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D2763

Sigma-Aldrich

Dihydroergotamine methanesulfonate salt

powder

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About This Item

Empirical Formula (Hill Notation):
C33H37N5O5 · CH4O3S
CAS Number:
6190-39-2
Molecular Weight:
679.78
EC Number:
228-235-6
MDL number:
MFCD00058615
UNSPSC Code:
12352200
PubChem Substance ID:
24277913
NACRES:
NA.77

form

powder

color

white

solubility

methanol: 21 mg/mL
45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 5.45 mg/mL
H2O: insoluble

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

Gene Information

human ... DRD2(1813)

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Biochem/physiol Actions

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

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

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
097K1459
105F0105

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Abraham J Nagy et al.
Neurology, 77(20), 1827-1832 (2011-11-04)
To determine dosing and side effects of dihydroergotamine as they affect outcomes in primary headache disorders. We audited our use of dihydroergotamine for inpatient management of disabling primary headache, focusing on the commonly treated problems. Of patients interviewed, 114 had
Alan M Rapoport
Neurological sciences : official journal of the Italian Neurological Society and of the Italian Society of Clinical Neurophysiology, 33 Suppl 1, S119-S125 (2012-06-01)
There are many categories and individual types of headache and most have a variety of treatment protocols, while a few are best treated by just one medication. This paper will concentrate on acute care medications for migraine and discuss some
Stewart J Tepper et al.
Headache, 52(1), 37-47 (2011-11-24)
Central sensitization develops once migraine attacks become established and can be clinically detected by the development of cutaneous allodynia. The efficacy of triptans for migraine resolution has been shown to be markedly reduced when administered in patients with established cutaneous
Anick Bérard et al.
Headache, 52(7), 1085-1093 (2012-05-23)
Dihydroergotamine (DHE) is perceived to be associated with a higher risk of adverse pregnancy events, but it has significantly less vasoconstrictive and uterotonic effects compared with ergotamine, and has demonstrated no teratogenic effect in animals. The objectives of this study
Stewart J Tepper et al.
Mayo Clinic proceedings, 86(10), 948-955 (2011-10-04)
To evaluate the efficacy of MAP0004, an orally inhaled dihydroergotamine, for acute treatment of migraine when administered at various time points from within 1 hour to more than 8 hours after migraine onset. This post hoc subanalysis was conducted using
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