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315-30-0

Basic Information
CAS No.: 315-30-0
Name: Allopurinol
Molecular Structure:
Molecular Structure of 315-30-0 (Allopurinol)
Formula: C5H4N4O
Molecular Weight: 136.13
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;
EINECS: 206-250-9
Density: 1.702 g/cm3
Melting Point: >300 °C(lit.)
Boiling Point: 423.27 °C at 760 mmHg
Flash Point: 209.787 °C
Solubility: 0.35 g/L (25 °C) in water
Appearance: white to off-white solid
Hazard Symbols: IrritantXi,ToxicT, HarmfulXn
Risk Codes: 25-43-36/37/38-20/21/22
Safety: 28-36/37-45-36/37/39-26-24-36
Transport Information: UN 2811 6.1/PG 3
PSA: 74.43000
LogP: -0.35380
Synthetic route
64-18-6

formic acid

25229-97-4

2-cyano-3-morpholinoacrylamide

315-30-0

4-hydroxypyrazolo(3,4-d)pyrimidine

Conditions
ConditionsYield
Stage #1: 2-cyano-3-morpholinoacrylamide With hydrazine hydrate In water at 90 - 100℃;
Stage #2: formic acid; formamide at 100 - 170℃;
96%
90914-36-6

3-methylthio-4-hydroxypyrazolo<3,4-d>pyrimidine

315-30-0

4-hydroxypyrazolo(3,4-d)pyrimidine

Conditions
ConditionsYield
nickel In ethanol for 40h; Heating;66%

1-({[4-(morpholinomethyl)-benzoyl]oxy}methyl)allopurinol

A

50-00-0

formaldehyd

B

62642-62-0

4-(morpholinomethyl)benzoic acid

C

315-30-0

4-hydroxypyrazolo(3,4-d)pyrimidine

Conditions
ConditionsYield
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;
29097-00-5

3-amino-1H-pyrazole-4-carboxylic acid methyl ester

315-30-0

4-hydroxypyrazolo(3,4-d)pyrimidine

Conditions
ConditionsYield
at 155℃; for 11h; Temperature;
315-30-0

4-hydroxypyrazolo(3,4-d)pyrimidine

allopurinol sodium

Conditions
ConditionsYield
With sodium hydroxide In water at 15 - 30℃; for 1h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;81.8%
315-30-0

4-hydroxypyrazolo(3,4-d)pyrimidine

144750-83-4

5-Iodo-4(3H)-oxo-7H-pyrazolo<3,4-d>pyrimidine

Conditions
ConditionsYield
With N-iodo-succinimide In N,N-dimethyl-formamide at 110℃; for 18h;81%
695-96-5

2-bromo-4-chlorophenol

315-30-0

4-hydroxypyrazolo(3,4-d)pyrimidine

4-chloro-2-[pyrazolo[3,4-d]pyrimidine-4-yloxy]phenol

Conditions
ConditionsYield
With caesium carbonate; copper(l) chloride In 1-methyl-pyrrolidin-2-one for 0.0833333h; Ullmann ether synthesis; microwave irradiation;80%
15529-49-4, 41756-81-4

tris(triphenylphosphine)ruthenium(II) chloride

315-30-0

4-hydroxypyrazolo(3,4-d)pyrimidine

C46H38Cl2N8O2P2Ru

Conditions
ConditionsYield
In methanol; dichloromethane for 4h; Schlenk technique; Reflux;80%
315-30-0

4-hydroxypyrazolo(3,4-d)pyrimidine

5399-92-8

4-chloro-1H-pyrazolo[3,4-d]pyrimidine

Conditions
ConditionsYield
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%
88496-72-4

RuCl2(1,4-bis(diphenylphosphino)butane)(PPh3)

315-30-0

4-hydroxypyrazolo(3,4-d)pyrimidine

C38H36Cl2N8O2P2Ru

Conditions
ConditionsYield
In methanol; dichloromethane at 20℃; for 0.5h; Schlenk technique;70%
961-07-9

2'-Deoxyguanosine

315-30-0

4-hydroxypyrazolo(3,4-d)pyrimidine

95087-12-0

8-aza-7-deaza-2'-deoxyinosine

Conditions
ConditionsYield
With purine nucleoside phosphorylase at 50℃; pH=7; aq. phosphate buffer; Enzymatic reaction;68%
315-30-0

4-hydroxypyrazolo(3,4-d)pyrimidine

101834-30-4

1-bromo-2-(10β-dihydroartemisinoxy)ethane

C39H56N4O11

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 2.5h;63.4%
315-30-0

4-hydroxypyrazolo(3,4-d)pyrimidine

95087-12-0

8-aza-7-deaza-2'-deoxyinosine

Conditions
ConditionsYield
With purine nucleoside phosphorylase; phosphopentomutase; ribokinase; potassium chloride; ATP; manganese(ll) chloride at 40℃; for 10h; pH=7.5; aq. buffer; Enzymatic reaction; regiospecific reaction;60%
98-16-8

3-trifluoromethylaniline

315-30-0

4-hydroxypyrazolo(3,4-d)pyrimidine

4-(3-trifluoromethylanilino)-1H-pyrazolo<3,4-d>pyrimidine

Conditions
ConditionsYield
With phosphorus pentoxide; triethylamine hydrochloride at 200℃; for 24h;59%
315-30-0

4-hydroxypyrazolo(3,4-d)pyrimidine

320-51-4

4-chloro-3-trifluoromethyl-aniline

(4-Chloro-3-trifluoromethyl-phenyl)-(1H-pyrazolo[3,4-d]pyrimidin-4-yl)-amine

Conditions
ConditionsYield
With phosphorus pentoxide; triethylamine hydrochloride at 200℃; for 3h;56%
108-42-9

3-chloro-aniline

315-30-0

4-hydroxypyrazolo(3,4-d)pyrimidine

(3-Chloro-phenyl)-(1H-pyrazolo[3,4-d]pyrimidin-4-yl)-amine

Conditions
ConditionsYield
With phosphorus pentoxide; triethylamine hydrochloride at 200℃; for 3h;50%
108-69-0

3,5-dimethylaminoaniline

315-30-0

4-hydroxypyrazolo(3,4-d)pyrimidine

(3,5-Dimethyl-phenyl)-(1H-pyrazolo[3,4-d]pyrimidin-4-yl)-amine

Conditions
ConditionsYield
With phosphorus pentoxide; triethylamine hydrochloride at 150℃; for 3h;48%
315-30-0

4-hydroxypyrazolo(3,4-d)pyrimidine

101834-30-4

1-bromo-2-(10β-dihydroartemisinoxy)ethane

C22H30N4O6

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 2.5h;35.2%
315-30-0

4-hydroxypyrazolo(3,4-d)pyrimidine

371-40-4

4-fluoroaniline

(4-Fluoro-phenyl)-(1H-pyrazolo[3,4-d]pyrimidin-4-yl)-amine

Conditions
ConditionsYield
With phosphorus pentoxide; triethylamine hydrochloride at 150℃; for 3h;31%

(2S,3R,4R,5S)-2-[N-benzyl-N-(p-toluenesulfonyl)]aminomethyl 3,4-dibenzyloxy-5-(p-toluenesulfonyl)methyl-1-N-(p-toluenesulfonyl)pyrrolidine

315-30-0

4-hydroxypyrazolo(3,4-d)pyrimidine

A

(2S,3R,4R,5S)-2-N-[benzyl-N-(p-toluenesulfonyl)]aminomethyl-3,4-bis(benzyloxy)-5-(N8-allopurinol)-1-N-(ptoluenesulfonyl)pyrrolidine

B

(2S,3R,4R,5S)-2-N-[benzyl-N-(p-toluenesulfonyl)]aminomethyl-3,4-bis(benzyloxy)-5-(N9-allopurinol)-1-N-(p-toluenesulfonyl)pyrrolidine

C

(2S,3R,4R,5S)-2-N-[benzyl-N-(p-toluenesulfonyl)]aminomethyl-3,4-bis(benzyloxy)-5-(N-2-allopurinol)-1-N-(p-toluenesulfonyl)pyrrolidine

Conditions
ConditionsYield
With 18-crown-6 ether; potassium carbonate In N,N-dimethyl-formamide at 85℃; for 8h;A 31%
B n/a
C n/a
106-47-8

4-chloro-aniline

315-30-0

4-hydroxypyrazolo(3,4-d)pyrimidine

ETP-45852

Conditions
ConditionsYield
With phosphorus pentoxide; triethylamine hydrochloride at 200℃; for 2.5h;26%
315-30-0

4-hydroxypyrazolo(3,4-d)pyrimidine

58-96-8

uridine

16220-07-8

1-β-D-ribofuranosyl-1H-pyrazolo<3,4-d>pyrimidin-4-one

Conditions
ConditionsYield
With dipotassium hydrogenphosphate at 36℃; for 144h; pH 7.2, purine nucleoside phosphorylase, uridine phosphorylase;24%
62-53-3

aniline

315-30-0

4-hydroxypyrazolo(3,4-d)pyrimidine

99973-41-8

N-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Conditions
ConditionsYield
With phosphorus pentoxide; triethylamine hydrochloride at 150℃; for 1.5h;21%
315-30-0

4-hydroxypyrazolo(3,4-d)pyrimidine

A

1,5-bis((6E)‐3,7,11‐trimethyldodeca‐2,6,10‐trien‐1‐yl)‐1,5‐dihydro‐4H-pyrazolo[3,4‐d]pyrimidin‐4‐one

B

2,7‐bis((6E)-3,7,11‐trimethyldodeca‐2,6,10‐trien‐1‐yl)‐2,7‐dihydro‐4H-pyrazolo[3,4‐d]pyrimidin‐4‐one

C

5‐((2E,6E)-3,7,11‐trimethyldodeca‐2,6,10‐trien‐1‐yl)‐5H-pyrazolo[3,4‐d]pyrimidin‐4‐ol

Conditions
ConditionsYield
Stage #1: 4-hydroxypyrazolo(3,4-d)pyrimidine With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: farnesyl bromide In N,N-dimethyl-formamide at 70℃; for 27h; Inert atmosphere;
A 12%
B 4%
C 21%

C10H10Cl4N2O2

315-30-0

4-hydroxypyrazolo(3,4-d)pyrimidine

2-(pyridin-2-yl)ethyl N-(2,2,2-trichloro-1-(4-hydroxy-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)carbamate

Conditions
ConditionsYield
In dichloromethane; acetonitrile at 20 - 60℃; Inert atmosphere;7.22%
6138-90-5

trans-geranyl bromide

315-30-0

4-hydroxypyrazolo(3,4-d)pyrimidine

(E)-5‐(3,7‐dimethylocta‐2,6‐dien‐1‐yl)‐5H-pyrazolo[3,4‐d]pyrimidin‐4‐ol

Conditions
ConditionsYield
Stage #1: 4-hydroxypyrazolo(3,4-d)pyrimidine With sodium carbonate; potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: trans-geranyl bromide In N,N-dimethyl-formamide for 24h; Inert atmosphere;
2%
50848-64-1

2E,6E,10E-geranylgeranyl bromide

315-30-0

4-hydroxypyrazolo(3,4-d)pyrimidine

1,5‐bis((2E,6E,10E)-3,7,11,15‐tetramethylhexadeca‐2,6,10,14‐tetraen‐1‐yl)‐1,5‐dihydro‐4H-pyrazolo[3,4‐d]pyrimidin‐4‐one

Conditions
ConditionsYield
Stage #1: 4-hydroxypyrazolo(3,4-d)pyrimidine With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: 2E,6E,10E-geranylgeranyl bromide In N,N-dimethyl-formamide for 27h; Inert atmosphere;
2%
315-30-0

4-hydroxypyrazolo(3,4-d)pyrimidine

2465-59-0

oxypurinol

Conditions
ConditionsYield
With ethylenediaminetetraacetic acid at 25℃; Mechanism; presence of xanthine-oxidase, pH=8; inhibition of xanthine-oxidase;
With sodium hydroxide; air; Mo(VI)-xanthine oxidase In phosphate buffer pH=7.5; Irradiation;
With bovine xanthine oxidase at 25℃; for 0.0833333h; pH=7.8; aq. buffer; Enzymatic reaction;
315-30-0

4-hydroxypyrazolo(3,4-d)pyrimidine

methanesulfonic acid 2-(7-amino-2-furan-2-yl-[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-yl)-octahydro-pyrido[1,2-a]pyrazin-7-ylmethyl ester

(7RS,9aRS)-2-furan-2-yl-5-[7-(1H-pyrazolo[3,4-d]pyrimidin-4-yloxymethyl)octahydropyrido[1,2-a]pyrazin-2-yl][1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ylamine

Conditions
ConditionsYield
Stage #1: 4-hydroxypyrazolo(3,4-d)pyrimidine With sodium hydride In N,N-dimethyl-formamide at 50℃; for 2h;
Stage #2: methanesulfonic acid 2-(7-amino-2-furan-2-yl-[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-yl)-octahydro-pyrido[1,2-a]pyrazin-7-ylmethyl ester In N,N-dimethyl-formamide at 100℃; for 24h;
Raw Materials
90914-36-6
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Chemistry

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

Uses

 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.

Toxicity Data With Reference

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

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

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): ToxicT,IrritantXi,HarmfulXn
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

Specification

 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.