667.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Amoxapine,1TMS,isomer #1	C[Si](C)(C)N1CCN(C2=NC3=CC=CC=C3OC3=CC=C(Cl)C=C23)CC1	2899.7	Semi standard non polar	33892256
Amoxapine,1TMS,isomer #1	C[Si](C)(C)N1CCN(C2=NC3=CC=CC=C3OC3=CC=C(Cl)C=C23)CC1	2748.2	Standard non polar	33892256
Amoxapine,1TMS,isomer #1	C[Si](C)(C)N1CCN(C2=NC3=CC=CC=C3OC3=CC=C(Cl)C=C23)CC1	4154.0	Standard polar	33892256
Amoxapine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCN(C2=NC3=CC=CC=C3OC3=CC=C(Cl)C=C23)CC1	3119.5	Semi standard non polar	33892256
Amoxapine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCN(C2=NC3=CC=CC=C3OC3=CC=C(Cl)C=C23)CC1	2939.5	Standard non polar	33892256
Amoxapine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCN(C2=NC3=CC=CC=C3OC3=CC=C(Cl)C=C23)CC1	4334.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Amoxapine GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-6190000000-1acb98762576326ae75b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Amoxapine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Amoxapine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-052b-4490000000-6bbd0d2c0c8fe332c636	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 - Amoxapine LC-ESI-qTof , Positive-QTOF	splash10-00dl-2690000000-0e598ca107ca857b8f06	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amoxapine , positive-QTOF	splash10-044i-0169000000-d1665f2e6d27a9efaa39	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amoxapine , positive-QTOF	splash10-002f-0940000000-9bf5c13f1f2b9b04f465	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amoxapine , positive-QTOF	splash10-00dl-2690000000-0e598ca107ca857b8f06	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amoxapine 75V, Positive-QTOF	splash10-006x-2950000000-2fb725746001d0be41d1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amoxapine 90V, Positive-QTOF	splash10-0006-0910000000-7df25fea8ffb96c66d50	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amoxapine 30V, Positive-QTOF	splash10-03k9-1059000000-99ec364d324293ba9191	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amoxapine 15V, Positive-QTOF	splash10-03di-0009000000-fb09780a1d33ba8eb3c8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amoxapine 45V, Positive-QTOF	splash10-00di-2090000000-046bbbcb38472a6b5a4c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amoxapine 60V, Positive-QTOF	splash10-00di-2290000000-47774f87a43619d76d34	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amoxapine 60V, Positive-QTOF	splash10-00di-2290000000-53b12cd961449d9ea634	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amoxapine 10V, Positive-QTOF	splash10-03di-0009000000-873be01dd22731e1f7a7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amoxapine 20V, Positive-QTOF	splash10-03di-0049000000-3989b74ad41770f20ee0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amoxapine 40V, Positive-QTOF	splash10-01r6-9440000000-54259557a6e11d912eb7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amoxapine 10V, Negative-QTOF	splash10-03di-0019000000-eaaa73a51b5bbc0bf28b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amoxapine 20V, Negative-QTOF	splash10-03di-0049000000-be3ce6855a4cc094b8fc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amoxapine 40V, Negative-QTOF	splash10-0006-9250000000-d2f001cf68189e0c19d4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amoxapine 10V, Negative-QTOF	splash10-03di-0009000000-c66d97d82d39ee90b585	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amoxapine 20V, Negative-QTOF	splash10-03di-0009000000-d2c945077b93a0423349	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amoxapine 40V, Negative-QTOF	splash10-00e9-4091000000-4a8bdcd3ca72bcad379c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amoxapine 10V, Positive-QTOF	splash10-03di-0009000000-06ad1e364d70213564e8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amoxapine 20V, Positive-QTOF	splash10-03di-0039000000-17396abffdd86c9873e9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amoxapine 40V, Positive-QTOF	splash10-05e9-1291000000-4d8a424af3692977794b	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
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 DB00543	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00543	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

DB00543

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2085

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Amoxapine

METLIN ID

Not Available

PubChem Compound

2170

PDB ID

Not Available

ChEBI ID

2675

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

References

Shin HC, Kim HR, Cho HJ, Yi H, Cho SM, Lee DG, Abd El-Aty AM, Kim JS, Sun D, Amidon GL: Comparative gene expression of intestinal metabolizing enzymes. Biopharm Drug Dispos. 2009 Nov;30(8):411-21. doi: 10.1002/bdd.675. [PubMed:19746353 ]

Enzyme Details

2. 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

Richelson E, Nelson A: Antagonism by antidepressants of neurotransmitter receptors of normal human brain in vitro. J Pharmacol Exp Ther. 1984 Jul;230(1):94-102. [PubMed:6086881 ]
Buckley NA, McManus PR: Can the fatal toxicity of antidepressant drugs be predicted with pharmacological and toxicological data? Drug Saf. 1998 May;18(5):369-81. [PubMed:9589848 ]

Enzyme Details

3. 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

Wei HB, Niu XY: [Comparison of the affinities of amoxapine and loxapine for various receptors in rat brain and the receptor down-regulation after chronic administration]. Yao Xue Xue Bao. 1990;25(12):881-5. [PubMed:1966571 ]
Nasu R, Matsuo H, Takanaga H, Ohtani H, Sawada Y: Quantitative prediction of catalepsy induced by amoxapine, cinnarizine and cyclophosphamide in mice. Biopharm Drug Dispos. 2000 May;21(4):129-38. [PubMed:11180191 ]

Enzyme Details

4. Alpha-1A adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins
Gene Name:: ADRA1A
Uniprot ID:: P35348
Molecular weight:: 51486.0

References

Wei HB, Niu XY: [Comparison of the affinities of amoxapine and loxapine for various receptors in rat brain and the receptor down-regulation after chronic administration]. Yao Xue Xue Bao. 1990;25(12):881-5. [PubMed:1966571 ]
Buckley NA, McManus PR: Can the fatal toxicity of antidepressant drugs be predicted with pharmacological and toxicological data? Drug Saf. 1998 May;18(5):369-81. [PubMed:9589848 ]

Enzyme Details

5. Gamma-aminobutyric acid receptor subunit alpha-1

General function:: Involved in ion transport
Specific function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:: GABRA1
Uniprot ID:: P14867
Molecular weight:: 51801.4

References

Buckley NA, McManus PR: Can the fatal toxicity of antidepressant drugs be predicted with pharmacological and toxicological data? Drug Saf. 1998 May;18(5):369-81. [PubMed:9589848 ]

Enzyme Details

6. D(1A) 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 activate adenylyl cyclase
Gene Name:: DRD1
Uniprot ID:: P21728
Molecular weight:: 49292.8

References

Nasu R, Matsuo H, Takanaga H, Ohtani H, Sawada Y: Quantitative prediction of catalepsy induced by amoxapine, cinnarizine and cyclophosphamide in mice. Biopharm Drug Dispos. 2000 May;21(4):129-38. [PubMed:11180191 ]

Enzyme Details

7. Muscarinic acetylcholine receptor M1

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
Gene Name:: CHRM1
Uniprot ID:: P11229
Molecular weight:: 51420.4

References

Richelson E: Antimuscarinic and other receptor-blocking properties of antidepressants. Mayo Clin Proc. 1983 Jan;58(1):40-6. [PubMed:6130192 ]
Buckley NA, McManus PR: Can the fatal toxicity of antidepressant drugs be predicted with pharmacological and toxicological data? Drug Saf. 1998 May;18(5):369-81. [PubMed:9589848 ]

Transporters

Enzyme Details

1. Sodium-dependent noradrenaline transporter

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

References

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 ]
Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [PubMed:9537821 ]

Enzyme Details

2. Sodium-dependent serotonin transporter

General function:: Involved in neurotransmitter:sodium symporter activity
Specific function:: Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into the pre-synaptic terminal for re-utilization. Plays a key role in mediating regulation of the availability of serotonin to other receptors of serotonergic systems. Terminates the action of serotonin and recycles it in a sodium-dependent manner.
Gene Name:: SLC6A4
Uniprot ID:: P31645
Molecular weight:: 70324.165

References

Spurlock G, Buckland P, O'Donovan M, McGuffin P: Lack of effect of antidepressant drugs on the levels of mRNAs encoding serotonergic receptors, synthetic enzymes and 5HT transporter. Neuropharmacology. 1994 Mar-Apr;33(3-4):433-40. [PubMed:7984281 ]
Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [PubMed:9537821 ]

Showing metabocard for Amoxapine (HMDB0014683)

MOL for HMDB0014683 (Amoxapine)

3D MOL for HMDB0014683 (Amoxapine)

3D SDF for HMDB0014683 (Amoxapine)

3D-SDF for HMDB0014683 (Amoxapine)

PDB for HMDB0014683 (Amoxapine)

3D PDB for HMDB0014683 (Amoxapine)

SMILES for HMDB0014683 (Amoxapine)

INCHI for HMDB0014683 (Amoxapine)

Structure for HMDB0014683 (Amoxapine)

3D Structure for HMDB0014683 (Amoxapine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References

References

References

Transporters

References

References