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Pinazepam

HCID 40391
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Basic information

CAS
52463-83-9
Standard SMILES
C#CCN1C(=O)CN=C(c2ccccc2)c2cc(Cl)ccc21
InChIKey
MFZOSKPPVCIFMT-UHFFFAOYSA-N
Molecular formula
C18H13ClN2O
Average molar mass
308.8 g/mol
Monoisotopic mass
308.0716407

Overview

Pinazepam is a benzodiazepine.

Names & identifiers

Preferred name
Pinazepam
IUPAC
7-chloro-5-phenyl-1-prop-2-ynyl-3H-1,4-benzodiazepin-2-one
English name
pinazepam
Molecular formula
C18H13ClN2O
Molecular weight
308.76

Names & synonyms

PinazepamDomar52463-83-9Pinazepamum7-Chloro-1,3-dihydro-5-phenyl-1-(2-propynyl)-2H-1,4-benzodiazepin-2-one7-Chloro-1-propargyl-5-phenyl-2H-1,4-benzodiazepin-2-one5286RBZ882DTXSID30234757-chloro-5-phenyl-1-(prop-2-yn-1-yl)-2,3-dihydro-1H-1,4-benzodiazepin-2-onepropazepamRefChem:929293DTXCID203475
Show more names
Zami-905pinazepam USP/EP/BP7-chloro-5-phenyl-1-prop-2-ynyl-3H-1,4-benzodiazepin-2-one2H-1,4-Benzodiazepin-2-one, 7-chloro-1,3-dihydro-5-phenyl-1-(2-propyn-1-yl)-
N05BA147-chloro-5-phenyl-1-propargyl-1,4-benzodiazepin-2-one257-934-9Pinazepam [INN]ZAMI 905DunaZ-9052H-1,4-Benzodiazepin-2-one, 7-chloro-1,3-dihydro-5-phenyl-1-(2-propynyl)-

Database identifiers

CAS
52463-83-9
PubChem CID
40391
DTXSID
DTXSID3023475
ChEMBL
CHEMBL1213352
ChEBI
CHEBI:135315
UNII
5286RBZ882
EC Number
257-934-9
Nikkaji
J9.933C

Properties

Computed structural properties

XLogP
3.1
Topological polar surface area
32.7 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
2
Heavy atoms
22
Formal charge
0
Complexity
500

Experimental & physicochemical properties

Drugs · 3 items

DEA NFLIS-Drug Category -> Benzodiazepines

DEA Schedule IV Controlled Substance -> Depressants

Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds

LogP2.87
Melting Point141 °C
Physical DescriptionSolid

Physicochemical properties

Melting point
140 · 140-142°
Boiling point
523.6 · 523.6±50.0 °C(Predicted)
Density
1.2151 · 1.2151 (rough estimate)
refractive index
1.58 · 1.5800 (estimate)
solubility
DMSO (Slightly), Methanol (Slightly)
form
Solid
pka
2.34 · pKa 2.34 (Uncertain)
color
Off-White to Pale Beige

Safety & regulation

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

Hazard information

Regulatory InformationDEA schedule IV controlled substance

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.

Chemistry & industry

Pharmacology

ATC Code · 2 items

N - Nervous system

QN - Nervous system

MeSH Pharmacological Classification · 1 item

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.

Cellular LocationsMembrane

Applications

UsesPinazepam is a is a benzodiazepine. Pinazepam possesses anxiolytic, anticonvulsant, sedative and skeletal muscle relaxant properties. Pinazepam is less toxic than Diazepam. This is a contolled substance (depressant). Anxiolytic.

Upstream & downstream products

Upstream raw materials

Phthalimido Acetyl ChlorideHydrazine hydratePropargyl bromide2-Amino-5-chlorobenzophenoneNordazepam

Additional notes

DefinitionChEBI: Pinazepam is a benzodiazepine.

Related reactions

2 records
New reaction record
HRID 1446802 reaction equation
HRID 1446802As productuspto-grants-1982_02
HRID 1446803 reaction equation
HRID 1446803As productuspto-grants-1982_02

Compound notes

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Stability
Light Sensitive
FDA UNII
5286 RBZ882 · 5286RBZ882
ATC code
5 BA14 · N05BA14
RIDADR
3249 · 3249
HazardClass
6.1 · 6.1(b)
PackingGroup
III
Toxicity
50 in · LD50 in mice, rats (mg/kg): 1355, 5819 orally; 266, 622 i.p. (Scrollini, 1975); Also reported as LD50 in mice (mg/kg): 670 orally (Podesva, Vagi)
DEA Controlled Substances
2883 CSA · CSCN: 2883CSA SCH: Schedule IVNARC: No
Carcinogen Classification
No indication of carcinogenicity to humans (not listed by IARC).

Safety data

ridadr
3249
Toxicity
LD50 in mice, rats (mg/kg): 1355, 5819 orally; 266, 622 i.p. (Scrollini, 1975); Also reported as LD50 in mice (mg/kg): 670 orally (Podesva, Vagi)
hazard_class
6.1(b)
packing_group
III
DEA Controlled Substances
CSCN: 2883CSA SCH: Schedule IVNARC: No