Anagyrine

Anagyrine
	Skeletal structure of anagyrine
	Ball-and-stick model of anagyrine
Names
	Systematic IUPAC name (7Ξ,7aR,14Ξ)-7,7a,8,9,10,11,13,14-Octahydro-4H,6H-7,14-methanodipyrido[1,2-a:1′,2′-e] [1,5]diazocin-4-one
	Other names Rhombinine; Anagyrin; Monolupin; Monolupine; Rhombinin; 3,4,5,6-Tetradehydrospartein-2-one; [7R-(7α,7aβ,14α)]-7,7a,8,9,10,11,13,14-Octahydro-7,14-methano-4H,6H-dipyrido[1,2-a:1′,2′-e] [1,5]diazocin-4-one
Identifiers
CAS Number	486-89-5 ;
3D model (JSmol)	Interactive image;
ChemSpider	9828;
ECHA InfoCard	100.215.995
PubChem CID	10246;
UNII	FYU1U980Q9 ;
CompTox Dashboard (EPA)	DTXSID40964091 ;
	InChI InChI=1S/C15H20N2O/c18-15-6-3-5-14-11-8-12(10-17(14)15)13-4-1-2-7-16(13)9-11/h3,5-6,11-13H,1-2,4,7-10H2/t11?,12?,13-/m1/s1 Key: FQEQMASDZFXSJI-WXRRBKDZSA-N;
	SMILES C1CCN2CC3CC(C2C1)CN4C3=CC=CC4=O;
Properties
Chemical formula	C15H20N2O
Molar mass	244.338 g·mol−1
Density	1.22 ±0.1 g/mL
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Anagyrine is a teratogenic alkaloid first isolated from (and named for) Anagyris foetida in the year 1885 by French biologists Hardy and Gallois. A. foetida (family Fabaceae), the Stinking Bean Trefoil, is a highly toxic shrub native to the Mediterranean region, with a long history of use in folk medicine. In the year 1939 Anagyrine was found by James Fitton Couch to be identical to an alkaloid present in many species belonging to the plant genus Lupinus (lupins). The toxin can cause crooked calf disease if a cow ingests the plant during certain periods of pregnancy.