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Merck

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

Key Documents

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Product Name

Ergotamine D-tartrate, ≥97.0% (calc. based on dry substance, NT)

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)

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Application

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

General description

Ergotamine D-tartrate is an ergot alkaloid.

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCBW1272
BCBS3200V
BCBN2989V
BCBK9725V
BCBG1436V

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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
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)
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
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.
J L Klotz et al.
Journal of animal science, 95(11), 5151-5160 (2018-01-03)
Mares grazing endophyte-infected () tall fescue () typically exhibit reproductive dysfunction rather than problems associated with peripheral vasoconstriction as a primary sign of the fescue toxicosis syndrome. Research using Doppler ultrasonography demonstrated that consumption of endophyte-infected tall fescue seed causes
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