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 is a semisynthetic ergot alkaloid with weaker oxytocic and vasoconstrictor properties than ergotamine. It is a full agonist at serotonin 5HT1B and 5HT1D receptors, and also acts on 5HT1A and 5HT1F receptors. It is one of the oldest agents for the treatment of migraine and acts as a potent vasoconstrictor and alpha-adrenergic antagonist. DIHYDROERGOTAMINE MESYLATE is a white to off-white solid.

Uses

Used in Pharmaceutical Industry:
DIHYDROERGOTAMINE MESYLATE is used as an α-Androgenic blocker with selective venoconstrictor properties for the treatment of migraine and orthostatic hypotension. It acts as a full agonist at vascular serotonin receptors and a partial agonist at alpha-adrenergic and dopamine D2 receptors, making it effective in managing migraine symptoms.
Used in Migraine Treatment:
DIHYDROERGOTAMINE MESYLATE is used as a vasoconstrictor and antimigraine agent for the relief of migraine headaches. Its action on serotonin receptors helps to constrict blood vessels and alleviate the pain associated with migraines.
Used in Vasoconstriction:
DIHYDROERGOTAMINE MESYLATE is used as a potent vasoconstrictor in various medical applications where constriction of blood vessels is required, such as in the treatment of orthostatic hypotension.

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 
• 3006-19-7 9,10-dihydrolysergic acid methyl ester 
• 5878-43-3 9,10-dihydrolysergic acid