4-Amino-1-butanol
Organic compound and GABA analogue and precursor
From Wikipedia, the free encyclopedia
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.
 | |
| 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) |
|
| ChemSpider | |
| ECHA InfoCard | 100.033.045 |
| EC Number |
|
PubChem CID |
|
CompTox Dashboard (EPA) |
|
| |
| |
| 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: | |
  | |
| 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).
| |
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]