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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:39 UTC

HMDB ID

HMDB0014548

Secondary Accession Numbers

HMDB14548

Metabolite Identification

Common Name

Alprazolam

Description

Alprazolam is only found in individuals that have used or taken this drug. It is a triazolobenzodiazepine compound with antianxiety and sedative-hypnotic actions, that is efficacious in the treatment of panic disorders, with or without agoraphobia, and in generalized anxiety disorders. (From AMA Drug Evaluations Annual, 1994, p238)Benzodiazepines bind nonspecifically to benzodiazepine receptors BNZ1, which mediates sleep, and BNZ2, which affects muscle relaxation, anticonvulsant activity, motor coordination, and memory. As benzodiazepine receptors are thought to be coupled to gamma-aminobutyric acid-A (GABA_A) receptors, this enhances the effects of GABA by increasing GABA affinity for the GABA receptor. Binding of the inhibitory neurotransmitter GABA to the site opens the chloride channel, resulting in a hyperpolarized cell membrane that prevents further excitation of the cell.

Structure

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

HMDB0014548
     RDKit          3D
Alprazolam
 35 38  0  0  0  0  0  0  0  0999 V2000
    4.0542   -0.3207   -1.0173 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3196    0.8914   -0.6330 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6141    2.1985   -0.9284 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6407    2.9998   -0.4462 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7354    2.2647    0.1456 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1761    0.9735    0.0206 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5065   -0.1846    0.5568 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3805   -1.1137    1.0333 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7801   -2.2307    1.6300 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3894   -2.3480    1.7179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3721   -3.7515    2.4626 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.4547   -1.3825    1.2267 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105   -0.2884    0.6348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8642    0.6723    0.1543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0968    0.1705   -0.4072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4335   -1.0950   -0.7164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6808   -1.4329   -1.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6755   -0.4964   -1.3180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3806    0.8306   -1.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1253    1.1271   -0.5765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6683    1.9655    0.2350 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4856    2.7134    0.7729 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0251   -0.4860   -0.5570 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4335   -1.2206   -1.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3728   -0.0893   -2.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4253   -0.9591    1.0035 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4114   -2.9915    2.0167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5396   -1.4162    1.3444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7060   -1.8877   -0.6909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9447   -2.4721   -1.4051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6696   -0.7089   -1.6607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1491    1.5964   -1.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9255    2.1852   -0.3462 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5498    2.5280    1.8622 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2757    3.7592    0.5120 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 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
 14 21  2  0
 21 22  1  0
  6  2  1  0
 13  7  1  0
 20 15  1  0
 22  5  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  8 26  1  0
  9 27  1  0
 12 28  1  0
 16 29  1  0
 17 30  1  0
 18 31  1  0
 19 32  1  0
 20 33  1  0
 22 34  1  0
 22 35  1  0
M  END

404
  Mrv0541 02231214392D          

 22 25  0  0  0  0            999 V2000
    1.6500   -0.2321    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.8159   -1.3269    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2284    0.4805    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1244   -1.5631    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7352   -2.2849    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0726   -0.9689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8890   -0.1645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5592   -0.9689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4034    0.4805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7428   -0.1645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9281   -2.1392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4517   -1.5630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0718    0.1014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0454    1.2238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6286   -1.3160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4374   -0.4783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3328   -2.7104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2227    1.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5102    1.9054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8648    2.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1523    2.6488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3296    2.7104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 16  1  0  0  0  0
  2  6  1  0  0  0  0
  2  8  1  0  0  0  0
  2 11  1  0  0  0  0
  3  9  2  0  0  0  0
  3 10  1  0  0  0  0
  4  5  1  0  0  0  0
  4  8  2  0  0  0  0
  5 11  2  0  0  0  0
  6  7  2  0  0  0  0
  6 12  1  0  0  0  0
  7  9  1  0  0  0  0
  7 13  1  0  0  0  0
  8 10  1  0  0  0  0
  9 14  1  0  0  0  0
 11 17  1  0  0  0  0
 12 15  2  0  0  0  0
 13 16  2  0  0  0  0
 14 18  2  0  0  0  0
 14 19  1  0  0  0  0
 15 16  1  0  0  0  0
 18 20  1  0  0  0  0
 19 21  2  0  0  0  0
 20 22  2  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014548

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=NN=C2CN=C(C3=CC=CC=C3)C3=C(C=CC(Cl)=C3)N12

> <INCHI_IDENTIFIER>
InChI=1S/C17H13ClN4/c1-11-20-21-16-10-19-17(12-5-3-2-4-6-12)14-9-13(18)7-8-15(14)22(11)16/h2-9H,10H2,1H3

> <INCHI_KEY>
VREFGVBLTWBCJP-UHFFFAOYSA-N

> <FORMULA>
C17H13ClN4

> <MOLECULAR_WEIGHT>
308.765

> <EXACT_MASS>
308.082874143

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
32.21940045856445

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
12-chloro-3-methyl-9-phenyl-2,4,5,8-tetraazatricyclo[8.4.0.0²,⁶]tetradeca-1(10),3,5,8,11,13-hexaene

> <ALOGPS_LOGP>
2.23

> <JCHEM_LOGP>
2.3741000000000003

> <ALOGPS_LOGS>
-3.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.2996362847328

> <JCHEM_PKA_STRONGEST_BASIC>
5.076680256062132

> <JCHEM_POLAR_SURFACE_AREA>
43.07

> <JCHEM_REFRACTIVITY>
98.87900000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.24e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
neurol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014548
     RDKit          3D
Alprazolam
 35 38  0  0  0  0  0  0  0  0999 V2000
    4.0542   -0.3207   -1.0173 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3196    0.8914   -0.6330 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6141    2.1985   -0.9284 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6407    2.9998   -0.4462 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7354    2.2647    0.1456 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1761    0.9735    0.0206 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5065   -0.1846    0.5568 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3805   -1.1137    1.0333 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7801   -2.2307    1.6300 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3894   -2.3480    1.7179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3721   -3.7515    2.4626 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.4547   -1.3825    1.2267 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105   -0.2884    0.6348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8642    0.6723    0.1543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0968    0.1705   -0.4072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4335   -1.0950   -0.7164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6808   -1.4329   -1.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6755   -0.4964   -1.3180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3806    0.8306   -1.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1253    1.1271   -0.5765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6683    1.9655    0.2350 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4856    2.7134    0.7729 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0251   -0.4860   -0.5570 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4335   -1.2206   -1.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3728   -0.0893   -2.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4253   -0.9591    1.0035 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4114   -2.9915    2.0167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5396   -1.4162    1.3444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7060   -1.8877   -0.6909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9447   -2.4721   -1.4051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6696   -0.7089   -1.6607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1491    1.5964   -1.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9255    2.1852   -0.3462 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5498    2.5280    1.8622 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2757    3.7592    0.5120 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 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
 14 21  2  0
 21 22  1  0
  6  2  1  0
 13  7  1  0
 20 15  1  0
 22  5  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  8 26  1  0
  9 27  1  0
 12 28  1  0
 16 29  1  0
 17 30  1  0
 18 31  1  0
 19 32  1  0
 20 33  1  0
 22 34  1  0
 22 35  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 404                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       3.080  -0.433   0.000  0.00  0.00          Cl+0
HETATM    2  N   UNK     0       8.990  -2.477   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       9.760   0.897   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      11.432  -2.918   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      10.706  -4.265   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       7.602  -1.809   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.259  -0.307   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.377  -1.809   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.220   0.897   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.720  -0.307   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.199  -3.993   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.443  -2.918   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.734   0.189   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.551   2.284   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.907  -2.457   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.550  -0.893   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.088  -5.059   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.016   2.399   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.419   3.557   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.348   3.787   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.751   4.944   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.215   5.059   0.000  0.00  0.00           C+0
CONECT    1   16                                                            
CONECT    2    6    8   11                                                  
CONECT    3    9   10                                                       
CONECT    4    5    8                                                       
CONECT    5    4   11                                                       
CONECT    6    2    7   12                                                  
CONECT    7    6    9   13                                                  
CONECT    8    2    4   10                                                  
CONECT    9    3    7   14                                                  
CONECT   10    3    8                                                       
CONECT   11    2    5   17                                                  
CONECT   12    6   15                                                       
CONECT   13    7   16                                                       
CONECT   14    9   18   19                                                  
CONECT   15   12   16                                                       
CONECT   16    1   13   15                                                  
CONECT   17   11                                                            
CONECT   18   14   20                                                       
CONECT   19   14   21                                                       
CONECT   20   18   22                                                       
CONECT   21   19   22                                                       
CONECT   22   20   21                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0014548
HETATM    1  C1  UNL     1       4.054  -0.321  -1.017  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.320   0.891  -0.633  1.00  0.00           C  
HETATM    3  N1  UNL     1       3.614   2.198  -0.928  1.00  0.00           N  
HETATM    4  N2  UNL     1       2.641   3.000  -0.446  1.00  0.00           N  
HETATM    5  C3  UNL     1       1.735   2.265   0.146  1.00  0.00           C  
HETATM    6  N3  UNL     1       2.176   0.973   0.021  1.00  0.00           N  
HETATM    7  C4  UNL     1       1.506  -0.185   0.557  1.00  0.00           C  
HETATM    8  C5  UNL     1       2.381  -1.114   1.033  1.00  0.00           C  
HETATM    9  C6  UNL     1       1.780  -2.231   1.630  1.00  0.00           C  
HETATM   10  C7  UNL     1       0.389  -2.348   1.718  1.00  0.00           C  
HETATM   11 CL1  UNL     1      -0.372  -3.751   2.463  1.00  0.00          CL  
HETATM   12  C8  UNL     1      -0.455  -1.382   1.227  1.00  0.00           C  
HETATM   13  C9  UNL     1       0.110  -0.288   0.635  1.00  0.00           C  
HETATM   14  C10 UNL     1      -0.864   0.672   0.154  1.00  0.00           C  
HETATM   15  C11 UNL     1      -2.097   0.171  -0.407  1.00  0.00           C  
HETATM   16  C12 UNL     1      -2.433  -1.095  -0.716  1.00  0.00           C  
HETATM   17  C13 UNL     1      -3.681  -1.433  -1.158  1.00  0.00           C  
HETATM   18  C14 UNL     1      -4.675  -0.496  -1.318  1.00  0.00           C  
HETATM   19  C15 UNL     1      -4.381   0.831  -1.015  1.00  0.00           C  
HETATM   20  C16 UNL     1      -3.125   1.127  -0.576  1.00  0.00           C  
HETATM   21  N4  UNL     1      -0.668   1.965   0.235  1.00  0.00           N  
HETATM   22  C17 UNL     1       0.486   2.713   0.773  1.00  0.00           C  
HETATM   23  H1  UNL     1       5.025  -0.486  -0.557  1.00  0.00           H  
HETATM   24  H2  UNL     1       3.434  -1.221  -1.218  1.00  0.00           H  
HETATM   25  H3  UNL     1       4.373  -0.089  -2.101  1.00  0.00           H  
HETATM   26  H4  UNL     1       3.425  -0.959   1.004  1.00  0.00           H  
HETATM   27  H5  UNL     1       2.411  -2.992   2.017  1.00  0.00           H  
HETATM   28  H6  UNL     1      -1.540  -1.416   1.344  1.00  0.00           H  
HETATM   29  H7  UNL     1      -1.706  -1.888  -0.691  1.00  0.00           H  
HETATM   30  H8  UNL     1      -3.945  -2.472  -1.405  1.00  0.00           H  
HETATM   31  H9  UNL     1      -5.670  -0.709  -1.661  1.00  0.00           H  
HETATM   32  H10 UNL     1      -5.149   1.596  -1.134  1.00  0.00           H  
HETATM   33  H11 UNL     1      -2.925   2.185  -0.346  1.00  0.00           H  
HETATM   34  H12 UNL     1       0.550   2.528   1.862  1.00  0.00           H  
HETATM   35  H13 UNL     1       0.276   3.759   0.512  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    3    6
CONECT    3    4
CONECT    4    5    5
CONECT    5    6   22
CONECT    6    7
CONECT    7    8    8   13
CONECT    8    9   26
CONECT    9   10   10   27
CONECT   10   11   12
CONECT   12   13   13   28
CONECT   13   14
CONECT   14   15   21   21
CONECT   15   16   16   20
CONECT   16   17   29
CONECT   17   18   18   30
CONECT   18   19   31
CONECT   19   20   20   32
CONECT   20   33
CONECT   21   22
CONECT   22   34   35
END

HMDB0014548
     RDKit          3D
Alprazolam
 35 38  0  0  0  0  0  0  0  0999 V2000
    4.0542   -0.3207   -1.0173 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3196    0.8914   -0.6330 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6141    2.1985   -0.9284 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6407    2.9998   -0.4462 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7354    2.2647    0.1456 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1761    0.9735    0.0206 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5065   -0.1846    0.5568 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3805   -1.1137    1.0333 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7801   -2.2307    1.6300 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3894   -2.3480    1.7179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3721   -3.7515    2.4626 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.4547   -1.3825    1.2267 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105   -0.2884    0.6348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8642    0.6723    0.1543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0968    0.1705   -0.4072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4335   -1.0950   -0.7164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6808   -1.4329   -1.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6755   -0.4964   -1.3180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3806    0.8306   -1.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1253    1.1271   -0.5765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6683    1.9655    0.2350 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4856    2.7134    0.7729 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0251   -0.4860   -0.5570 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4335   -1.2206   -1.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3728   -0.0893   -2.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4253   -0.9591    1.0035 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4114   -2.9915    2.0167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5396   -1.4162    1.3444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7060   -1.8877   -0.6909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9447   -2.4721   -1.4051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6696   -0.7089   -1.6607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1491    1.5964   -1.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9255    2.1852   -0.3462 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5498    2.5280    1.8622 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2757    3.7592    0.5120 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 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
 14 21  2  0
 21 22  1  0
  6  2  1  0
 13  7  1  0
 20 15  1  0
 22  5  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  8 26  1  0
  9 27  1  0
 12 28  1  0
 16 29  1  0
 17 30  1  0
 18 31  1  0
 19 32  1  0
 20 33  1  0
 22 34  1  0
 22 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
8-Chloro-1-methyl-6-phenyl-4H-S-triazolo(4,3-a)(1,4)benzodiazepine	ChEBI
Xanax	ChEBI
TUS-1	HMDB
Alphapharm brand OF alprazolam	HMDB
Alprazolam orion brand	HMDB
Alprazolam pfizer brand	HMDB
Apotex brand OF alprazolam	HMDB
Kalma	HMDB
Kenral brand OF alprazolam	HMDB
Nu alpraz	HMDB
Pfizer brand OF alprazolam	HMDB
Temmler brand OF alprazolam	HMDB
Trankimazin	HMDB
Alprazolam kenral brand	HMDB
Alprazolam novopharm brand	HMDB
Alprazolam nu-pharm brand	HMDB
Apo alpraz	HMDB
Apo-alpraz	HMDB
Arzneimittelwerk dresden brand OF alprazolam	HMDB
Cassadan	HMDB
NuAlpraz	HMDB
Alprazolam alphapharm brand	HMDB
ApoAlpraz	HMDB
Novo alprazol	HMDB
Novo-alprazol	HMDB
NovoAlprazol	HMDB
Nu pharm brand OF alprazolam	HMDB
Nu-pharm brand OF alprazolam	HMDB
Alprazolam apotex brand	HMDB
Alprazolam temmler brand	HMDB
Alprazolan	HMDB
Alprox	HMDB
D-65MT	HMDB
D65MT	HMDB
Esparon	HMDB
Novopharm brand OF alprazolam	HMDB
Nu-alpraz	HMDB
Orion brand OF alprazolam	HMDB
Ralozam	HMDB
Tafil	HMDB

Chemical Formula

C₁₇H₁₃ClN₄

Average Molecular Weight

308.765

Monoisotopic Molecular Weight

308.082874143

IUPAC Name

12-chloro-3-methyl-9-phenyl-2,4,5,8-tetraazatricyclo[8.4.0.0²,⁶]tetradeca-1(10),3,5,8,11,13-hexaene

Traditional Name

neurol

CAS Registry Number

28981-97-7

SMILES

CC1=NN=C2CN=C(C3=CC=CC=C3)C3=C(C=CC(Cl)=C3)N12

InChI Identifier

InChI=1S/C17H13ClN4/c1-11-20-21-16-10-19-17(12-5-3-2-4-6-12)14-9-13(18)7-8-15(14)22(11)16/h2-9H,10H2,1H3

InChI Key

VREFGVBLTWBCJP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1,2,4-triazolo[4,3-a][1,4]benzodiazepines. These are aromatic compounds containing a 1,4-benzodiazepine fused to and sharing a nitrogen atom with a 1,2,4-triazole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodiazepines

Sub Class

1,4-benzodiazepines

Direct Parent

1,2,4-triazolo[4,3-a][1,4]benzodiazepines

Alternative Parents

Substituents

1,2,4-triazolo[4,3-a][1,4]benzodiazepine
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Azole
1,2,4-triazole
Heteroaromatic compound
Ketimine
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Azacycle
Organopnictogen compound
Organic nitrogen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Imine
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organochlorine compound (CHEBI:2611 )
triazolobenzodiazepine (CHEBI:2611 )

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

Cytoplasm (HMDB: HMDB0014548)
Membrane (HMDB: HMDB0014548)

Source

Exogenous

Exogenous (HMDB: HMDB0014548)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Anxiolytic drug (HMDB: HMDB0014548)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	228 - 228.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.032 g/L	Not Available
LogP	4.9	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	171.5	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.032 g/L	ALOGPS
logP	2.23	ALOGPS
logP	2.37	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	18.3	ChemAxon
pKa (Strongest Basic)	5.08	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.07 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	98.88 m³·mol⁻¹	ChemAxon
Polarizability	32.22 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	201.179	30932474
DeepCCS	[M+Na]+	176.406	30932474
AllCCS	[M+H]+	170.0	32859911
AllCCS	[M+H-H2O]+	166.4	32859911
AllCCS	[M+NH4]+	173.3	32859911
AllCCS	[M+Na]+	174.3	32859911
AllCCS	[M-H]-	173.1	32859911
AllCCS	[M+Na-2H]-	172.1	32859911
AllCCS	[M+HCOO]-	171.2	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.	5.93 minutes	32390414
Predicted by Siyang on May 30, 2022	11.7852 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.31 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	45.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1648.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	313.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	156.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	187.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	143.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	416.9 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	410.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	146.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1013.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	386.9 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	1148.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	306.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	332.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	277.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	145.9 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	55.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Alprazolam	CC1=NN=C2CN=C(C3=CC=CC=C3)C3=C(C=CC(Cl)=C3)N12	3929.3	Standard polar	33892256
Alprazolam	CC1=NN=C2CN=C(C3=CC=CC=C3)C3=C(C=CC(Cl)=C3)N12	2901.8	Standard non polar	33892256
Alprazolam	CC1=NN=C2CN=C(C3=CC=CC=C3)C3=C(C=CC(Cl)=C3)N12	2864.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Alprazolam GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-4090000000-d08d3360d39ebeeb87f8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Alprazolam GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0kdi-4792000000-9f1cdda14e36000955d3	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 - Alprazolam LC-ESI-qTof , Positive-QTOF	splash10-0a4i-0910000000-9efa6a8a3dea17fc1ce7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Alprazolam LC-ESI-QTOF , positive-QTOF	splash10-0a59-0079000000-e4c35fb4df41aa5cc62e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Alprazolam , positive-QTOF	splash10-0bt9-0169000000-0e6779728f3bdec2acf1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Alprazolam , positive-QTOF	splash10-0a4i-0910000000-9efa6a8a3dea17fc1ce7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Alprazolam -1V, Positive-QTOF	splash10-0a59-0069000000-a0ce5531f8b2cb70eb28	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Alprazolam 35V, Positive-QTOF	splash10-0a59-0097000000-5b89356bc4e59b202968	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alprazolam 10V, Positive-QTOF	splash10-0a4i-0009000000-be2bb3a7878fa113efc8	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alprazolam 20V, Positive-QTOF	splash10-0a4i-0039000000-7bd62157388fecd0e430	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alprazolam 40V, Positive-QTOF	splash10-0o93-3390000000-307fd2f8dd5a9c4f7eac	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alprazolam 10V, Negative-QTOF	splash10-0a4i-0029000000-ceec7f24f309605ec6fb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alprazolam 20V, Negative-QTOF	splash10-0a4i-0097000000-d61397bd13173381fc0d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alprazolam 40V, Negative-QTOF	splash10-0udi-3290000000-370bd9e4b8fa73925c04	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alprazolam 10V, Negative-QTOF	splash10-0a4i-0009000000-4c14e6d547df7e93b204	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alprazolam 20V, Negative-QTOF	splash10-0a4i-0019000000-4e5c057a93f515a3aad6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alprazolam 40V, Negative-QTOF	splash10-001i-9021000000-63a97e91d4073b1a51cb	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alprazolam 10V, Positive-QTOF	splash10-0a4i-0009000000-f3356a9af159cd5dbe12	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alprazolam 20V, Positive-QTOF	splash10-0a4i-0009000000-f3356a9af159cd5dbe12	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alprazolam 40V, Positive-QTOF	splash10-004i-1090000000-a69b3052aba45b714693	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00404	21059682	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00404	21059682	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	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

DB00404

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2034

KEGG Compound ID

C06817

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Alprazolam

METLIN ID

Not Available

PubChem Compound

2118

PDB ID

Not Available

ChEBI ID

2611

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

Wolf B, Griffiths RR: Physical dependence on benzodiazepines: differences within the class. Drug Alcohol Depend. 1991 Dec 31;29(2):153-6. [PubMed:1686752 ]
Haque W, Watson DJ, Bryant SG: Death following suspected alprazolam withdrawal seizures: a case report. Tex Med. 1990 Jan;86(1):44-7. [PubMed:2300914 ]
Risse SC, Whitters A, Burke J, Chen S, Scurfield RM, Raskind MA: Severe withdrawal symptoms after discontinuation of alprazolam in eight patients with combat-induced posttraumatic stress disorder. J Clin Psychiatry. 1990 May;51(5):206-9. [PubMed:2335496 ]
Hori A: Pharmacotherapy for personality disorders. Psychiatry Clin Neurosci. 1998 Feb;52(1):13-9. [PubMed:9682928 ]
Garcia-Algar O, Lopez-Vilchez MA, Martin I, Mur A, Pellegrini M, Pacifici R, Rossi S, Pichini S: Confirmation of gestational exposure to alprazolam by analysis of biological matrices in a newborn with neonatal sepsis. Clin Toxicol (Phila). 2007;45(3):295-8. [PubMed:17453885 ]

Showing metabocard for Alprazolam (HMDB0014548)

MOL for HMDB0014548 (Alprazolam)

3D MOL for HMDB0014548 (Alprazolam)

3D SDF for HMDB0014548 (Alprazolam)

3D-SDF for HMDB0014548 (Alprazolam)

PDB for HMDB0014548 (Alprazolam)

3D PDB for HMDB0014548 (Alprazolam)

SMILES for HMDB0014548 (Alprazolam)

INCHI for HMDB0014548 (Alprazolam)

Structure for HMDB0014548 (Alprazolam)

3D Structure for HMDB0014548 (Alprazolam)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra