6,9-dihydro-1H-purine
mercaptopurine
CAS: 50-44-2
Molecular Formula: C5H4N4S
6,9-dihydro-1H-purine - Names and Identifiers
| Name | mercaptopurine |
| Synonyms | 6-MP mern nsc755 mercapurin THIOPURINE nci-c04886 mercaptopurin mercaptopurine purine-6-thiol merkaptopuryna 6-Mercaptopurine 6H-purine-6-thione 6,9-dihydro-1H-purine 3,5-dihydro-6H-purine-6-thione |
| CAS | 50-44-2 |
| EINECS | 200-037-4 |
| InChI | InChI=1/C5H6N4/c1-4-5(8-2-6-1)9-3-7-4/h2-3H,1H2,(H,6,8)(H,7,9) |
6,9-dihydro-1H-purine - Physico-chemical Properties
| Molecular Formula | C5H4N4S |
| Molar Mass | 152.18 |
| Density | 1.463 (estimate) |
| Melting Point | 241-244°C |
| Boling Point | 498.6±37.0 °C(Predicted) |
| Flash Point | 238.663°C |
| Water Solubility | 124mg/L(25 ºC) |
| Solubility | Dimethyl Sulfoxide, Methanol |
| Vapor Presure | 0mmHg at 25°C |
| Appearance | solid |
| pKa | 7.77, 11.17(at 25℃) |
| Storage Condition | Inert atmosphere,2-8°C |
| Refractive Index | 1.5605 (estimate) |
| Physical and Chemical Properties | This product is yellow crystalline powder; Odorless, slightly sweet taste. Slightly soluble in water and ethanol, practically insoluble in ether. Water of crystallization was lost at 140 °c. Soluble in alkaline aqueous solution, but unstable, slow hydrolysis, light notes into black in the air. Soluble in boiling water. mp313-314. |
| Use | Used as an antineoplastic agent |
6,9-dihydro-1H-purine - Risk and Safety
| UN IDs | 3249 |
| Hazard Class | 6.1(b) |
| Packing Group | III |
| Toxicity | LD50 oral in rat: 277mg/kg |
6,9-dihydro-1H-purine - Introduction
Mercaptopurine (6-MP) is a drug widely used in the treatment of leukemia, and it is also an immunosuppressive drug. It inhibits the synthesis of new purines by integrating the methyltransferase metabolites of mercaptopurine into DNA and RNA
Last Update：2022-10-16 17:25:33
6,9-dihydro-1H-purine - Reference Information
| (IARC) carcinogen classification | 3 (Vol. 26, Sup 7) 1987 |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| indications | mercaptopurine (6-MP) is used to treat acute lymphoblastic leukemia (ALL), chronic myeloid leukemia (CML), Crohn's disease and ulcerative colitis. For acute lymphoblastic leukemia, it is usually used with methotrexate. It's oral. For the maintenance treatment of acute lymphoblastic and acute non-lymphocytic leukemia, the acute phase of chronic myeloid leukemia; suitable for choriocarcinoma, malignant hydatidiform mole. |
| Side effects | Common side effects of 6-mercaptopurine include bone marrow suppression, hepatotoxicity, vomiting and loss of appetite. Other serious side effects include an increased risk of cancer and pancreatitis in the future. People with defects in the thiopurine S-methyltransferase gene have a higher risk of side effects. Use during pregnancy may harm the baby. |
| use | antineoplastic drugs. The treatment of acute and chronic leukemia, choriocarcinoma and malignant hydatidiform mole is also effective for malignant lymphadenopathy and multiple myeloma. Adverse reactions mainly include nausea, vomiting, decreased appetite, and sometimes diarrhea, stomatitis and oral ulcers. Blood should be strictly checked during medication, and liver function tests should be performed. Patients with liver and kidney dysfunction should reduce the amount with caution. When combined with allopurinol, allopurinol should be reduced to 25%-50% of the original dose. for biochemical research and anti-tumor drugs. This product is a drug that interferes with nucleosynthesis by hypoxanthines, also known as anti-metabolic drugs. Prevent the synthesis of nucleic acids, stop the division and reproduction of cancer cells, and even because DNA synthesis is blocked but protein synthesis does not stop, unbalanced growth occurs and cancer cells die. Mercaptopurine is a cycle-specific drug, which mainly acts on the S phase and also has a delaying effect on the G1 phase; it also has an inhibitory effect on humoral immunity and cellular immunity. Mainly used for leukemia. This product is also a biochemical reagent. The LD50 injected intraperitoneally in mice was 157mg/kg. Used as an antineoplastic agent |
| Production method | The 6-hydroxypurine (C5H4N4O) is cyclized with 4, 5-diamino-6-hydroxypyrimidine (see 1160) and formic acid, and then mixed with phosphorus pentasulfide. 4, 5-diamino-6-hydroxypyrimidine and formic acid are added to the reaction pot, stirred, heated and dissolved, heated and refluxed for 4 hours, and formic acid is recovered under reduced pressure. Add sodium hydroxide solution to dissolve, add activated carbon to decolorize, and filter. The filtrate is cooled and the pH is adjusted to 6 with glacial acetic acid. After being placed, crystals, namely 6-hydroxypurine, are filtered out. 6-hydroxyenyl and phosphorus pentasulfide are added into pyridine, stirred and dissolved, and reacted at 118 ℃ for 4h to generate mercaptopurine, which is refined after post-treatment to obtain a finished product with a yield of nearly 60%. It is made from hypoxanthine and phosphorus pentasulfide. the mass ratio of 2-mercapto-4-amino-6-hydroxypyrimidine is ethyl cyanoacetate: thiourea: sodium ethoxide = 1:0.75:3.75. Anhydrous ethanol and sodium ethoxide are stirred and heated to 76°C in a dry reactor, thiourea is added, ethyl cyanoacetate is added dropwise under reflux, refluxed for 4h after addition, and cooled to 30°C. Filter, add 3.5 times of water to dissolve the filter cake and decolorize with activated carbon, filter, heat the filtrate to 90 ℃, add 40% acetic acid dropwise to pH4-5, cool and filter the product. Ethyl cyanoacetate [sodium ethoxide, thiourea, anhydrous ethanol] →[76 ℃, 4h; 90 ℃, pH4-5] 2-mercapto-4-amino-6-hydroxypyrimidine 2-mercapto-4, 5-diamino-6-hydroxypyrimidine The mass ratio of feeding is 2-mercapto-4-amino-6-hydroxypyrimidine: hydrochloric acid (volume): nitric acid: sodium nitrite: sodium sulfite = 1:0.31:0.47:0.48:2.5. Dissolve 2-mercapto -6-amino -6-hydroxypyrimidine with water, add hydrochloric acid and nitric acid, add sodium nitrite dropwise at 15 ℃, react under pH3-4 conditions for 2h after adding, filter, wash the filter cake to neutral, add water, add hydrosulfite when cooled to below 20 ℃, react below 25 ℃ for 0.5h, react at 35 ℃ for 2h, and filter to obtain the product. 2-thio-4-amino-6-hydroxypyrimidine [sodium nitrite, hydrochloric acid, nitric acid] →[2h, pH3-4] 2-mercapto-4-amino-5-nitroso-6-hydroxypyrimidine [sodium dithionite] →[<25 ℃, 0.5h; 35 ℃, 2h] 2-mercapto-4, 5-diamino-6-hydroxypyrimidine 4, the mass ratio of preparation of 5-diamino-6-hydroxypyrimidine is 2-mercapto 4, 5-diamino-6-hydroxypyrimidine: sodium carbonate: activated nickel: glacial acetic acid (volume) = 1:0.75:1.5:1. 2-mercapto -4, 5-diamino-6-hydroxypyrimidine, sodium carbonate and appropriate amount of water were heated, stirred and dissolved, and activated nickel was added to reflux at 90-98 ℃ for 4 hours. Filtration, glacial acetic acid adjusts the pH of the filtrate to 7.5, reduces pressure and concentrates, then cools and filters to obtain the product. Preparation of 2-mercapto-4-, 5-diamino-6-hydroxypyrimidine [sodium carbonate, nickel] →[90-98 ℃, 4h]4, 5-diamino-6-hydroxypyrimidine 6-mercaptopurine with a feed ratio of 4, 5-diamino-6-hydroxypyrimidine (m): formic acid (V): pyridine (V): phosphorus pentasulfide (m)= 1:12:13:2.7. 4, 5-diamino-6-hydroxypyrimidine and formic acid are stirred, heated and dissolved, refluxed for 4 hours, formic acid is recovered under reduced pressure, 6mol/L sodium hydroxide solution is added for dissolution, decolorization and filtration, filtrate is cooled to 20 ℃, glacial acetic acid is adjusted to pH6, placed overnight, filtered, filter cake, pyridine and phosphorus pentasulfide are put into a reactor for heating and dissolution, reacted at 118 ℃ for 4 hours, pyridine is recovered under reduced pressure, cooled, and water is added, coarse crystals are recrystallized with water to make fine products. 4, 5-diamino-6-hydroxypyrimidine [formic acid, 4h]→ [phosphorus pentasulfide, 118 ℃, 4h] 6-mercaptopurine. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-10 22:29:15
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