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Details

Stereochemistry ACHIRAL
Molecular Formula C9H8N2
Molecular Weight 144.1732
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 1H-1,2-BENZODIAZEPINE

SMILES

N1N=CC=CC2=CC=CC=C12

InChI

InChIKey=SVUOLADPCWQTTE-UHFFFAOYSA-N
InChI=1S/C9H8N2/c1-2-6-9-8(4-1)5-3-7-10-11-9/h1-7,11H

HIDE SMILES / InChI

Molecular Formula C9H8N2
Molecular Weight 144.1732
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Benzodiazepines represent a group of two-ring heterocyclic compounds consisting of a benzene ring fused to a diazepine ring. Benzodiazepines (BZDs) are one of the most widely prescribed pharmacologic agents in the United States (more than 112 million prescriptions in 2007). BZDs are used for numerous indications, including anxiety, insomnia, muscle relaxation, relief from spasticity caused by central nervous system pathology, and epilepsy. BZDs are also used intraoperatively because of their amnesic and anxiolytic properties. However, these properties become undesired side effects in nearly all other clinical instances. BZDs act as positive allosteric modulators on the gamma amino butyric acid (GABA)-A receptor. The GABA-A receptor is a ligand-gated chloride-selective ion channel. Benzodiazepines are a large drug class and have a long history of development, starting with the first FDA-approvals in the 1960s. All benzodiazepines are listed as DEA schedule IV controlled substances. As controlled substances, all benzodiazepines have the potential for abuse, addiction and diversion.

Approval Year

PubMed

PubMed

TitleDatePubMed
High dose benzodiazepines prolong reaction times in chronic users who have major depressive and/or anxiety disorders.
2014-03
Optimization of (arylpiperazinylbutyl)oxindoles exhibiting selective 5-HT₇ receptor antagonist activity.
2011-10-13
Clinical pattern of toxicity associated with the novel synthetic cathinone mephedrone.
2011-04
Pro-2-PAM therapy for central and peripheral cholinesterases.
2010-09-06
Pentobarbital coma for refractory intra-cranial hypertension after severe traumatic brain injury: mortality predictions and one-year outcomes in 55 patients.
2010-08
Limited clinical value of bacterial cocaine esterase in cocaine toxicity.
2010-05
Cocaine and beta-blockers: the paradigm.
2010-04
Hyperammoneic encephalopathy, valproic acid, and benzodiazepine withdrawal: a case series.
2010-03
Alcoholic and cocaine-associated cardiomyopathies.
2010-01-30
Cognitive-behavioural, pharmacological and psychosocial predictors of outcome during tapered discontinuation of benzodiazepine.
2008-12-31
Cardiovascular manifestations of sedatives and analgesics in the critical care unit.
2008-12-19
Abuse liability of intra-nasal midazolam in inhaled-cocaine abusers.
2008-10
Safety evaluation of the concomitant use of clozapine and benzodiazepines: a retrospective, cross-sectional chart review.
2008-09
Nausea and vomiting.
2008-04
Alterations of GABA A-receptor function and allosteric modulation during development of status epilepticus.
2008-03
The impact of benzodiazepine use on methadone maintenance treatment outcomes.
2008
[Optical hallucinosis during benzodiazepine withdrawal in low-dose dependence].
1997-11
[Myoclonus resulting from high-dose epidural and intravenous morphine infusion].
1997-05-15
[Benzodiazepine withdrawal presenting as pseudo-surgical abdominal pain].
1997
Catatonia after benzodiazepine withdrawal.
1996-08
Cocaine-associated myocardial infarction.
1996-08
Bilateral forearm compartment syndromes resulting from neuroleptic malignant syndrome.
1996-03
[Acne induced by amineptin: adnexal toxiderma].
1996
Benzodiazepine-insensitive mice generated by targeted disruption of the gamma 2 subunit gene of gamma-aminobutyric acid type A receptors.
1995-08-15
Urinary retention related to phenytoin therapy.
1995-07
Benzodiazepine receptor mediation of the anxiolytic-like effect of (-)-nicotine in mice.
1994-11
Neuropsychiatric adverse drug reactions: passive reports to Health and Welfare Canada's adverse drug reaction database (1965-present).
1994
Benzodiazepine amplification of valproate teratogenic effects in children of mothers with absence epilepsy.
1993-04
[Confusion induced by the combination cimetidine-benzodiazepine; apropos of a case report].
1990-01
Clinical experience with the benzodiazepine antagonist flumazenil in suspected benzodiazepine or ethanol poisoning.
1990
Clotiazepam-induced acute hepatitis.
1989-09
Adjunctive buspirone in benzodiazepine treatment of four patients with panic disorder.
1989-07
Mania precipitated by benzodiazepine withdrawal.
1989-04
Complications of phenylpropanolamine.
1989-04
Delusional depression following benzodiazepine withdrawal.
1988-10
Controlled study of extrapyramidal reactions in the management of delirious, medically ill patients: intravenous haloperidol versus intravenous haloperidol plus benzodiazepines.
1988-05
Obsessive-compulsive disorder--a complication of benzodiazepine withdrawal.
1987-02
Review of the side-effect profile of buspirone.
1986-03-31
[Memory gaps and hypercomplex automatisms after a single oral dose of benzodiazepines: clinical and medico-legal aspects].
1986-01
Chronic use of benzodiazepines and psychomotor and cognitive test performance.
1986
Toxic "ictal" confusion in middle age: treatment with benzodiazepines.
1985-05
Alcohol withdrawal syndromes: clinical management with lofexidine.
1985-03-01
[Benzodiazepine abstinence syndrome. Case report].
1985-01-01
Depression following withdrawal from long-term benzodiazepine use: a report of four cases.
1984-11
[Reversal of benzodiazepine depression with aminophylline].
1984-07-01
Rebound anxiety in anxious patients after abrupt withdrawal of benzodiazepine treatment.
1984-07
[Respiratory arrest in a 19-year-old patient following low-dose benzodiazepines].
1983-10-21
Cimetidine and prolonged post-operative somnolence.
1981-09
Tonic status epilepticus precipitated by intravenous benzodiazepine in five patients with Lennox-Gastaut syndrome.
1972-07
Increased aggression and toxicity in grouped male mice treated with tranquilizing benzodiazepines.
1971
Patents
Substance Class Chemical
Created
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on Mon Mar 31 19:25:17 GMT 2025
Edited
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Record UNII
M0Q7802G2B
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Name Type Language
1H-1,2-BENZODIAZEPINE
Preferred Name English
Code System Code Type Description
CAS
264-60-8
Created by admin on Mon Mar 31 19:25:17 GMT 2025 , Edited by admin on Mon Mar 31 19:25:17 GMT 2025
PRIMARY
PUBCHEM
134664
Created by admin on Mon Mar 31 19:25:17 GMT 2025 , Edited by admin on Mon Mar 31 19:25:17 GMT 2025
PRIMARY
FDA UNII
M0Q7802G2B
Created by admin on Mon Mar 31 19:25:17 GMT 2025 , Edited by admin on Mon Mar 31 19:25:17 GMT 2025
PRIMARY