γ-Aminobutyraldehyde
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| IUPAC name
4-aminobutanal
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| Other names
γ-Aminobutyraldehyde; gamma-Aminobutyraldehyde; ABAL; GABAL; GABAAL; 4-Aminobutanol; 4-Aminobutyraldehyde; γ-Aminobutanol; gamma-Aminobutanol
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3D model (JSmol)
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PubChem CID
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CompTox Dashboard (EPA)
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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).
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γ-Aminobutyraldehyde (ABAL, GABAL), also known as 4-aminobutanal or 4-aminobutyraldehyde, 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] However, biosynthesis of GABA from polyamines like putrescine is a minor metabolic pathway in the brain.[1] Monoacetylputrescine can be converted into ABAL via monoamine oxidase (MAO).[3]
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.[4][5] 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]
References
[edit]- ^ 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. doi:10.1016/j.plantsci.2012.06.001. PMID 22794926.
- ^ 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].
- ^ 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.