Swainsonine

This article may be too technical for most readers to understand. Please help improve it to make it understandable to non-experts, without removing the technical details. (January 2022) (Learn how and when to remove this message)

Swainsonine

Names
Preferred IUPAC name (1S,2R,8R,8aR)-Octahydroindolizine-1,2,8-triol
Other names Tridolgosir
Identifiers
CAS Number	72741-87-8 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:9367 N
ChEMBL	ChEMBL371197 Y
ChemSpider	46788 Y
DrugBank	DB02034 Y
ECHA InfoCard	100.123.531
KEGG	C10173 Y
PubChem CID	51683
UNII	RSY4RK37KQ Y
CompTox Dashboard (EPA)	DTXSID5046356
InChI InChI=1S/C8H15NO3/c10-5-2-1-3-9-4-6(11)8(12)7(5)9/h5-8,10-12H,1-4H2/t5-,6-,7-,8-/m1/s1 Y Key: FXUAIOOAOAVCGD-WCTZXXKLSA-N Y InChI=1/C8H15NO3/c10-5-2-1-3-9-4-6(11)8(12)7(5)9/h5-8,10-12H,1-4H2/t5-,6-,7-,8-/m1/s1 Key: FXUAIOOAOAVCGD-WCTZXXKLBP InChI=1S/C8H15NO3/c10-5-2-1-3-9-4-6(11)8(12)7(5)9/h5-8,10-12H,1-4H2/t5-,6-,7-,8-/m1/s1 Key: FXUAIOOAOAVCGD-WCTZXXKLSA-N
SMILES C1C[C@H]([C@@H]2[C@@H]([C@@H](CN2C1)O)O)O
Properties
Chemical formula	C8H15NO3
Molar mass	173.2
Melting point	143 to 144 °C (289 to 291 °F; 416 to 417 K)
Solubility in water	10 mg/1 mL
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Swainsonine is an indolizidine alkaloid. It is a potent inhibitor of Golgi alpha-mannosidase II, an immunomodulator, and a potential chemotherapy drug.^[1] As a toxin in locoweed (likely its primary toxin^[2]) it also is a significant cause of economic losses in livestock industries, particularly in North America. It was first isolated from Swainsona canescens.^[3]