MedKoo Cat#: 413989 | Name: Ergotoxine Free Base

Description:

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

Ergotoxine Free Base is a mixture of three different ergotaman-3',6',18-triones; toxic ergot alkaloid mixture of equal parts of erocornine, ergocristine & ergocryptine; has alpha adrenergic blocking action, stimulates smooth muscle & antagonizes serotonin; used as oxytocic & in peripheral vascular disorders.

Chemical Structure

Ergotoxine Free Base
Ergotoxine Free Base
CAS#8006-25-5 (free base)

Theoretical Analysis

MedKoo Cat#: 413989

Name: Ergotoxine Free Base

CAS#: 8006-25-5 (free base)

Chemical Formula: C28H33N5O5

Exact Mass: 519.2482

Molecular Weight: 519.60

Elemental Analysis: C, 64.72; H, 6.40; N, 13.48; O, 15.40

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 #
8047-28-7 (esylate) 8006-25-5 (free) 8047-29-8 (phosphate)
Synonym
Ergotoxine Free Base; Ecboline; Ergotoxin
IUPAC/Chemical Name
(6aR,9R)-N-((2R,10aS,10bS)-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
XLMJRFCCCWFQRE-SJRQCXNHSA-N
InChi Code
InChI=1S/C28H33N5O5/c1-15(2)27(26(36)33-14-23(34)32-9-5-8-22(32)28(33,37)38-27)30-25(35)17-10-19-18-6-4-7-20-24(18)16(12-29-20)11-21(19)31(3)13-17/h4,6-7,10,12,15,17,21-22,29,37H,5,8-9,11,13-14H2,1-3H3,(H,30,35)/t17-,21-,22+,27-,28+/m1/s1
SMILES Code
CC([C@]1(O[C@]2([C@@H]3CCCN3C(CN2C1=O)=O)O)NC([C@H]4CN([C@@H]5Cc(c[nH]6)c7c6cccc7C5=C4)C)=O)C
Appearance
Solid powder
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 519.60 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: Kanto J. Clinical pharmacokinetics of ergotamine, dihydroergotamine, ergotoxine, bromocriptine, methysergide, and lergotrile. Int J Clin Pharmacol Ther Toxicol. 1983 Mar;21(3):135-42. PMID: 6133838. 2: Barger G, Dale HH. Ergotoxine and some other Constituents of Ergot. Biochem J. 1907;2(5-6):240-99. doi: 10.1042/bj0020240. PMID: 16742070; PMCID: PMC1276214. 3: Dale HH. On the action of ergotoxine; with special reference to the existence of sympathetic vasodilators. J Physiol. 1913 Jun 19;46(3):291-300. doi: 10.1113/jphysiol.1913.sp001592. PMID: 16993202; PMCID: PMC1420444. 4: Moir C. CLINICAL COMPARISON OF ERGOTOXINE AND ERGOTAMINE: A REPORT TO THE THERAPEUTIC TRIALS COMMITTEE OF THE MEDICAL RESEARCH COUNCIL. Br Med J. 1932 Jun 4;1(3726):1022-4. doi: 10.1136/bmj.1.3726.1022. PMID: 20776878; PMCID: PMC2521092. 5: SHELESNYAK MC. Failure of adrenalectomy to interfere with ergotoxine-induced interruption of early pregnancy in the rat. J Endocrinol. 1956 Aug;14(1):37-9. doi: 10.1677/joe.0.0140037. PMID: 13357679. 6: Iwangoff P, Meier-Ruge W, Schieweck C, Enz A. The uptake of DH-ergotoxine by different parts of the cat brain. Pharmacology. 1976;14(1):27-38. doi: 10.1159/000136576. PMID: 989171. 7: Brace DE, Reid LC. THE USE OF ERGOTOXINE AND ERGOTAMINE IN THE SURGICAL MANAGEMENT OF THYROTOXICOSIS. Ann Surg. 1941 Jan;113(1):62-72. doi: 10.1097/00000658-194101000-00008. PMID: 17857716; PMCID: PMC1385655. 8: Fioravanti M, Nakashima T, Xu J, Garg A. A systematic review and meta- analysis assessing adverse event profile and tolerability of nicergoline. BMJ Open. 2014 Jul 30;4(7):e005090. doi: 10.1136/bmjopen-2014-005090. PMID: 25079927; PMCID: PMC4120366. 9: BUCHANAN AR, ROBERTS JE, ROBINSON BE. Ergotoxine hyper- and hypothermia in albino rats. Proc Soc Exp Biol Med. 1948 May;68(1):143-50. doi: 10.3181/00379727-68-16418. PMID: 18863702. 10: MATANIC V. [The treatment of ulcus cruris, diabetic gangrene and thrombophlebitis with hydrogenated alkaloids of the ergotoxine group]. Wien Med Wochenschr. 1961 Aug 5;111:511-3. German. PMID: 13768027.