Ergovaline

CAS: 2873-38-3

Ref. TR-E600050

Product Information

• Name: Ergovaline
• Synonyms: (5'a)-12'-Hydroxy-2'-methyl-5'-(1-methylethyl)-ergotaman-3',6',18-trione, 8H-Oxazolo[3,2-a]pyrrolo[2,1-c]pyrazine, ergotaman-3',6',18-trione deriv., 4,6,6a,7,8,9-hexahydro-7-methyl-N-(octahydro-10b-hydroxy-5-isopropyl-2-methyl-3,6-dioxo-8H-oxazolo[3,2-a]pyrrolo[2,1-c]pyrazin-2-yl)- indolo[4,3-fg]quinoline-9-carboxamide, (5'alpha)-9,10-Dihydro-12'-hydroxy-2'-methyl-5'-(1-methylethyl)ergotaman-3',6',18-trione, (5′α)-12′-Hydroxy-2′-methyl-5′-(1-methylethyl)ergotaman-3′,6′,18-trione, 8H-Oxazolo[3,2-a]pyrrolo[2,1-c]pyrazine, ergotaman-3′,6′,18-trione deriv., Ergotaman-3′,6′,18-trione, 12′-hydroxy-2′-methyl-5′-(1-methylethyl)-, (5′α)-, Indolo[4,3-fg]quinoline, ergotaman-3′,6′,18-trione deriv., Indolo[4,3-fg]quinoline-9-carboxamide, 4,6,6a,7,8,9-hexahydro-7-methyl-N-(octahydro-10b-hydroxy-5-isopropyl-2-methyl-3,6-dioxo-8H-oxazolo[3,2-a]pyrrolo[2,1-c]pyrazin-2-yl)-
• CAS: 2873-38-3

Description

Stability Unstable in solution
Applications Ergovaline is an ergopetine alkaloid commonly found in endophyte-infected species of tall grass fescue. Ergovaline is known to cause tall fescue toxicosis and is toxic to cattle feeding on the infected grass as it inhibits vesicular glutamate transporter activity in cow cerebral synatic vesicles.
References Xue, Y., et al.: J. Dairy. Sci., 94, 3331 (2011); Najafabdi, A.S., et al.: Res. Pharm. Sci., 5, 135 (2010); Foote, A.P., et al.: J. Animial. Sci., 89, 2944 (2011); Reed, K.F., et al.: Animal. Prod. Sci., 51, 1098 (2011);

• Brand: TRC

Chemical properties

• Molecular weight: 533.6187
• Formula: C₂₉H₃₅N₅O₅
• Color/Form: Neat
• 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
• InChI key: InChIKey=BGHDUTQZGWOQIA-VQSKNWBGSA-N
• SMILES: CC(C)[C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@@](C)(NC(=O)[C@@H]3C=C4c5cccc6[nH]cc(c56)C[C@H]4N(C)C3)C(=O)N12