{{Chembox <!-- Images --> | ImageFile = Amabiline.svg | ImageSize = 200px <!-- Names --> | PIN = [(7a''S'')-5,6,7,7a-Tetrahydro-3''H''-pyrrolizin-1-yl]methyl (2''S'')-2-hydroxy-2-[(1''S'')-1-hydroxyethyl]-3-methylbutanoate | OtherNames = <!-- Sections --> | Section1 = {{Chembox Identifiers | CASNo = 17958-43-9 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = HG6G8EU69E | PubChem = 442706 | ChEBI = 2617 | KEGG = C10263 | ChemSpiderID = 391061 | StdInChI=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 | StdInChIKey = DRVWTOSBCBKXOR-WHOFXGATSA-N | SMILES = C[C@@H]([C@@](C(C)C)(C(=O)OCC1=CCN2[C@H]1CCC2)O)O }} | Section2 = {{Chembox Properties | C=15|H=25|N=1|O=4 | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} | Section3 = {{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }}
'''Amabiline''' is a pyrrolizidine alkaloid first isolated in 1967 from ''Cynoglossum amabile''.<ref>{{cite journal | doi = 10.1071/CH9672499 | title = The alkaloids of Cynoglossum australe R.Br. And C. Amabile Stapf & Drummond | journal = Australian Journal of Chemistry | volume = 20 | issue = 11 | pages = 2499 | year = 1967 | last1 = Culvenor | first1 = CCJ | last2 = Smith | first2 = LW }}</ref> It is also found in the seeds and flowers of borage (''Borago officinalis'')<ref>{{cite journal | doi = 10.1021/np50046a045 | title = Pyrrolizidine Alkaloids from Borage (Borago officinalis) Seeds and Flowers | journal = Journal of Natural Products | volume = 49 | issue = 4 | pages = 727–728 | year = 1986 | last1 = Dodson | first1 = Craig D. | last2 = Stermitz | first2 = Frank R. | bibcode = 1986JNAtP..49..727D }}</ref> and in borage seed oil.<ref>{{cite journal | title = TLC detection of pyrrolizidine alkaloids in oil extracted from the seeds of Borago officinalis |author1=Parvais, O. |author2=Vander Stricht, B. |author3=Vanhaelen-Fastre, R. |author4=Vanhaelen, M. | journal = Journal of Planar Chromatography--Modern TLC | year = 1994 | volume = 7 | issue = 1 | pages = 80–82}}</ref><ref>{{cite journal |author1=Wretensjoe, Inger |author2=Karlberg, Bo. | title = Pyrrolizidine alkaloid content in crude and processed borage oil from different processing stages | journal = Journal of the American Oil Chemists' Society | year = 2003 | volume = 80 | issue = 10 | pages = 963–970 | doi = 10.1007/s11746-003-0804-z|s2cid=94575246 }}</ref>
Chemically, it is the ester derived from viridifloric acid and supinidine.<ref>{{cite book | title = The Alkaloids: Chemistry and Physiology | publisher = Academic Press | date = 1970 | pages = 302–303 }}</ref>
Amabiline is hepatotoxic and may contribute to the potential liver damage caused by consumption of borage and its seed oil.<ref>{{cite web | url = https://www.mskcc.org/cancer-care/integrative-medicine/herbs/borage | title = Borage | date = 31 March 2022 | publisher = Memorial Sloan Kettering Cancer Center }}</ref>
==References== {{reflist}}
Category:pyrrolizidine alkaloids Category:Esters Category:Diols