NP-MRD: Showing NP-Card for N-Demethyldiazepam (NP0047059)

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Record Information

Version

2.0

Created at

2022-03-17 20:33:56 UTC

Updated at

2022-03-17 20:33:56 UTC

NP-MRD ID

NP0047059

Secondary Accession Numbers

None

Natural Product Identification

Common Name

N-Demethyldiazepam

Description

Nordiazepam, also known as desmethyldiazepam or dealkylprazepam, 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. It is contraindicated in patients who are on long-term benzodiazepines, those who have ingested a substance that lowers the seizure threshold, or in patients who have tachycardia or a history of seizures. Nordiazepam is a moderately basic compound (based on its pKa). Outside of the human body, Nordiazepam has been detected, but not quantified in, a few different foods, such as common wheats, corns, and potato. This could make nordiazepam a potential biomarker for the consumption of these foods. 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. Nordiazepam is a potentially toxic compound. As benzodiazepine receptors are thought to be coupled to gamma-aminobutyric acid-A (GABAA) receptors, this enhances the effects of GABA by increasing GABA affinity for the GABA receptor. Benzodiazepines bind nonspecifically to benzodiazepine receptors BNZ1, which mediates sleep, and BNZ2, which affects affects muscle relaxation, anticonvulsant activity, motor coordination, and memory. As a general rule, medical observation and supportive care are the mainstay of treatment of benzodiazepine overdose. It is recommended only if benzodiazepines have been taken in combination with other drugs that may benefit from decontamination. In particular, flumazenil is very effective at reversing the CNS depression associated with benzodiazepines but is less effective at reversing respiratory depression. Dialysis is of limited value. Flumazenil (Anexate) is a competitive benzodiazepine receptor antagonist that can be used as an antidote for benzodiazepine overdose. N-Demethyldiazepam is found in Apis cerana, Glycine max, Homo sapiens and Lens culinaris. N-Demethyldiazepam was first documented in 1977 (PMID: 16622). General supportive measures should be employed, along with intravenous fluids, and an adequate airway maintained (PMID: 19604) (PMID: 360230) (PMID: 367407).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241221402D          

 19 21  0  0  0  0            999 V2000
   -1.5519   -1.6408    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.8374   -1.2283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1230   -1.6408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5915   -1.2283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5915   -0.4033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2365    0.1111    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0408   -0.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5552    0.5725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3988   -0.8158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0408   -1.5591    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2365   -1.7427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0529   -2.5470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6577   -3.1081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4741   -3.9124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6858   -4.1556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0810   -3.5945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2646   -2.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1230    0.0092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8374   -0.4033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
  5 18  2  0  0  0  0
 18 19  1  0  0  0  0
  2 19  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0047059

> <DATABASE_NAME>
NP-MRD

> <SMILES>
ClC1=CC=C2NC(=O)CN=C(C3=CC=CC=C3)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H11ClN2O/c16-11-6-7-13-12(8-11)15(17-9-14(19)18-13)10-4-2-1-3-5-10/h1-8H,9H2,(H,18,19)

> <INCHI_KEY>
AKPLHCDWDRPJGD-UHFFFAOYSA-N

> <FORMULA>
C15H11ClN2O

> <MOLECULAR_WEIGHT>
270.714

> <EXACT_MASS>
270.055990691

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
27.408062774131473

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-chloro-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one

> <ALOGPS_LOGP>
2.79

> <JCHEM_LOGP>
3.2120204986666656

> <ALOGPS_LOGS>
-4.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.299820888817013

> <JCHEM_PKA_STRONGEST_BASIC>
2.8480504744474846

> <JCHEM_POLAR_SURFACE_AREA>
41.46

> <JCHEM_REFRACTIVITY>
76.69600000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.19e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nordiazepam

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1 Cl   UNK     0      -2.897  -3.063   0.000  0.00  0.00          Cl+0
HETATM    2  C   UNK     0      -1.563  -2.293   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.230  -3.063   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.104  -2.293   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.104  -0.753   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       2.308   0.207   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       3.809  -0.135   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.770   1.069   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.478  -1.523   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       3.809  -2.910   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       2.308  -3.253   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.965  -4.754   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.094  -5.802   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.752  -7.303   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.280  -7.757   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.151  -6.710   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.494  -5.208   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.230   0.017   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.563  -0.753   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6   18                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    4   12                                                  
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18    5   19                                                       
CONECT   19   18    2                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Value	Source
1-Demethyldiazepam	ChEBI
7-Chloro-1,3-dihydro-5-phenyl-(2H)-1,4-benzodiazepin-2-one	ChEBI
7-Chloro-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one	ChEBI
7-Chloro-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one	ChEBI
Chlordesmethyldiazepam	ChEBI
Dealkylprazepam	ChEBI
Desmethyldiazepam	ChEBI
N-Demethyldiazepam	ChEBI
N-Deoxydemoxepam	ChEBI
N-Desmethyldiazepam	ChEBI
N1-Desmethyldiazepam	ChEBI
Nordazepamum	ChEBI
Norprazepam	ChEBI
Calmday	Kegg
Nordiazepam	ChEBI
N-Descyclopropylmethylprazepam	MeSH
Tranxilium N	MeSH
Vegesan	MeSH
N Descyclopropylmethyl prazepam	MeSH
N Desalkylhalazepam	MeSH
N Destrifluoroethylhalazepam	MeSH
N Descyclopropylmethylprazepam	MeSH
Nordaz	MeSH
Nordazepam	MeSH
Demethyldiazepam	MeSH
N-Descyclopropylmethyl-prazepam	MeSH
N-Destrifluoroethylhalazepam	MeSH
Deoxydemoxepam	MeSH
N-Desalkylhalazepam	MeSH

Chemical Formula

C₁₅H₁₁ClN₂O

Average Mass

270.7140 Da

Monoisotopic Mass

270.05599 Da

IUPAC Name

7-chloro-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one

Traditional Name

nordiazepam

CAS Registry Number

1088-11-5

SMILES

ClC1=CC=C2NC(=O)CN=C(C3=CC=CC=C3)C2=C1

InChI Identifier

InChI=1S/C15H11ClN2O/c16-11-6-7-13-12(8-11)15(17-9-14(19)18-13)10-4-2-1-3-5-10/h1-8H,9H2,(H,18,19)

InChI Key

AKPLHCDWDRPJGD-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Apis cerana	LOTUS Database	35616633
Glycine max	LOTUS Database	35616633
Homo sapiens	LOTUS Database	35616633
Lens culinaris	LOTUS Database	35616633
Solanum tuberosum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Triticum aestivum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Zea mays L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

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
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Cyclic carboximidic acid
Ketimine
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Azacycle
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Imine
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organochlorine compound (CHEBI:111762 )
1,4-benzodiazepinone (CHEBI:111762 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.79	ALOGPS
logP	3.21	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	12.3	ChemAxon
pKa (Strongest Basic)	2.85	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	41.46 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	76.7 m³·mol⁻¹	ChemAxon
Polarizability	27.41 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0060538

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB007124

KNApSAcK ID

Not Available

Chemspider ID

2890

KEGG Compound ID

C07486

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Desmethyldiazepam

METLIN ID

Not Available

PubChem Compound

2997

PDB ID

Not Available

ChEBI ID

111762

Good Scents ID

Not Available

References

General References

Andreoli V, Maffei F, Montanaro N, Morandini G: Double-blind cross-over clinical comparison of two 2'-chloro benzodiazepines: 7-chloro-5-(2-chlorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one (chlordesmethyldiazepam) versus 7-chloro-5-(o-chlorophenyl)-1,3-dihydro-3-hydroxy-2H-1,4-benzodiazepin-2-one (lorazepam) in neurotic anxiety. Arzneimittelforschung. 1977 Feb;27(2):436-9. [PubMed:16622 ]
Traversa U, de Angelis L, Vertua R: On the hypnogenic and anticonvulsant activities of demethyldiazepam and chlordemethyldiazepam: time-effect relations. J Pharm Pharmacol. 1977 Aug;29(8):504-6. doi: 10.1111/j.2042-7158.1977.tb11380.x. [PubMed:19604 ]
Babbini M, Gaiardi M, Bartoletti M: Influence of the 2'-chloro substitution on central activity of desmethyldiazepam. Pharmacology. 1978;17(3):121-7. doi: 10.1159/000136845. [PubMed:360230 ]
Klotz U, Muller-Seydlitz P: Altered elimination of desmethyldiazepam in the elderly. Br J Clin Pharmacol. 1979 Jan;7(1):119-20. doi: 10.1111/j.1365-2125.1979.tb00908.x. [PubMed:367407 ]

Showing NP-Card for N-Demethyldiazepam (NP0047059)

MOL for NP0047059 (N-Demethyldiazepam)

3D MOL for NP0047059 (N-Demethyldiazepam)

3D SDF for NP0047059 (N-Demethyldiazepam)

3D-SDF for NP0047059 (N-Demethyldiazepam)

PDB for NP0047059 (N-Demethyldiazepam)

3D PDB for NP0047059 (N-Demethyldiazepam)

SMILES for NP0047059 (N-Demethyldiazepam)

INCHI for NP0047059 (N-Demethyldiazepam)

Structure for NP0047059 (N-Demethyldiazepam)

3D Structure for NP0047059 (N-Demethyldiazepam)