Nimetazepam

HCID 4496CAS 2011-67-8

Basic information

Standard SMILES
CN1C(=O)CN=C(c2ccccc2)c2cc([N+](=O)[O-])ccc21
InChIKey
GWUSZQUVEVMBPI-UHFFFAOYSA-N
Molecular formula
C16H13N3O3
Average molar mass
295.29 g/mol
Monoisotopic mass
295.09569128

Overview

Nimetazepam is a nitrazepam which is substituted at positions 1 by a methyl group. It is used as an anticonvulsant and as a hypnotic for the short-term management of insomnia. It has a role as an anticonvulsant, a sedative, a GABA modulator and an antispasmodic drug. It is a 1,4-benzodiazepinone and a C-nitro compound. It is functionally related to a nitrazepam.

Names & identifiers

Preferred name
Nimetazepam
IUPAC
1-methyl-7-nitro-5-phenyl-3H-1,4-benzodiazepin-2-one
English name
Nimetazepam
Molecular formula
C16H13N3O3
Molecular weight
295.29

Names & synonyms

nimetazepam2011-67-81-MethylnitrazepamEriminMethylnitrazepam1,3-Dihydro-1-methyl-7-nitro-5-phenyl-2H-1,4-benzodiazepin-2-oneNimetazepamumRo 5-3453S 1530DTXSID60233691-Methyl-5-phenyl-7-nitro-1,3-dihydro-2H-1,4-benzodiazepin-2-oneS-1530
Show more names
EliminHypnonro5-3453NimetazamN-MethylmogadonNimetazepam (CRM)Nimetazepam solution
1-Methyl-7-nitro-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-oneCHEBI:31912DTXCID3033694532264KW61-methyl-7-nitro-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one1-methyl-7-nitro-5-phenyl-3H-1,4-benzodiazepin-2-oneRefChem:854155217-931-5

Database identifiers

CAS
2011-67-8
PubChem CID
4496
DTXSID
DTXSID6023369
ChEMBL
CHEMBL13341
ChEBI
CHEBI:31912
UNII
4532264KW6
EC Number
217-931-5
Nikkaji
J4.431H

Properties

Computed structural properties

XLogP
2.2
Topological polar surface area
78.5 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
4
Rotatable bonds
1
Heavy atoms
22

Experimental & physicochemical properties

Drugs · 3 items

DEA NFLIS-Drug Category -> Benzodiazepines

DEA Schedule IV Controlled Substance -> Depressants

Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds

Collision Cross Section169.7 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated]

Physicochemical properties

Melting point
156.5 · 156.5-157.5°
Boiling point
436.98 °C · 436.98°C (rough estimate)
Density
1.1952 · 1.1952 (rough estimate)
refractive index
1.65 · 1.6500 (estimate)
Flash point
9 ℃ · 9℃
storage temp.
-20 °C · -20°C

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationDEA schedule IV controlled substance
Hazard Classes and CategoriesAcute Tox. 4 (100%)

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).

Safety data

wgk
1
ridadr
UN1230 - class 3 - PG 2 - Methanol, solution
Toxicity
LD50 in male, female mice, rats (mg/kg): 910, 750, 1150, 970 orally; 970, 840, 970, 980 i.p.; 1500, 1500, 1000, 1000 s.c. (Sakai)
risk_code
11-23/24/25-39/23/24/25
Signal word
Danger
Symbol(GHS)
GHS02,GHS06,GHS08

Chemistry & industry

Pharmacology

ATC Code · 2 items

N - Nervous system

QN - Nervous system

MeSH Pharmacological Classification · 4 items

Drugs used to prevent SEIZURES or reduce their severity.

Drugs used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.

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.

Applications

UsesSedative, hypnotic. Controlled substance.

Upstream & downstream products

Additional notes

DefinitionChEBI: A nitrazepam which is substituted at positions 1 by a methyl groups. It is used as an anticonvulsant and as a hypnotic for the short-term management of insomnia.

Related reactions

6 records

Linked notes

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