Ergovaline

Ergovaline
Identifiers
CAS Number	2873-38-3 ;
PubChem CID	104843;
ChemSpider	94635 ;
UNII	059E2O9IV4;
CompTox Dashboard (EPA)	DTXSID10893243 ;
Chemical and physical data
Formula	C29H35N5O5
Molar mass	533.629 g·mol−1
3D model (JSmol)	Interactive image;
	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;
	InChI InChI=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 ; Key:BGHDUTQZGWOQIA-VQSKNWBGSA-N ;
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Ergovaline is an ergopeptine and one of the ergot alkaloids. It is usually found in endophyte-infected species of grass like Tall fescue^[1] or Perennial Ryegrass.^[2] It is toxic to cattle feeding on infected grass, probably because it acts as a vasoconstrictor.^[1]^[3]

References

^ ^a ^b Browning R (2003). "Tall Fescue Endophyte Toxicosis in Beef Cattle: Clinical Mode of Action and Potential Mitigation through Cattle Genetics" (PDF). Beef Improvement Federation. {{cite journal}}: Cite journal requires |journal= (help)
^ Hovermale JT, Craig AM (July 2001). "Correlation of ergovaline and lolitrem B levels in endophyte-infected perennial ryegrass (Lolium perenne)". Journal of Veterinary Diagnostic Investigation. 13 (4): 323–7. doi:10.1177/104063870101300407. PMID 11478604.
^ Schnitzius JM, Hill NS, Thompson CS, Craig AM (May 2001). "Semiquantitative determination of ergot alkaloids in seed, straw, and digesta samples using a competitive enzyme-linked immunosorbent assay". Journal of Veterinary Diagnostic Investigation. 13 (3): 230–7. doi:10.1177/104063870101300307. PMID 11482600.

External links

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[Browning-1] Browning R (2003). "Tall Fescue Endophyte Toxicosis in Beef Cattle: Clinical Mode of Action and Potential Mitigation through Cattle Genetics" (PDF). Beef Improvement Federation. {{cite journal}}: Cite journal requires |journal= (help)

[2] Hovermale JT, Craig AM (July 2001). "Correlation of ergovaline and lolitrem B levels in endophyte-infected perennial ryegrass (Lolium perenne)". Journal of Veterinary Diagnostic Investigation. 13 (4): 323–7. doi:10.1177/104063870101300407. PMID 11478604.

[3] Schnitzius JM, Hill NS, Thompson CS, Craig AM (May 2001). "Semiquantitative determination of ergot alkaloids in seed, straw, and digesta samples using a competitive enzyme-linked immunosorbent assay". Journal of Veterinary Diagnostic Investigation. 13 (3): 230–7. doi:10.1177/104063870101300307. PMID 11482600.

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[2]

[3]

v t e Ergolines
Lysergic acid derivatives	2-Bromo-LSD (BOL-148) Amesergide Bromocriptine Cabergoline Dihydroergocornine Dihydroergocristine Dihydroergocryptine Dihydroergometrine (Dihydroergonovine, Dihydroergobasine) Dihydroergosine Dihydroergotamine Epicriptine Ergine (LSA; LA-111; Lysergamide) Ergocornine Ergocristine Ergocryptine Ergoloid (Dihydroergotoxine) Ergometrine (Ergonovine, Ergobasine) Ergometrinine Ergostine Ergotamine Ergotoxine Ergovaline Lisuride LY-215,840 LSH Lysergic acid Lysergic acid methyl ester Lysergol Mesulergine Metergoline MIPLA Methysergide Sergolexole
Psychedelic lysergamides	1B-LSD 1cP-LSD 1P-ETH-LAD 1P-LSD AL-LAD ALD-52 BU-LAD CYP-LAD Diallyllysergamide (DAL) Dimethyllysergamide (DAM-57) ECPLA Ergonovine ETFELA ETH-LAD IP-LAD LAMPA LAE-32 LSD LPD-824 LSM-775 LSH LSD-Pip Lysergic Acid 2-Butylamide Lysergic Acid 2,4-Dimethylazetidide Lysergic Acid 3-Pentylamide Lysergic acid cyclobutylamide Lysergic acid cyclopentylamide Methylergometrine (Methylergonovine, Methylergobasine) MIPLA MLD-41 PARGY-LAD PRO-LAD
Clavines	9-Deacetoxyfumigaclavine C Agroclavine Chanoclavine Chanoclavine II Costaclavin Cycloclavine Elymoclavine Epoxyagroclavine Festuclavine Fumigaclavine A Fumigaclavine B Fumigaclavine C Paliclavine Penniclavine Setoclavine
Other ergolines	Acetergamine CY-208,243 Ergoline Lergotrile Nicergoline Pergolide
Natural sources	Achnatherum robustum (Sleepy Grass) Claviceps spp. (Ergot) Morning glory: Argyreia nervosa (Hawaiian Baby Woodrose), Ipomoea spp.(Morning Glory, Tlitliltzin, Badoh Negro), Rivea corymbosa (Coaxihuitl, Ololiúqui)

Ergovaline

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Identifiers

CAS Number	2873-38-3^Y
PubChem CID	104843
ChemSpider	94635^N
UNII	059E2O9IV4
CompTox Dashboard (EPA)	DTXSID10893243
Chemical and physical data
Formula	C₂₉H₃₅N₅O₅
Molar mass	533.629 g·mol⁻¹
3D model (JSmol)	Interactive image
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
InChI InChI=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^N Key:BGHDUTQZGWOQIA-VQSKNWBGSA-N^N
^NY (what is this?) (verify)

Ergovaline

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