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Nordazepam

Nordiazepam

HCID 2997
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Grundinformationen

CAS
1088-11-5
Standard-SMILES
O=C1CN=C(c2ccccc2)c2cc(Cl)ccc2N1
InChIKey
AKPLHCDWDRPJGD-UHFFFAOYSA-N
Summenformel
C15H11ClN2O
Durchschnittliche Molmasse
270,71 g/mol
Monoisotopische Masse
270,05599065

Überblick

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.

Namen und Bezeichner

Bevorzugter Name
Nordiazepam
IUPAC
7-chloro-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one
Lokaler Name
Nordazepam
Englischer Name
Nordazepam
Summenformel
C15H11ClN2O
Molmasse
270.71

Namen und Synonyme

NordazepamNordiazepamdesmethyldiazepamNorprazepam1088-11-5N-DesmethyldiazepamN-DemethyldiazepamN-DeoxydemoxepamMadar1-DemethyldiazepamN1-DesmethyldiazepamDemethyldiazepam
Weitere Namen anzeigen
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

Datenbank-Bezeichner

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

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
2,9
Polarare Oberfläche (TPSA)
41,5 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
1
Schwere Atome
19
Formalladung
0
Komplexität
376

Experimentelle und physikochemische Eigenschaften

Chemical ClassesPharmaceutical
Drugs · 5 Einträge

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)]

Physikochemische Eigenschaften

Schmelzpunkt
208 · 208-210°C
Siedepunkt
453.1 · 453.1±45.0 °C(Predicted)
Dichte
1.2576 · 1.2576 (rough estimate)
Brechungsindex
1.633 · 1.6330 (estimate)

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 5 Einträge

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.

Gefahrenhinweise

Regulatory Information · 3 Einträge

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%)

Toxikologische Informationen

Treatment · 1 Eintrag

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.

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 3 Einträge

N05BA16

N - Nervous system

QN - Nervous system

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

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

Verwendung und Herstellung

Use Classification · 2 Einträge

Pharmaceuticals

Pharmaceuticals -> Transformation products

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

BenzophenonDiphenylaminMethenamin

Zugehörige Reaktionen

32
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 103397
HRID 103397als ProduktTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
Reaktionsgleichung von HRID 106654
HRID 106654als ProduktTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
Reaktionsgleichung von HRID 262942
HRID 262942als Produktuspto-grants-1979_05
Reaktionsgleichung von HRID 262943
HRID 262943als Eduktuspto-grants-1979_05
Reaktionsgleichung von HRID 328109
HRID 328109als Eduktuspto-grants-1977_04
Reaktionsgleichung von HRID 462039
HRID 462039als Eduktuspto-grants-1977_12
Reaktionsgleichung von HRID 663836
HRID 663836als EduktTraining data from https://doi.org/10.1039/C8SC04228D (3/10)
Reaktionsgleichung von HRID 704543
HRID 704543als Produktuspto-grants-1991_01
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Flammpunkt
11 °C · 11 °C
storage temp.
2 · 2-8°C
Löslichkeit
10 mg/mL · DMSO: >10mg/mL
pka
3.5 · pKa 3.5 12.0 (5%MeOH in H2O t=20 I=0.15) (Uncertain)
Aggregatzustand
neat &_& powder
Farbe
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
NIST chemische Informationen
Nordazepam(1088-11-5)
EPA chemische Informationen
2 H-1,4-Benzodiazepin-2-one, · 2H-1,4-Benzodiazepin-2-one, 7-chloro-1,3-dihydro-5-phenyl- (1088-11-5)
Toxicity Summary · 1 Eintrag

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 Einträge

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 Einträge

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

Sicherheitsdaten

wgk
3
ridadr
3249
hs_code
2933910000
RTECS-Nr.
DF1750000
risk_code
22-39/23/24/25-23/24/25-11
Toxizität
LD50 in mice (mg/kg): 2750 orally, >400 i.p. (Randall); LD50 in mice, rats (mg/kg): 1300, >5200 orally (company communication)
hazard_code
Xn,T,F
safety_code
7-16-36/37-45
hazard_class
6.1(b)
packing_group
III
Speicherklasse
3 - Flammable liquids
Hazard Classifications
Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralFlam. Liq. 2STOT SE 1
Essigsure

Nachgelagerte Produkte

BENZP-DINITRIDE-THIO-KETONEPinazepam

Ergänzende Hinweise

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.