Ergovaline

{{Short description|Chemical compound}}

{{Drugbox

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| verifiedrevid = 424781850

| IUPAC_name =

| image = Ergovaline.svg

| width = 250px

| tradename =

| pregnancy_US_comment = 4 months

| pregnancy_category =

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| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 2873-38-3

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 059E2O9IV4

| ATC_prefix =

| ATC_suffix =

| PubChem = 104843

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| ChemSpiderID = 94635

| SMILES = O=C3N1CCC[C@H]1[C@]2(O)O[C@](C(=O)N2[C@H]3C(C)C)(NC(=O)[C@@H]7/C=C6/c4cccc5c4c(c[nH]5)C[C@H]6N(C)C7)C

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C29H35N5O5/c1-15(2)24-26(36)33-10-6-9-22(33)29(38)34(24)27(37)28(3,39-29)31-25(35)17-11-19-18-7-5-8-20-23(18)16(13-30-20)12-21(19)32(4)14-17/h5,7-8,11,13,15,17,21-22,24,30,38H,6,9-10,12,14H2,1-4H3,(H,31,35)/t17-,21-,22+,24+,28-,29+/m1/s1

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| StdInChIKey = BGHDUTQZGWOQIA-VQSKNWBGSA-N

| C=29 | H=35 | N=5 | O=5

}}

Ergovaline is an ergopeptine and one of the ergot alkaloids. It is usually found in endophyte-infected species of grass like Tall fescue{{cite journal |title=Tall Fescue Endophyte Toxicosis in Beef Cattle: Clinical Mode of Action and Potential Mitigation through Cattle Genetics| first = Richard | last = Browning | name-list-style = vanc |publisher=Beef Improvement Federation |year=2003 |url= http://www.bifconference.com/bif2003/BIFsymposium_pdfs/Browning.pdf }} or Perennial Ryegrass.{{cite journal | vauthors = Hovermale JT, Craig AM | title = Correlation of ergovaline and lolitrem B levels in endophyte-infected perennial ryegrass (Lolium perenne) | journal = Journal of Veterinary Diagnostic Investigation | volume = 13 | issue = 4 | pages = 323–7 | date = July 2001 | pmid = 11478604 | doi = 10.1177/104063870101300407 | doi-access = free }} It is toxic to cattle feeding on infected grass, probably because it acts as a vasoconstrictor.{{cite journal | vauthors = Schnitzius JM, Hill NS, Thompson CS, Craig AM | title = Semiquantitative determination of ergot alkaloids in seed, straw, and digesta samples using a competitive enzyme-linked immunosorbent assay | journal = Journal of Veterinary Diagnostic Investigation | volume = 13 | issue = 3 | pages = 230–7 | date = May 2001 | pmid = 11482600 | doi = 10.1177/104063870101300307 | doi-access = free }}