4-Amino-1-butanol

4-Amino-1-butanol
Names
IUPAC name
4-aminobutan-1-ol
Other names
4-Amino-1-butanol; 4-Aminobutanol; 4-Hydroxybutylamine; 4-Hydroxy-n-butylamine; N-(4-Hydroxybutyl)amine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.033.045 Edit this at Wikidata
EC Number
  • 236-364-4
  • InChI=1S/C4H11NO/c5-3-1-2-4-6/h6H,1-5H2
    Key: BLFRQYKZFKYQLO-UHFFFAOYSA-N
  • C(CCO)CN
Properties
C4H11NO
Molar mass 89.138 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

4-Amino-1-butanol, or 4-aminobutanol, also known as 4-hydroxybutylamine, is an alkanolamine and an analogue and precursor of the neurotransmitter γ-aminobutyric acid (GABA).[1][2][3][4]

The structural relation of 1,4-butanediol (1,4-BD) to γ-hydroxybutyric acid (GHB) is analogous to the relation of 4-amino-1-butanol to GABA.[1] 1,4-BD is a known prodrug of GHB which is converted into it through the actions of alcohol dehydrogenase (ADH) and aldehyde dehydrogenase (ALDH).[5][6] γ-Hydroxybutyraldehyde (GHBAL) is an intermediate in this pathway,[5][6] whereas the analogous intermediate structure for 4-amino-1-butanol and GABA is γ-aminobutyraldehyde (GABAL).[7][8][9] Similar to the conversion of 1,4-BD into GHB, 4-amino-1-butanol is converted into GABAL by aldehyde reductase (ALR) and GABAL is converted into GABA by ALDH.[2][7][8][9]

References

  1. ^ a b "4-Amino-1-butanol". PubChem. Retrieved 8 September 2024.
  2. ^ a b Storer, R. James; Ferrante, Antonio (10 October 1997). "Radiochemical Assay of Diamine Oxidase". Polyamine Protocols. Methods in Molecular Biology. Vol. 79. New Jersey: Humana Press. pp. 91–96. doi:10.1385/0-89603-448-8:91. ISBN 978-0-89603-448-8. PMID 9463822. In biological mixtures γ-aminobutyraldehyde may be alternatively oxidized by aldehyde dehydrogenases (EC 1.2.1.3) to γ-aminobutyric acid (GABA) (11—13). The formation of 4-amino-1-butanol is also possible through reduction by aldehyde dehydrogenase and/or alcohol dehydrogenase (13,14), thus preventing cyclization. Other fates of putrescine in biological mixtures include the acetylation to acetylputrescine by an N-acetyltransferase and then oxidation by monoamine oxidase (EC 1.4.3.4) (11,17). [...] Fig 1 Fates of putrescine in biological mixtures
  3. ^ Takahashi H, Uchikura K, Takahashi H (June 1961). "Relationship between pharmacological actions on the mammalian ileum and chemical structure of gamma-aminobutyric acid". Jpn J Physiol. 11 (3): 229–237. doi:10.2170/jjphysiol.11.229. PMID 13774871.
  4. ^ Takahashi H, Koshino C, Ikeda O (February 1962). "Relationship between the hypotensive activity and chemical structure of gamma-aminobutyric acid in the rabbit". Jpn J Physiol. 12: 97–105. doi:10.2170/jjphysiol.12.97. PMID 13919036.
  5. ^ a b 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.
  6. ^ a b 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.
  7. ^ a b 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].
  8. ^ a b 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.
  9. ^ a b 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].


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