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552410

Sigma-Aldrich

5-Amino-4-imidazolecarboxamide

95%

Sinónimos:

4-Amino-5-carbamoylimidazole, 4-Aminoimidazole-5-carboxamide, 4-Carbamoyl-5-aminoimidazole, 4-Carboxamido-5-aminoimidazole, 5-Amino-1H-imidazole-4-carboxamide, 5-Amino-1H-imidazole-4-carboxylic acid amide, 5-Amino-3H-imidazole-4-carboxamide

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About This Item

Fórmula empírica (notación de Hill):
C4H6N4O
Número de CAS:
360-97-4
Peso molecular:
126.12
EC Number:
206-641-4
MDL number:
MFCD02181040
UNSPSC Code:
12352005
PubChem Substance ID:
24879267
NACRES:
NA.22

assay

95%

form

solid

mp

164-170 °C (lit.)

SMILES string

NC(=O)c1nc[nH]c1N

InChI

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

Inchi Key

DVNYTAVYBRSTGK-UHFFFAOYSA-N

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Application

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).

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Synthesis of guanosine and its derivatives from 5-amino-l-?-D-ribofuranosyl-4-imidazolecarboxamide. III. Formation of a novel cycloimidazole nucleoside and its cleavage reactions.
Okutsu M and Yamazaki A.
Nucleic Acids Research, 3(1), 237-250 (1976)
Preparation of 5-Amino-1-?-ribosyl-4-imidazolecarboxamide-5'-phosphate and N-(5-Amino-1-?-D-ribosyl-4-imidazolecarbonyl)-L-aspartic Acid 5'-Phosphate.
Huang HT.
Biochemistry, 4(1), 58-62 (1965)
James P White et al.
American journal of physiology. Endocrinology and metabolism, 304(10), E1042-E1052 (2013-03-28)
Although catabolic signaling has a well-established role in muscle wasting during cancer cachexia, the suppression of anabolic signaling also warrants further investigation. In cachectic tumor-bearing mice, circulating IL-6 levels are associated with suppressed muscle protein synthesis and mTORC1 signaling. We
Jang Han Lee et al.
American journal of physiology. Renal physiology, 304(6), F686-F697 (2013-01-18)
The epithelial-mesenchymal transition (EMT) is a novel mechanism that promotes renal fibrosis. Transforming growth factor-β (TGF-β), angiotensin II, aldosterone, high glucose, and urinary albumin are well-known causes of EMT and renal fibrosis. We examined whether and how activation of AMP-activated
Melissa M Thomas et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 28(5), 2098-2107 (2014-02-14)
AMP-activated protein kinase (AMPK) is a master regulator of metabolism. While muscle-specific AMPK β1β2 double-knockout (β1β2M-KO) mice display alterations in metabolic and mitochondrial capacity, their severe exercise intolerance suggested a secondary contributor to the observed phenotype. We find that tibialis
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