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).[2][3][4][5] Its formula is H2NCH2CH2CH2CH2OH. It is a colorless liquid.
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| Names | |
|---|---|
| Preferred 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) |
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| ChemSpider | |
| ECHA InfoCard | 100.033.045 |
| EC Number |
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PubChem CID |
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CompTox Dashboard (EPA) |
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| Properties | |
| C4H11NO | |
| Molar mass | 89.138 g·mol−1 |
| Appearance | Colorless liquid[1] |
| Odor | Amine-like[1] |
| Density | 0.967 g/ml[1] |
| Melting point | 16–18 °C (61–64 °F; 289–291 K)[1] |
| Boiling point | 206 °C (403 °F; 479 K)[1] |
| Soluble[1] | |
| Solubility | Miscible with dichloromethane[1] |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards |
Severe skin burns and eye damage |
| GHS labelling: | |
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| Danger | |
| H302, H314 | |
| P260, P264, P270, P280, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P330, P363, P405, P501 | |
| Flash point | 107 °C (225 °F; 380 K)[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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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.[2] 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).[6][7] γ-Hydroxybutyraldehyde (GHBAL) is an intermediate in this pathway,[6][7] whereas the analogous intermediate structure for 4-amino-1-butanol and GABA is γ-aminobutyraldehyde (GABAL).[8][9][10] 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.[3][8][9][10]
References
edit- 1 2 3 4 5 6 7 8 LOBA Chemie. "4-AMINO-1-BUTANOL FOR SYNTHESIS". www.lobachemie.com. Retrieved 11 April 2026.
- 1 2 "4-Amino-1-butanol". PubChem. Retrieved 8 September 2024.
- 1 2 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
- ↑ 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.
- ↑ 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.
- 1 2 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.
- 1 2 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.
- 1 2 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].
- 1 2 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.
- 1 2 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].