Imidazole-4-acetaldehyde

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
CAS Number	645-14-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:27398;
ChemSpider	132948;
KEGG	C05130;
PubChem CID	150841;
CompTox Dashboard (EPA)	DTXSID60214747 ;
	InChI InChI=1S/C5H6N2O/c8-2-1-5-3-6-4-7-5/h2-4H,1H2,(H,6,7) Key: MQSRGWNVEZRLDK-UHFFFAOYSA-N;
	SMILES C1=C(NC=N1)CC=O;
Properties
Chemical formula	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). Infobox references

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

Biological inactivation of histamine

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

In a study of imidazole-4-acetaldehyde presence in the reaction mixture during the coupling reaction of fungal amine oxidase and bacterial aldehyde oxidase for histamine elimination, imidazole 4-acetaldehyde was not detected, which suggests that imidazole 4-acetaldehyde was not produced as a result of the coupling reaction between fungal amine oxidase and aldehyde oxidase, as such, its absence in the reaction mixture implies that the fungal amine oxidase-aldehyde oxidase coupling reaction likely proceeded directly from histamine to imidazole-4-acetic acid with an apparent yield of 100%, without the intermediate formation of imidazole 4-acetaldehyde.^[4]

Postoperative opioid prediction

In a 2022 observational study aimed to identify preoperative serum metabolites that could predict postoperative opioid consumption, the role of imidazole-4-acetaldehyde was identified as one of the metabolites that showed different trends between gastric cancer patients with high postoperative opioid consumption and those with low opioid consumption group. The results suggest that imidazole-4-acetaldehyde, along with other metabolites, was significantly different between the two groups, so that that imidazole-4-acetaldehyde may serve as a potential biomarker for predicting postoperative opioid consumption in gastric cancer patients, still, the results of this study is inconclusive.^[5]

References

^ ^a ^b Bähre H, Kaever V (2017). "Analytical Methods for the Quantification of Histamine and Histamine Metabolites". Handb Exp Pharmacol. Handbook of Experimental Pharmacology. 241: 3–19. doi:10.1007/164_2017_22. ISBN 978-3-319-58192-7. PMID 28321587.
^ Ambroziak W, Maśliński C (April 1988). "Participation of aldehyde dehydrogenase in the oxidative deamination pathway of histamine and putrescine". Agents Actions. 23 (3–4): 311–3. doi:10.1007/BF02142573. PMID 3394581. S2CID 8283492.
^ Shen C, Yang L, Miller SL, Oró J (1987). "Prebiotic synthesis of imidazole-4-acetaldehyde and histidine". Orig Life Evol Biosph. 17 (3–4): 295–305. Bibcode:1987OrLi...17..295S. doi:10.1007/BF02386469. PMID 2957640. S2CID 19561011.
^ Usui M, Kubota H, Ishihara M, Matsuki H, Kawabe S, Sugiura Y, Kataoka N, Matsushita K, Ano Y, Akakabe Y, Hours RA, Yakushi T, Adachi O (September 2022). "Histamine elimination by a coupling reaction of fungal amine oxidase and bacterial aldehyde oxidase†". Biosci Biotechnol Biochem. 86 (10): 1438–1447. doi:10.1093/bbb/zbac121. PMID 35876648.
^ Li J, Li S, Yu L, Wei J, Sun H, Yang C, Tan H (March 2022). "Identification of Preoperative Serum Metabolites Associated With Postoperative Opioid Consumption in Gastric Cancer Patients by Extreme Phenotype Sampling". Pain Physician. 25 (2): E385–E396. PMID 35322994.

[pmid28321587-1] Bähre H, Kaever V (2017). "Analytical Methods for the Quantification of Histamine and Histamine Metabolites". Handb Exp Pharmacol. Handbook of Experimental Pharmacology. 241: 3–19. doi:10.1007/164_2017_22. ISBN 978-3-319-58192-7. PMID 28321587.

[pmid3394581-2] Ambroziak W, Maśliński C (April 1988). "Participation of aldehyde dehydrogenase in the oxidative deamination pathway of histamine and putrescine". Agents Actions. 23 (3–4): 311–3. doi:10.1007/BF02142573. PMID 3394581. S2CID 8283492.

[pmid2957640-3] Shen C, Yang L, Miller SL, Oró J (1987). "Prebiotic synthesis of imidazole-4-acetaldehyde and histidine". Orig Life Evol Biosph. 17 (3–4): 295–305. Bibcode:1987OrLi...17..295S. doi:10.1007/BF02386469. PMID 2957640. S2CID 19561011.

[pmid35876648-4] Usui M, Kubota H, Ishihara M, Matsuki H, Kawabe S, Sugiura Y, Kataoka N, Matsushita K, Ano Y, Akakabe Y, Hours RA, Yakushi T, Adachi O (September 2022). "Histamine elimination by a coupling reaction of fungal amine oxidase and bacterial aldehyde oxidase†". Biosci Biotechnol Biochem. 86 (10): 1438–1447. doi:10.1093/bbb/zbac121. PMID 35876648.

[pmid35322994-5] Li J, Li S, Yu L, Wei J, Sun H, Yang C, Tan H (March 2022). "Identification of Preoperative Serum Metabolites Associated With Postoperative Opioid Consumption in Gastric Cancer Patients by Extreme Phenotype Sampling". Pain Physician. 25 (2): E385–E396. PMID 35322994.

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