methyprylon
- CAS No.
- 125-64-4
- Chemical Name:
- methyprylon
- 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
- CBNumber:
- CB5890862
- Molecular Formula:
- C10H17NO2
- Molecular Weight:
- 183.25
- MDL Number:
- MOL File:
- 125-64-4.mol
| 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) |
| EWG's Food Scores | 1 |
| FDA UNII | CUT48I42ON |
| EPA Substance Registry System | 2,4-Piperidinedione, 3,3-diethyl-5-methyl- (125-64-4) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |   GHS07,GHS05 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Danger | |||||||||
| Hazard statements | H302-H335-H315-H318-H317 | |||||||||
| Precautionary statements | P264-P270-P301+P312-P330-P501-P264-P280-P302+P352-P321-P332+P313-P362-P261-P272-P280-P302+P352-P333+P313-P321-P363-P501-P280-P305+P351+P338-P310 | |||||||||
| NFPA 704 |
|
methyprylon Chemical Properties,Uses,Production
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).
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)
Hazard
Abuse may cause addiction.