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.^[1] It is also found in the seeds and flowers of borage (Borago officinalis)^[2] and in borage seed oil.^[3]^[4]

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]

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. 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.