ContaminantDB: Nitrazepam

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (24)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:28:55 UTC

Update Date

2026-05-14 17:10:11 UTC

Accession Number

CHEM002403

Identification

Common Name

Nitrazepam

Class

Small Molecule

Description

Nitrazepam is only found in individuals that have used or taken this drug. It is a benzodiazepine derivative used as an anticonvulsant and hypnotic. Nitrazepam belongs to a group of medicines called benzodiazepines. It acts on benzodiazepine receptors in the brain which are associated with the GABA receptors causing an enhanced binding of GABA (gamma amino butyric acid) to GABAA receptors. GABA is a major inhibitory neurotransmitter in the brain, involved in inducing sleepiness, muscular relaxation and control of anxiety and fits, and slows down the central nervous system. The anticonvulsant properties of nitrazepam and other benzodiazepines may be in part or entirely due to binding to voltage-dependent sodium channels rather than benzodiazepine receptors. Sustained repetitive firing seems to be limited by benzodiazepines effect of slowing recovery of sodium channels from inactivation.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
Suspected Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amide
Amine
Anti-Anxiety Agent
Anticonvulsant
Drug
GABA Modulator
Human Neurotoxin
Hypnotic and Sedative
Metabolite
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,3-Dihydro-7-nitro-5-phenyl-2H-1,4-benzodiazepin-2-one	ChEBI
2,3-Dihydro-7-nitro-5-phenyl-1H-1,4-benzodiazepin-2-one	ChEBI
7-Nitro-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one	ChEBI
7-Nitro-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one	ChEBI
Apodorm	ChEBI
Atempol	ChEBI
Benzalin	ChEBI
Calsmin	ChEBI
Dormicum	ChEBI
Eatan	ChEBI
Eunoctin	ChEBI
Gerson	ChEBI
Hipnax	ChEBI
Hipsal	ChEBI
Ibrovek	ChEBI
Imeson	ChEBI
Imesont	ChEBI
Mogadon	ChEBI
N-Desmethylnimetazepam	ChEBI
Nelbon	ChEBI
Nelmat	ChEBI
Neozepam	ChEBI
Neuchlonic	ChEBI
Nitrados	ChEBI
Nitrazepamum	ChEBI
Paxisyn	ChEBI
Pelson	ChEBI
Persopit	ChEBI
Radedorm	ChEBI
Relact	ChEBI
Remnos	ChEBI
Ro 4-5360	ChEBI
Ro 5-3059	ChEBI
Somitran	ChEBI
Sonebon	ChEBI
Sonnolin	ChEBI
Surem	ChEBI
Trazenin	ChEBI
Unisomnia	ChEBI
1, 3-Dihydro-7-nitro-5-phenyl-2H-1,4-benzodiazepin-2-one	HMDB
2,3-Dihydro-7-nitro-5-phenyl-1H-1,4-benzodiazepin-2-ON	HMDB
7-Nitro-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one	HMDB
Alter brand OF nitrazepam	HMDB
CSP Brand OF nitrazepam	HMDB
DDSA brand OF nitrazepam	HMDB
Desitin brand OF nitrazepam	HMDB
Nitrazepam al	HMDB
Nitrazepam-neuraxpharm	HMDB
Nitrodiazepam	HMDB
Novanox	HMDB
Taurus brand OF nitrazepam	HMDB
CT-Arzneimittel brand OF nitrazepam	HMDB
Aliud brand OF nitrazepam	HMDB
Alphapharma brand OF nitrazepam	HMDB
Dormicum brand OF nitrazepam	HMDB
Nitrazadon	HMDB
Nitrazep	HMDB
Norgine brand OF nitrazepam	HMDB
Rhoxalpharma brand OF nitrazepam	HMDB
Scheurich brand OF nitrazepam	HMDB
Serenade	HMDB
Dermatech brand OF nitrazepam	HMDB
ICN brand OF nitrazepam	HMDB
Imadorm	HMDB
Pfleger brand OF nitrazepam	HMDB
Rhoxal-nitrazepam	HMDB
Wernigerode brand OF nitrazepam	HMDB
Allphar brand OF nitrazepam	HMDB
Alodorm	HMDB
Alpharma brand OF nitrazepam	HMDB
Dormalon	HMDB
Dormo-puren	HMDB
Protea brand OF nitrazepam	HMDB
Somnite	HMDB
United drug brand OF nitrazepam	HMDB
Neuraxpharm brand OF nitrazepam	HMDB
Rhoxal nitrazepam	HMDB
Nitrazepam neuraxpharm	HMDB

Chemical Formula

C₁₅H₁₁N₃O₃

Average Molecular Mass

281.266 g/mol

Monoisotopic Mass

281.080 g/mol

CAS Registry Number

146-22-5

IUPAC Name

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

Traditional Name

gerson

SMILES

[O-][N+](=O)C1=CC2=C(NC(=O)CN=C2C2=CC=CC=C2)C=C1

InChI Identifier

InChI=1S/C15H11N3O3/c19-14-9-16-15(10-4-2-1-3-5-10)12-8-11(18(20)21)6-7-13(12)17-14/h1-8H,9H2,(H,17,19)

InChI Key

KJONHKAYOJNZEC-UHFFFAOYSA-N

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
Alpha-amino acid or derivatives
Nitroaromatic compound
Monocyclic benzene moiety
Benzenoid
Carboxamide group
Ketimine
Lactam
C-nitro compound
Organic nitro compound
Secondary carboxylic acid amide
Carboxylic acid derivative
Azacycle
Organic oxoazanium
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Imine
Organonitrogen compound
Organooxygen compound
Carbonyl group
Organic zwitterion
Organopnictogen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

C-nitro compound (CHEBI:7581 )
1,4-benzodiazepinone (CHEBI:7581 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	225°C
Boiling Point	Not Available
Solubility	2.99e-02 g/L

Predicted Properties

Property	Value	Source
Water Solubility	0.03 g/L	ALOGPS
logP	1.95	ALOGPS
logP	2.55	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	11.66	ChemAxon
pKa (Strongest Basic)	2.65	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	84.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	78.21 m³·mol⁻¹	ChemAxon
Polarizability	27.67 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0il0-0190000000-e010be5805d1bd8c4980	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-001i-0090000000-8f7713c4e618326c1d9b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0udi-0090000000-d514d232dff7c473d32f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0udi-0090000000-e2a1a64f13da7ed85586	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0uk9-0190000000-f22bb948e3a20dfd2bff	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-006x-0980000000-f78bdd1a7e391dbaad48	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-014l-0920000000-d334a1a23130e08b3d55	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-014i-1900000000-3808670d5ccc91bd0e38	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0uxu-3900000000-1fc08ceb9c88d5c734ca	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0udi-5900000000-cbcd46c7ea13a9ff18cb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00lr-0090000000-bc49e652f5e2e4f4b760	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-001i-0090000000-c63c1250878b61e6d0da	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-001i-0090000000-02d4e0b73c57e157d6b0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0019-0090000000-6623ad5dc09e01b5a573	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-000i-0390000000-38d5874ebcc0e05f411c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-053r-0970000000-ce2d7caefc3860d70fa4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-053r-0930000000-670ac85a651f0faf0d7d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0udi-1900000000-f96a507afa68e1b3a438	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0udi-2900000000-c9082e2a3a5a56cfe408	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0udi-3900000000-310a824d6452fa47d987	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0090000000-561625e5abacb4f46f7d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0090000000-4283a0fd03dc5d34141a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-054k-9310000000-06affddb11ec02837252	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0090000000-fb59c905972aefb50fef	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0090000000-5f6a8e538799be95e46b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-cf06cb39768b75fb66c0	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0zgi-2490000000-84b5bf7df62c745f8414	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Bioavailability is 53-94% following oral administration.

Mechanism of Toxicity

Nitrazepam belongs to a group of medicines called benzodiazepines. It acts on benzodiazepine receptors in the brain which are associated with the GABA receptors causing an enhanced binding of GABA (gamma amino butyric acid) to GABAA receptors. GABA is a major inhibitory neurotransmitter in the brain, involved in inducing sleepiness, muscular relaxation and control of anxiety and fits, and slows down the central nervous system. The anticonvulsant properties of nitrazepam and other benzodiazepines may be in part or entirely due to binding to voltage-dependent sodium channels rather than benzodiazepine receptors. Sustained repetitive firing seems to be limited by benzodiazepines effect of slowing recovery of sodium channels from inactivation.

Metabolism

It is long acting, is lipophilic and is metabolised hepatically via oxidative pathways. [Wikipedia] Half Life: 15-38 hours (mean elimination half life 26 hours).

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Used to treat short-term sleeping problems (insomnia), such as difficulty falling asleep, frequent awakenings during the night, and early-morning awakening.

Minimum Risk Level

Not Available

Health Effects

They cause slurred speech, disorientation and "drunken" behavior. They are physically and psychologically addictive. May cause a potentially dangerous rash that may develop into Stevens Johnson syndrome, an extremely rare but potentially fatal skin disease.

Symptoms

Nitrazepam is a drug which is very frequently involved in drug intoxication, including overdose. Nitrazepam overdose may result in stereotypical symptoms of benzodiazepine overdose including intoxication, impaired balance, slurred speech. In cases of severe overdose this may progress to a comatose state with the possibility of death.

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.

Concentrations

Not Available

External Links

DrugBank ID

DB01595

HMDB ID

HMDB0015534

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID