Imidazole-4-acetaldehyde

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Imidazole-4-acetaldehyde
Names
Other names
1H-Imidazole-5-acetaldehyde, 1H-Imidazole-5-acetaldehyde, Imidazole-4-acetaldehyde, 1H-Imidazole-4-acetaldehyde, Imidazole-5-acetaldehyde, 4-Imidazolylacetaldehyde, 2-(1H-Imidazol-4-yl)acetaldehyde, 2-(1H-Imidazol-5-yl)acetaldehyde
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
  • InChI=1S/C5H6N2O/c8-2-1-5-3-6-4-7-5/h2-4H,1H2,(H,6,7)
    Key: MQSRGWNVEZRLDK-UHFFFAOYSA-N
  • C1=C(NC=N1)CC=O
Properties
C5H6N2
Molar mass 94.117 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Imidazole-4-acetaldehyde is a metabolite of histamine in biological species.

The process of histamine inactivation in biological species involves its metabolism through the oxidative deamination of its primary amino group. This reaction is catalyzed by the enzyme diamine oxidase (DAO). The metabolite produced from this reaction is imidazole-4-acetaldehyde.[1][2]

Imidazole-4-acetaldehyde is then further oxidized by a NAD-dependent aldehyde dehydrogenase, leading to imidazole-4-acetic acid.[1]

Synthesis under prebiotic conditions

Under prebiotic conditions, imidazole-4-acetaldehyde can be synthesized from erythrose, formamidine, formaldehyde, and ammonia.[3]

Role in fungal amine oxidase and bacterial aldehyde oxidase

Postoperative opioid prediction

References

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