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45510

Sigma-Aldrich

Ergotamine D-tartrate

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

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Empirical Formula (Hill Notation):
C33H35N5O5 · 0.5C4H6O6
CAS Number:
379-79-3
Molecular Weight:
656.70
Beilstein:
6173437
EC Number:
206-835-9
MDL number:
MFCD08277639
UNSPSC Code:
12352005
PubChem Substance ID:
57650423
NACRES:
NA.22

Quality Level

100

Assay

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

mp

~195 °C (dec.) (lit.)

storage temp.

2-8°C

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

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

InChI key

CJMJLDQKTOJACI-BGQAIRJTSA-N

Gene Information

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

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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

Signal Word

Danger

Hazard Statements

H301 + H311 + H331,H361

Hazard Classifications

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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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
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.
Santiago Acle et al.
Revista medica de Chile, 139(12), 1597-1600 (2012-03-27)
Ergotism is a complication of the acute intoxication or chronic abuse of ergot derivatives. It may be manifested by a vasomotor syndrome with peripheral vascular disease frequently involving extremities. We report three patients infected with human immunodeficiency virus (HIV), in
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