4-Amino-1-butanol

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]

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
CAS Number	13325-10-5
3D model (JSmol)	Interactive image
ChemSpider	24099
ECHA InfoCard	100.033.045
EC Number	236-364-4
PubChem CID	25868
CompTox Dashboard (EPA)	DTXSID70158027
InChI InChI=1S/C4H11NO/c5-3-1-2-4-6/h6H,1-5H2 Key: BLFRQYKZFKYQLO-UHFFFAOYSA-N
SMILES C(CCO)CN
Properties
Chemical formula	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). Infobox references

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]