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1202005

USP

Dihydroergotamine mesylate

United States Pharmacopeia (USP) Reference Standard

Synonym(s):

Dihydroergotamine methanesulfonate salt

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About This Item

Empirical Formula (Hill Notation):
C33H37N5O5 · CH4O3S
CAS Number:
6190-39-2
Molecular Weight:
679.78
MDL number:
MFCD00058615
UNSPSC Code:
41116107
PubChem Substance ID:
329749596

grade

pharmaceutical primary standard

API family

dihydroergotamine

manufacturer/tradename

USP

application(s)

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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Related Categories

Application

Dihydroergotamine mesylate USP reference standard, intended for use in specified quality tests and assays as specified in the USP compendia.

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

Sales restrictions may apply.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
Stephen Silberstein
Expert opinion on pharmacotherapy, 13(13), 1961-1968 (2012-08-07)
Dihydroergotamine mesylate (DHE) has been used as an acute migraine treatment since 1945, although tolerability with intravenous administration has limited its use. MAP0004 is a novel, orally inhaled, aerosol formulation of DHE that provides pulmonary drug delivery using a pressurized
John A Morren et al.
Expert opinion on pharmacotherapy, 11(18), 3085-3093 (2010-11-18)
Migraine affects approximately 18% of women and 6% of men, and has an immense impact on quality of life and productivity. Advancement in therapeutic options has been slow. For many patients with difficult-to-treat migraine, the appropriate use of dihydroergotamine mesylate
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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