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MedKoo Cat#: 146128 | Name: Ergocristine

Description:

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

Ergocristine is an ergot alkaloid derived from Claviceps purpurea, a fungus that infects cereal crops, and is known for its vasoconstrictive and neuroactive properties. It has been studied for its potential use in treating conditions such as migraines, hypertension, and certain neurological disorders due to its ability to influence serotonin and dopamine receptors. Ergocristine works by binding to these receptors, regulating vasoconstriction and neurotransmitter release, which helps in alleviating symptoms of vascular headaches and other related conditions.

Chemical Structure

Ergocristine
Ergocristine
CAS#511-08-0

Theoretical Analysis

MedKoo Cat#: 146128

Name: Ergocristine

CAS#: 511-08-0

Chemical Formula: C35H39N5O5

Exact Mass: 609.2951

Molecular Weight: 609.73

Elemental Analysis: C, 68.95; H, 6.45; N, 11.49; O, 13.12

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
Ergocristine;
IUPAC/Chemical Name
(6aR,9R)-N-((2R,5S,10aS,10bS)-5-benzyl-10b-hydroxy-2-isopropyl-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
HEFIYUQVAZFDEE-MKTPKCENSA-N
InChi Code
1S/C35H39N5O5/c1-20(2)34(37-31(41)23-16-25-24-11-7-12-26-30(24)22(18-36-26)17-27(25)38(3)19-23)33(43)40-28(15-21-9-5-4-6-10-21)32(42)39-14-8-13-29(39)35(40,44)45-34/h4-7,9-12,16,18,20,23,27-29,36,44H,8,13-15,17,19H2,1-3H3,(H,37,41)/t23-,27-,28+,29+,34-,35+/m1/s1
SMILES Code
[H][C@@]12CCCN1C(=O)[C@H](CC3=CC=CC=C3)N4C(=O)[C@](NC(=O)[C@H]5CN(C)[C@]6([H])CC7=CNC8=CC=CC(=C78)C6=C5)(O[C@@]24O)C(C)C
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 609.73 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: Cherewyk JE, Parker SE, Blakley BR, Al-Dissi AN. Sustained vascular contractile response induced by an R- and S-epimer of the ergot alkaloid ergocristine and attenuation by a noncompetitive antagonist. J Anim Sci. 2022 Sep 1;100(9):skac235. doi: 10.1093/jas/skac235. PMID: 35775420; PMCID: PMC9492154. 2: Rudolph W, Remane D, Wissenbach DK, Peters FT. Comparative study on the metabolism of the ergot alkaloids ergocristine, ergocryptine, ergotamine, and ergovaline in equine and human S9 fractions and equine liver preparations. Xenobiotica. 2019 Oct;49(10):1149-1157. doi: 10.1080/00498254.2018.1542187. Epub 2019 Jan 9. PMID: 30623698. 3: Rudolph W, Remane D, Wissenbach DK, Peters FT. Liquid chromatography-mass spectrometry-based determination of ergocristine, ergocryptine, ergotamine, ergovaline, hypoglycin A, lolitrem B, methylene cyclopropyl acetic acid carnitine, N-acetylloline, N-formylloline, paxilline, and peramine in equine hair. J Chromatogr B Analyt Technol Biomed Life Sci. 2019 Jun 1;1117:127-135. doi: 10.1016/j.jchromb.2019.04.016. Epub 2019 Apr 5. PMID: 31009898. 4: Roquebert J, Demichel P. Agonist/antagonist activity of ergocristine at alpha-adrenoceptors in the rat. Fundam Clin Pharmacol. 1987;1(1):23-33. doi: 10.1111/j.1472-8206.1987.tb00542.x. PMID: 2822556. 5: Reifel CW, Shin SH, Leather RA. Extensive ultrastructural changes in rat mammotrophs following administration of the dopamine agonist ergocristine- reflecting inhibition of prolactin release. Cell Tissue Res. 1983;232(2):249-56. doi: 10.1007/BF00213784. PMID: 6688378. 6: Shin SH. Effect of ergocristine on prolactin secretion in the male rat with pituitaries grafted beneath the kidney capsule. Can J Physiol Pharmacol. 1979 Nov;57(11):1313-6. doi: 10.1139/y79-195. PMID: 42476. 7: Coufal-Majewski S, Stanford K, McAllister T, Blakley B, McKinnon J, Chaves AV, Wang Y. Impacts of Cereal Ergot in Food Animal Production. Front Vet Sci. 2016 Feb 25;3:15. doi: 10.3389/fvets.2016.00015. PMID: 26942186; PMCID: PMC4766294. 8: Cherewyk JE, Blakley BR, Al-Dissi AN. Investigation of the relationship between ergocristinine and vascular receptors. Toxicol Rep. 2023 May 14;10:604-611. doi: 10.1016/j.toxrep.2023.05.005. PMID: 37213815; PMCID: PMC10199403. 9: Chung SWC. A critical review of analytical methods for ergot alkaloids in cereals and feed and in particular suitability of method performance for regulatory monitoring and epimer-specific quantification. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2021 Jun;38(6):997-1012. doi: 10.1080/19440049.2021.1898679. Epub 2021 Mar 30. PMID: 33784227. 10: Peterková M, Kakác B, Matousová O. Stanovení trimepranolu, chlorthalidonu, DH-ergokristinu a amiloridu vedle sebe [Determination of trimepranol, chlorthalidone, DH-ergocristine and amiloride simultaneously]. Cesk Farm. 1980 Sep;29(7):241-3. Czech. PMID: 6110484. 11: Carbonell-Rozas L, Mahdjoubi CK, Arroyo-Manzanares N, García-Campaña AM, Gámiz-Gracia L. Occurrence of Ergot Alkaloids in Barley and Wheat from Algeria. Toxins (Basel). 2021 Apr 28;13(5):316. doi: 10.3390/toxins13050316. PMID: 33925104; PMCID: PMC8145663. 12: Schummer C, Zandonella I, van Nieuwenhuyse A, Moris G. Epimerization of ergot alkaloids in feed. Heliyon. 2020 Jun 30;6(6):e04336. doi: 10.1016/j.heliyon.2020.e04336. PMID: 32637710; PMCID: PMC7330613. 13: Jakob K, Schwack W, Morlock GE. All-in-one 2LabsToGo system for analysis of ergot alkaloids in whole rye. Food Chem. 2024 Sep 30;453:139593. doi: 10.1016/j.foodchem.2024.139593. Epub 2024 May 11. PMID: 38761724. 14: Klotz JL, Kirch BH, Aiken GE, Bush LP, Strickland JR. Contractile response of fescue-naive bovine lateral saphenous veins to increasing concentrations of tall fescue alkaloids. J Anim Sci. 2010 Jan;88(1):408-15. doi: 10.2527/jas.2009-2243. Epub 2009 Sep 25. PMID: 19783700. 15: Foote AP, Harmon DL, Strickland JR, Bush LP, Klotz JL. Effect of ergot alkaloids on contractility of bovine right ruminal artery and vein. J Anim Sci. 2011 Sep;89(9):2944-9. doi: 10.2527/jas.2010-3626. Epub 2011 Apr 21. PMID: 21512122. 16: Klotz JL, McDowell KJ. Tall fescue ergot alkaloids are vasoactive in equine vasculature. J Anim Sci. 2017 Nov;95(11):5151-5160. doi: 10.2527/jas2017.1852. PMID: 29293720; PMCID: PMC6292298. 17: Puras G, Santafé J, Segarra J, Garrido M, Melena J. The effect of topical natural ergot alkaloids on the intraocular pressure and aqueous humor dynamics in rabbits with alpha-chymotrypsin-induced ocular hypertension. Graefes Arch Clin Exp Ophthalmol. 2002 Apr;240(4):322-8. doi: 10.1007/s00417-002-0446-2. Epub 2002 Mar 9. PMID: 11981648. 18: Poapolathep S, Klangkaew N, Zhang Z, Giorgi M, Logrieco AF, Poapolathep A. Simultaneous Determination of Ergot Alkaloids in Swine and Dairy Feeds Using Ultra High-Performance Liquid Chromatography-Tandem Mass Spectrometry. Toxins (Basel). 2021 Oct 13;13(10):724. doi: 10.3390/toxins13100724. PMID: 34679017; PMCID: PMC8540808. 19: Almousa A, Yonpiam R, Blakley B, Al-Dissi AN. Prolonged absorption and susceptibility to enterohepatic circulation after oral administration of ergot alkaloids in ewes. Can J Vet Res. 2022 Apr;86(2):108-112. PMID: 35388236; PMCID: PMC8978282. 20: Yonpiam R, Gobbet J, Jadhav A, Desai K, Blakley B, Al-Dissi A. Vasoactive Effects of Acute Ergot Exposure in Sheep. Toxins (Basel). 2021 Apr 20;13(4):291. doi: 10.3390/toxins13040291. PMID: 33924041; PMCID: PMC8072561.