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125-33-7

Basic Information
CAS No.: 125-33-7
Name: Primidone
Article Data: 16
Molecular Structure:
Molecular Structure of 125-33-7 (Primidone)
Formula: C12H14N2O2
Molecular Weight: 218.255
Synonyms: 2-Deoxyphenobarbital;2-Desoxyphenobarbital;5-Ethyl-5-phenylhexahydropyrimidine-4,6-dione;5-Ethyldihydro-5-phenyl-4,6(1H,5H)-pyrimidinedione;Resimatil;Roe101;Primakton;Primidon;Pyrimidone Medi-pets;Primacone;Primaclone;Lepimidin;Misodine;Mizolin;Mylepsin;Mysoline;Neurosyn;Sertan;5-Phenyl-5-ethyl-hexahydropyrimidine-4,6-dione;Hexamidine(antiepileptic);Hexamydin;5-Ethylhexahydro-5-phenylpyrimidine-4,6-dione;
EINECS: 204-737-0
Density: 1.138 g/cm3
Melting Point: 281-282 °C
Boiling Point: 520.7 °C at 760 mmHg
Flash Point: 228.2 °C
Solubility: <0.1 g/100 mL at 19 °C
Appearance: Crystalline solid
Hazard Symbols: HarmfulXn
Risk Codes: 22-40
Safety: 22-36-45
Transport Information: UN 3249
PSA: 58.20000
LogP: 1.19550
Synthetic route
2753-74-4

5-ethyl-5-phenyl-2-thiobarbituric acid

125-33-7

pirimidone

Conditions
ConditionsYield
With sodium tetrahydroborate; nickel dichloride In methanol at 20℃; for 5.75h;81%
With ethanol; nickel
Multi-step reaction with 2 steps
1: 44 percent / 17 h / 22 °C / Irradiation
2: 42 percent / butan-1-ol / 17 h / 22 °C / Irradiation
View Scheme
64-18-6

formic acid

7206-76-0

2-ethyl-2-phenylmalonamide

125-33-7

pirimidone

Conditions
ConditionsYield
for 2h; Product distribution; Further Variations:; reaction time, effect of microwave activation; heterocyclization; Heating;79%
7206-76-0

2-ethyl-2-phenylmalonamide

125-33-7

pirimidone

Conditions
ConditionsYield
at 210℃; for 6h; heterocyclization;54%
117752-97-3

2-Ethoxy-5-ethyl-2-dihydro-5-phenyl-4,6(1H,5H)-pyrimidinedione

125-33-7

pirimidone

Conditions
ConditionsYield
In butan-1-ol at 22℃; for 17h; Irradiation;42%
With formamide durch Reduktion;
With formic acid durch Reduktion;
694447-38-6

5-ethyl-5-phenyl-1H-pyrimidine-4,6-dione

125-33-7

pirimidone

Conditions
ConditionsYield
With Pd/SrCO3; ethanol Hydrogenation;
With hydrogen; nickel
With ethanol; Pd/CaCO3 Hydrogenation;
With hydrogen; nickel
7206-76-0

2-ethyl-2-phenylmalonamide

125-33-7

pirimidone

Conditions
ConditionsYield
With formamide
With formamide
50-06-6

phenobarbital

125-33-7

pirimidone

Conditions
ConditionsYield
durch elektrochemische Reduktion;
durch elektrochemische Reduktion;
857411-80-4

5-ethyl-2-methoxy-5-phenyl-1H-pyrimidine-4,6-dione

125-33-7

pirimidone

Conditions
ConditionsYield
With ethanol; nickel
With ethanol; nickel
343339-89-9, 343339-90-2, 156546-57-5

S-methyl-2-thiophenobarbital

125-33-7

pirimidone

Conditions
ConditionsYield
With ethanol; nickel
With ethanol; nickel
7206-76-0

2-ethyl-2-phenylmalonamide

144-62-7

oxalic acid

125-33-7

pirimidone

Downstream Products
7206-76-0
50-06-6
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Chemistry

The chemical name of 2-DESOXYPHENOBARBITAL(125-33-7) is Primidone,the IUPAC name is 5-ethyl-5-phenyl-1,3-diazinane-4,6-dione.its molecular formula is C12H14N2O2,with the formula weight is 218.25 g/mol.
CAS No.: 125-33-7
EINECS: 204-737-0
RTECS: UV9100000
RTECS Class: Tumorigen; Drug; Mutagen; Reproductive Effector; Human Data 
The density of 2-DESOXYPHENOBARBITAL(125-33-7) is 1.138 g/cm3 and it has a flash point of 228.2 °C,The boiling point is 520.7 °C at 760 mmHg .The appearance of 2-DESOXYPHENOBARBITAL(125-33-7) is odorless white crystalline powder. it is slightly bitter taste,no acidic properties and insoluble in water .Following is the structure of 2-DESOXYPHENOBARBITAL(125-33-7):

              
The chemical synonymous of 2-DESOXYPHENOBARBITAL(125-33-7) are 2-deoxyphenobarbital;2-DESOXYPHENOBARBITAL;5-ETHYLDIHYDRO-5-PHENYL-4,6(1H,5H)-PYRIMIDINEDIONE;5-phenyl-5-ethyl-hexahydropyrimidine-4,6-dione;PRIMIDONE;4,6(1H,5H)-Pyrimidinedione, 5-ethyldihydro-5-phenyl-;5-Aethyl-5-phenyl-hexahydropyrimidin-4,6-dion;5-Ethyl-5-phenyldihydro-4,6(1H,5H)-pyrimidinedione.

Uses

2-DESOXYPHENOBARBITAL(125-33-7) is used for epilepsy grand mal and psychomotor seizures and uesd as Anticonvulsant.

Production

Product Categories about 2-DESOXYPHENOBARBITAL(125-33-7) are Intermediates & Fine Chemicals;Pharmaceuticals;GABA/Glycine receptor

Toxicity Data With Reference

1.   

mmo-sat 6666 µg/plate

   ENMUDM    Environmental Mutagenesis. 8 (Suppl 7)(1986),1.
2.   

cyt-hmn:leu 1 mg/L

   AJOGAH    American Journal of Obstetrics and Gynecology. 116 (1973),867.
3.   

orl-wmn TDLo:38 g/kg/7Y-I

   DICPBB    Drug Intelligence and Clinical Pharmacy. 17 (1983),551.
4.   

orl-rat LD50:1500 mg/kg

   NIIRDN    “Drugs in Japan. Ethical Drugs, 6th Edition 1982“ Edited by Japan Pharmaceutical Information Center. 6 (1982),691.
5.   

ipr-rat LD50:240 mg/kg

   PCJOAU    Pharmaceutical Chemistry Journal (English Translation). Translation of KHFZAN. 25 (1991),305.
6.   

orl-mus LD50:280 mg/kg

   TXAPA9    Toxicology and Applied Pharmacology. 34 (1975),271.
7.   

ipr-mus LD50:332 mg/kg

   PCJOAU    Pharmaceutical Chemistry Journal (English Translation). Translation of KHFZAN. 15 (1981),403.

child     TDLo     oral   625mg/kg (625mg/kg)   BEHAVIORAL: GENERAL ANESTHETICBEHAVIORAL: SLEEPBEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)   British Medical Journal. Vol. 1, Pg. 90, 1957.
mouse     LD50     intraperitoneal   332mg/kg (332mg/kg)   BEHAVIORAL:   ANTICONVULSANT Pharmaceutical Chemistry Journal Vol. 15, Pg. 403, 1981.
mouse     LD50     oral   280mg/kg (280mg/kg)     Toxicology and Applied Pharmacology. Vol. 34, Pg. 271, 1975.
mouse     LD50     unreported   340mg/kg (340mg/kg)   BEHAVIORAL: ANTICONVULSANT Russian Pharmacology and Toxicology Vol. 43, Pg. 73, 1980.
rat     LD50     intraperitoneal   240mg/kg (240mg/kg)     Pharmaceutical Chemistry Journal Vol. 25, Pg. 305, 1991.
rat     LD50     oral   1500mg/kg (1500mg/kg)     Drugs in Japan Vol. 6, Pg. 691, 1982.
rat     LD50     unreported   > 2gm/kg (2000mg/kg)     British Journal of Pharmacology and Chemotherapy. Vol. 8, Pg. 230, 1953.
women     TDLo     oral   5mg/kg (5mg/kg)   BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)BEHAVIORAL: HEADACHE
GASTROINTESTINAL:   NAUSEA OR VOMITING   Lancet. Vol. 266, Pg. 102, 1954.
women     TDLo     oral   450mg/kg (450mg/kg)   BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)BEHAVIORAL: ATAXIA
BEHAVIORAL:   ANTIPSYCHOTIC Archives of Neurology Vol. 30, Pg. 255, 1974.
women     TDLo     oral   38gm/kg/7Y-I (38000mg/kg)   BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"BEHAVIORAL:   TOXIC PSYCHOSIS   Drug Intelligence and Clinical Pharmacy. Vol. 17, Pg. 551, 1983.

Safety Profile

Poison by ingestion and intraperitoneal routes. Human teratogenic effects include developmental abnormalities of the craniofacial area, skin and skin appendages, and cardiovascular system. Human reproductive effects: effects on newborn, including unusual growth statistics, drug dependence, physical and other neonatal changes. Experimental teratogenic and reproductive effects. Human mutation data reported. An addictive drug. When heated to decomposition it emits toxic fumes of NOx. See also BARBITURATES.
Hazard Codes:
    Xn: Harmful 
Risk Statements about 2-DESOXYPHENOBARBITAL(125-33-7):
    R22 Harmful if swallowed.
    R40 Limited evidence of a carcinogenic effect.
Safety Statements about 2-DESOXYPHENOBARBITAL(125-33-7):
    S22 Do not breathe dust.
    S36 Wear suitable protective clothing.
    S45 In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

Specification

1. Storage: Keep in a cool, dry, dark location in a tightly sealed container or cylinder. Keep away from incompatible materials, ignition sources and untrained individuals.Protect containers/cylinders from physical damage.
2. Handling: All chemicals should be considered hazardous. Avoid direct physical contact. Use appropriate, approved safety equipment. Untrained individuals should not handle this chemical or its container. Handling should occur in a chemical fume hood.
3. Personal Protection: Chemical splash goggles in compliance with OSHA regulations are advised; however, OSHA regulations also permit other type safety glasses. Whre chemical resistant gloves. To prevent repeated or prolonged skin contact, wear impervious clothing and boots.