Prazepam

HCID 4890CAS 2955-38-6

Basic information

Standard SMILES
O=C1CN=C(c2ccccc2)c2cc(Cl)ccc2N1CC1CC1
InChIKey
MWQCHHACWWAQLJ-UHFFFAOYSA-N
Molecular formula
C19H17ClN2O
Average molar mass
324.8 g/mol
Monoisotopic mass
324.1029409

Names & identifiers

Preferred name
Prazepam
IUPAC
7-chloro-1-(cyclopropylmethyl)-5-phenyl-3H-1,4-benzodiazepin-2-one
English name
PRAZEPAM
Molecular formula
C19H17ClN2O
Molecular weight
324.8

Names & synonyms

prazepamCentraxDemetrinTrepidan2955-38-6PrazepamumW 4020Prazepam civDTXSID40211812H-1,4-Benzodiazepin-2-one, 7-chloro-1-(cyclopropylmethyl)-1,3-dihydro-5-phenyl-7-Chloro-1-(cyclopropylmethyl)-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-oneW-4020
Show more names
w4020K-373SettimaPrazeneVerstranSedapran
NSC-277179Q30VCC064MDTXCID1011817-Chloro-1-(cyclopropylmethyl)-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one7-chloro-1-(cyclopropylmethyl)-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-oneMono DemetrinRefChem:55907N05BA11

Database identifiers

CAS
2955-38-6
PubChem CID
4890
DTXSID
DTXSID4021181
ChEMBL
CHEMBL969
ChEBI
CHEBI:8362
UNII
Q30VCC064M
EC Number
220-975-8
Nikkaji
J3.397I

Properties

Computed structural properties

XLogP
3.6
Topological polar surface area
32.7 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
3
Heavy atoms
23

Experimental & physicochemical properties

LogP · 2 items

3.73

3.73

Solubility3.99e-03 g/L
Melting Point · 2 items

145-146 °C

145 - 146 °C

Physical DescriptionSolid
Kovats Retention Index · 2 items

2648;2651;2624;2624;2630;2652;2652;2676;2679;2694;2638;2610;2655;2641;2676;2650.1;2620;2619;2656;2641

2746.9;2646.3;2633.2;2676;2660.5;2660.5;2685

Collision Cross Section174 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]

Physicochemical properties

Melting point
145 · 145-146°
Boiling point
538.5 · 538.5±50.0 °C(Predicted)
Density
1.166 · 1.1660 (rough estimate)
refractive index
1.579 · 1.5790 (estimate)
Flash point
11 °C · 11 °C
storage temp.
2 · 2-8°C

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 33.3% (1 of 3) of reports.

Warning

H336 (66.7%): May cause drowsiness or dizziness [Warning Specific target organ toxicity, single exposure; Narcotic effects];H361 (66.7%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity];H362 (33.3%): May cause harm to breast-fed children [Reproductive toxicity, effects on or via lactation]

P203, P260, P261, P263, P264, P270, P271, P280, P304+P340, P318, P319, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 3 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Reported as not meeting GHS hazard criteria per 1 of 3 reports by companies.;There are 2 notifications provided by 2 of 3 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Regulatory Information · 2 items

DEA schedule IV controlled substance

2H-1,4-Benzodiazepin-2-one, 7-chloro-1-(cyclopropylmethyl)-1,3-dihydro-5-phenyl-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Other Safety Information · 1 item

IMAP assessments - 2H-1,4-Benzodiazepin-2-one, 7-chloro-1-(cyclopropylmethyl)-1,3-dihydro-5-phenyl-: Human health tier I assessment;IMAP assessments - 2H-1,4-Benzodiazepin-2-one, 7-chloro-1-(cyclopropylmethyl)-1,3-dihydro-5-phenyl-: Environment tier I assessment

Hazard Classes and CategoriesSTOT SE 3 (66.7%);Repr. 2 (66.7%);Lact. (33.3%)

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.

Health EffectsThey cause slurred speech, disorientation and "drunken" behavior. They are physically and psychologically addictive.
Exposure RoutesOral
Toxicity Summary · 1 item

Prazepam is believed to stimulate GABA receptors in the ascending reticular activating system. Since GABA is inhibitory, receptor stimulation increases inhibition and blocks both cortical and limbic arousal following stimulation of the brain stem reticular formation.

Signs and SymptomsSymptoms of overdose include somnolence, confusion, coma, and diminished reflexes. Respiration, pulse and blood pressure should be monitored.
Carcinogen Classification · 6 items

Prazepam

Group 3: Not classifiable as to its carcinogenicity to humans

Volume 66: (1996) Some Pharmaceutical Drugs

1996

1996

3, not classifiable as to its carcinogenicity to humans. (L135)

Regulatory information

Regulatory Information · 2 items

DEA schedule IV controlled substance

2H-1,4-Benzodiazepin-2-one, 7-chloro-1-(cyclopropylmethyl)-1,3-dihydro-5-phenyl-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Safety data

wgk
2
rtecs
DF2368000
ridadr
3249
hs_code
2933910000
risk_code
11-23/24/25-39/23/24/25
Signal word
Danger

Chemistry & industry

Pharmacology

ATC Code · 3 items

N05BA11

N - Nervous system;N05 - Psycholeptics;N05B - Anxiolytics;N05BA - Benzodiazepine derivatives;N05BA11 - Prazepam

QN - Nervous system;QN05 - Psycholeptics;QN05B - Anxiolytics;QN05BA - Benzodiazepine derivatives;QN05BA11 - Prazepam

Pharmacodynamics · 1 item

Prazepam is a benzodiazepine derivative with anxiolytic, anticonvulsant, sedative and skeletal muscle relaxant activity. Benzodiazepines may be habit-forming (causing mental or physical dependence), especially when taken for a long time or in high doses.

Mechanism of Action · 1 item

Prazepam is believed to stimulate GABA receptors in the ascending reticular activating system. Since GABA is inhibitory, receptor stimulation increases inhibition and blocks both cortical and limbic arousal following stimulation of the brain stem reticular formation.

Biological Half-Life36-200 hours
Metabolism/Metabolites · 2 items

Hepatic.

Hepatic. Prazepam is metabolised into descyclopropylmethylprazepam (also known as desmethyldiazepam) and 3-hydroxyprazepam which is further metabolised into oxazepam. [Wikipedia] Half Life: 36-200 hours

MeSH Pharmacological Classification · 2 items

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.

Uses & manufacturing

Uses · 2 items

Use (kg; approx.) in Germany (2009): >25;Use (kg) in France (2004): 2166;Consumption (g per capita; approx.) in Germany (2009): 0.000305;Consumption (g per capita) in France (2004): 0.0358;Calculated removal (%): 33.7

For the treatment of anxiety disorders.

Use ClassificationPharmaceuticals
Applications · 4 items

DescriptionPrazepam (Item No. 18358) is an analytical reference material categorized as a benzodiazepine. Prazepam is regulated as a Schedule IV compound in the United States. This product is intended for research and forensic applications.

DescriptionPrazepam (CRM) (Item No. 21701) is a certified reference material categorized as a benzodiazepine. Prazepam is regulated as a Schedule IV compound in the United States. Prazepam (CRM) (Item No. 21701) is provided as a DEA exempt preparation. This product is intended for research and forensic applications.

UsesSedative-hypnotic.

General DescriptionPrazepam, 7-chloro-1-(cyclopropylmethyl)-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepine-2-one(Verstran), has a long overall half-life. Extensive N-dealkylationoccurs to yield active nordazepam. 3-Hydroxylation ofboth prazepam and nordazepam occurs.

Additional notes

DefinitionChEBI: Prazepam is a benzodiazepine.

Related reactions

1 records

Linked notes

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