478-94-4

Basic information

• Product Name: 9,10-didehydro-6-methylergoline-8beta-carboxamide
• Synonyms: 9,10-didehydro-6-methylergoline-8beta-carboxamide
• CAS NO: 478-94-4
• Molecular Formula: C₁₆H₁₇N₃O
• Molecular Weight: 267.33
• EINECS: 207-524-0
• Product Categories: Amines;Aromatics;Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 478-94-4.mol
• Article Data: 1

Chemical Properties

• Melting Point: >200°C (dec.)
• Boiling Point: 410.51°C (rough estimate)
• Flash Point: 299.9°C
• Appearance: /
• Density: 1.0724 (rough estimate)
• Vapor Pressure: 4.18E-13mmHg at 25°C
• Refractive Index: 1.7210 (estimate)
• Storage Temp.: Amber Vial, -20?C Freezer, Under Inert Atmosphere
• PKA: 15.87±0.20(Predicted)
• CAS DataBase Reference: 9,10-didehydro-6-methylergoline-8beta-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: 9,10-didehydro-6-methylergoline-8beta-carboxamide(478-94-4)
• EPA Substance Registry System: 9,10-didehydro-6-methylergoline-8beta-carboxamide(478-94-4)

Safety Data

• Hazardous Substances Data: 478-94-4(Hazardous Substances Data)

Usage

Description

9,10-Didehydro-6-methylergoline-8beta-carboxamide is an ergot alkaloid, a class of chemical compounds that are derived from the ergot fungus. It is structurally similar to other ergot alkaloids such as ergonovine and ergotamine, and has been found to have vasoconstrictive properties.

Uses

Used in Pharmaceutical Industry:
9,10-Didehydro-6-methylergoline-8beta-carboxamide is used as a vasoconstrictive agent for its ability to cause vasoconstriction similar to that of ergonovine and ergotamine. This property makes it a potential candidate for the treatment of conditions that require constriction of blood vessels, such as migraines and other vascular disorders.

Purification Methods

The (-)-hydrochloride has m 208-210o(dec, from MeOH). [Kornfeld et al. J Am Chem Soc 76 5256 1954, Kornfeld et al. J Am Chem Soc 78 3087 1956, Beilstein 25 III/IV 934,]

InChI:InChI=1/C16H17N3O/c1-19-8-10(16(17)20)5-12-11-3-2-4-13-15(11)9(7-18-13)6-14(12)19/h2-5,7,10,14,18H,6,8H2,1H3,(H2,17,20)/t10-,14-/m1/s1

Upstream product

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Relevant articles and documents

Novel ergopeptides as dual ligands for adenosine and dopamine receptors

Multivalent ligands are promising pharmacological tools that may be more efficacious for several diseases than highly selective single-target drugs. A combined therapy using dopaminergic agonists and adenosinergic antagonists is currently being evaluated for the treatment of Parkinson's disease. [(a) Kanda, T.; et al. Exp. Neurol. 2000, 162, 321-327. (b) Jenner, P. Expert Opin. Invest. Drugs 2005, 14, 729-738. (c) Kase, H.; et al. Neurology 2003, 61 (Suppl 6), S97-S100.] Here we prepared dual ligands acting on adenosine and dopamine receptors by applying a combinatorial approach based on the ergolene privileged structure. The potency and efficacy of these novel compounds were determined by radioligand binding studies and intracellular cAMP production assays in cells expressing adenosine and dopamine receptors. Selected compounds displayed dual dopamine agonist and adenosine antagonist activity. Molecules with this pharmacological profile are potentially useful for studying dopamine-adenosine cross-talk in the central nervous system and for testing the therapeutic potential of multivalent drugs for Parkinson's disease.