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Tetrazepam

HCID 25215
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
10379-14-3
Standard SMILES
CN1C(=O)CN=C(C2=CCCCC2)c2cc(Cl)ccc21
InChIKey
IQWYAQCHYZHJOS-UHFFFAOYSA-N
Molecular formula
C16H17ClN2O
Average molar mass
288.77 g/mol
Monoisotopic mass
288.1029409

Overview

Tetrazepam is a benzodiazepine.

Names & identifiers

Preferred name
Tetrazepam
IUPAC
7-chloro-5-(cyclohexen-1-yl)-1-methyl-3H-1,4-benzodiazepin-2-one
English name
TETRAZEPAM
Molecular formula
C16H17ClN2O
Molecular weight
288.77

Names & synonyms

TetrazepamMyolastanMusarilClinoxan10379-14-3CB 4261CB-4261FO92091VP8DTXSID001460587-chloro-5-(cyclohex-1-en-1-yl)-1-methyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one7-chloro-5-(1-cyclohexen-1-yl)-1,3-dihydro-1-methyl-2h-1,4-benzodiazepin-2-oneRefChem:188914
Show more names
epineCS-3124261cb4361cbcb42614361 CB
DTXCID8068549233-837-7Ro 06-66574261 CB7-Chloro-5-(cyclohexen-1-yl)-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one2H-1,4-BENZODIAZEPIN-2-ONE, 7-CHLORO-5-(1-CYCLOHEXEN-1-YL)-1,3-DIHYDRO-1-METHYL-Tetrazepam (INN)7-Chloro-5-(1-cyclohexenyl)-1-methyl-2-oxo-2,3-dihydro-1H-(1,4)-benzo(f)diazepine

Database identifiers

CAS
10379-14-3
PubChem CID
25215
DTXSID
DTXSID00146058
ChEMBL
CHEMBL2105527
ChEBI
CHEBI:135198
UNII
FO92091VP8
EC Number
233-837-7
Nikkaji
J10.468J

Properties

Computed structural properties

XLogP
3.2
Topological polar surface area
32.7 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
1
Heavy atoms
20
Formal charge
0
Complexity
457

Experimental & physicochemical properties

Drugs · 5 items

DEA NFLIS-Drug Category -> Benzodiazepines

DEA Schedule IV Controlled Substance -> Depressants

Pharmaceuticals

Pharmaceuticals -> Benzodiazepines

Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds

LogP · 2 items

3.20

2.76

Melting Point144 °C
Physical DescriptionSolid

Physicochemical properties

Melting point
144 ° · 144°
Boiling point
502.1 · 502.1±50.0 °C(Predicted)
Density
1.1741 · 1.1741 (rough estimate)
refractive index
1.58 · 1.5800 (estimate)
solubility
Practically insoluble in water, freely soluble in methylene chloride, soluble in acetonitrile.
pka
4.1 · 4.10±0.10(Predicted)

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Danger

H301 (40%): Toxic if swallowed [Danger Acute toxicity, oral]

P203, P261, P262, P264, P270, P271, P272, P273, P280, P301+P316, P301+P317, P302+P352, P304+P340, P316, P318, P319, P321, P330, P333+P317, P361+P364, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 5 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 2 items

DEA schedule IV controlled substance

2H-1,4-Benzodiazepin-2-one, 7-chloro-5-(1-cyclohexen-1-yl)-1,3-dihydro-1-methyl-: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and CategoriesAcute Tox. 3 (40%)

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.

Chemistry & industry

Pharmacology

ATC Code · 2 items

M - Musculo-skeletal system

QM - Musculo-skeletal system

MeSH Pharmacological Classification · 1 item

A heterogeneous group of drugs used to produce muscle relaxation, excepting the neuromuscular blocking agents. They have their primary clinical and therapeutic uses in the treatment of muscle spasm and immobility associated with strains, sprains, and injuries of the back and, to a lesser degree, injuries to the neck. They have been used also for the treatment of a variety of clinical conditions that have in common only the presence of skeletal muscle hyperactivity, for example, the muscle spasms that can occur in MULTIPLE SCLEROSIS. (From Smith and Reynard, Textbook of Pharmacology, 1991, p358)

Cellular LocationsMembrane

Uses & manufacturing

Uses · 2 items

Use (kg; approx.) in Germany (2009): >2500

Tetrazepam is used to treat muscle spasm, anxiety disorders such as panic attacks, or more rarely to treat depression, premenstrual syndrome or agoraphobia.

Applications

UsesTetrazepam is a muscle relaxant (skeletal). This is a controlled substance (depressant).

Additional notes

DefinitionChEBI: Tetrazepam is a benzodiazepine.

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
CAS DataBase Reference
10379 · 10379-14-3
EWG's Food Scores
1 · 1
FDA UNII
92091 VP8 · FO92091VP8
ATC code
3 BX07 · M03BX07
Toxicity
50 in · LD50 in mice (mg/kg): 415 i.p.; 2000 orally (Schmitt)
DEA Controlled Substances
2886 CSA · CSCN: 2886CSA SCH: Schedule IVNARC: No
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).
Drug Induced Liver Injury · 4 items

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

Tetrazepam

DILI Positive

DOI:10.1016/j.drudis.2019.09.022

Safety data

Toxicity
LD50 in mice (mg/kg): 415 i.p.; 2000 orally (Schmitt)
DEA Controlled Substances
CSCN: 2886CSA SCH: Schedule IVNARC: No