Primidone
Names
[ CAS No. ]:
125-33-7
[ Name ]:
Primidone
[Synonym ]:
Prysoline
Primidon
Mysoline
Misodine
MFCD00038662
Sertan
Primidone
EINECS 204-737-0
5-ethyl-5-phenyl-dihydro-pyrimidine-4,6-dione
Mylepsinum
Liskantin
Mizodin
5-ethyl-5-phenyl-1,3-diazinane-4,6-dione
Primaclone
5-Ethyl-5-phenylhexahydropyrimidine-4,6-dione
2-Deoxyphenobarbital
2-Desoxyphenobarbital,5-Ethyl-5-phenylhexahydropyrimidine-4,6-dione
Biological Activity
[Description]:
[Related Catalog]:
[References]
[Related Small Molecules]
Chemical & Physical Properties
[ Density]:
1.138g/cm3
[ Boiling Point ]:
520.7ºC at 760mmHg
[ Melting Point ]:
281-282°C
[ Molecular Formula ]:
C12H14N2O2
[ Molecular Weight ]:
218.25200
[ Flash Point ]:
228.2ºC
[ Exact Mass ]:
218.10600
[ PSA ]:
58.20000
[ LogP ]:
1.19550
[ Vapour Pressure ]:
6.08E-11mmHg at 25°C
[ Index of Refraction ]:
1.528
[ Storage condition ]:
Store at RT
[ Water Solubility ]:
<0.1 g/100 mL at 19 ºC
MSDS
Toxicological Information
CHEMICAL IDENTIFICATION
- RTECS NUMBER :
- UV9100000
- CHEMICAL NAME :
- 4,6(1H,5H)-Pyrimidinedione, 5-ethyldihydro-5-phenyl-
- CAS REGISTRY NUMBER :
- 125-33-7
- BEILSTEIN REFERENCE NO. :
- 0218034
- LAST UPDATED :
- 199712
- DATA ITEMS CITED :
- 33
- MOLECULAR FORMULA :
- C12-H14-N2-O2
- MOLECULAR WEIGHT :
- 218.28
- WISWESSER LINE NOTATION :
- T6MV DVMTJ C2 CR
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Human - woman
- DOSE/DURATION :
- 38 gm/kg/7Y-I
- TOXIC EFFECTS :
- Behavioral - hallucinations, distorted perceptions Behavioral - toxic psychosis
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 1500 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 240 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Unreported
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- >2 gm/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 280 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 332 mg/kg
- TOXIC EFFECTS :
- Behavioral - anticonvulsant
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Unreported
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 340 mg/kg
- TOXIC EFFECTS :
- Behavioral - anticonvulsant
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 10500 mg/kg/14D-C
- TOXIC EFFECTS :
- Behavioral - ataxia Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 17062 mg/kg/13W-C
- TOXIC EFFECTS :
- Liver - other changes Nutritional and Gross Metabolic - weight loss or decreased weight gain
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 27440 mg/kg/14D-C
- TOXIC EFFECTS :
- Behavioral - ataxia Related to Chronic Data - death
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 89 gm/kg/13W-C
- TOXIC EFFECTS :
- Behavioral - somnolence (general depressed activity) Behavioral - ataxia Related to Chronic Data - death
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Primate - monkey
- DOSE/DURATION :
- 2 gm/kg/4D-I
- TOXIC EFFECTS :
- Behavioral - altered sleep time (including change in righting reflex) Behavioral - ataxia
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 10350 mg/kg
- SEX/DURATION :
- female 1-39 week(s) after conception
- TOXIC EFFECTS :
- Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - skin and skin appendages Reproductive - Specific Developmental Abnormalities - cardiovascular (circulatory) system
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 10350 mg/kg
- SEX/DURATION :
- female 1-39 week(s) after conception
- TOXIC EFFECTS :
- Reproductive - Effects on Newborn - other neonatal measures or effects Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 2025 mg/kg
- SEX/DURATION :
- female 1-39 week(s) after conception
- TOXIC EFFECTS :
- Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - cardiovascular (circulatory) system Reproductive - Effects on Newborn - Apgar score (human only)
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Unreported
- DOSE :
- 10640 mg/kg
- SEX/DURATION :
- female 1-38 week(s) after conception
- TOXIC EFFECTS :
- Reproductive - Effects on Newborn - drug dependence Reproductive - Effects on Newborn - physical
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 330 mg/kg
- SEX/DURATION :
- female 6-16 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Specific Developmental Abnormalities - musculoskeletal system
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 990 mg/kg
- SEX/DURATION :
- female 6-16 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Specific Developmental Abnormalities - Central Nervous System
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 875 mg/kg
- SEX/DURATION :
- male 5 day(s) pre-mating
- TOXIC EFFECTS :
- Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 275 mg/kg
- SEX/DURATION :
- female 6-16 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)
- TYPE OF TEST :
- Sperm Morphology
MUTATION DATA
- TYPE OF TEST :
- Micronucleus test
- TEST SYSTEM :
- Rodent - hamster Embryo
- DOSE/DURATION :
- 250 mg/L
- REFERENCE :
- MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 392,61,1997 *** REVIEWS *** TOXICOLOGY REVIEW DICPBB Drug Intelligence and Clinical Pharmacy. (POB 42435, Cincinnati, OH 45242) V.3- 1969- Volume(issue)/page/year: 8,690,1974 TOXICOLOGY REVIEW AUHPAI Australian Journal of Hospital Pharmacy. (B.R. Miller, POB 125, Heidelberg, Vic., Australia) V.1- 1971- Volume(issue)/page/year: 4(1),5,1974 TOXICOLOGY REVIEW DRUGAY Drugs. International Journal of Current Therapeutics and Applied Pharmacology Reviews. (ADIS Press International Inc., Suite B-30, Oxford Ct. Business Center, 582 Middletown Blvd., Langhorne, PA 19047) V.1- 1971- Volume(issue)/page/year: 8,354,1974 TOXICOLOGY REVIEW PRSMA4 Proceedings of the Royal Society of Medicine. (New York, NY) V.1-70, 1907-77. For publisher information, see JRSMD9. Volume(issue)/page/year: 63,48,1970 TOXICOLOGY RIVIEW BMJOAE British Medical Journal. (British Medical Assoc., BMA House, Tavistock Sq., London WC1H 9JR, UK) V.1- 1857- Volume(issue)/page/year: 2,442,1973 TOXICOLOGY REVIEW AJDCAI American Journal of Diseases of Children. (AMA, 535 N. Dearborn St., Chicago, IL 60610) V.1-80(3), 1911-50; V.100- 1960- Volume(issue)/page/year: 131,1337,1977 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X4105 No. of Facilities: 416 (estimated) No. of Industries: 3 No. of Occupations: 6 No. of Employees: 11085 (estimated) No. of Female Employees: 6869 (estimated)
Safety Information
[ Symbol ]:
GHS07, GHS08
[ Signal Word ]:
Warning
[ Hazard Statements ]:
H302-H351
[ Precautionary Statements ]:
P280-P301 + P312 + P330
[ Personal Protective Equipment ]:
Eyeshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges
[ Hazard Codes ]:
Xn: Harmful;
[ Risk Phrases ]:
R22
[ Safety Phrases ]:
S22-S36-S45
[ RIDADR ]:
3249
[ WGK Germany ]:
3
[ RTECS ]:
UV9100000
[ Packaging Group ]:
III
[ Hazard Class ]:
6.1(b)
Synthetic Route
Precursor & DownStream
Precursor
DownStream
Articles
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Carrier Mediated Distribution System (CAMDIS): a new approach for the measurement of octanol/water distribution coefficients.Eur. J. Pharm. Sci. 68 , 68-77, (2015)
Here we present a miniaturized assay, referred to as Carrier-Mediated Distribution System (CAMDIS) for fast and reliable measurement of octanol/water distribution coefficients, log D(oct). By introduc...
How did phenobarbital's chemical structure affect the development of subsequent antiepileptic drugs (AEDs)?Epilepsia 53 Suppl 8 , 3-11, (2012)
Phenobarbital has been in clinical use as an antiepileptic drug (AED) since 1912. The initial clinical success of phenobarbital and other barbiturates affected the design of subsequent AEDs (e.g., phe...