TEMAZEPAM

TEMAZEPAM Basic information
Product Name:TEMAZEPAM
Synonyms:Planum;Remestan;Restoril;Ro 5-5345;ro5-5345;Ro-5-5354;Signopam;WY 2917
CAS:846-50-4
MF:C16H13ClN2O2
MW:300.74
EINECS:212-688-1
Product Categories:Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Isotope Labeled Compounds;Heterocycles, Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals;pharmaceutical intermediate
Mol File:846-50-4.mol
TEMAZEPAM Structure
TEMAZEPAM Chemical Properties
Melting point 119-121°C
Boiling point 211°C (rough estimate)
density 1.2682 (rough estimate)
refractive index 1.5200 (estimate)
Fp 11 °C
storage temp. 2-8°C
solubility Practically insoluble in water, freely soluble in methylene chloride, sparingly soluble in ethanol (96 per cent).
pkapKa 1.6 (Uncertain)
BCS Class2
CAS DataBase Reference846-50-4(CAS DataBase Reference)
IARC3 (Vol. 66) 1996
EPA Substance Registry SystemTemazepam (846-50-4)
Safety Information
Hazard Codes Xn,T,F
Risk Statements 22-39/23/24/25-23/24/25-11
Safety Statements 16-36/37-45-7
RIDADR UN 1230 3/PG 2
WGK Germany 3
RTECS DF1225000
HS Code 2933910000
ToxicityLD50 oral in rat: 2gm/kg
MSDS Information
ProviderLanguage
SigmaAldrich English
TEMAZEPAM Usage And Synthesis
Chemical PropertiesCrystalline Solid
OriginatorLevanxol,Carlo Erba,Italy,1970
UsesPharmacologically active metabolite of Diazepam. Controlled substance (depressant). Sedative, hypnotic
UsesPharmacologically active labelled metabolite of Diazepam. Controlled substance (depressant). Sedative, hypnotic
UsesTemazepam, is pharmacologically active metabolite of Diazepam (D416855). It is Sedative, and hypnotic. Controlled substance (depressant).
DefinitionChEBI: Temazepam is a benzodiazepine.
Manufacturing ProcessAccording to British Patent 1,022,645 3.4 g of 3-acetoxy-7-chloro-1-methyl-5- phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one suspended in 80 ml alcohol was treated with 6 ml of 4 N NaOH. After complete solution had taken place, a solid precipitated; this solid was redissolved by the addition of 80 ml of water. The solution was acidified with acetic acid to give white crystals which were recrystallized from alcohol to yield 7-chloro-3-hydroxy-5-phenyl-1- methyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one, MP 119° to 121°C.
Brand nameRestoril (Tyco); Temaz (Quantum Pharmics).
Therapeutic FunctionTranquilizer
World Health Organization (WHO)Temazepam is a widely used benzodiazepine derivative. As with other drugs in this class, cases of misuse and drug dependence are known.
General DescriptionTemazepam, 7-chloro-1,3-dihydro-3-hydroxy-1-methyl-5-phenyl -2H-1,4-benzodiazepine-2-one(Restoril), also occurs as a minor metabolite of diazepam.It can be visualized as N-methyl oxazepam, and indeed, asmall amount of N-demethylation occurs slowly. However,metabolism proceeds mainly through glucuronidationof the 3-hydroxyl group, thus, it is intermediate acting andmarketed as a hypnotic said to have little or no residualeffect.
Clinical UseBenzodiazepine:
Insomnia (short-term use)
Pre-med anxiolytic prior to minor procedures
Drug interactionsPotentially hazardous interactions with other drugs
Antibacterials: metabolism possibly increased by rifampicin.
Antipsychotics: increased sedative effects; risk of serious adverse effects in combination with clozapine.
Antivirals: concentration possibly increased by ritonavir.
Disulfiram: metabolism of temazepam inhibited (increased toxicity).
Sodium oxybate: enhanced effects of sodium oxybate - avoid.
MetabolismTemazepam is metabolised mainly in the liver. It is excreted mainly in the urine in the form of its inactive glucuronide conjugate together with small amounts of the demethylated derivative, oxazepam, also in conjugated form.
TEMAZEPAM Preparation Products And Raw materials
Raw materialsSodium hydroxide
TEMAZEPAM IMPURITY F 7-chloro-5-(2-fluorophenyl)-1,3-dihydro-3-hydroxy-1-methyl-2H-1,4-benzodiazepin-2-one 3-hydroxyhalazepam camazepam Temazepam acetate TEMAZEPAM - CONTROLLED DRUG - SCHEDULE 3 TEMAZEPAM IMPURITY C Temazepam -D-Glucuronide Temazepam mercury(II)dichloride LORMETAZEPAM ANTI-TEMAZEPAM TEMAZEPAM IMP. A (EP): [5-CHLORO-2-(METHYLAMINO)PHENYL]PHENYLMETHANONE(5-CHLORO-2-(METHYLAMINO)BENZOPHENONE) AURORA KA-7114 AURORA KA-7115 TEMAZEPAM-D5,100/MLINMETHANOL,TEMAZEPAM-D5 Doxefazepam Cinolazepam TEMAZEPAM

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