Nordiazepam

HCID 2997CAS 1088-11-5

Basic information

Standard SMILES
O=C1CN=C(c2ccccc2)c2cc(Cl)ccc2N1
InChIKey
AKPLHCDWDRPJGD-UHFFFAOYSA-N
Molecular formula
C15H11ClN2O
Average molar mass
270.71 g/mol
Monoisotopic mass
270.05599065

Overview

Nordazepam is a 1,4-benzodiazepinone having phenyl and chloro substituents at positions 5 and 7 respectively; it has anticonvulsant, anxiolytic, muscle relaxant and sedative properties but is used primarily in the treatment of anxiety. It has a role as an anxiolytic drug, an anticonvulsant, a sedative, a GABA modulator and a human metabolite. It is a 1,4-benzodiazepinone and an organochlorine compound.

Names & identifiers

Preferred name
Nordiazepam
IUPAC
7-chloro-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one
English name
Nordazepam
Molecular formula
C15H11ClN2O
Molecular weight
270.71

Names & synonyms

NordazepamNordiazepamdesmethyldiazepamNorprazepam1088-11-5N-DesmethyldiazepamN-DemethyldiazepamN-DeoxydemoxepamMadar1-DemethyldiazepamN1-DesmethyldiazepamDemethyldiazepam
Show more names
NDZNDDDmdzA 101NordazCalmday
StilnyPraxadiumDemadarNordazepamumNordazepam CIV7-Chloro-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-oneN-Descyclopropylmethylprazepam7-chloro-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one

Database identifiers

CAS
1088-11-5
PubChem CID
2997
DTXSID
DTXSID2049000
ChEMBL
CHEMBL523
ChEBI
CHEBI:111762
UNII
67220MCM01
EC Number
214-123-4
Nikkaji
J7.250H

Properties

Computed structural properties

XLogP
2.9
Topological polar surface area
41.5 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
2
Rotatable bonds
1
Heavy atoms
19

Experimental & physicochemical properties

Chemical ClassesPharmaceutical
Drugs · 5 items

DEA NFLIS-Drug Category -> Benzodiazepines

DEA Schedule IV Controlled Substance -> Depressants

Pharmaceuticals -> Benzodiazepines

Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds

Pharmaceuticals -> Listed in ZINC15

Solubility>40.6 [ug/mL] (The mean of the results at pH 7.4)
Human DrugsPharmaceuticals
Collision Cross Section160.1 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]

Physicochemical properties

Melting point
208 · 208-210°C
Boiling point
453.1 · 453.1±45.0 °C(Predicted)
Density
1.2576 · 1.2576 (rough estimate)
refractive index
1.633 · 1.6330 (estimate)
Flash point
11 °C · 11 °C
storage temp.
2 · 2-8°C

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 8.3% (4 of 48) of reports.

Warning

H302 (89.6%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 48 reports by companies from 4 notifications to the ECHA C&L Inventory.

Hazard information

Regulatory Information · 3 items

DEA schedule IV controlled substance

Status: Active Update: 04-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/21623

2H-1,4-Benzodiazepin-2-one, 7-chloro-1,3-dihydro-5-phenyl-: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and CategoriesAcute Tox. 4 (89.6%)

Toxicology

Treatment · 1 item

General supportive measures should be employed, along with intravenous fluids, and an adequate airway maintained. Hypotension may be combated by the use of norepinephrine or metaraminol. Dialysis is of limited value. Flumazenil (Anexate) is a competitive benzodiazepine receptor antagonist that can be used as an antidote for benzodiazepine overdose. In particular, flumazenil is very effective at reversing the CNS depression associated with benzodiazepines but is less effective at reversing respiratory depression. Its use, however, is controversial as it has numerous contraindications. 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. As a general rule, medical observation and supportive care are the mainstay of treatment of benzodiazepine overdose. Although benzodiazepines are absorbed by activated charcoal, gastric decontamination with activated charcoal is not beneficial in pure benzodiazepine overdose as the risk of adverse effects often outweigh any potential benefit from the procedure. It is recommended only if benzodiazepines have been taken in combination with other drugs that may benefit from decontamination. Gastric lavage (stomach pumping) or whole bowel irrigation are also not recommended.

Toxicity Summary · 1 item

Benzodiazepines bind nonspecifically to benzodiazepine receptors BNZ1, which mediates sleep, and BNZ2, which affects affects muscle relaxation, anticonvulsant activity, motor coordination, and memory. 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. 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.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury · 4 items

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

Nordazepam

DILI Positive

DOI:10.1016/j.drudis.2019.09.022

USGS Health-Based Screening Levels for Evaluating Water-Quality · 3 items

Nordiazepam

Pharmaceutical

Smith, C.D. and Nowell, L.H., 2024. Health-Based Screening Levels for evaluating water-quality data (3rd ed.). DOI:10.5066/F71C1TWP

Safety data

wgk
3
rtecs
DF1750000
ridadr
3249
hs_code
2933910000
Toxicity
LD50 in mice (mg/kg): 2750 orally, >400 i.p. (Randall); LD50 in mice, rats (mg/kg): 1300, >5200 orally (company communication)
risk_code
22-39/23/24/25-23/24/25-11

Chemistry & industry

Pharmacology

ATC Code · 3 items

N05BA16

N - Nervous system

QN - Nervous system

Metabolism/MetabolitesNordiazepam has known human metabolites that include Oxazepam.
MeSH Pharmacological Classification · 2 items

Agents that alleviate ANXIETY, tension, and ANXIETY DISORDERS, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions. ADRENERGIC BETA-ANTAGONISTS are commonly used in the symptomatic treatment of anxiety but are not included here.

Substances that do not act as agonists or antagonists but do affect the GAMMA-AMINOBUTYRIC ACID receptor-ionophore complex. GABA-A receptors (RECEPTORS, GABA-A) appear to have at least three allosteric sites at which modulators act: a site at which BENZODIAZEPINES act by increasing the opening frequency of GAMMA-AMINOBUTYRIC ACID-activated chloride channels; a site at which BARBITURATES act to prolong the duration of channel opening; and a site at which some steroids may act. GENERAL ANESTHETICS probably act at least partly by potentiating GABAergic responses, but they are not included here.

Tissue LocationsKidney
Cellular LocationsCytoplasm

Uses & manufacturing

Use Classification · 2 items

Pharmaceuticals

Pharmaceuticals -> Transformation products

Applications

UsesThe primary metabolite of Diazepam. A ligand for the GABAA receptor benzodiazepine modulatory site. Anxiolytic. Controlled substance (depressant).

Upstream & downstream products

Additional notes

DefinitionChEBI: A 1,4-benzodiazepinone having phenyl and chloro substituents at positions 5 and 7 respectively; it has anticonvulsant, anxiolytic, muscle relaxant and sedative properties but is used primarily in the treatment of anxiety.

Related reactions

32 records

Linked notes

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