Product Name

  • Name

    Warfarin

  • EINECS 201-377-6
  • CAS No. 81-81-2
  • Article Data72
  • CAS DataBase
  • Density 1.308 g/cm3
  • Solubility Practically insoluble
  • Melting Point 162-164 °C(lit.)
  • Formula C19H16O4
  • Boiling Point 515.155 °C at 760 mmHg
  • Molecular Weight 308.334
  • Flash Point 188.828 °C
  • Transport Information UN 2811 6.1/PG 1
  • Appearance crystalline solid
  • Safety 53-45-61-52
  • Risk Codes 61-48/25-52/53
  • Molecular Structure Molecular Structure of 81-81-2 (Warfarin)
  • Hazard Symbols ToxicT
  • Synonyms Coumarin,3-(a-acetonylbenzyl)-4-hydroxy- (7CI,8CI);(RS)-Warfarin;1-(4'-Hydroxy-3'-coumarinyl)-1-phenyl-3-butanone;3-(1'-Phenyl-2'-acetylethyl)-4-hydroxycoumarin;3-(a-Acetonylbenzyl)-4-hydroxycoumarin;3-(a-Phenyl-b-acetylethyl)-4-hydroxycoumarin;4-Hydroxy-3-(3-oxo-1-phenylbutyl)-2H-chromen-2-one;Athrombine-K;Brumolin;Co-Rax;Compound 42;Coumafen;Coumaphen;Coumefene;DL-3-(a-Acetonylbenzyl)-4-hydroxycoumarin;Kumader;Kumadu;Ratron;Rodafarin;Rodafarin C;Rodex;Vampirinip II;Vampirinip III;W.A.R.F. 42;WARF compound 42;Warfarin;Zoocoumarin;rac-Warfarin;
  • PSA 67.51000
  • LogP 3.60960

Synthetic route

4-hydroxy[1]benzopyran-2-one
1076-38-6

4-hydroxy[1]benzopyran-2-one

1-Phenylbut-1-en-3-one
122-57-6

1-Phenylbut-1-en-3-one

Conditions
ConditionsYield
With C23H24N2O6S*Li(1+) In tetrahydrofuran; dimethyl sulfoxide at 0℃; for 48h; Reagent/catalyst; Michael Addition;99%
With lipase In water at 50℃; for 168h; Temperature; Michael Addition; Enzymatic reaction;99.1%
With N-ethyl-N,N-diisopropylamine In water for 20h; Michael Addition; Reflux;93%

warfarin
81-81-2

warfarin

Conditions
ConditionsYield
With polystyrene-divinylbenzene support prepared cyclohexanol as porogen with immobilized 1,5,7-triazabicyclo[4.4.0]dec-5-ene at 100℃; for 96h; Reagent/catalyst; Solvent; Temperature; Time; Michael Addition; Green chemistry;96%
With L-proline In dimethyl sulfoxide at 20℃; for 15h; Michael addition;85%
With rac-Pro-OH In dimethyl sulfoxide at 20℃; for 24h;80%
With cetyltrimethylammonim bromide; 1,4-dihydropyridine-enolate In water at 20℃; for 10h; Michael addition;50%
4-hydroxy[1]benzopyran-2-one
1076-38-6

4-hydroxy[1]benzopyran-2-one

2-phenylethanol
60-12-8

2-phenylethanol

D,L-valine
516-06-3

D,L-valine

warfarin
81-81-2

warfarin

Conditions
ConditionsYield
In dimethyl sulfoxide at 20℃; for 16h;84%
4-hydroxy[1]benzopyran-2-one
1076-38-6

4-hydroxy[1]benzopyran-2-one

warfarin
81-81-2

warfarin

Conditions
ConditionsYield
With cyclopentene In chlorobenzene; toluene at 100℃; for 8h; Inert atmosphere; regioselective reaction;83%
3-(phenyl-λ3-iodanylidene)chromane-2,4-dione
86795-49-5

3-(phenyl-λ3-iodanylidene)chromane-2,4-dione

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

warfarin
81-81-2

warfarin

Conditions
ConditionsYield
In acetonitrile at 80℃; for 12h;76%
(+/-)-Warfarin 4-methyl ether
38063-51-3

(+/-)-Warfarin 4-methyl ether

warfarin
81-81-2

warfarin

Conditions
ConditionsYield
With boron tribromide In dichloromethane -78 up to 0 deg C;
2-methoxywarfarin
102077-97-4

2-methoxywarfarin

warfarin
81-81-2

warfarin

Conditions
ConditionsYield
With boron tribromide In dichloromethane -78 up to 0 deg C;
4-hydroxy[1]benzopyran-2-one
1076-38-6

4-hydroxy[1]benzopyran-2-one

water
7732-18-5

water

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

warfarin
81-81-2

warfarin

4-hydroxy[1]benzopyran-2-one
1076-38-6

4-hydroxy[1]benzopyran-2-one

2-Methoxypropene
116-11-0

2-Methoxypropene

benzaldehyde
100-52-7

benzaldehyde

warfarin
81-81-2

warfarin

Conditions
ConditionsYield
Stage #1: 4-hydroxy[1]benzopyran-2-one; 2-Methoxypropene; benzaldehyde With ethylenediamine diacetic acid In 1,4-dioxane at 90℃; for 4h; tandem Knoevenagel-hetero-Diels-Alder reaction;
Stage #2: With hydrogenchloride; silica gel In water; trifluoroacetic acid at 20℃;
quat-ammonium salt

quat-ammonium salt

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

warfarin
81-81-2

warfarin

Conditions
ConditionsYield
In water
benzaldehyde
100-52-7

benzaldehyde

warfarin
81-81-2

warfarin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1-n-butyl-3-methylimidazolim bromide; bovine serum albumin; tetrabutylammomium bromide / 4 h / 60 °C / Inert atmosphere; Enzymatic reaction
2: 48 h
View Scheme
Multi-step reaction with 2 steps
1: sodium hydroxide / water / Microwave irradiation
2: N-ethyl-N,N-diisopropylamine / water / 20 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1: Fe3O4(at)L-proline/Pd2 NCs / 24 h / 70 °C / Sealed tube
2: water / 12 h / 100 °C
View Scheme
warfarin
81-81-2

warfarin

(1R,2S,5R)-menthyl chloroformate
14602-86-9

(1R,2S,5R)-menthyl chloroformate

Carbonic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 2-oxo-3-(3-oxo-1-phenyl-butyl)-2H-chromen-4-yl ester

Carbonic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 2-oxo-3-(3-oxo-1-phenyl-butyl)-2H-chromen-4-yl ester

Conditions
ConditionsYield
With TEA In 1,2-dichloro-ethane for 0.5h; Ambient temperature;100%
warfarin
81-81-2

warfarin

N-methoxylamine hydrochloride
593-56-6

N-methoxylamine hydrochloride

4-hydroxy-3-(3-(methoxyimino)-1-phenylbutyl)-2H-1-benzopyran-2-one
1103877-12-8

4-hydroxy-3-(3-(methoxyimino)-1-phenylbutyl)-2H-1-benzopyran-2-one

Conditions
ConditionsYield
With pyridine In methanol at 20℃; for 18h;99%
warfarin
81-81-2

warfarin

A

dehydrowarfarin
67588-18-5

dehydrowarfarin

B

C18H12O3

C18H12O3

Conditions
ConditionsYield
With copper(l) iodide In pyridine at 55 - 60℃; for 5h; air;A 98%
B n/a
warfarin
81-81-2

warfarin

Methylenetriphenylphosphorane
19493-09-5

Methylenetriphenylphosphorane

4-hydroxy-3-(3-methyl-1-phenyl-3-butenyl)-2H-1-benzopyran-2-one
92824-18-5

4-hydroxy-3-(3-methyl-1-phenyl-3-butenyl)-2H-1-benzopyran-2-one

Conditions
ConditionsYield
In tetrahydrofuran; dimethyl sulfoxide95%
In tetrahydrofuran; dimethyl sulfoxide65%
warfarin
81-81-2

warfarin

3-nitro-benzaldehyde
99-61-6

3-nitro-benzaldehyde

4-hydroxy-3-[5-(3-nitro-phenyl)-3-oxo-1-phenyl-pent-4-enyl]-chromen-2-one
1189759-41-8

4-hydroxy-3-[5-(3-nitro-phenyl)-3-oxo-1-phenyl-pent-4-enyl]-chromen-2-one

Conditions
ConditionsYield
With sodium hydroxide In water at 20℃;95%
warfarin
81-81-2

warfarin

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

4-hydroxy-3-[5-(4-chloro-phenyl)-3-oxo-1-phenyl-pent-4-enyl]-chromen-2-one
1189759-36-1

4-hydroxy-3-[5-(4-chloro-phenyl)-3-oxo-1-phenyl-pent-4-enyl]-chromen-2-one

Conditions
ConditionsYield
With sodium hydroxide In water at 20℃;93%
warfarin
81-81-2

warfarin

2-chloro-benzaldehyde
89-98-5

2-chloro-benzaldehyde

4-hydroxy-3-[5-(2-chloro-phenyl)-3-oxo-1-phenyl-pent-4-enyl]-chromen-2-one
1189759-37-2

4-hydroxy-3-[5-(2-chloro-phenyl)-3-oxo-1-phenyl-pent-4-enyl]-chromen-2-one

Conditions
ConditionsYield
With sodium hydroxide In water at 20℃;93%
warfarin
81-81-2

warfarin

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

4-hydroxy-3-[5-(4-nitro-phenyl)-3-oxo-1-phenyl-pent-4-enyl]-chromen-2-one
1189759-40-7

4-hydroxy-3-[5-(4-nitro-phenyl)-3-oxo-1-phenyl-pent-4-enyl]-chromen-2-one

Conditions
ConditionsYield
With sodium hydroxide In water at 20℃;93%
warfarin
81-81-2

warfarin

3-fluoro-3-(1-phenyl-3-oxobutyl)-2H-benzopyran-2,4-dione
910618-41-6

3-fluoro-3-(1-phenyl-3-oxobutyl)-2H-benzopyran-2,4-dione

Conditions
ConditionsYield
With N-fluorobis<(trifluoromethyl)sulfonyl>imide In chloroform; water at 35℃; for 0.25h;92%
poly(ethylene glycol), MW=2000, activated to carboxylic groups by succinic anhydride

poly(ethylene glycol), MW=2000, activated to carboxylic groups by succinic anhydride

warfarin
81-81-2

warfarin

A

warfarin conjugated with poly(ethylene glycol), MW=2000

warfarin conjugated with poly(ethylene glycol), MW=2000

B

1,3-Dicyclohexylurea
2387-23-7

1,3-Dicyclohexylurea

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 5h;A 85%
B n/a
furfural
98-01-1

furfural

warfarin
81-81-2

warfarin

4-hydroxy-3-(5-furan-2-yl-3-oxo-1-phenyl-pent-4-enyl)-chromen-2-one
1253372-65-4

4-hydroxy-3-(5-furan-2-yl-3-oxo-1-phenyl-pent-4-enyl)-chromen-2-one

Conditions
ConditionsYield
With sodium hydroxide In water at 20℃;85%
warfarin
81-81-2

warfarin

benzaldehyde
100-52-7

benzaldehyde

4-hydroxy-3-(3-oxo-1,5-diphenyl-pent-4-enyl)-chromen-2-one
1189759-35-0

4-hydroxy-3-(3-oxo-1,5-diphenyl-pent-4-enyl)-chromen-2-one

Conditions
ConditionsYield
With sodium hydroxide In water at 20℃;85%
warfarin
81-81-2

warfarin

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

4-hydroxy-3-[5-(4-methoxy-phenyl)-3-oxo-1-phenyl-pent-4-enyl]-chromen-2-one
1189759-38-3

4-hydroxy-3-[5-(4-methoxy-phenyl)-3-oxo-1-phenyl-pent-4-enyl]-chromen-2-one

Conditions
ConditionsYield
With sodium hydroxide In water at 20℃;85%
warfarin
81-81-2

warfarin

potassium warfarin
2610-86-8

potassium warfarin

Conditions
ConditionsYield
With pyrographite; potassium hydroxide In water; isopropyl alcohol at 75℃; for 8h; pH=7.8 - 8; Product distribution / selectivity; Inert atmosphere;81%
warfarin
81-81-2

warfarin

Warfarin-oxim

Warfarin-oxim

Conditions
ConditionsYield
With pyridine; sodium hydroxide; hydroxylamine hydrochloride In ethanol 1) 12 h, 2) reflux, 6 h;77%
warfarin
81-81-2

warfarin

vanadium(IV) fluoride
10049-16-8

vanadium(IV) fluoride

difluorovanadium(IV)di(4-oxo-3-(oxo-1-phenylbutyl)2H-1-benzopyran-2-one)

difluorovanadium(IV)di(4-oxo-3-(oxo-1-phenylbutyl)2H-1-benzopyran-2-one)

Conditions
ConditionsYield
In methanol methanolic soln. of VF4 added to methanolic soln. of C19H16O4 dropwise with stirring, mixt. had pH 3, refluxed for 2 h, kept overnight with stirring at room temp.; solvent removed on a rotary apparatus under reduced pressure; recrystn. (MeOH/n-hexane, 1/1); elem. anal., detd. by thermal anal.;77%
warfarin
81-81-2

warfarin

1-oxyl-4-carboxyl-2,2,6,6-tetramethylpiperidine
37149-18-1

1-oxyl-4-carboxyl-2,2,6,6-tetramethylpiperidine

2-oxo-3-[(RS)-3-oxo-1-phenylbutyl]-2H-chromen-4-yl 2,2,6,6-tetramethylpiperidine-1-oxyl-4-carboxylate

2-oxo-3-[(RS)-3-oxo-1-phenylbutyl]-2H-chromen-4-yl 2,2,6,6-tetramethylpiperidine-1-oxyl-4-carboxylate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 26h; Inert atmosphere;75%
warfarin
81-81-2

warfarin

acetic anhydride
108-24-7

acetic anhydride

4-acetoxy-3-(3-oxo-1-phenylbutyl)-2H-1-benzopyran-2-one
5979-00-0

4-acetoxy-3-(3-oxo-1-phenylbutyl)-2H-1-benzopyran-2-one

Conditions
ConditionsYield
for 1h; Heating;71.4%
warfarin
81-81-2

warfarin

benzaldehyde
100-52-7

benzaldehyde

methylamine
74-89-5

methylamine

[3',4':5,6]pyrano[3,2-c]pyridine-6(7H)-one

[3',4':5,6]pyrano[3,2-c]pyridine-6(7H)-one

Conditions
ConditionsYield
In ethanol; water Heating; stereoselective reaction;68%
warfarin
81-81-2

warfarin

Benzyl bromoacetate
5437-45-6

Benzyl bromoacetate

C28H24O6

C28H24O6

Conditions
ConditionsYield
In acetone at 45℃; for 48h;65%
warfarin
81-81-2

warfarin

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

trifluoro-methanesulfonic acid 2-oxo-3-(3-oxo-1-phenyl-butyl)-2H-chromen-4-yl ester
929551-51-9

trifluoro-methanesulfonic acid 2-oxo-3-(3-oxo-1-phenyl-butyl)-2H-chromen-4-yl ester

Conditions
ConditionsYield
With triethylamine In chloroform at -5 - 25℃;62%
warfarin
81-81-2

warfarin

Trimethylboroxine
823-96-1

Trimethylboroxine

C20H18O4

C20H18O4

Conditions
ConditionsYield
With pentamethylcyclopentadienyl(benzene)cobalt(III) hexafluorophosphate; potassium carbonate; silver carbonate In 2-methyltetrahydrofuran at 60℃; for 16h; Inert atmosphere; Sealed tube;56%
methanol
67-56-1

methanol

warfarin
81-81-2

warfarin

2-methoxy-2-methyl-4-phenyl-3,4-dihydropyrano[3,2-c]chromen-5(2H)-one
518-20-7, 54288-87-8, 54288-88-9, 64753-99-7, 64754-00-3, 64754-01-4, 65207-43-4, 94902-10-0

2-methoxy-2-methyl-4-phenyl-3,4-dihydropyrano[3,2-c]chromen-5(2H)-one

2-methoxy-2-methyl-4-phenyl-3,4-dihydro-2H-pyrano[3,2-c]chromen-5-one

2-methoxy-2-methyl-4-phenyl-3,4-dihydro-2H-pyrano[3,2-c]chromen-5-one

Conditions
ConditionsYield
With hydrogenchloride for 23h; Reflux;A 53%
B 9%
warfarin
81-81-2

warfarin

benzyl bromide
100-39-0

benzyl bromide

C26H22O4

C26H22O4

Conditions
ConditionsYield
With potassium carbonate In acetone at 25℃; for 24h;38%
warfarin
81-81-2

warfarin

4'-Hydroxywarfarin
24579-14-4

4'-Hydroxywarfarin

Conditions
ConditionsYield
With culture of Cunninghamella bainieri In water for 144h; Product distribution; Ph7 phosphate buffer; metabolism of warfarin to 4'-hydroxywarfarin using the fungus Cunninghamella bainiery, possible mechanism of aromatic hydroxylation, primary isotope effect; inhibition of hydroxylation by CO;2 mg

Warfarin History

1. The early 1920s saw the outbreak of a previously unrecognized disease of cattle in the northern United States and Canada. Cattle would die of uncontrollable bleeding from very minor injuries, or sometimes drop dead of internal hemorrhage with no external signs of injury. In 1921, Frank Schofield, a Canadian veterinarian, determined that the cattle were ingesting moldy silage made from sweet clover that functioned as a potent anticoagulant.In 1929, North Dakota veterinarian Dr L.M. Roderick demonstrated that the condition was due to a lack of functioning prothrombin.
2. After an incident in 1951, where a US Army inductee unsuccessfully attempted suicide with warfarin and recovered fully,studies began in the use of warfarin as a therapeutic anticoagulant
3. A 2003 theory posits that warfarin was used by a conspiracy of Lavrenty Beria, Nikita Khrushchev and others to poison Soviet leader Joseph Stalin.
 

Warfarin Specification

The CAS registry number of Warfarin is 81-81-2. The IUPAC name is 4-hydroxy-3-(3-oxo-1-phenylbutyl)-2H-chromen-2-one. Its EINECS registry number is 201-377-6. In addition, the molecular formula is C19H16O4 and the molecular weight is 308.33. It is a kind of white to off-white crystalline powder and belongs to the classes of Coumarins; Insecticide; Intermediates & Fine Chemicals; Pharmaceuticals; Miscellaneous Compounds. And it is a synthetic derivative of dicoumarol, a 4-hydroxycoumarin-derived mycotoxin anticoagulant originally discovered in spoiled sweet clover-based animal feeds.

Physical properties about this chemical are: (1)ACD/LogP: 3.13 ; (2)ACD/LogD (pH 5.5): 2; (3)ACD/LogD (pH 7.4): 1; (4)ACD/BCF (pH 5.5): 21; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 157; (7)ACD/KOC (pH 7.4): 3; (8)#H bond acceptors: 4; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 5; (11)Polar Surface Area: 63.6 Å2; (12)Index of Refraction: 1.635; (13)Molar Refractivity: 84.447 cm3; (14)Molar Volume: 235.758 cm3; (15)Polarizability: 33.477 ×10-24cm3; (16)Surface Tension: 58.658 dyne/cm; (17)Density: 1.308 g/cm3; (18)Flash Point: 188.828 °C; (19)Enthalpy of Vaporization: 82.854 kJ/mol; (20)Boiling Point: 515.155 °C at 760 mmHg.

Preparation of Warfarin: it can be prepared by 4-hydroxy-chromen-2-one and 4-phenyl-but-3-en-2-one. This reaction will need catalyst triethylbenzylammonium chloride and solvent H2O. The reaction time is 2 hours by heating. The yield is about 82%.

Warfarin can be prepared by 4-hydroxy-chromen-2-one and 4-phenyl-but-3-en-2-one

Uses of Warfarin: is used to decrease the tendency for thrombosis or as secondary prophylaxis (prevention of further episodes) in those individuals that have already formed a blood clot (thrombus). And is also used in antiphospholipid syndrome. It has been used occasionally after heart attacks (myocardial infarctions), but is far less effective at preventing new thromboses in coronary arteries. In addition, it can be used to get 3-fluoro-3-(3-oxo-1-phenyl-butyl)-chroman-2,4-dione. This reaction will need reagent (CF3SO2)2NF and solvent CHCl3 and H2O. The reaction time is 15 minutes at reaction temperature of 35 °C. The yield is about 92%.

Warfarin can be used to get 3-fluoro-3-(3-oxo-1-phenyl-butyl)-chroman-2,4-dione

When you are using this chemical, please be cautious about it as the following:
It is toxic if swallowed and may cause harm to the unborn child. And it has danger of serious damage to health by prolonged exposure. In addition, it is harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment. It is refer to special instructions/safety data sheets. Avoid exposure - obtain special instructions before use. During using it, not recommended for interior use on large surface areas. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.). You should avoid release to the environment.

You can still convert the following datas into molecular structure:
(1)SMILES: CC(=O)CC(C\1=C(/O)c2ccccc2OC/1=O)c3ccccc3
(2)InChI: InChI=1/C19H16O4/c1-12(20)11-15(13-7-3-2-4-8-13)17-18(21)14-9-5-6-10-16(14)23-19(17)22/h2-10,15,21H,11H2,1H3
(3)InChIKey: PJVWKTKQMONHTI-UHFFFAOYAW

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 oral 6mg/kg (6mg/kg)   Defense des Vegetaux. Vol. 32, Pg. 27, 1978.
chicken LD50 oral 942mg/kg (942mg/kg) PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BLOOD: HEMORRHAGE
Bulletin of Environmental Contamination and Toxicology. Vol. 37, Pg. 544, 1986.
dog LD50 oral 3mg/kg (3mg/kg)   Defense des Vegetaux. Vol. 43(255-256), Pg. 20, 1989.
guinea pig LD50 oral 180mg/kg (180mg/kg)   Defense des Vegetaux. Vol. 32, Pg. 27, 1978.
human LDLo oral 6667ug/kg (6.667mg/kg)   Yakkyoku. Pharmacy. Vol. 28, Pg. 329, 1977.
man TDLo oral 10200ug/kg (10.2mg/kg) BLOOD: HEMORRHAGE "Clinical Memoranda on Economic Poisons," U.S. Dept. HEW, Public Health Service, Communicable Disease Center, Atlanta, GA, 1956Vol. -, Pg. 1, 1956.
mouse LD50 intraperitoneal 750mg/kg (750mg/kg)   European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 30, Pg. 531, 1995.
mouse LD50 intravenous 165mg/kg (165mg/kg)   "Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. 274, 1973.
mouse LD50 oral 3mg/kg (3mg/kg)   Defense des Vegetaux. Vol. 43(255-256), Pg. 20, 1989.
mouse LD50 unreported 60mg/kg (60mg/kg)   Yakkyoku. Pharmacy. Vol. 30, Pg. 397, 1979.
mouse LDLo subcutaneous 800mg/kg (800mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: FOOD INTAKE (ANIMAL)
Trudy, VNIIVS. Transactions of the All-Union Scientific Research Institute of Veterinary Sanitation. Vol. 58, Pg. 122, 1977.
pig LD50 oral 1mg/kg (1mg/kg)   Defense des Vegetaux. Vol. 32, Pg. 27, 1978.
rabbit LD50 oral 800mg/kg (800mg/kg)   Defense des Vegetaux. Vol. 32, Pg. 27, 1978.
rat LC50 inhalation 320mg/m3 (320mg/m3)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 22(7), Pg. 49, 1978.
rat LD50 oral 1600ug/kg (1.6mg/kg)   Toxicology and Applied Pharmacology. Vol. 11, Pg. 327, 1967.
rat LD50 skin 1400mg/kg (1400mg/kg) SENSE ORGANS AND SPECIAL SENSES: CHROMODACYRORREA: EYE

KIDNEY, URETER, AND BLADDER: HEMATURIA

BEHAVIORAL: MUSCLE WEAKNESS
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 22(7), Pg. 49, 1978.
rat LD50 unreported 50mg/kg (50mg/kg)   Yakkyoku. Pharmacy. Vol. 30, Pg. 397, 1979.
rat LDLo intraperitoneal 420mg/kg (420mg/kg)   Toxicology and Applied Pharmacology. Vol. 1, Pg. 156, 1959.
women TDLo oral 250ug/kg/2D-I (0.25mg/kg) VASCULAR: STRICTIRA; CJAMGES OM VESSE;S American Journal of Emergency Medicine. Vol. 16, Pg. 541, 1998.
women TDLo oral 15mg/kg/21W-I (15mg/kg) GASTROINTESTINAL: ULCERATION OR BLEEDING FROM SMALL INTESTINE

BLOOD: CHANGE IN CLOTTING FACTORS
Southern Medical Journal. Vol. 75, Pg. 242, 1982.

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