3413-72-7

Basic information

• Product Name: MTIC
• Synonyms: 5-(3-methyl-1-triazenyl)-1h-imidazole-4-carboxamid;5(or4)-(3-methyl-1-triazeno)-imidazole-4(or5)-carboxamid;mtic;nsc407347;MonomethylTriaizenoImidazoleCarboxamide,3-Methyl-(triazen-yl)-imidazole-4-carboxamide,NSC407347,;Monomethyl Triaizeno Imidazole Carboxamide, 3-Methyl(triazenyl)imidazole-4-carboxamide, 5-(3-Methyltriazen-1-yl)imidazole-4-carboxamide, NSC 407347;MONOMETHYL-TRIAZENOIMIDAZOLE-CARBOXAMIDE;5-(3-Methyl-1-triazenyl)-1H-imidazole-4-carboxamide
• CAS NO: 3413-72-7
• Molecular Formula: C₅H₈N₆O
• Molecular Weight: 168.15662
• Product Categories: Various Metabolites and Impurities;Metabolites & Impurities
• Mol File: 3413-72-7.mol
• Article Data: 1

Chemical Properties

• Melting Point: 178 °C
• Boiling Point: 297.08°C (rough estimate)
• Flash Point: 139.3°C
• Appearance: /
• Density: 1.6600
• Vapor Pressure: 0.000758mmHg at 25°C
• Refractive Index: 1.7290 (estimate)
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated, Sonicated), Water (Slightly, Heated
• PKA: 10.07±0.10(Predicted)
• CAS DataBase Reference: MTIC(CAS DataBase Reference)
• NIST Chemistry Reference: MTIC(3413-72-7)
• EPA Substance Registry System: MTIC(3413-72-7)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 3413-72-7(Hazardous Substances Data)

Usage

Description

MTIC, also known as a metabolite of Temozolomide, is a monocarboxylic acid amide derived from Dacarbazine with one of the methyl groups replaced by a hydrogen. It is the active metabolite of Dacarbazine and is also produced by the spontaneous hydrolysis of Temozolomide in the body. MTIC is an off-white solid and has significant applications in the pharmaceutical industry due to its antineoplastic properties.

Uses

Used in Pharmaceutical Industry:
MTIC is used as an antineoplastic agent for its ability to inhibit tumor growth and progression. It is particularly effective in treating various types of cancer by modulating oncological signaling pathways and demonstrating synergistic effects when combined with conventional chemotherapeutic drugs, enhancing chemo-sensitivity and efficacy in resistant cases.
Used in Drug Development:
MTIC is utilized in the development of novel drug delivery systems to overcome limitations and enhance its applications and efficacy against cancer cells. Various organic and metallic nanoparticles have been employed as carriers for MTIC delivery, aiming to improve its delivery, bioavailability, and therapeutic outcomes.

InChI:InChI=1/C5H8N6O/c1-7-11-10-5-3(4(6)12)8-2-9-5/h2,7,11H,1H3,(H2,6,12)/b10-5+

Synthetic route

methylamine hydrochloride (593-51-1) + 5-diazoimidazole-4-carboxamide (7008-85-7) → 5-(3-methyltriazen-1-yl)imidazole-4-carboxamide (3413-72-7)

Conditions	Yield
With potassium carbonate 1.) water, ethyl acetate, 25 deg C, 18 h; 2.) ethyl acetate, 18 h; Yield given. Multistep reaction;

8-carbamoyl-3-methylimidazo<5,1-d>-1,2,3,5-tetrazin-4(3H)-one → 5-(3-methyltriazen-1-yl)imidazole-4-carboxamide (3413-72-7)

Conditions	Yield
With 5 percent NaCO3 In water at 25℃; for 0.333333h;	0.09 g

Upstream product

• 593-51-1 methylamine hydrochloride 
• 7008-85-7 5-diazoimidazole-4-carboxamide 

Relevant articles and documents

Antitumour Imidazotetrazines. Part 12. Reactions of Mitozolomide and its 3-Alkyl Congeners with Oxygen, Nitrogen, Halogen, and Carbon Nucleophiles

Mitozolomide (1) and its 3-alkyl congeners ring-open in aqueous sodium carbonate to form 5-(3-alkyltriazen-1-yl)imidazole-4-carboxamides.The 3-methyl and 3-ethyl analogues of mitozolomide decompose in alcohols to form 2-azahypoxanthine and 5-amino-1-alkoxycarbonylimidazole-4-carboxamides.In hydrazine hydrate mitozolomide yields, principally, 5-azidoimidazole-4-carboxamide, whereas the 3-alkyl-derivatives form 5-amino-4-carbamoylimidazole-1-carbohydrazide. 5-Diazoimidazole-4-carboxamide, generated by thermolysis of mitozolomide in acetic acid or pyridine, can be trapped by reactive methylenic ketones, nitriles or esters to afford imidazotriazines.