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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-13 11:54:55 UTC

Update Date

2022-03-07 02:57:15 UTC

HMDB ID

HMDB0042029

Secondary Accession Numbers

HMDB42029

Metabolite Identification

Common Name

Tetrazepam

Description

Allergic reactions can develop to tetrazepam and it is considered to be a potential allergen. Drug rash and drug-induced eosinophilia with systemic symptoms is a known complication of tetrazepam exposure. These hypersensitive allergic reactions can be of the delayed type. Drowsiness is a common side effect of tetrazepam. A reduction in muscle force can occur. Myasthenia gravis, a condition characterised by severe muscle weakness is another potential adverse effect from tetrazepam. Cardiovascular and respiratory adverse effects can occur with tetrazepam similar to other benzodiazepines. Prolonged use, as with all benzodiazepines, should be avoided, as tolerance occurs and there is a risk of benzodiazepine dependence and a benzodiazepine withdrawal syndrome after stopping or reducing dosage. Tetrazepam (is marketed under the following brand names, Clinoxan, Epsipam, Myolastan, Musaril, Relaxam and Spasmorelax) is a benzodiazepine derivative with anticonvulsant, anxiolytic, hypnotic and muscle relaxant properties. It is used mainly in Austria, France, Belgium, Germany and Spain to treat muscle spasm, anxiety disorders such as panic attacks, or more rarely to treat depression, premenstrual syndrome or agoraphobia. Tetrazepam has relatively little sedative effect at low doses while still producing useful muscle relaxation and anxiety relief. Tetrazepam is an unusual benzodiazepine in its molecular structure as it has cyclohexenyl group which has substituted the typical 5-phenyl moiety seen in other benzodiazepines. Tetrazepam, is rapidly absorbed after oral administration, within 45 mins and reaches peak plasma levels in less than 2 hours. It is classed as an intermediate acting benzodiazepine with an elimination half-life of approximately 15 hours. It is primarily metabolised to the inactive metabolites 3-hydroxy-tetrazepam and norhydroxytetrazepam. The pharmacological effects of tetrazepam are significantly less potent when compared against diazepam, in animal studies. Tetrazepam is a benzodiazepine site agonist and binds unselectively to type 1 and type 2 benzodiazepine site types as well as to peripheral benzodiazepine receptors. The muscle relaxant properties of tetrazepam are most likely due to a reduction of calcium influx. Small amounts of diazepam as well as the active metabolites of diazepam are produced from metabolism of tetrazepam. The metabolism of tetrazepam has led to false accusations of prisoners prescribed tetrazepam of taking illicit diazepam; this can lead to increased prison sentences for prisoners. Tetrazepam, like other benzodiazepines is a drug which is very frequently used in overdoses. These overdoses are often mixed overdoses, i.e. a mixture of other benzodiazepines or other drug classes with tetrazepam.

Structure

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

HMDB0042029
     RDKit          3D
Tetrazepam
 37 39  0  0  0  0  0  0  0  0999 V2000
   -3.9528    1.6676    0.4118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8637    1.0763   -0.2848 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4700    1.5541   -1.5905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0222    2.6314   -1.9122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5094    0.9223   -2.5627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2303    0.7098   -1.9153 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0815    0.1560   -0.7444 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4725    0.0986   -0.3735 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4212    0.4603   -1.2866 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8659    0.4441   -1.0333 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2706   -0.1345    0.2597 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2047   -1.0357    0.8234 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9588   -0.1519    0.9874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9084   -0.4567    0.0912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4357   -1.5899    0.7002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2620   -2.2702    1.5812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7011   -3.7168    2.3960 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.5613   -1.8182    1.8492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0165   -0.6849    1.2249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1933   -0.0284    0.3626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0588    2.7146    0.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7897    1.7415    1.5123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9282    1.1802    0.1761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3323    1.6559   -3.3737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9326    0.0157   -3.0250 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0032    0.7700   -2.2447 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1792    1.5377   -1.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4378    0.0211   -1.9054 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2571   -0.6652    0.1976 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4732    0.6809    1.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9380   -1.7687    0.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4909   -1.4965    1.7745 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4485    0.8552    1.3433 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3111   -0.4724    1.7652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5381   -1.9507    0.4393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1968   -2.3599    2.5421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9871   -0.2926    1.3872 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
  7 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 20  2  1  0
 13  8  1  0
 20 14  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  5 24  1  0
  5 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 15 35  1  0
 18 36  1  0
 19 37  1  0
M  END

  Mrv0541 09131211542D          

 20 22  0  0  0  0            999 V2000
    3.4479    2.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0808   -2.2457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8691   -2.0025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4760   -1.6845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0527   -1.1982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6596   -0.8802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5575    1.5066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2720    1.9191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2720    0.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7938    1.0941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4479   -0.6370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5575    0.6816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9865    0.6816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9865    1.5066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4358    1.8374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6315    0.1673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8431    0.2691    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.4358    0.3508    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6315    2.0210    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9502    2.4825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  8  7  2  0  0  0  0
 11  5  2  0  0  0  0
 11  6  1  0  0  0  0
 12  7  1  0  0  0  0
 12  9  2  0  0  0  0
 13  9  1  0  0  0  0
 14  8  1  0  0  0  0
 14 13  2  0  0  0  0
 15 10  1  0  0  0  0
 16 11  1  0  0  0  0
 16 13  1  0  0  0  0
 17 12  1  0  0  0  0
 18 10  1  0  0  0  0
 18 16  2  0  0  0  0
 19  1  1  0  0  0  0
 19 14  1  0  0  0  0
 19 15  1  0  0  0  0
 20 15  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0042029

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C2=C(C=C(Cl)C=C2)C(=NCC1=O)C1=CCCCC1

> <INCHI_IDENTIFIER>
InChI=1S/C16H17ClN2O/c1-19-14-8-7-12(17)9-13(14)16(18-10-15(19)20)11-5-3-2-4-6-11/h5,7-9H,2-4,6,10H2,1H3

> <INCHI_KEY>
IQWYAQCHYZHJOS-UHFFFAOYSA-N

> <FORMULA>
C16H17ClN2O

> <MOLECULAR_WEIGHT>
288.772

> <EXACT_MASS>
288.102940883

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
30.778432769769793

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-chloro-5-(cyclohex-1-en-1-yl)-1-methyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one

> <ALOGPS_LOGP>
3.53

> <JCHEM_LOGP>
3.138270967000001

> <ALOGPS_LOGS>
-3.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
3.241219004676963

> <JCHEM_POLAR_SURFACE_AREA>
32.67

> <JCHEM_REFRACTIVITY>
81.7173

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.23e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tetrazepam

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0042029
     RDKit          3D
Tetrazepam
 37 39  0  0  0  0  0  0  0  0999 V2000
   -3.9528    1.6676    0.4118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8637    1.0763   -0.2848 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4700    1.5541   -1.5905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0222    2.6314   -1.9122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5094    0.9223   -2.5627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2303    0.7098   -1.9153 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0815    0.1560   -0.7444 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4725    0.0986   -0.3735 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4212    0.4603   -1.2866 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8659    0.4441   -1.0333 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2706   -0.1345    0.2597 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2047   -1.0357    0.8234 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9588   -0.1519    0.9874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9084   -0.4567    0.0912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4357   -1.5899    0.7002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2620   -2.2702    1.5812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7011   -3.7168    2.3960 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.5613   -1.8182    1.8492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0165   -0.6849    1.2249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1933   -0.0284    0.3626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0588    2.7146    0.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7897    1.7415    1.5123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9282    1.1802    0.1761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3323    1.6559   -3.3737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9326    0.0157   -3.0250 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0032    0.7700   -2.2447 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1792    1.5377   -1.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4378    0.0211   -1.9054 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2571   -0.6652    0.1976 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4732    0.6809    1.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9380   -1.7687    0.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4909   -1.4965    1.7745 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4485    0.8552    1.3433 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3111   -0.4724    1.7652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5381   -1.9507    0.4393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1968   -2.3599    2.5421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9871   -0.2926    1.3872 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
  7 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 20  2  1  0
 13  8  1  0
 20 14  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  5 24  1  0
  5 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 15 35  1  0
 18 36  1  0
 19 37  1  0
M  END

HEADER    PROTEIN                                 13-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-SEP-12         0                                  
HETATM    1  C   UNK     0       6.436   5.274   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.751  -4.192   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.222  -3.738   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.622  -3.144   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.565  -2.237   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.965  -1.643   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.907   2.812   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.241   3.582   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.241   0.502   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.948   2.042   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.436  -1.189   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.907   1.272   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.575   1.272   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.575   2.812   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.280   3.430   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.779   0.312   0.000  0.00  0.00           C+0
HETATM   17 Cl   UNK     0       1.574   0.502   0.000  0.00  0.00          Cl+0
HETATM   18  N   UNK     0       8.280   0.655   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0       6.779   3.773   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0       9.240   4.634   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3   11                                                       
CONECT    6    4   11                                                       
CONECT    7    8   12                                                       
CONECT    8    7   14                                                       
CONECT    9   12   13                                                       
CONECT   10   15   18                                                       
CONECT   11    5    6   16                                                  
CONECT   12    7    9   17                                                  
CONECT   13    9   14   16                                                  
CONECT   14    8   13   19                                                  
CONECT   15   10   19   20                                                  
CONECT   16   11   13   18                                                  
CONECT   17   12                                                            
CONECT   18   10   16                                                       
CONECT   19    1   14   15                                                  
CONECT   20   15                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0042029
HETATM    1  C1  UNL     1      -3.953   1.668   0.412  1.00  0.00           C  
HETATM    2  N1  UNL     1      -2.864   1.076  -0.285  1.00  0.00           N  
HETATM    3  C2  UNL     1      -2.470   1.554  -1.590  1.00  0.00           C  
HETATM    4  O1  UNL     1      -3.022   2.631  -1.912  1.00  0.00           O  
HETATM    5  C3  UNL     1      -1.509   0.922  -2.563  1.00  0.00           C  
HETATM    6  N2  UNL     1      -0.230   0.710  -1.915  1.00  0.00           N  
HETATM    7  C4  UNL     1       0.082   0.156  -0.744  1.00  0.00           C  
HETATM    8  C5  UNL     1       1.473   0.099  -0.374  1.00  0.00           C  
HETATM    9  C6  UNL     1       2.421   0.460  -1.287  1.00  0.00           C  
HETATM   10  C7  UNL     1       3.866   0.444  -1.033  1.00  0.00           C  
HETATM   11  C8  UNL     1       4.271  -0.134   0.260  1.00  0.00           C  
HETATM   12  C9  UNL     1       3.205  -1.036   0.823  1.00  0.00           C  
HETATM   13  C10 UNL     1       1.959  -0.152   0.987  1.00  0.00           C  
HETATM   14  C11 UNL     1      -0.908  -0.457   0.091  1.00  0.00           C  
HETATM   15  C12 UNL     1      -0.436  -1.590   0.700  1.00  0.00           C  
HETATM   16  C13 UNL     1      -1.262  -2.270   1.581  1.00  0.00           C  
HETATM   17 CL1  UNL     1      -0.701  -3.717   2.396  1.00  0.00          CL  
HETATM   18  C14 UNL     1      -2.561  -1.818   1.849  1.00  0.00           C  
HETATM   19  C15 UNL     1      -3.016  -0.685   1.225  1.00  0.00           C  
HETATM   20  C16 UNL     1      -2.193  -0.028   0.363  1.00  0.00           C  
HETATM   21  H1  UNL     1      -4.059   2.715   0.066  1.00  0.00           H  
HETATM   22  H2  UNL     1      -3.790   1.742   1.512  1.00  0.00           H  
HETATM   23  H3  UNL     1      -4.928   1.180   0.176  1.00  0.00           H  
HETATM   24  H4  UNL     1      -1.332   1.656  -3.374  1.00  0.00           H  
HETATM   25  H5  UNL     1      -1.933   0.016  -3.025  1.00  0.00           H  
HETATM   26  H6  UNL     1       2.003   0.770  -2.245  1.00  0.00           H  
HETATM   27  H7  UNL     1       4.179   1.538  -1.009  1.00  0.00           H  
HETATM   28  H8  UNL     1       4.438   0.021  -1.905  1.00  0.00           H  
HETATM   29  H9  UNL     1       5.257  -0.665   0.198  1.00  0.00           H  
HETATM   30  H10 UNL     1       4.473   0.681   1.024  1.00  0.00           H  
HETATM   31  H11 UNL     1       2.938  -1.769   0.036  1.00  0.00           H  
HETATM   32  H12 UNL     1       3.491  -1.497   1.774  1.00  0.00           H  
HETATM   33  H13 UNL     1       2.448   0.855   1.343  1.00  0.00           H  
HETATM   34  H14 UNL     1       1.311  -0.472   1.765  1.00  0.00           H  
HETATM   35  H15 UNL     1       0.538  -1.951   0.439  1.00  0.00           H  
HETATM   36  H16 UNL     1      -3.197  -2.360   2.542  1.00  0.00           H  
HETATM   37  H17 UNL     1      -3.987  -0.293   1.387  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   20
CONECT    3    4    4    5
CONECT    5    6   24   25
CONECT    6    7    7
CONECT    7    8   14
CONECT    8    9    9   13
CONECT    9   10   26
CONECT   10   11   27   28
CONECT   11   12   29   30
CONECT   12   13   31   32
CONECT   13   33   34
CONECT   14   15   15   20
CONECT   15   16   35
CONECT   16   17   18   18
CONECT   18   19   36
CONECT   19   20   20   37
END

HMDB0042029
     RDKit          3D
Tetrazepam
 37 39  0  0  0  0  0  0  0  0999 V2000
   -3.9528    1.6676    0.4118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8637    1.0763   -0.2848 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4700    1.5541   -1.5905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0222    2.6314   -1.9122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5094    0.9223   -2.5627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2303    0.7098   -1.9153 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0815    0.1560   -0.7444 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4725    0.0986   -0.3735 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4212    0.4603   -1.2866 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8659    0.4441   -1.0333 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2706   -0.1345    0.2597 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2047   -1.0357    0.8234 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9588   -0.1519    0.9874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9084   -0.4567    0.0912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4357   -1.5899    0.7002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2620   -2.2702    1.5812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7011   -3.7168    2.3960 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.5613   -1.8182    1.8492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0165   -0.6849    1.2249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1933   -0.0284    0.3626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0588    2.7146    0.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7897    1.7415    1.5123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9282    1.1802    0.1761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3323    1.6559   -3.3737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9326    0.0157   -3.0250 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0032    0.7700   -2.2447 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1792    1.5377   -1.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4378    0.0211   -1.9054 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2571   -0.6652    0.1976 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4732    0.6809    1.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9380   -1.7687    0.0359 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4909   -1.4965    1.7745 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4485    0.8552    1.3433 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3111   -0.4724    1.7652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5381   -1.9507    0.4393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1968   -2.3599    2.5421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9871   -0.2926    1.3872 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
  7 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 20  2  1  0
 13  8  1  0
 20 14  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  5 24  1  0
  5 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 15 35  1  0
 18 36  1  0
 19 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Myolastan	Kegg
Clinoxan	HMDB
Musaril	HMDB
Lichtenstein brand OF tetrazepam	HMDB
Mobiforton	HMDB
Musapam	HMDB
Tetramdura	HMDB
Tetrazep 1a pharma	HMDB
1a Brand OF tetrazepam	HMDB
AbZ brand OF tetrazepam	HMDB
Gry brand OF tetrazepam	HMDB
Krewel brand OF tetrazepam	HMDB
MTW-Tetrazepam	HMDB
Panos	HMDB
Tetra-saar	HMDB
MTW Brand OF tetrazepam	HMDB
Merck dura brand OF tetrazepam	HMDB
Sanofi synthelabo brand OF tetrazepam	HMDB
Tethexal	HMDB
Tetrarelax	HMDB
Tetrazep abz	HMDB
Mibe brand OF tetrazepam	HMDB
Fornet brand OF tetrazepam	HMDB
Hexal brand OF tetrazepam	HMDB
MIP brand OF tetrazepam	HMDB
Myospasmal	HMDB
Rilex	HMDB
TAD brand OF tetrazepam	HMDB
CT-Arzneimittel brand OF tetrazepam	HMDB
Tetrazep von CT	HMDB

Chemical Formula

C₁₆H₁₇ClN₂O

Average Molecular Weight

288.772

Monoisotopic Molecular Weight

288.102940883

IUPAC Name

7-chloro-5-(cyclohex-1-en-1-yl)-1-methyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one

Traditional Name

tetrazepam

CAS Registry Number

10379-14-3

SMILES

CN1C2=C(C=C(Cl)C=C2)C(=NCC1=O)C1=CCCCC1

InChI Identifier

InChI=1S/C16H17ClN2O/c1-19-14-8-7-12(17)9-13(14)16(18-10-15(19)20)11-5-3-2-4-6-11/h5,7-9H,2-4,6,10H2,1H3

InChI Key

IQWYAQCHYZHJOS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1,4-benzodiazepines. These are organic compounds containing a benzene ring fused to a 1,4-azepine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodiazepines

Sub Class

1,4-benzodiazepines

Direct Parent

1,4-benzodiazepines

Alternative Parents

Substituents

1,4-benzodiazepine
Alpha-amino acid or derivatives
Aryl chloride
Aryl halide
Benzenoid
Tertiary carboxylic acid amide
Carboxamide group
Ketimine
Lactam
Carboxylic acid derivative
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organochloride
Organohalogen compound
Hydrocarbon derivative
Imine
Organic nitrogen compound
Organic oxide
Carbonyl group
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0042029)

Source

Exogenous

Exogenous (HMDB: HMDB0042029)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	144 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	3.20	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.042 g/L	ALOGPS
logP	3.53	ALOGPS
logP	3.14	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Basic)	3.24	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	32.67 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	81.72 m³·mol⁻¹	ChemAxon
Polarizability	30.78 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
DeepCCS	[M+H]+	167.196	30932474
DeepCCS	[M-H]-	164.838	30932474
DeepCCS	[M-2H]-	198.243	30932474
DeepCCS	[M+Na]+	173.47	30932474
AllCCS	[M+H]+	165.5	32859911
AllCCS	[M+H-H2O]+	161.9	32859911
AllCCS	[M+NH4]+	168.9	32859911
AllCCS	[M+Na]+	169.9	32859911
AllCCS	[M-H]-	171.1	32859911
AllCCS	[M+Na-2H]-	171.0	32859911
AllCCS	[M+HCOO]-	170.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tetrazepam	CN1C2=C(C=C(Cl)C=C2)C(=NCC1=O)C1=CCCCC1	3824.8	Standard polar	33892256
Tetrazepam	CN1C2=C(C=C(Cl)C=C2)C(=NCC1=O)C1=CCCCC1	2436.8	Standard non polar	33892256
Tetrazepam	CN1C2=C(C=C(Cl)C=C2)C(=NCC1=O)C1=CCCCC1	2446.5	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 - Tetrazepam GC-MS (Non-derivatized) - 70eV, Positive	splash10-06z9-0190000000-e89bbe3f5be5dd2d8ef6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tetrazepam GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0udr-2690000000-03229b9979372af89a08	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 - Tetrazepam LC-ESI-QFT , positive-QTOF	splash10-000i-0090000000-648ea07cfb54da221938	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetrazepam LC-ESI-QFT , positive-QTOF	splash10-000i-0090000000-6fa6feb988c28cea9701	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetrazepam LC-ESI-QFT , positive-QTOF	splash10-000i-0190000000-133e43f99f45b667ff8d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetrazepam LC-ESI-QFT , positive-QTOF	splash10-0fc0-1690000000-9b2cabcfe30f022505fa	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetrazepam LC-ESI-QFT , positive-QTOF	splash10-005a-2940000000-160b387e0e158e114ad3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetrazepam LC-ESI-QFT , positive-QTOF	splash10-003s-1920000000-afce32e992dcf0ffa799	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetrazepam 15V, Positive-QTOF	splash10-000i-0090000000-648ea07cfb54da221938	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetrazepam 30V, Positive-QTOF	splash10-000i-0090000000-ed241329da9c26f2ad1e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetrazepam 60V, Positive-QTOF	splash10-0fc0-1690000000-44693634010667152d40	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetrazepam 45V, Positive-QTOF	splash10-000i-0090000000-78f3056f8d14c06bdee3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetrazepam 90V, Positive-QTOF	splash10-003s-1920000000-2eb3baa6cda1930497c8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetrazepam 75V, Positive-QTOF	splash10-005a-2940000000-2402a3bd2d4706d4b407	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrazepam 10V, Positive-QTOF	splash10-000i-0090000000-481bd9921daf23c25723	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrazepam 20V, Positive-QTOF	splash10-000i-1090000000-1da96f135036ef7911eb	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrazepam 40V, Positive-QTOF	splash10-0f6x-9330000000-4698b4ebfdf65cd11c90	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrazepam 10V, Negative-QTOF	splash10-000i-0090000000-13675d06f8c473dd2019	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrazepam 20V, Negative-QTOF	splash10-000i-0090000000-0b2235e8dd6ef6442946	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrazepam 40V, Negative-QTOF	splash10-0a4i-9430000000-ec79a12e3355732a7950	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrazepam 10V, Negative-QTOF	splash10-000i-0090000000-7183d771e959d0a76d02	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrazepam 20V, Negative-QTOF	splash10-000i-1090000000-fba0c8f7d5e70241e1ff	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrazepam 40V, Negative-QTOF	splash10-0019-5090000000-2a383ea900ba4439bcfb	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrazepam 10V, Positive-QTOF	splash10-000i-0090000000-28b936e03152b6596fcd	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrazepam 20V, Positive-QTOF	splash10-000i-0090000000-130637d1f671d168362f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrazepam 40V, Positive-QTOF	splash10-01wo-1190000000-a458f36dd23549f29d15	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

DB13324

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

23551

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tetrazepam

METLIN ID

Not Available

PubChem Compound

25215

PDB ID

Not Available

ChEBI ID

Not Available

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 Tetrazepam (HMDB0042029)

MOL for HMDB0042029 (Tetrazepam)

3D MOL for HMDB0042029 (Tetrazepam)

3D SDF for HMDB0042029 (Tetrazepam)

3D-SDF for HMDB0042029 (Tetrazepam)

PDB for HMDB0042029 (Tetrazepam)

3D PDB for HMDB0042029 (Tetrazepam)

SMILES for HMDB0042029 (Tetrazepam)

INCHI for HMDB0042029 (Tetrazepam)

Structure for HMDB0042029 (Tetrazepam)

3D Structure for HMDB0042029 (Tetrazepam)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra