4-Aminobutanal
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| IUPAC name 4-aminobutanal | |
| Other names γ-Aminobutyraldehyde; gamma-Aminobutyraldehyde; 4-Aminobutyraldehyde; GABA aldehyde | |
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3D model (JSmol) |
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| Properties | |
| C4H9NO | |
| Molar mass | 87.122 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
4-Aminobutanal, also known as γ-aminobutyraldehyde, 4-aminobutyraldehyde, or GABA aldehyde, is a metabolite of putrescine and a biological precursor of γ-aminobutyric acid (GABA).[1][2] It can be converted into GABA by the actions of diamine oxidase (DAO) and aminobutyraldehyde dehydrogenase (ABALDH) (e.g., ALDH9A1).[1] Putrescine is converted into 4-aminobutanal via monoamine oxidase B (MAO-B).[3][4][5] However, biosynthesis of GABA from polyamines like putrescine is a minor metabolic pathway in the brain.[1]
The related compound γ-hydroxybutyraldehyde (GHBAL) is a prodrug of γ-hydroxybutyric acid (GHB) as well as a metabolic intermediate in the conversion of 1,4-butanediol (1,4-BD) into GHB.[6][7] However, aliphatic aldehydes like GHBAL are caustic, strong-smelling, and foul-tasting, and ingestion is likely to be unpleasant and result in severe nausea and vomiting.[citation needed]
See also
- N-Acetyl-γ-aminobutyraldehyde (N-acetyl-GABAL)
References
- ^ a b c Rashmi, Deo; Zanan, Rahul; John, Sheeba; Khandagale, Kiran; Nadaf, Altafhusain (2018). "γ-Aminobutyric Acid (GABA): Biosynthesis, Role, Commercial Production, and Applications". Studies in Natural Products Chemistry. Vol. 57. Elsevier. pp. 413–452. doi:10.1016/b978-0-444-64057-4.00013-2. ISBN 978-0-444-64057-4.
Alternate pathways of GABA synthesis from putrescine and other polyamines have also been reported [207–211]. Here, γ-aminobutyraldehyde, an intermediate from polyamine degradation reaction via combined activities of diamine oxidase (DAO, E.C. 1.4.3.6) and 4-aminobutyraldehyde dehydrogenase (ABALDH), leads to the synthesis of GABA [205,212,213]. In response to abiotic stresses, GABA is also reported to be synthesized from proline via D1-pyrroline intermediate formation [47,205,214] and also by a nonenzymatic reaction [214]. However, GABA synthesis from polyamine pathways is minor in the brain, [215] although they play a significant role in the developing brain [216] and retina [217]. But GABA can be formed from putrescine in the mammalian brain [218].
- ^ Shelp BJ, Bozzo GG, Trobacher CP, Zarei A, Deyman KL, Brikis CJ (September 2012). "Hypothesis/review: contribution of putrescine to 4-aminobutyrate (GABA) production in response to abiotic stress". Plant Sci. 193–194: 130–135. Bibcode:2012PlnSc.193..130S. doi:10.1016/j.plantsci.2012.06.001. PMID 22794926.
- ^ Nam MH, Sa M, Ju YH, Park MG, Lee CJ (April 2022). "Revisiting the Role of Astrocytic MAOB in Parkinson's Disease". Int J Mol Sci. 23 (8): 4453. doi:10.3390/ijms23084453. PMC 9028367. PMID 35457272.
- ^ Benedetti MS, Dostert P (1994). "Contribution of amine oxidases to the metabolism of xenobiotics". Drug Metab Rev. 26 (3): 507–535. doi:10.3109/03602539408998316. PMID 7924902.
MAO also catalyses the deamination of a natural brain constituent, monoacetyl-putrescine, producing y-acetylaminobutyraldehyde, which in turn participates in the formation of brain GABA [13].
- ^ Cho HU, Kim S, Sim J, Yang S, An H, Nam MH, Jang DP, Lee CJ (July 2021). "Redefining differential roles of MAO-A in dopamine degradation and MAO-B in tonic GABA synthesis". Exp Mol Med. 53 (7): 1148–1158. doi:10.1038/s12276-021-00646-3. PMC 8333267. PMID 34244591.
- ^ Felmlee MA, Morse BL, Morris ME (January 2021). "γ-Hydroxybutyric Acid: Pharmacokinetics, Pharmacodynamics, and Toxicology". AAPS J. 23 (1): 22. doi:10.1208/s12248-020-00543-z. PMC 8098080. PMID 33417072.
- ^ Tay E, Lo WK, Murnion B (2022). "Current Insights on the Impact of Gamma-Hydroxybutyrate (GHB) Abuse". Subst Abuse Rehabil. 13: 13–23. doi:10.2147/SAR.S315720. PMC 8843350. PMID 35173515.