Anagyrine
 Skeletal structure of anagyrine
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| Names | |
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IUPAC name
7,14-Methano-4H,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocin-4-one, 7,7a,8,9,10,11,13,14-octahydro-, [7R-(7α,7aβ,14α)]-
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| Other names
Rhombinine; Anagyrin; Monolupin; Monolupine; Rhombinin; 3,4,5,6-Tetradehydrospartein-2-one
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PubChem CID
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| Properties | |
| C15H20N2O1 | |
| Molar mass | 244.33 g/mol |
| Density | 1.22 ±0.1 g/mL |
| Boiling point | 455.6 °C |
| Hazards | |
| Flash point | 216.3 °C |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |
Anagyrine is a teratogenic alkaloid commonly found in many species of lupinus plants. The toxin can cause crooked calf disease if a cow ingests the plant during certain periods of pregnancy.
The toxicity of certain species of lupinus plants has been known for several years. The plant is very common in western North America and is sometimes used in feed for cattle if the toxicity of the given lupine is low enough. The toxicity of the plant comes from a variety of toxins, however out of these chemicals anagyrine is the most well known for causing crooked calf disease when ingested by cows. The discovery of anagyrine occurred in 1885 by E.Hardy and N. Gallois and the earliest isolation of anagyrine from a lupinus plant was recorded in 1939. The toxin can be found in growing leaf material in a young lupinus plant and in the flower and seed of a mature plant, though varying concentrations of the alkaloid are present throughout lupines that contain anagyrine. The first correlation between anagyrine and crooked calf disease was made by Richard Keeler in 1973. Recently there have been a few successful syntheses of anagyrine recorded, most notably one completed by Diane Gray and Timothy Gallagher.
Anagyrine causes crooked calf disease if 1.44g/kg of the substance is ingested by the mother cow between days 40 and 70 of pregnancy. Out of the hundreds of varieties of lupinus plants, 23 (listed below) are known to contain high enough concentrations of anagyrine to be dangerous to cattle. The IC50 of anagyrine is 132 μM at muscarinic receptors and 2,096 μM at nicotinic receptors.
Known symptoms of crooked cow disease include athrogryposis (permanently flexed joints), torticollis (twisting of the neck), scoliosis (curving of the spine), kyphosis (humpback), and cleft plate. It is thought that teratogenic alkaloids like anagyrine cause the deformities by sedating the fetus, causing it to remain fixed in an abnormal position as it grows. Lasting malformations of the calf can occur even in mild poisonings of the cow because fetal movement depression persists much longer between doses of teratogenic alkaloids than the signs of toxicity in the cow.
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Wikipedia