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360-97-4

360-97-4 Structure

360-97-4 Structure
IdentificationMore
[Name]

5-Amino-4-imidazolecarboxamide
[CAS]

360-97-4
[Synonyms]

4(5)-AMINO-5(4)-IMIDAZOLECARBOXAMIDE
4-AMINO-1H-IMIDAZOLE-5-CARBOXAMIDE
4-AMINO-5-IMIDAZOLECARBOXAMIDE
4-AMINOIMIDAZOLE-5-CARBOXAMIDE
5-AMINO-1H-IMIDAZOLE-4-CARBOXAMIDE
5-amino-4-imidazolecarboxamide
5-AMINOIMIDAZOLE-4-CARBOXAMIDE
4-amino-5-imidazolecarboxamid
5-amino-1h-imidazole-4-carboxamid
5-Amino-4-glyoxalinecarboxamide
5-amino-imidazole-4-carboxamid
aic
aminoimidazolecarboxamide
ba2756
diazol-c
1H-Imidazole-4-carboxamide, 5-amino-
5-amino-4-imidazolylcarboxamide
4-Amino-5-imidazolecarboxamide monohydrate
AICA, 4-Amino-5-carbamoylimidazole,
4-Amino-5-imodazole
[EINECS(EC#)]

206-641-4
[Molecular Formula]

C4H6N4O
[MDL Number]

MFCD02181040
[Molecular Weight]

126.12
[MOL File]

360-97-4.mol
Chemical PropertiesBack Directory
[Appearance]

White to Off-White Solid
[Melting point ]

164-170 °C(lit.)
[Boiling point ]

234.22°C (rough estimate)
[density ]

1.3659 (rough estimate)
[refractive index ]

1.8500 (estimate)
[storage temp. ]

Keep in dark place,Sealed in dry,Room Temperature
[solubility ]

DMSO (Slightly), Methanol (Slightly), Water (Slightly)
[form ]

Powder
[pka]

11.97±0.10(Predicted)
[color ]

White
[Water Solubility ]

Soluble in DMSO, Methanol, Water.
[Usage]

A metabolite of Temozolomide
[InChI]

InChI=1S/C4H6N4O/c5-3-2(4(6)9)7-1-8-3/h1H,5H2,(H2,6,9)(H,7,8)
[InChIKey]

DVNYTAVYBRSTGK-UHFFFAOYSA-N
[SMILES]

C1NC(N)=C(C(N)=O)N=1
[CAS DataBase Reference]

360-97-4(CAS DataBase Reference)
[EPA Substance Registry System]

360-97-4(EPA Substance)
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H319-H335
[Precautionary statements ]

P261-P264-P271-P280-P302+P352-P305+P351+P338
[Hazard Codes ]

Xi
[Risk Statements ]

R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
[RIDADR ]

UN2811
[WGK Germany ]

3
[RTECS ]

NI3910000
[TSCA ]

Yes
[HazardClass ]

6.1
[HS Code ]

29332900
[Storage Class]

11 - Combustible Solids
[Hazard Classifications]

Eye Irrit. 2
Skin Irrit. 2
STOT SE 3
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Glycinamide
[Preparation Products]

Temozolomide-->Dacarbazine-->5-(Amino-1-(N-methyl Carbamoyl)-->Ethyl 4-amino-5-imidazolecarboxylate-->Temozolomide Impurity
Questions And AnswerBack Directory
[Description]

5-Amino-4-imidazolecarboxamide may be used in the synthesis of 4-(N′-benzoylcarbamoyl)amino-5-imidazolecarboxamide and 5-amino-1-β-D-ribosyl-4-imidazolecarboxamide-5′-phosphate (AICAR).It is an imidazole derivative which is a metabolite of the antineoplastic agents BIC and DIC. By itself, or as the ribonucleotide, it is used as a condensation agent in the preparation of nucleosides and nucleotides. When compounded with orotic acid, it is used to treat liver diseases.
[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.
Hazard InformationBack Directory
[Chemical Properties]

White to Off-White Solid
[Uses]

A metabolite of Temozolomide
[Application]

5-Amino-4-imidazolecarboxamide ribonucleotide (AICAR) is an analog of AMP and an activator of AMP-dependent protein kinase (AMPK). It prevents/reverses drug-induced mitochondrial and hepatocellular damage by regulating mitochondrial fusion and mitophagy in acetaminophen and diclofenac-induced hepatic cell toxicity of murine and human origin[1].
[Definition]

ChEBI: An aminoimidazole in which the amino group is at C-5 with a carboxamido group at C-4.
[storage]

Store at -20°C
[References]

[1] Alamri, R. D., Elmeligy, M. A., Albalawi, G. A., Alquayr, S. M., Alsubhi, S. S., & El-Ghaiesh, S. H. (2021). Leflunomide an immunomodulator with antineoplastic and antiviral potentials but drug-induced liver injury: A comprehensive review. International Immunopharmacology, 93, Article 107398. https://doi.org/10.1016/j.intimp.2021.107398
Spectrum DetailBack Directory
[Spectrum Detail]

5-Amino-4-imidazolecarboxamide(360-97-4)MS
5-Amino-4-imidazolecarboxamide(360-97-4)1HNMR
5-Amino-4-imidazolecarboxamide(360-97-4)IR1
5-Amino-4-imidazolecarboxamide(360-97-4)IR2
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

5-Aminoimidazole-4-carboxamide, 95%(360-97-4)
[Sigma Aldrich]

360-97-4(sigmaaldrich)
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