Global InformationAnagyrine information
 Skeletal structure of anagyrine
| |
 Ball-and-stick model of anagyrine[1][2]
| |
| 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] 3,4,5,6-Tetradehydrospartein-2-one;[4] [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[3]
| |
| Identifiers | |
CAS Number
|
|
3D model (JSmol)
|
|
| ECHA InfoCard | 100.215.995 |
PubChem CID
|
|
| UNII |
|
CompTox Dashboard (EPA)
|
|
InChI
| |
SMILES
| |
| Properties | |
Chemical formula
|
C15H20N2O |
| Molar mass | 244.338 g·mol−1 |
| Density | 1.22 ±0.1 g/mL[5] |
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.[6] 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.[7][8] 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).[9] The toxin can cause crooked calf disease if a cow ingests the plant during certain periods of pregnancy.
- ^ Turgunov, K.K.; Rakhimov, S.B.; Vinogradova, V.I.; Tashkhodjaev, B. (2015). "CSD Entry: UHUHOW". Cambridge Structural Database: Access Structures. Cambridge Crystallographic Data Centre. doi:10.5517/cc14ll5h. Retrieved 2022-07-28.
- ^ Turgunov, K. K.; Rakhimov, S. B.; Vinogradova, V. I.; Tashkhodjaev, B. (2015). "Crystal structure of anagyrine perchlorate". Acta Crystallogr. E. 71 (5): o343–o344. Bibcode:2015AcCrE..71O.343T. doi:10.1107/S2056989015007781. PMC 4420039. PMID 25995939. S2CID 22686042.
- ^ a b P.J. Linstrom and W.G. Mallard, Eds., NIST Chemistry WebBook, NIST Standard Reference Database Number 69, National Institute of Standards and Technology, Gaithersburg MD, 20899, doi:10.18434/T4D303, (retrieved April 21, 2017)
- ^ "3,4,5,6-Tetradehydrospartein-2-one." 3,4,5,6-Tetradehydrospartein-2-one | C15H20N2O | ChemSpider. Royal Society of Chemistry, n.d. Web. 25 Apr. 2017.
- ^ 486-89-5(ANAGYRINE) Product Description." ChemicalBook---Chemical Search Engine. N.p., n.d. Web. 21 Apr. 2017.
- ^ Hardy and Gallois, Comptes-rendus et Mémoires de la Société de Biologie, 13th June 1885
- ^ Pedanius Dioscorides, De materia medica Book 3: "Roots of Akanthoda (= Prickly Plants) No. 167 "Anaguris [Onaguris]" http://www.cancerlynx.com/BOOKTHREEROOTS.PDF
- ^ Partheil and Spassky, Apoth. Ztg. 1895, 10, 903 https://pubs.rsc.org/en/Image/Get?imageInfo.ImageType=GA&imageInfo.ImageIdentifier.ManuscriptID=JR9330000504&imageInfo.ImageIdentifier.Year=1933 Retrieved at 11.59 on 28/11/22.
- ^ Couch, James Fitton. "Lupine Studies. XIV.1 The Isolation of Anagyrine FromLupinus Laxiflorusvar.silvicola C. P. Smith." Journal of the American Chemical Society 61.12 (1939): 3327-328. https://pubs.acs.org/doi/pdf/10.1021/ja01267a027 Retrieved at 12.18 on 28/11/22.