Amabiline

Amabiline is a pyrrolizidine alkaloid first isolated in 1967 from Cynoglossum amabile.^[1] It is also found in the seeds and flowers of borage (Borago officinalis)^[2] and in borage seed oil.^[3][4]

Amabiline

Names
Preferred IUPAC name [(7aS)-5,6,7,7a-Tetrahydro-3H-pyrrolizin-1-yl]methyl (2S)-2-hydroxy-2-[(1S)-1-hydroxyethyl]-3-methylbutanoate
Identifiers
CAS Number	17958-43-9
3D model (JSmol)	Interactive image
ChEBI	CHEBI:2617
ChemSpider	391061
KEGG	C10263
PubChem CID	442706
UNII	HG6G8EU69E Y
CompTox Dashboard (EPA)	DTXSID60939241
InChI InChI=1S/C15H25NO4/c1-10(2)15(19,11(3)17)14(18)20-9-12-6-8-16-7-4-5-13(12)16/h6,10-11,13,17,19H,4-5,7-9H2,1-3H3/t11-,13-,15-/m0/s1 Key: DRVWTOSBCBKXOR-WHOFXGATSA-N
SMILES C[C@@H]([C@@](C(C)C)(C(=O)OCC1=CCN2[C@H]1CCC2)O)O
Properties
Chemical formula	C15H25NO4
Molar mass	283.368 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

Chemically, it is the ester derived from viridifloric acid and supinidine.^[5]

Amabiline is hepatotoxic and may contribute to the potential liver damage caused by consumption of borage and its seed oil.^[6]