125-64-4

Basic information

• Product Name: methyprylon
• Synonyms: Methyprylone;2,4-Piperidinedione, 3,3-diethyl-5-methyl-;(+)-Noludar;Ro-1-6463;3,3-diethyl-5-methyl-piperidine-2,4-quinone;2,4-Dioxo-3,3-diethyl-5-methylpiperidine;Nodular;NSC 30442
• CAS NO: 125-64-4
• Molecular Formula: C₁₀H₁₇NO₂
• Molecular Weight: 183.28
• EINECS: 204-745-4
• Mol File: 125-64-4.mol
• Article Data: 0

Chemical Properties

• Melting Point: 74-77°
• Boiling Point: 316.93°C (rough estimate)
• Flash Point: 143.1°C
• Appearance: /
• Density: 1.0612 (rough estimate)
• Vapor Pressure: 8.93E-05mmHg at 25°C
• Refractive Index: 1.4730 (estimate)
• PKA: 12.11±0.70(Predicted)
• Water Solubility: 76g/L(25 oC)
• CAS DataBase Reference: methyprylon(CAS DataBase Reference)
• NIST Chemistry Reference: methyprylon(125-64-4)
• EPA Substance Registry System: methyprylon(125-64-4)

Safety Data

• Hazardous Substances Data: 125-64-4(Hazardous Substances Data)

Usage

Chemical Properties

Nearly white, crystalline powder; slightcharacteristic odor; bitter taste. Melting range 74–77C. Soluble in water; very soluble in alcohol, chlo-roform, ether, and benzene.

Originator

Noludar,Roche,US,1955

Uses

Medicine (sedative, hypnotic).

Manufacturing Process

24 parts by weight of powdered sodium are suspended in 100 parts by volume of absolute benzene and to this suspension is added a freshly prepared solution of 150 parts by weight of methyl formate and 165 parts by weight of 2,4-dioxo-3,3-diethyl-piperidine in 900 parts by volume of absolute benzene. By cooling with cold water, the temperature is maintained at 25° to 28°C. After being stirred for 12 hours 200 parts by volume of 0.6 N sodium hydroxide are added while cooling. The aqueous layer is separated and acidified to Congo red by means of 35% hydrochloric acid. The 2,4-dioxo-3,3- diethyl-5-oxymethylenepiperidine is precipitated in good yield as a solid. After having been recrystallized in chloroform/petroleum ether it melts at 140° to 141°C.5 parts by weight of 2,4-dioxo-3,3-diethyl-5-oxymethylene-piperidine are hydrogenated in 25 parts by volume of methanol in the presence of about 2 parts by weight of Raney nickel at 120°C and under an elevated pressure of 100 atm. Once 2 mols of hydrogen are absorbed, the hydrogenation is interrupted, the solution is separated from the catalyst and concentrated and the residue is distilled in vacuo. The distillate, boiling between 178° and 185°C under a pressure of 16 mm, consists of 2,4-dioxo-3,3-diethyl-5-methylpiperidine, which melts at 74° to 75°C.The same compound is obtained when proceeding according to the following alternative procedure. A mixture of 39.4 parts by weight of 2,4-dioxo-3,3- diethyl-5-oxymethylenepiperidine and 27 parts by weight of dibutylamine are heated to 150°C in a closed vessel. The 2,4-dioxo-3,3-diethyl-5-dibutylaminomethylene-piperidine formed melts at 77°C after having been recrystallized in petroleum ether.31 parts by weight of the latter compound are hydrogenated in 150 parts by volume of alcohol, containing 6 parts by weight of acetic acid, in the presence of 10 parts by weight of Raney nickel, at 120°C and under an elevated pressure of 100 atm. The catalyst is separated and the solution is distilled in vacuo. The 2,4-dioxo-3,3-diethyl-5-methyl-piperidine boils between 178° and 185°C under a pressure of 16 mm and melts at 74° to 75°C.

Brand name

Nolurate.

Therapeutic Function

Sedative, Hypnotic

World Health Organization (WHO)

Methyprylon, a piperidine derivative, was introduced in 1955 for use as a sedative-hypnotic drug. Habituation, tolerance, physical dependence and addiction can occur and methyprylon is controlled under Schedule IV of the 1971 Convention on Psychotropic Substances. (Reference: (UNCPS4) United Nations Convention on Psychotropic Substances (IV), , , 1971)

Hazard

Abuse may cause addiction.

InChI:InChI=1/C10H17NO2/c1-4-10(5-2)8(12)7(3)6-11-9(10)13/h7H,4-6H2,1-3H3,(H,11,13)

Upstream product

• 77-04-3 3,3-diethyl-2,4(1H,3H)-pyridinedione 
• 64-17-5 ethanol 
• 64-19-7 acetic acid 
• 20096-03-1 3,3-diethyl-5-hydroxymethyl-1H-pyridine-2,4-dione 

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1.1. A controlled clinical comparison has been made of placebo, pentobarbital, secobarbital, phenobarbital, methyprylon (Noludar), and meprobamate (Miltown Equanil), in 46 chronically ill patients.2.2. The effects of two dose levels of each drug on induction and duration of sleep, and over-all p...detailed

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Single oral doses of 300 mg of methyprylon were administered to 10 healthy volunteers. Plasma concentrations of methyprylon and its dehydro metabolite were measured using a recently developed HPLC assay. Plasma concentration–time data were fitted to a two-compartment model with either first-ord...detailed

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