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Name |
Allopurinol |
EINECS | 206-250-9 |
CAS No. | 315-30-0 | Density | 1.702 g/cm3 |
PSA | 74.43000 | LogP | -0.35380 |
Solubility | 0.35 g/L (25 °C) in water | Melting Point |
>300 °C(lit.) |
Formula | C5H4N4O | Boiling Point | 423.27 °C at 760 mmHg |
Molecular Weight | 136.113 | Flash Point | 209.787 °C |
Transport Information | UN 2811 6.1/PG 3 | Appearance | white to off-white solid |
Safety | 28-36/37-45-36/37/39-26-24-36 | Risk Codes | 25-43-36/37/38-20/21/22 |
Molecular Structure | Hazard Symbols | Xi,T, Xn | |
Synonyms |
4H-Pyrazolo(3,4-d)pyrimidin-4-one;Hexanuret;Apulonga;1H-Pyrazolo(3,4-d)pyrimidin-4-ol;Zyloric;4-Hydroxy-1H-pyrazolo[3,4-d]pyrimidine;Lopurin;Monarch;Takanarumin;Dabrosin;Uricemil;Suspendol;2,4,8,9-tetrazabicyclo[4.3.0]nona-1,3,6-trien-5-one;BW 56-158;Urbol;1,5-Dihydro-4H-pyrazolo(3,4-d)pyrimidine-4-one;Alositol;Allozym;Foligan;Milurit;Apurin;Alopurinol [INN-Spanish];Allopurinolum [INN-Latin];Allopurinol (JP14/USP);1, 5-Dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one;4-Hydroxypyrazolyl(3,4-d)pyrimidine;Dura Al;Zyloprim (TN);Urtias 100;Ailural;4H-Pyrazolo[3, 4-d]pyrimidin-4-one, 1,5-dihydro-;Urolit;4-Hydroxypyrazolyl[3, 4-d]pyrimidine;4H-Pyrazolo[3,4-d]pyrimidin-4-one,1,5- dihydro-;Epuric;1H-Pyrazolo[3, 4-d]pyrimidin-4-ol;Gotax;4-Hydroxypyrazolo[3,4-d]pyrimidine;Anoprolin;4-Hydroxy-1H-pyrazolo(3,4-d)pyrimidine;Aluline;Cellidrin;HPP;4-Hydroxypyrazolol(3,4-d)pyrimidine;Allo-Puren;4-Hydroxypyrazolopyrimidine;Nektrohan;Geapur; |
Article Data | 25 |
formic acid
2-cyano-3-morpholinoacrylamide
formamide
4-hydroxypyrazolo(3,4-d)pyrimidine
Conditions | Yield |
---|---|
Stage #1: 2-cyano-3-morpholinoacrylamide With hydrazine hydrate In water at 90 - 100℃; Stage #2: formic acid; formamide at 100 - 170℃; | 96% |
3-methylthio-4-hydroxypyrazolo<3,4-d>pyrimidine
4-hydroxypyrazolo(3,4-d)pyrimidine
Conditions | Yield |
---|---|
nickel In ethanol for 40h; Heating; | 66% |
A
formaldehyd
B
4-(morpholinomethyl)benzoic acid
C
4-hydroxypyrazolo(3,4-d)pyrimidine
Conditions | Yield |
---|---|
In water at 37℃; Product distribution; phosphate buffer pH=7.4, human plasma; other N-subst. N-<<<(aminomethyl)benzoyl>oxy>methyl> drug derivatives; time course of the reaction; |
formamide
3-amino-1H-pyrazole-4-carboxylic acid methyl ester
4-hydroxypyrazolo(3,4-d)pyrimidine
Conditions | Yield |
---|---|
at 155℃; for 11h; Temperature; |
4-hydroxypyrazolo(3,4-d)pyrimidine
Conditions | Yield |
---|---|
With sodium hydroxide In water at 15 - 30℃; for 1h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere; | 81.8% |
4-hydroxypyrazolo(3,4-d)pyrimidine
5-Iodo-4(3H)-oxo-7H-pyrazolo<3,4-d>pyrimidine
Conditions | Yield |
---|---|
With N-iodo-succinimide In N,N-dimethyl-formamide at 110℃; for 18h; | 81% |
Conditions | Yield |
---|---|
With caesium carbonate; copper(l) chloride In 1-methyl-pyrrolidin-2-one for 0.0833333h; Ullmann ether synthesis; microwave irradiation; | 80% |
tris(triphenylphosphine)ruthenium(II) chloride
4-hydroxypyrazolo(3,4-d)pyrimidine
Conditions | Yield |
---|---|
In methanol; dichloromethane for 4h; Schlenk technique; Reflux; | 80% |
Conditions | Yield |
---|---|
With N,N-dimethyl-formamide; trichlorophosphate for 12h; Reflux; | 76% |
With trichlorophosphate In N,N-dimethyl-aniline for 1h; Reflux; | 72% |
With trichlorophosphate In N,N-dimethyl-aniline at 80℃; for 2h; | 70% |
RuCl2(1,4-bis(diphenylphosphino)butane)(PPh3)
4-hydroxypyrazolo(3,4-d)pyrimidine
Conditions | Yield |
---|---|
In methanol; dichloromethane at 20℃; for 0.5h; Schlenk technique; | 70% |
Molecular Structure of Allopurinol (CAS NO.315-30-0):
Molecular Formula: C5H4N4O
Formula Weight: 136.11
Melting point: >300 °C(lit.)
H bond acceptors: 5
H bond donors: 2
Freely Rotating Bonds: 0
Polar Surface Area: 74.69 Å2
Index of Refraction: 1.816
Molar Refractivity: 34.684 cm3
Molar Volume: 79.973 cm3
Surface Tension: 126.431 dyne/cm
Flash Point: 209.787 °C
Enthalpy of Vaporization: 70.382 kJ/mol
Boiling Point: 423.27 °C at 760 mmHg
Vapour Pressure: 0 mmHg at 25°C
Water Solubility: 0.35 g/L (25 °C)
Index of Refraction: 1.902
Density: 1.89 g/cm3
InChI
InChI=1/C5H4N4O/c10-5-3-1-8-9-4(3)6-2-7-5/h1-2H,(H2,6,7,8,9,10)
Smiles
c12c(ncnc1O)[nH]nc2
EINECS: 206-250-9
Product Categories: Pyrimidine; Miscellaneous Natural Products; Heterocyclic Compounds; Antitumors for Research and Experimental Use; Chemical Reagents for Pharmacology Research; Biochemistry; Nucleobases and their analogs; Nucleosides, Nucleotides & Related Reagents; Heterocycles; Intermediates & Fine Chemicals; Pharmaceuticals; Fused Ring Systems;API's; Miscellaneous Enzyme
Allopurinol (CAS NO.315-30-0) is a drug commonly used in treatment of hyperuricemia and chronic gout. Also used to prevent tumor lysis with certain types of cancer.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
man | TDLo | oral | 21429ug/kg/5D (21.429mg/kg) | BEHAVIORAL: MUSCLE WEAKNESS LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED" BLOOD: THROMBOCYTOPENIA | Annals of the Rheumatic Diseases. Vol. 40, Pg. 245, 1981. |
man | TDLo | oral | 120mg/kg/4W-I (120mg/kg) | BLOOD: OTHER CHANGES SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER SYSTEMIC EXPOSURE" SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" | Clinical and Experimental Dermatology. Vol. 19, Pg. 243, 1994. |
mouse | LD50 | intraperitoneal | 214mg/kg (214mg/kg) | BEHAVIORAL: FOOD INTAKE (ANIMAL) BEHAVIORAL: FLUID INTAKE BEHAVIORAL: ATAXIA | Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 64, Pg. 108, 1968. |
mouse | LD50 | oral | 78mg/kg (78mg/kg) | Pharmaceutical Chemistry Journal Vol. 7, Pg. 735, 1973. | |
mouse | LD50 | subcutaneous | 298mg/kg (298mg/kg) | Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 23, Pg. 715, 1981. | |
rabbit | LD | oral | > 100mg/kg (100mg/kg) | Pharmaceutical Chemistry Journal Vol. 7, Pg. 735, 1973. | |
rat | LD | oral | > 500mg/kg (500mg/kg) | Pharmaceutical Chemistry Journal Vol. 7, Pg. 735, 1973. | |
rat | LD50 | intraperitoneal | 900mg/kg (900mg/kg) | Advances in Teratology. Vol. 3, Pg. 181, 1968. | |
rat | LD50 | subcutaneous | 2450mg/kg (2450mg/kg) | Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 11, Pg. 763, 1969. | |
women | LDLo | oral | 88mg/kg/22D-I (88mg/kg) | BLOOD: LEUKOPENIA | Annals of the Rheumatic Diseases. Vol. 40, Pg. 245, 1981. |
women | TDLo | oral | 42mg/kg/7D-I (42mg/kg) | KIDNEY, URETER, AND BLADDER: OTHER CHANGES SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" | American Journal of Medicine. Vol. 76, Pg. 47, 1984 |
Reported in EPA TSCA Inventory.
Human poison by ingestion. Poison experimentally by intraperitoneal and subcutaneous routes. An experimental teratogen. Human systemic effects by ingestion: blood leukopenia, dermatitis, jaundice, muscle weakness, thrombocytopenia. When heated to decomposition it emits toxic fumes of NOx. An FDA proprietary drug used as a xanthine oxidase inhibitor.
Hazard Codes of Allopurinol (CAS NO.315-30-0): T,Xi,Xn
Risk Statements: 25-43-36/37/38-20/21/22
R25: Toxic if swallowed.
R43: May cause sensitization by skin contact.
R36/37/38: Irritating to eyes, respiratory system and skin.
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 28-36/37-45-36/37/39-26-24-36
S28: After contact with skin, wash immediately with plenty of soap-suds.
S36/37: Wear suitable protective clothing and gloves.
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S24: Avoid contact with skin.
S36: Wear suitable protective clothing.
RIDADR: UN 2811 6.1/PG 3
WGK Germany: 2
RTECS: UR0785000
HazardClass: 6.1
PackingGroup: III
Allopurinol , with CAS number of 315-30-0, can be called 4-Hydroxypyrazol[3,4-D]pyrimidine ; 1H-pyrazolo[3,4-d]pyrimidin-4-ol (IM OCS) ; 1,5-Dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one ; 4-Hydroxypyrazolo(3,4-d)pyrimidine ; 1H-Pyrazolo[3,4-d]pyrimidin-4-ol ; 4-Hydroxypyrazolopyrimidine . Allopurinol (CAS NO.315-30-0) is very slightly soluble in cold water. Insoluble in diethyl ether. It is very slightly soluble in alcohol.