Amabiline

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 ;
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

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

Chemically, it is the ester derived from viridifloric acid and supinidine.

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

References

↑ Culvenor, CCJ; Smith, LW (1967). "The alkaloids of Cynoglossum australe R.Br. And C. Amabile Stapf & Drummond". Australian Journal of Chemistry. 20 (11): 2499. doi:10.1071/CH9672499.
↑ Dodson, Craig D.; Stermitz, Frank R. (1986). "Pyrrolizidine Alkaloids from Borage (Borago officinalis) Seeds and Flowers". Journal of Natural Products. 49 (4): 727–728. Bibcode:1986JNAtP..49..727D. doi:10.1021/np50046a045.
↑ Parvais, O.; Vander Stricht, B.; Vanhaelen-Fastre, R.; Vanhaelen, M. (1994). "TLC detection of pyrrolizidine alkaloids in oil extracted from the seeds of Borago officinalis". Journal of Planar Chromatography--Modern TLC. 7 (1): 80–82.
↑ Wretensjoe, Inger; Karlberg, Bo. (2003). "Pyrrolizidine alkaloid content in crude and processed borage oil from different processing stages". Journal of the American Oil Chemists' Society. 80 (10): 963–970. doi:10.1007/s11746-003-0804-z. S2CID 94575246.
↑ The Alkaloids: Chemistry and Physiology. Academic Press. 1970. pp. 302–303.
↑ "Borage". Memorial Sloan Kettering Cancer Center. 31 March 2022.