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MedKoo Cat#: 146116 | Name: Ergovalinine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Ergovalinine is a naturally occurring ergot alkaloid primarily found in fungi of the Claviceps genus, and it is known for its vasoconstrictive and neurotoxic effects. It has been studied for its potential role in causing ergotism, a condition resulting from the consumption of contaminated rye, which can lead to symptoms like gangrene, convulsions, and hallucinations. Ergovalinine exerts its effects by binding to serotonin and dopamine receptors, influencing vasoconstriction and altering neurotransmitter activity.

Chemical Structure

Ergovalinine
Ergovalinine
CAS#3263-56-7

Theoretical Analysis

MedKoo Cat#: 146116

Name: Ergovalinine

CAS#: 3263-56-7

Chemical Formula: C29H35N5O5

Exact Mass: 533.2638

Molecular Weight: 533.63

Elemental Analysis: C, 65.27; H, 6.61; N, 13.12; O, 14.99

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Ergovalinine;
IUPAC/Chemical Name
(6aR,9S)-N-((2R,5S,10aS,10bS)-10b-hydroxy-5-isopropyl-2-methyl-3,6-dioxooctahydro-8H-oxazolo[3,2-a]pyrrolo[2,1-c]pyrazin-2-yl)-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide
InChi Key
BGHDUTQZGWOQIA-KPUJGURZSA-N
InChi Code
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-/m0/s1
SMILES Code
[H][C@@]12CCCN1C(=O)[C@H](C(C)C)N3C(=O)[C@](C)(NC(=O)[C@@H]4CN(C)[C@]5([H])CC6=CNC7=CC=CC(=C67)C5=C4)O[C@@]23O
Appearance
To be determined
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 -4 C for short term (days to weeks) or -20 C for long term(months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 533.63 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Klotz JL, Aiken GE, Bussard JR, Foote AP, Harmon DL, Goff BM, Schrick FN, Strickland JR. Vasoactivity and Vasoconstriction Changes in Cattle Related to Time off Toxic Endophyte-Infected Tall Fescue. Toxins (Basel). 2016 Sep 22;8(10):271. doi: 10.3390/toxins8100271. PMID: 27669299; PMCID: PMC5086632. 2: McDowell KJ, Moore ES, Parks AG, Bush LP, Horohov DW, Lawrence LM. Vasoconstriction in horses caused by endophyte-infected tall fescue seed is detected with Doppler ultrasonography. J Anim Sci. 2013 Apr;91(4):1677-84. doi: 10.2527/jas.2012-5852. Epub 2013 Feb 28. PMID: 23449860. 3: Britt JL, Greene MA, Wilbanks SA, Bertrand JK, Klotz JL, Bridges W Jr, Aiken G, Andrae JG, Duckett SK. Feeding Tall Fescue Seed Reduces Ewe Milk Production, Lamb Birth Weight and Pre-Weaning Growth Rate. Animals (Basel). 2020 Dec 3;10(12):2291. doi: 10.3390/ani10122291. PMID: 33287449; PMCID: PMC7761808. 4: Britt JL, Greene MA, Bridges WC, Klotz JL, Aiken GE, Andrae JG, Pratt SL, Long NM, Schrick FN, Strickland JR, Wilbanks SA, Miller MF, Koch BM, Duckett SK. Ergot alkaloid exposure during gestation alters. I. Maternal characteristics and placental development of pregnant ewes1. J Anim Sci. 2019 Apr 3;97(4):1874-1890. doi: 10.1093/jas/skz068. PMID: 30895321; PMCID: PMC6447248. 5: Britt JL, Greene MA, Klotz JL, Justice SM, Powell RR, Noorai RE, Bruce TF, Duckett SK. Mycotoxin ingestion during late gestation alters placentome structure, cotyledon transcriptome, and fetal development in pregnant sheep. Hum Exp Toxicol. 2022 Jan-Dec;41:9603271221119177. doi: 10.1177/09603271221119177. PMID: 35947831. 6: Ji H, Fannin F, Klotz J, Bush L. Tall fescue seed extraction and partial purification of ergot alkaloids. Front Chem. 2014 Dec 11;2:110. doi: 10.3389/fchem.2014.00110. PMID: 25566528; PMCID: PMC4263182. 7: Shappell NW, Smith DJ. Ergovaline movement across Caco-2 cells. In Vitro Cell Dev Biol Anim. 2005 Sep-Oct;41(8-9):245-51. doi: 10.1290/0504026R.1. PMID: 16409109. 8: Smith DJ, Shappell NW. Technical note: epimerization of ergopeptine alkaloids in organic and aqueous solvents. J Anim Sci. 2002 Jun;80(6):1616-22. doi: 10.2527/2002.8061616x. PMID: 12078743. 9: Greene MA, Britt JL, Bertrand JK, Klotz JL, Bridges W Jr, Andrae JG, Duckett SK. Feeding Tall Fescue Seed during Mid and Late Gestation Influences Subsequent Postnatal Growth, Puberty, and Carcass Quality of Offspring. Animals (Basel). 2020 Oct 12;10(10):1859. doi: 10.3390/ani10101859. PMID: 33053893; PMCID: PMC7601090. 10: Jia Y, Li Q, Burris WR, Aiken GE, Bridges PJ, Matthews JC. Forms of selenium in vitamin-mineral mixes differentially affect serum prolactin concentration and hepatic glutamine synthetase activity of steers grazing endophyte-infected tall fescue. J Anim Sci. 2018 Mar 6;96(2):715-727. doi: 10.1093/jas/skx068. PMID: 29385471; PMCID: PMC6140910. 11: Egert AM, Klotz JL, McLeod KR, Harmon DL. Development of a methodology to measure the effect of ergot alkaloids on forestomach motility using real-time wireless telemetry. Front Chem. 2014 Oct 13;2:90. doi: 10.3389/fchem.2014.00090. PMID: 25353021; PMCID: PMC4195290. 12: Jia Y, Son K, Burris WR, Bridges PJ, Matthews JC. Forms of selenium in vitamin-mineral mixes differentially affect serum alkaline phosphatase activity, and serum albumin and blood urea nitrogen concentrations, of steers grazing endophyte-infected tall fescue. J Anim Sci. 2019 May 30;97(6):2569-2582. doi: 10.1093/jas/skz109. PMID: 30957833; PMCID: PMC6541827. 13: Reinhard H, Rupp H, Zoller O. Ergot alkaloids: Quantitation and recognition challenges. Mycotoxin Res. 2008 Mar;24(1):7-13. doi: 10.1007/BF02985264. PMID: 23606074.