5-Aminoimidazole-4-carboxamide (HCID 9679)

Overview

5-aminoimidazole-4-carboxamide is an aminoimidazole in which the amino group is at C-5 with a carboxamido group at C-4. It has a role as a mouse metabolite. It is an aminoimidazole and a monocarboxylic acid amide.

Names & identifiers

Preferred name: 5-Aminoimidazole-4-carboxamide
IUPAC: 4-amino-1H-imidazole-5-carboxamide
English name: 5-Amino-4-imidazolecarboxamide
Molecular formula: C4H6N4O
Molecular weight: 126.12

Names & synonyms

360-97-44-Amino-1H-imidazole-5-carboxamide5-Aminoimidazole-4-carboxamide5-amino-1H-imidazole-4-carboxamide4-Amino-5-imidazolecarboxamideAICAAminoimidazole carboxamide5-Aminoimidazol-4-carboxamideIMIDAZOLE-4-CARBOXAMIDE, 5-AMINO-4-Amino-5-imidazole carboxamide4-amino-5-carbamoylimidazole5-Amino-4-imidazolecarboxyamide

Show more names

aic4-AMINOIMIDAZOLE-5-CARBOXAMIDE5-amino-1h-imidazole-4-carboxamidba2756NSC 7784diazol-c4-Amino-5-imodazoleDacarbazine Impurity

3V0Y2PDE6KDTXSID8059891NSC-7784CHEBI:20305(4)-amino-4(5)-imidazolecarboxamideBA-2756Carboxamide, AminoimidazoleRefChem:557551

Database identifiers

CAS: 360-97-4
PubChem CID: 9679
DTXSID: DTXSID8059891
ChEMBL: CHEMBL1610
ChEBI: CHEBI:2030
UNII: 3V0Y2PDE6K
EC Number: 206-641-4
Nikkaji: J37.792I

Properties

Computed structural properties

XLogP: -0.5
Topological polar surface area: 97.8 Å²
Hydrogen bond donors: 3
Hydrogen bond acceptors: 3
Rotatable bonds: 1
Heavy atoms: 9
Formal charge: 0
Complexity: 126

Experimental & physicochemical properties

LogP-1.10

Solubility>18.9 [ug/mL] (The mean of the results at pH 7.4)

Physical DescriptionSolid

Physicochemical properties

Melting point: 164 · 164-170 °C(lit.)
Boiling point: 234.22 °C · 234.22°C (rough estimate)
Density: 1.3659 · 1.3659 (rough estimate)
refractive index: 1.85 · 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 · 11.97±0.10(Predicted)
color: White
Water Solubility: Soluble in DMSO, Methanol, Water.
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 · 360-97-4(CAS DataBase Reference)
EWG's Food Scores: 1 · 1
FDA UNII: 3 V0Y2PDE6K · 3V0Y2PDE6K
EPA Substance Registry System: 1 H-Imidazole-4-carboxamide, · 1H-Imidazole-4-carboxamide, 5-amino- (360-97-4)
UNSPSC Code: 41116107 · 41116107
NACRES: 24 · NA.24
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
target organs: Respiratory system
PPE: 95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38
Safety Statements: 26 · 26-36
RIDADR: 2811 · UN2811
WGK Germany: 3 · 3
RTECS: 3910000 · NI3910000
TSCA: TSCA listed
HazardClass: 6.1 · 6.1
HS Code: 29332900 · 29332900
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3
Limited Quantities: 5 kg · 5.0 kg (11 lbs) (solid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 1.9% (1 of 54) of reports.

Warning

H315 (96.3%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 54 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (96.3%)

Safety data

PPE: dust mask type N95 (US), Eyeshields, Gloves
wgk: 3
tsca: TSCA listed
rtecs: NI3910000
ridadr: UN2811
hs_code: 29332900
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 26-36
hazard_class: 6.1
Storage Class: 11 - Combustible Solids
target organs: Respiratory system
Hazard statements: H315-H319-H335
Limited Quantities: 5.0 kg (11 lbs) (solid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Hazard Classifications: Eye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements: P261-P264-P271-P280-P302+P352-P305+P351+P338

Chemistry & industry

Pharmacology

Tissue LocationsFibroblasts

Cellular LocationsCytoplasm

Metabolite PathwaysAdenine phosphoribosyltransferase deficiency (APRT)

Uses & manufacturing

General Manufacturing Information1H-Imidazole-4-carboxamide, 5-amino-: INACTIVE

Applications · 4 items

Description5-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.

UsesA metabolite of Temozolomide

Uses4-Aminoimidazole-5-carboxamide is used as Catalytic agent, Petrochemical additive. It is metabolite of temozolomide.

Uses5-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).