1202005

USP

Dihydroergotamine mesylate

United States Pharmacopeia (USP) Reference Standard

Synonym(s):
Dihydroergotamine methanesulfonate salt
Empirical Formula (Hill Notation):
C33H37N5O5 · CH4O3S
CAS Number:
Molecular Weight:
679.78
MDL number:
PubChem Substance ID:

grade

pharmaceutical primary standard

form

neat

manufacturer/tradename

USP

Featured Industry

Pharmaceutical (small molecule)

format

neat

storage temp.

2-8°C

SMILES string

CS(O)(=O)=O.[H][C@@]12Cc3c[nH]c4cccc(C1C[C@H](CN2C)C(=O)N[C@]5(C)O[C@]6(O)N([C@@H](Cc7ccccc7)C(=O)N8CCC[C@@]68[H])C5=O)c34

InChI

1S/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

InChI key

ADYPXRFPBQGGAH-WVVAGBSPSA-N

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Biochem/physiol Actions

Agonist at vascular serotonin receptors; partial agonist at α-adrenergic and dopamine D2 receptors; vasoconstrictor.

Analysis Note

These products are for test and assay use only. They are not meant for administration to humans or animals and cannot be used to diagnose, treat, or cure diseases of any kind.  ​

Other Notes

USP issued SDS can be found here.
Sales restrictions may apply.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

S B Shrewsbury et al.
British journal of pharmacology, 154(6), 1254-1265 (2008-05-27)
The effects of intrapulmonary artery (i.p.a.) administration of dihydroergotamine mesylate (DHE) were evaluated. Conscious beagle dogs (n=4) were given DHE via the i.p.a. or i.v. route as two 0.014 mg kg(-1) doses and a 0.14 mg kg(-1) dose given 60...
Xiaoyan Chen et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 768(2), 267-275 (2002-03-13)
A sensitive and specific procedure for the simultaneous determination of dihydroergotamine (DHE) and its 8'-hydroxylated metabolite (8'-OH-DHE) in human plasma was developed and validated. The analytes were extracted from plasma samples by liquid-liquid extraction, separated through a Zorbax C18 column...
Drugs in R&D, 4(6), 376-377 (2003-10-31)
MT 300 is an injectable formulation of dihydroergotamine mesylate (DHE; a serotonin 5-HT1 receptor agonist) that is being developed by POZEN for the acute treatment of migraine. POZEN intends to present MT 300 as a prefilled syringe that can be...
J A Barone et al.
Pharmacotherapy, 6(4 Pt 2), 3S-11S (1986-07-01)
Dihydroergotamine(DHE)-heparin combination offers a unique treatment modality for the prevention of deep vein thrombosis. The combination appears to affect all 3 limbs of Virchow's triad: hypercoagulability, venous stasis, and endothelial damage. In most efficacy studies, data indicated that the combination...
R B Lipton
Headache, 37 Suppl 1, S33-S41 (1997-01-01)
Ergotamine tartrate (ET) and dihydroergotamine mesylate (DHE) have been widely and effectively used in the treatment of migraine for many decades, although few randomized, controlled clinical trials have been conducted with these compounds. To compare their safety profiles, the world...

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