6-Mercaptopurine Chemical Properties

Melting point:

241-244°C

Boiling point:

498.6±37.0 °C(Predicted)

Density 

1.463 (estimate)

refractive index 

1.5605 (estimate)

storage temp. 

Inert atmosphere,2-8°C

solubility 

DMSO : 35.71 mg/mL (234.66 mM; Need ultrasonic)

pka

7.77, 11.17(at 25℃)

form 

solid

Water Solubility 

124mg/L(25 ºC)

CAS DataBase Reference

50-44-2(CAS DataBase Reference)

IARC

3 (Vol. 26, Sup 7) 1987

EPA Substance Registry System

Mercaptopurine (50-44-2)

Safety Information

RIDADR 

3249

HazardClass 

6.1(b)

PackingGroup 

III

HS Code 

2933599590

Hazardous Substances Data

50-44-2(Hazardous Substances Data)

Toxicity

LD50 oral in rat: 277mg/kg

6-Mercaptopurine Usage And Synthesis

Chemical Properties

Yellowish-Greenish Solid

Originator

Purinethol,Sandoz,France,1950

Uses

Has a cytotoxicity effect

Uses

6-Mercaptopurine (6-MP) is a antineoplastic, immonusupressant; inhibits purine nucleotide synthesis and metabolism. 6-MP have been used for several decades in the treatment of leukemia and certain other neoplastic diseases. 6-Mercaptopurine is used for maintenance therapy of acute lymphocytic and acute myelogenous leukemia.

Definition

A sulfurcontaining purine base not found in animal nucleoproteins.

Manufacturing Process

7.5 g of 4-amino-6-chloro-5-nitropyrimidine was suspended in 200 ml of 1 N potassium hydrosulfide and heated on the steam bath for 2 hours while passing hydrogen sulfide through the reaction mixture. The reaction mixture was allowed to cool slowly, acidified with 10 N sulfuric acid and chilled. The precipitate consisted of 4,5-diamino-6-mercaptopyrimidine and sulfur. It was boiled with 300 ml of water, filtered hot and then chilled. The product precipitated as pale yellow needles (4.2 g); an additional 0.95 g was obtained by concentration of the mother liquors to 100 ml.
A mixture of 2 g of 4,5-diamino-6-mercaptopyrimidine and 10 ml of 98% formic acid was heated at 70°C for two hours and then evaporated to dryness on the steam bath to give as a residue, 7-amino-thiazolo (5,4-d) pyrimidine.
To 820 mg of 7-amino-thiazolo[5,4-d]pyrimidine was added 2.5 cc of 2 N sodium hydroxide. The water was removed under reduced pressure. The sodium salt was then heated at 240°C for one hour, during which time it melted, gave off water and resolidified. The sodium salt of 6-mercaptopurine was dissolved in 15 ml of water and acidified to pH 5 with acetic acid. Yellow crystals of 6-mercaptopurine hydrate precipitated, according to US Patent 2,933,498.

brand name

Purinethol (Teva).

Therapeutic Function

Cancer chemotherapy

Hazard

Questionable carcinogen.

Safety Profile

Poison by ingestion, intraperitoneal, subcutaneous, parenteral, and intravenous routes. Human systemic effects by ingestion: dermatitis. Experimental teratogenic and reproductive effects. Questionable human carcinogen producing Hodgkin's disease and leukemia. Human mutation data reported. When heated to decomposition it emits very toxic fumes of SOx and NOx. See also MERCAPTANS.

Veterinary Drugs and Treatments

Veterinary uses of mercaptopurine include adjunctive therapy of lymphosarcoma, acute leukemias, and severe rheumatoid arthritis. It may have potential benefit in treating other autoimmune conditions (e.g., unresponsive ulcerative colitis) as well.

6-Mercaptopurine (50-44-2)Related Product Information

• POTASSIUM THIOGLYCOLATE
• 6-Mercaptohexan-1-ol
• Sodium thioglycolate
• 3-Mercaptopropionic acid
• ISOOCTYL 3-MERCAPTOPROPIONATE
• Mercaptoacetic acid
• Calcium thioglycolate
• Purine
• 2-Ethylhexyl mercaptoacetate
• 6-THIOGUANOSINE
• 6-(Methylthio)purine
• 2-Mercaptoethanol
• 6-Thioguanine
• Malathion
• 6-MERCAPTOPURINE RIBOSIDE
• 2,6-Dithiopurine
• 2-AMINO-6-HYDROXY-8-MERCAPTOPURINE 97%
• 6-MERCAPTOPURINE extrapure,MERCAPTOPURINE,MONOHYDRATE,USP,6-Mercaptopurine monohydrate, 99.5+%