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
Show more names
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
- Formal charge
- 0
- Complexity
- 376
Experimental & physicochemical properties
Drugs
DEA NFLIS-Drug Category -> Benzodiazepines
DEA Schedule IV Controlled Substance -> Depressants
Pharmaceuticals -> Benzodiazepines
Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds
Pharmaceuticals -> Listed in ZINC15
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
- solubility
- 10 mg/mL · DMSO: >10mg/mL
- pka
- 3.5 · pKa 3.5 12.0 (5%MeOH in H2O t=20 I=0.15) (Uncertain)
- form
- neat &_& powder
- color
- white to light tan
- Major Application
- clinical testing
- 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)
- InChIKey
- AKPLHCDWDRPJGD-UHFFFAOYSA-N
- SMILES
- Clc1ccc2NC(=O)CN=C(c3ccccc3)c2c1
- LogP
- 2.93 · 2.930
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 67220 MCM01 · 67220MCM01
- ATC code
- 5 BA16 · N05BA16
- NIST Chemistry Reference
- Nordazepam(1088-11-5)
- EPA Substance Registry System
- 2 H-1,4-Benzodiazepin-2-one, · 2H-1,4-Benzodiazepin-2-one, 7-chloro-1,3-dihydro-5-phenyl- (1088-11-5)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302
- Precautionary statements
- 264 · P264-P270-P301+P312-P501
- target organs
- Eyes,Central nervous system
- Hazard Codes
- Xn,T,F
- Risk Statements
- 22 · 22-39/23/24/25-23/24/25-11
- Safety Statements
- 7 · 7-16-36/37-45
- RIDADR
- 3249 · 3249
- WGK Germany
- 3 · 3
- RTECS
- 1750000 · DF1750000
- HazardClass
- 6.1 · 6.1(b)
- PackingGroup
- III
- HS Code
- 2933910000 · 2933910000
- Storage Class
- 3 · 3 - Flammable liquids
- Hazard Classifications
- 3 DermalAcute · Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralFlam. Liq. 2STOT SE 1
- Toxicity
- 50 in · LD50 in mice (mg/kg): 2750 orally, >400 i.p. (Randall); LD50 in mice, rats (mg/kg): 1300, >5200 orally (company communication)
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
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
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
Toxicology
Treatment
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
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.
Drug Induced Liver Injury
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
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
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn,T,F
- safety_code
- 7-16-36/37-45
- hazard_class
- 6.1(b)
- Storage Class
- 3 - Flammable liquids
- packing_group
- III
- target organs
- Eyes,Central nervous system
- Hazard statements
- H302
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralFlam. Liq. 2STOT SE 1
- Precautionary statements
- P264-P270-P301+P312-P501
Chemistry & industry
Pharmacology
ATC Code
N05BA16
N - Nervous system
QN - Nervous system
MeSH Pharmacological Classification
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.
Uses & manufacturing
Use Classification
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
Upstream raw materials
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
Linked notes
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