50-44-2 Usage
Chemical Properties
Yellowish-Greenish Solid
Originator
Purinethol,Sandoz,France,1950
Uses
Different sources of media describe the Uses of 50-44-2 differently. You can refer to the following data:
1. antineoplastic,
immonusupressant;inhibits purine nucleotide synthesis and metabolism
2. Has a cytotoxicity effect
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.
Check Digit Verification of cas no
The CAS Registry Mumber 50-44-2 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 0 respectively; the second part has 2 digits, 4 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 50-44:
(4*5)+(3*0)+(2*4)+(1*4)=32
32 % 10 = 2
So 50-44-2 is a valid CAS Registry Number.
InChI:InChI=1/C5H6N4/c1-4-5(8-2-6-1)9-3-7-4/h2-3H,1H2,(H,6,8)(H,7,9)
50-44-2Relevant articles and documents
A THIONATION PROCESS AND A THIONATING AGENT
-
Page/Page column 18, (2012/08/27)
A process for transforming a group >C=O (I) in a compound into a group >C=S (II) or into a tautomeric form of group (II) in a reaction giving a thionated reaction product, by use of crystalline P2S5·2 C5H5N as a thionating agent. A thionating agent which is crystalline P2S5·2 C5H5N
Thionations using a P4S10-pyridine complex in solvents such as acetonitrile and dimethyl sulfone
Bergman, Jan,Pettersson, Birgitta,Hasimbegovic, Vedran,Svensson, Per H.
experimental part, p. 1546 - 1553 (2011/06/11)
Tetraphosphorus decasulfide (P4S10) in pyridine has been used as a thionating agent for a long period of time. The moisture-sensitive reagent has now been isolated in crystalline form, and the detailed structure has been determined by X-ray crystallography. The thionating power of this storable reagent has been studied and transferred to solvents such as acetonitrile in which it has proven to be synthetically useful and exceptionally selective. Its properties have been compared with the so-called Lawesson reagent (LR). Particularly interesting are the results from thionations at relatively high temperatures (165 °C) in dimethyl sulfone as solvent. Under these conditions, for instance, acridone and 3-acetylindole could quickly be transformed to the corresponding thionated derivatives. Glycylglycine similarly gave piperazinedithione. At these temperatures, LR is inefficient due to rapid decomposition. The thionated products are generally cleaner and more easy to obtain because in the crystalline reagent, impurities which invariably are present in the conventional reagents, P4S 10 in pyridine or LR, have been removed. 2011 American Chemical Society.
Chemical transformations of 6-[(1-methyl-4-nitro-5-imidazolyl)-thio]purine (azathioprine)
Kochergin,Aleksandrova,Korsunskii
, p. 311 - 318 (2007/10/03)
The chemical transformations of 6-[(1-methyl-4-nitro-5-imidazolyl)thio]purine (azathiopurine)- hydrogenation, acetylation, alkylation by lower alkyl halides at positions 7 and 9 of the purine ring, hydrolytic cleavage at the C(6)-S and S-C(5) bonds - were studied.
