6190-39-2

Basic information

• Product Name: DIHYDROERGOTAMINE MESYLATE
• Synonyms: 5'-Benzyl-12'-hydroxy-2'-methyl-3',6',18-trioxo-9,10-dihydroergotaman;9,10-Dihydro-12'-hydroxy-2'-methyl-5'-(phenylmethyl)ergotoman-3',6',18-trionemonomethanesulfonate;9,10-dihydroergotaminemesylate;9,10-dihydro-ergotaminmonomethanesulfonate(salt);Agit;Angionorm;D.H.E. 45;Dergotamine
• CAS NO: 6190-39-2
• Molecular Formula: CH₄O₃S*C₃₃H₃₇N₅O₅
• Molecular Weight: 679.78
• EINECS: 228-235-6
• Product Categories: Organics;Ergot Alkaloids;Neurobiology;Pharmacologicals;Adrenoceptor;Aromatics;Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;MIGRANAL
• Mol File: 6190-39-2.mol
• Article Data: 0

Chemical Properties

• Melting Point: 232°C
• Boiling Point: 899.5 °C at 760 mmHg
• Flash Point: 497.8 °C
• Appearance: white/powder
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: -20 ° (C=0.25, JP Method)
• Storage Temp.: Store at RT
• Solubility: methanol: 21 mg/mL
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 2 months.
• Merck: 14,3174
• CAS DataBase Reference: DIHYDROERGOTAMINE MESYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: DIHYDROERGOTAMINE MESYLATE(6190-39-2)
• EPA Substance Registry System: DIHYDROERGOTAMINE MESYLATE(6190-39-2)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36
• RIDADR: 1544
• WGK Germany: 3
• RTECS: KE7920000
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 6190-39-2(Hazardous Substances Data)

Usage

Description

Dihydroergotamine mesylate (6190-39-2) is a full agonist at serotonin 5HT1B and 5HT1D receptors, IC50= 2 and 2.2 nM respectively1 and also at 5HT1A and 5HT1F receptors2. One of the oldest agents for treatment of migraine.3 Also acts as a potent vasoconstrictor and alpha-adrenergic antagonist.4

Chemical Properties

White to Off-White Solid

Uses

Different sources of media describe the Uses of 6190-39-2 differently. You can refer to the following data:
1. α-Androgenic blocker with selective venoconstrictor properties. Also binds to serotonin 5HT1-receptors. Antimigraine.
2. vasoconstrictor, antimigraine
3. Agonist at vascular serotonin receptors; partial agonist at alpha-adrenergic and dopamine D2 receptors

Definition

ChEBI: The methanesulfonic acid salt of dihydroergotamine, a semisynthetic ergot alkaloid with weaker oxytocic and vasoconstrictor properties than ergotamine. Both the mesylate and the tartrate salts are used for the treatment of migraine and orthostatic hypotens on.

Biological Activity

Partial α -adrenergic agonist. Partial D 2 dopaminergic receptor agonist. Competitive 5-HT antagonist.

References

Lesage et al. (1998), Agnostic properties of alniditan, sumatriptan and dihydroergotamine on human 5-HT1B and 5-HT1D receptors expressed in various mammalian cell lines; J. Pharmacol., 123 1655 Silberstein (1997), The pharmacology of ergotamine and dihydroergotamine; Headache, 37 Suppl 1 S15 Silberstein and McCrory (2003), Ergotamine and dihydroergotamine: history, pharmacology, and efficacy; Headache, 43 144 Lipton (1997), Ergotamine tartrate and dihydroergotamine mesylate: safety profiles; Headache, 37 Suppl.1 S33

InChI:InChI=1/C33H37N5O5.CH4O3S/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;1-5(2,3)4/h3-6,8-11,17,21,23,25-27,34,42H,7,12-16,18H2,1-2H3,(H,35,39);1H3,(H,2,3,4)/t21-,23?,25-,26+,27+,32?,33?;/m1./s1

Downstream Products

• 1416417-27-0 2-CF₃-dihydroergotamine 
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• 5878-43-3 9,10-dihydrolysergic acid