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Merck
CN

45510

Ergotamine D-tartrate

≥97.0% (calc. based on dry substance, NT)

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About This Item

Empirical Formula (Hill Notation):
C33H35N5O5 · 0.5C4H6O6
CAS Number:
379-79-3
Molecular Weight:
656.70
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
57650423
EC Number:
206-835-9
Beilstein/REAXYS Number:
6173437
MDL number:
MFCD08277639
Assay:
≥97.0% (calc. based on dry substance, NT)

Key Documents

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InChI key

CJMJLDQKTOJACI-BGQAIRJTSA-N

InChI

1S/2C33H35N5O5.C4H6O6/c2*1-32(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;5-1(3(7)8)2(6)4(9)10/h2*3-6,8-11,15,17,21,25-27,34,42H,7,12-14,16,18H2,1-2H3,(H,35,39);1-2,5-6H,(H,7,8)(H,9,10)/t2*21-,25-,26+,27+,32-,33+;1-,2-/m111/s1

SMILES string

O[C@H]([C@@H](O)C(O)=O)C(O)=O.CN1C[C@@H](C=C2C1Cc3c[nH]c4cccc2c34)C(=O)N[C@]5(C)O[C@@]6(O)C7CCCN7C(=O)[C@H](Cc8ccccc8)N6C5=O.CN9C[C@@H](C=C%10C9Cc%11c[nH]c%12cccc%10c%11%12)C(=O)N[C@]%13(C)O[C@@]%14(O)C%15CCCN%15C(=O)[C@H](Cc%16ccccc%16)N%14C%13=O

assay

≥97.0% (calc. based on dry substance, NT)

mp

~195 °C (dec.) (lit.)

functional group

amide, carboxylic acid, ether, hydroxyl, phenyl

storage temp.

2-8°C

Quality Level

100

Gene Information

human ... ADRA1A(148), ADRA1B(147), ADRA1D(146), ADRA2A(150), ADRA2B(151), ADRA2C(152), HTR1D(3352)

General description

Ergotamine D-tartrate is an ergot alkaloid.

Application

Ergotamine D-tartrate has been used as a standard in myograph protocol to study its effect on vasoconstriction of bovine mesenteric vasculature.

Other Notes

Sales restrictions may apply

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Repr. 2

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
BCBW1272
BCBS3200V
BCBN2989V
BCBK9725V
BCBG1436V

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Stefan Merkel et al.
Analytical and bioanalytical chemistry, 404(8), 2489-2497 (2012-09-13)
The degradation and epimerization of ergot alkaloids (EAs) in rye flour were investigated after baking cookies and subsequently subjecting them to an in vitro digestion model. Different steps of digestion were analyzed using salivary, gastric, and duodenal juices. The degradation
Interaction of isoflavones and endophyte-infected tall fescue seed extract on vasoactivity of bovine mesenteric vasculature.
Jia Y, et al.
Frontiers in nutrition, 2 (2015)
Priyanka Reddy et al.
Scientific reports, 10(1), 9714-9714 (2020-06-18)
The complex ergot alkaloids, ergovaline and ergotamine, cause dysregulation of physiological functions, characterised by vasoconstriction as well as thermoregulatory and cardiovascular effects in grazing livestock. To assess the effect of the mycotoxins, blood pressure and heart rate of male mice
Christopher J Derry et al.
The Cochrane database of systematic reviews, 2(2), CD009664-CD009664 (2012-02-18)
Migraine is a highly disabling condition for the individual and also has wide-reaching implications for society, healthcare services, and the economy. Sumatriptan is an abortive medication for migraine attacks, belonging to the triptan family. Rectal administration may be preferable to
Dennis Mulac et al.
Molecular nutrition & food research, 56(3), 475-485 (2011-12-08)
Ergot alkaloids are secondary metabolites of Claviceps spp. and they have been in the focus of research for many years. Experiments focusing on ergotamine as a former migraine drug referring to the ability to reach the brain revealed controversial results.
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