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MedKoo Cat#: 333108 | Name: Ergotaminine

Description:

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

Ergotaminine is an ergot alkaloid formed by, among others, the fungus Claviceps purpurea on cereal grains and grasses during the growth process. Ergotaminine is a stereoisomer of Ergotamine, which has CAS#113-15-5. Ergotamine is an ergopeptine and part of the ergot family of alkaloids. Ergotamine is used medicinally for treatment of acute migraine attacks (sometimes in combination with caffeine). This product is not available (it is a DEA controlled substance).

Chemical Structure

Ergotaminine
Ergotaminine
CAS#639-81-6 (free base),

Theoretical Analysis

MedKoo Cat#: 333108

Name: Ergotaminine

CAS#: 639-81-6 (free base),

Chemical Formula: C33H35N5O5

Exact Mass: 581.2638

Molecular Weight: 581.67

Elemental Analysis: C, 68.14; H, 6.07; N, 12.04; O, 13.75

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 #
379-79-3 (tartrate) 639-81-6 (free base) 113-15-5 (Ergotamine)
Synonym
Ergotaminine; Isoergotamine;
IUPAC/Chemical Name
(6aR,9S)-N-((2R,5S,10aS,10bS)-5-benzyl-10b-hydroxy-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
XCGSFFUVFURLIX-BRMNWJGKSA-N
InChi Code
InChI=1S/C33H35N5O5/c1-32(35-29(39)21-15-23-22-10-6-11-24-28(22)20(17-34-24)16-25(23)36(2)18-21)31(41)38-26(14-19-8-4-3-5-9-19)30(40)37-13-7-12-27(37)33(38,42)43-32/h3-6,8-11,15,17,21,25-27,34,42H,7,12-14,16,18H2,1-2H3,(H,35,39)/t21-,25+,26-,27-,32+,33-/m0/s1
SMILES Code
O[C@@]12N([C@@H](CC3=CC=CC=C3)C(=O)N4[C@]1(CCC4)[H])C(=O)[C@@](NC(=O)[C@H]5C=C6C=7C=8C(C[C@]6(N(C)C5)[H])=CNC8C=CC7)(C)O2
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 581.67 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: Jamir E, Sarma H, Priyadarsinee L, Kiewhuo K, Nagamani S, Sastry GN. Polypharmacology guided drug repositioning approach for SARS-CoV2. PLoS One. 2023 Aug 9;18(8):e0289890. doi: 10.1371/journal.pone.0289890. PMID: 37556478; PMCID: PMC10411734. 2: da Fonseca AM, Caluaco BJ, Madureira JMC, Cabongo SQ, Gaieta EM, Djata F, Colares RP, Neto MM, Fernandes CFC, Marinho GS, Dos Santos HS, Marinho ES. Screening of Potential Inhibitors Targeting the Main Protease Structure of SARS- CoV-2 via Molecular Docking, and Approach with Molecular Dynamics, RMSD, RMSF, H-Bond, SASA and MMGBSA. Mol Biotechnol. 2023 Jul 25. doi: 10.1007/s12033-023-00831-x. Epub ahead of print. PMID: 37490200. 3: Kim Y, Shin SJ, Lee JW, Kim YS, You HS, Kim J, Kang HT. Association Between Migraine and Ischemic Cardio-Cerebrovascular Disease (CCVD) and Effects of Triptans and Ergotamine on the Risk of Ischemic CCVD in Patients with Migraine in the Korean NHIS-HEALS Cohort. Clin Drug Investig. 2023 Jul;43(7):541-550. doi: 10.1007/s40261-023-01290-7. Epub 2023 Jul 17. PMID: 37460781. 4: Drugs and Lactation Database (LactMed®) [Internet]. Bethesda (MD): National Institute of Child Health and Human Development; 2006–. Ergotamine. 2023 Jul 15. PMID: 30000392. 5: Shakeel F, Alam P, Alqarni MH, Haq N, Bar FMA, Iqbal M. A Rapid and Sensitive Stability-Indicating Eco-Friendly HPTLC Assay for Fluorescence Detection of Ergotamine. Molecules. 2023 Jun 29;28(13):5101. doi: 10.3390/molecules28135101. PMID: 37446763; PMCID: PMC10343250. 6: Ngo M, Tadi P. Ergotamine/Caffeine. 2023 Jul 4. In: StatPearls [Internet]. Treasure Island (FL): StatPearls Publishing; 2023 Jan–. PMID: 32310413. 7: Fischer MA, Jan A. Medication-Overuse Headache. 2023 Jun 26. In: StatPearls [Internet]. Treasure Island (FL): StatPearls Publishing; 2023 Jan–. PMID: 30844177. 8: Chauhan A, Singh J, Sangwan N, Singh H, Prakash A, Medhi B, Avti PK. Designing the 5HT2BR structure and its modulation as a therapeutic target for repurposing approach in drug-resistant epilepsy. Epilepsy Res. 2023 Aug;194:107168. doi: 10.1016/j.eplepsyres.2023.107168. Epub 2023 May 30. PMID: 37302343. 9: Drugs for migraine. Med Lett Drugs Ther. 2023 Jun 12;65(1678):89-96. doi: 10.58347/tml.2023.1678a. PMID: 37266987. 10: Jacob H, Braekow P, Schwarz R, Höhm C, Kirchhefer U, Hofmann B, Neumann J, Gergs U. Ergotamine Stimulates Human 5-HT4-Serotonin Receptors and Human H2-Histamine Receptors in the Heart. Int J Mol Sci. 2023 Mar 1;24(5):4749. doi: 10.3390/ijms24054749. PMID: 36902177; PMCID: PMC10003312. 11: Shi H, Yu P. Using Molecular Spectroscopic Techniques (NIR and ATR-FT/MIR) Coupling with Various Chemometrics to Test Possibility to Reveal Chemical and Molecular Response of Cool-Season Adapted Wheat Grain to Ergot Alkaloids. Toxins (Basel). 2023 Feb 13;15(2):151. doi: 10.3390/toxins15020151. PMID: 36828464; PMCID: PMC9962322. 12: Chauhan A, Sangwan N, Singh J, Prakash A, Medhi B, Avti PK. Allosteric modulation of conserved motifs and helices in 5HT2BR: Advances drug discovery and therapeutic approach towards drug resistant epilepsy. J Biomol Struct Dyn. 2023 Feb 21:1-14. doi: 10.1080/07391102.2023.2178508. Epub ahead of print. PMID: 36809314. 13: Zhou Z, Lu Y, Gu Z, Sun Q, Fang W, Yan W, Ku X, Liang Z, Hu G. HNRNPA2B1 as a potential therapeutic target for thymic epithelial tumor recurrence: An integrative network analysis. Comput Biol Med. 2023 Mar;155:106665. doi: 10.1016/j.compbiomed.2023.106665. Epub 2023 Feb 11. PMID: 36791552. 14: Dali P, Shende P. Use of 3D applicator for intranasal microneedle arrays for combinational therapy in migraine. Int J Pharm. 2023 Mar 25;635:122714. doi: 10.1016/j.ijpharm.2023.122714. Epub 2023 Feb 10. PMID: 36773727. 15: Doi Y, Wakana D, Kitaoka S, Sato F, Tanaka E, Takeda H, Hosoe T. Ergot alkaloids in sclerotia collected in Japan: synthetic profiles and induction of apoptosis by Clavine-type compounds. J Nat Med. 2023 Mar;77(2):306-314. doi: 10.1007/s11418-022-01673-8. Epub 2023 Jan 12. PMID: 36635416. 16: Dali P, Shende P. Self-Assembled Lipid Polymer Hybrid Nanoparticles Using Combinational Drugs for Migraine Via Intranasal Route. AAPS PharmSciTech. 2022 Dec 16;24(1):20. doi: 10.1208/s12249-022-02479-3. PMID: 36526821. 17: Alexandrov V, Kirpich A, Kantidze O, Gankin Y. A multi-reference poly- conformational method for in silico design, optimization, and repositioning of pharmaceutical compounds illustrated for selected SARS-CoV-2 ligands. PeerJ. 2022 Nov 24;10:e14252. doi: 10.7717/peerj.14252. PMID: 36447514; PMCID: PMC9701500. 18: Malhotra H, Kumar A, Afaq Y. Molecular docking analysis of FDA approved drugs with the glycoprotein from Junin and Machupo viruses. Bioinformation. 2022 Feb 28;18(2):119-126. doi: 10.6026/97320630018119. PMID: 36420432; PMCID: PMC9649494. 19: Khalil IA, Razeq SAA, Mohammed SA. Validated HPLC-DAD and Spectrophotometric Methods for Simultaneous Determination of Ternary Mixture of Analgin, Caffeine, and Ergotamine. J AOAC Int. 2023 Mar 1;106(2):296-308. doi: 10.1093/jaoacint/qsac134. PMID: 36326356. 20: Yang X, Xing X, Liu Y, Zheng Y. Screening of potential inhibitors targeting the main protease structure of SARS-CoV-2 via molecular docking. Front Pharmacol. 2022 Oct 5;13:962863. doi: 10.3389/fphar.2022.962863. PMID: 36278156; PMCID: PMC9579442.

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