360-97-4

Basic information

• Product Name: 5-Amino-4-imidazolecarboxamide
• Synonyms: 4-AMINOIMIDAZOLE-5-CARBOXAMIDE;5-amino-4-imidazolecarboxamide;5-AMINOIMIDAZOLE-4-CARBOXAMIDE;5-AMINO-1H-IMIDAZOLE-4-CARBOXAMIDE;4(5)-AMINO-5(4)-IMIDAZOLECARBOXAMIDE;4-amino-5-imidazolecarboxamid;5-amino-1h-imidazole-4-carboxamid;5-Amino-4-glyoxalinecarboxamide
• CAS NO: 360-97-4
• Molecular Formula: C₄H₆N₄O
• Molecular Weight: 126.12
• EINECS: 206-641-4
• Product Categories: pharmacetical;Imidazol&Benzimidazole;Various Metabolites and Impurities;Bases & Related Reagents;Metabolites & Impurities;Nucleotides;Building Blocks;Heterocyclic Building Blocks;Imidazoles;Amines;Amines, Metabolites & Impurities, Nucleotides, Bases & Related Reagents
• Mol File: 360-97-4.mol
• Article Data: 17

Chemical Properties

• Melting Point: 164-170 °C(lit.)
• Boiling Point: 234.22°C (rough estimate)
• Flash Point: 269.6 °C
• Appearance: White/Powder
• Density: 1.3659 (rough estimate)
• Vapor Pressure: 2.59E-10mmHg at 25°C
• Refractive Index: 1.8500 (estimate)
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• PKA: 11.97±0.10(Predicted)
• Water Solubility: Soluble in DMSO, Methanol, Water.
• CAS DataBase Reference: 5-Amino-4-imidazolecarboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Amino-4-imidazolecarboxamide(360-97-4)
• EPA Substance Registry System: 5-Amino-4-imidazolecarboxamide(360-97-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: NI3910000
• TSCA: Yes
• Hazardous Substances Data: 360-97-4(Hazardous Substances Data)

Usage

Description

5-Amino-4-imidazolecarboxamide is an imidazole derivative that serves as a metabolite of the antineoplastic agents BIC and DIC. It is a white to off-white solid and is used as a condensation agent in the preparation of nucleosides and nucleotides. When compounded with orotic acid, it is utilized to treat liver diseases.

Uses

1. Used in Pharmaceutical Industry:
5-Amino-4-imidazolecarboxamide is used as a metabolite for the synthesis of various antineoplastic agents, such as temozolomide, which are crucial in cancer treatment.
2. Used in Petrochemical Industry:
5-Amino-4-imidazolecarboxamide is used as a catalytic agent and petrochemical additive, contributing to the efficiency and effectiveness of chemical reactions in this industry.
3. Used in Synthesis of Specific Compounds:
5-Amino-4-imidazolecarboxamide is used as a starting material for the synthesis of 4-(N′-benzoylcarbamoyl)amino-5-imidazolecarboxamide and 5-amino-1-β-D-ribosyl-4-imidazolecarboxamide-5′-phosphate (AICAR), which have potential applications in various fields.
4. Used in the Treatment of Liver Diseases:
When combined with orotic acid, 5-Amino-4-imidazolecarboxamide is used to treat liver diseases, providing therapeutic benefits to patients suffering from such conditions.

Reference

3. Black, S. L., M. J. Black, and J. H. Mangum. "A rapid assay for 5-amino-4-imidazolecarboxamide ribotide transformylase." Analytical Biochemistry90.1(1978):397-401.

InChI:InChI=1/C5H8N4/c1-3(6)4-5(7)9-2-8-4/h2H,1,6-7H2,(H,8,9)

Upstream product

• 100191-43-3 2-formylamino-malonomonoimidic acid diamide 
• 37842-62-9 ethyl N-(carbamoylcyanomethyl)formamidate 
• 6313-33-3 formamidine hydrochloride 
• 6719-21-7 2-Amino-2-cyanoacetamide 
• 85622-95-3 mitozolomide 
• 2627-69-2 AICA riboside 
• 76055-09-9 4⁽⁵⁾-oxoimidazole-5⁽⁴⁾-carbonitrile 
• 82647-13-0 5-<3-(2-fluoroethyl)-1-triazenyl>-imidazole-4-carboxamide 
• 85622-93-1 temozolomide 
• 85623-02-5 3-benzyl-8-carbamoyl-[3H]-imidazo[5,1-d]-1,2,3,5-tetrazin-4-one 
• 7664-93-9 sulfuric acid 
• 68-94-0 1,7-dihydro-6H-purin-6-one 
• 479071-08-4 N-α-{3-(2-chloroethyl)-3,4-dihydro-4-oxoimidazo[5,1-d]-1,2,3,5-tetrazin-8-carbonyl}-L-lysine methyl ester 
• 420-04-2 CYANAMID 

Downstream Products

• 83296-78-0 5-amino-2-(4-bromo-phenylazo)-1⁽³⁾H-imidazole-4-carboxylic acid amide 
• 3031-94-5 5-aminoimidazole-4-carboxamide ribonucleotide 
• 69-89-6 xanthin 
• 74180-78-2 4-amino-5-imidazolecarboxamide 
• 77856-27-0 4-carbamoyl-5-amino-1-<<2-(benzoyloxy)ethoxy>methyl>imidazole 
• 96445-86-2 2-<(4-amino-5-carbamoyl-1H-imidazol-1-yl)methoxy>ethyl benzoate 
• 74180-77-1 thioguanine 
• 91026-74-3 5-Acetamidoimidazole-4-carboxamide 
• 74180-76-0 8-azaguanine 
• 60298-05-7 3-benzoyl-1,4-dihydro-4-oxoimidazo<5,1-c><1,2,4>triazine-8-carboxamide 
• 60297-99-6 ethyl 2-(4-carbamoylimidazol-5-ylhydrazono)benzoylacetate 
• 111105-72-7 5-{[1-Phenyl-meth-(E)-ylidene]-amino}-1H-imidazole-4-carboxylic acid amide 
• 82145-23-1 5-Benzamidoimidazole-4-carboxamide 
• 74180-74-8 guanine 

Relevant articles and documents

Studies on the biosynthesis of nucleic acids. IV. Synthesis of labeled 4-aminoimidazole-5-carboxamide from barium carbonate-14C.

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Screening of microorganisms producing 5 amino 4 imidazole carboxamide and D ribose from 5 amino 4 imidazole carboxamide riboside

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Development of a One-Step Synthesis of 5-Amino-1 H-imidazole-4-carboxamide

An innovative and efficient synthesis of 5-amino-1H-imidazole-4-carboxamide (AIC) from commercially available hypoxanthine (～$30/kg) is described. The development of the key hydrolysis step and a practical isolation enables a highly efficient one-step manufacturing process for AIC with minimal environmental impact and significant reduction of production cost.

Optimized synthesis process of anticancer drug dacarbazine

The invention provides an optimized synthesis process of an anticancer drug dacarbazine. The optimized synthesis process of the anticancer drug dacarbazine comprises the following steps: synthesis ofglycine methyl ester, synthesis of N-formylglycine methyl ester, synthesis of alpha-methyl isocyanoacetate, synthesis of alpha-isocyanoacetamide, synthesis of 5-amino-4-imidazolecarboxamide and synthesis of dacarbazine. Synthesis of the glycine methyl ester comprises the following steps: weighing 7.5 g of glycine and adding the glycine into a 500 mL round-bottom flask, taking 200 mL of redistilledmethanol as a solvent and cooling with stirring in an ice bath for 15 min; weighing 22 mL of thionyl chloride by a syringe and slowly dropwise adding the thionyl chloride into the reaction flask to react overnight at room temperature; and removing excess thionyl chloride and methanol by rotary evaporation at the room temperature, dissolving the residues by using as little hot methanol as possible, quickly adding a large amount of cold diethyl ether, and cooling in the reaction bottle in an ice bath. By improving the synthesis process of the anticancer drug dacarbazine, the optimized synthesisprocess of the anticancer drug dacarbazine has the advantages of reasonable synthesis circuit, cheap raw materials, mild reaction conditions and high total yield, thereby effectively solving the problems and defects in the prior art.