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Oxazolam

HCID 4617
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
24143-17-7
Standard SMILES
CC1CN2CC(=O)Nc3ccc(Cl)cc3C2(c2ccccc2)O1
InChIKey
VCCZBYPHZRWKFY-UHFFFAOYSA-N
Molecular formula
C18H17ClN2O2
Average molar mass
328.8 g/mol
Monoisotopic mass
328.0978555

Overview

Oxazolam is a hemiaminal ether and an organic molecular entity.

Names & identifiers

Preferred name
Oxazolam
IUPAC
10-chloro-2-methyl-11b-phenyl-2,3,5,7-tetrahydro-[1,3]oxazolo[3,2-d][1,4]benzodiazepin-6-one
English name
OXAZOLAM METHANOL SOLUTION
Molecular formula
C18H17ClN2O2
Molecular weight
328.79

Names & synonyms

oxazolamOxazolazepamTranquitHializan24143-17-7Oxazolamum1V2WI2NA1CDTXSID502340110-Chloro-2-methyl-11b-phenyl-2,3,7,11b-tetrahydro(1,3)oxazolo(3,2-d)(1,4)benzodiazepin-6(5H)-one10-Chloro-2-methyl-11b-phenyl-2,3,7,11b-tetrahydro[1,3]oxazolo[3,2-d][1,4]benzodiazepin-6(5H)-oneRefChem:857082DTXCID80209312
Show more names
NebusnToccataSerenal (Japanese)o-2-methyl-11b-phenyl-OXAZOLAM METHANOL SOLUTION
10-chloro-2,3,7,11b-tetrahydro-2-methyl-11b-phenylbenzo(6,7)(1,4)diazepino(5,4-b) oxazol-6-one13-chloro-4-methyl-2-phenyl-3-oxa-6,9-diazatricyclo(8.4.0.0^(2,6))tetradeca-1(10),11,13-trien-8-one246-032-0SerenalSerenal [Japanese]10-Chloro-2,3,7,11b-tetrahydro-2-methyl-11b-phenyloxazolo(3,2-d)(1,4)benzodiazepin-6(5H)-one10-Chloro-2,3,7,11b-tetrahydro-2-methyl-11b-phenyloxazolo[3,2-d][1,4]benzodiazepin-6(5H)-oneBenzo(6,7)-1,4-diazepino-(5,4-b)-oxazol-6-one, 10-chloro-2,3,5,6,7,11b-hexahydro-2-methyl-11b-phenyl-

Database identifiers

CAS
24143-17-7
PubChem CID
4617
DTXSID
DTXSID5023401
ChEMBL
CHEMBL2104805
ChEBI
CHEBI:31944
UNII
1V2WI2NA1C
EC Number
246-032-0
Nikkaji
J3.472J

Properties

Computed structural propertiesFilling in

XLogP
3
Topological polar surface area
41.6 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
3
Rotatable bonds
1
Heavy atoms
23
Formal charge
0
Complexity
468

Experimental & physicochemical properties

Drugs · 2 items

DEA NFLIS-Drug Category -> Benzodiazepines

DEA Schedule IV Controlled Substance -> Depressants

Physicochemical properties

Melting point
187 °C · 187°C
Boiling point
495.8 · 495.8±45.0 °C(Predicted)
Density
1.2065 · 1.2065 (rough estimate)
refractive index
1.54 · 1.5400 (estimate)
Flash point
11 °C · 11 °C
storage temp.
2 · 2-8°C
solubility
Chloroform (Slightly), Methanol (Slightly)
pka
12.85 · 12.85±0.60(Predicted)
form
A solid
FDA UNII
1 V2WI2NA1C · 1V2WI2NA1C
Symbol(GHS)
6 · GHS06
Signal word
Danger

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 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 39 reports by companies from 1 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. 3 (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.

Chemistry & industry

Applications

UsesA psychotropic agent with anxiolytic, anticonvulsant, sedative and skeletal muscle relaxant properties. It is a precursor to the active substance Desmethyldiazepam (D291595).

Upstream & downstream products

Upstream raw materials

5-CHLORO-2-CHLOROACETYLAMINOBENZOPHENONE(S)-(+)-1-Amino-2-propanol

Additional notes

DefinitionChEBI: Oxazolam is an organic molecular entity and a hemiaminal ether.

Related reactions

7 records
New reaction record
HRID 328480 reaction equation
HRID 328480As productuspto-grants-1977_04
HRID 328492 reaction equation
HRID 328492As productuspto-grants-1977_04
HRID 597626 reaction equation
HRID 597626As productuspto-grants-1977_03
HRID 1658603 reaction equation
HRID 1658603As productuspto-grants-1976_06
HRID 1973526 reaction equation
HRID 1973526As productuspto-grants-1976_12
HRID 2071945 reaction equation
HRID 2071945As productuspto-grants-1977_09
HRID 2071959 reaction equation
HRID 2071959As productuspto-grants-1977_09

Compound notes

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Hazard statements
301 · H301-H319-H315-H331
Precautionary statements
264 · P264-P280-P302+P352-P321-P332+P313-P362-P261-P271-P304+P340-P311-P321-P403+P233-P405-P501-P264-P270-P301+P310-P321-P330-P405-P501-P264-P280-P305+P351+P338-P337+P313P
Hazard Codes
F,T
Risk Statements
11 · 11-23/24/25-39/23/24/25-36/38-23/25
Safety Statements
16 · 16-36/37-45-24
Toxicity
50 orl-mus: · LD50 orl-mus: 5200 mg/kg NYKZAU 66,107,70
DEA Controlled Substances
2839 CSA · CSCN: 2839CSA 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).

Safety data

Toxicity
LD50 orl-mus: 5200 mg/kg NYKZAU 66,107,70
risk_code
11-23/24/25-39/23/24/25-36/38-23/25
Signal word
Danger
Symbol(GHS)
GHS06
hazard_code
F,T
safety_code
16-36/37-45-24
Hazard statements
H301-H319-H315-H331
Precautionary statements
P264-P280-P302+P352-P321-P332+P313-P362-P261-P271-P304+P340-P311-P321-P403+P233-P405-P501-P264-P270-P301+P310-P321-P330-P405-P501-P264-P280-P305+P351+P338-P337+P313P
DEA Controlled Substances
CSCN: 2839CSA SCH: Schedule IVNARC: No