| Identification | Back Directory | [Name]
methyprylon | [CAS]
125-64-4 | [Synonyms]
Nodular
NSC 30442
Ro-1-6463
(+)-Noludar
Methyprylone
METHYPRYLON USP/EP/BP
Methyprylon (1.0 mg/mL in Methanol)
2,4-Dioxo-3,3-diethyl-5-methylpiperidine
2,4-Piperidinedione, 3,3-diethyl-5-methyl-
3,3-diethyl-5-methyl-piperidine-2,4-quinone | [EINECS(EC#)]
204-745-4 | [Molecular Formula]
C10H17NO2 | [MOL File]
125-64-4.mol | [Molecular Weight]
183.25 |
| Chemical Properties | Back Directory | [Appearance]
Nearly white, crystalline powder; slightcharacteristic odor; bitter taste. Melting range 74–77C. Soluble in water; very soluble in alcohol, chlo-roform, ether, and benzene. | [Melting point ]
74-77° | [Boiling point ]
316.93°C (rough estimate) | [density ]
1.0612 (rough estimate) | [refractive index ]
1.4730 (estimate) | [solubility ]
Chloroform: soluble; Ethanol: soluble | [form ]
A crystalline solid | [pka]
12.11±0.70(Predicted) | [Water Solubility ]
76g/L(25 ºC) | [Uses]
Medicine (sedative, hypnotic). | [EPA Substance Registry System]
2,4-Piperidinedione, 3,3-diethyl-5-methyl- (125-64-4) |
| Hazard Information | Back Directory | [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. | [Hazard]
Abuse may cause addiction. | [Originator]
Noludar,Roche,US,1955 | [Definition]
ChEBI: Methyprylon is an organic molecular entity. | [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) |
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