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TEMAZEPAM

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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
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TEMAZEPAM Chemical Properties

Melting point:
119-121°C
Boiling point:
211°C (rough estimate)
Density 
1.2682 (rough estimate)
refractive index 
1.5200 (estimate)
Flash point:
11 °C
storage temp. 
2-8°C
solubility 
Practically insoluble in water, freely soluble in methylene chloride, sparingly soluble in ethanol (96 per cent).
pka
pKa 1.6 (Uncertain)
BCS Class
2
CAS DataBase Reference
846-50-4(CAS DataBase Reference)
IARC
3 (Vol. 66) 1996
EPA Substance Registry System
Temazepam (846-50-4)
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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
Toxicity
LD50 oral in rat: 2gm/kg

MSDS

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TEMAZEPAM Usage And Synthesis

Chemical Properties

Crystalline Solid

Originator

Levanxol,Carlo Erba,Italy,1970

Uses

Pharmacologically active metabolite of Diazepam. Controlled substance (depressant). Sedative, hypnotic

Uses

Pharmacologically active labelled metabolite of Diazepam. Controlled substance (depressant). Sedative, hypnotic

Uses

Temazepam, is pharmacologically active metabolite of Diazepam (D416855). It is Sedative, and hypnotic. Controlled substance (depressant).

Definition

ChEBI: Temazepam is a benzodiazepine.

Manufacturing Process

According 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 name

Restoril (Tyco); Temaz (Quantum Pharmics).

Therapeutic Function

Tranquilizer

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 Description

Temazepam, 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 Use

Benzodiazepine:
Insomnia (short-term use)
Pre-med anxiolytic prior to minor procedures

Drug interactions

Potentially 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.

Metabolism

Temazepam 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.

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