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B2134

Sigma-Aldrich

2-Bromo-α-ergocryptine methanesulfonate salt

solid

Synonym(s):

(+)-2-Bromo-12′-hydroxy-2′-(1-methylethyl)-5′-(2-methylpropyl)ergotaman-3′,6′-18-trione methanesulfonate salt, (+)-Bromocriptine methanesulfonate salt, Bromocriptine mesylate salt

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About This Item

Empirical Formula (Hill Notation):
C32H40BrN5O5 · CH4SO3
CAS Number:
22260-51-1
Molecular Weight:
750.70
Beilstein:
4115238
EC Number:
244-881-1
MDL number:
MFCD00069218
UNSPSC Code:
12352200
PubChem Substance ID:
24277885
NACRES:
NA.77

form

solid

optical activity

[α]20/D +95°, c = 1 in methanol: methylene chloride (1:1)(lit.)

color

white

solubility

H2O: 0.8 mg/mL
ethanol: 23 mg/mL

storage temp.

2-8°C

SMILES string

CS(O)(=O)=O.[H][C@@]12Cc3c(Br)[nH]c4cccc(C1=CC(CN2C)C(=O)N[C@@]5(O[C@]6(O)N([C@@H](CC(C)C)C(=O)N7CCC[C@@]67[H])C5=O)C(C)C)c34

InChI

1S/C32H40BrN5O5.CH4O3S/c1-16(2)12-24-29(40)37-11-7-10-25(37)32(42)38(24)30(41)31(43-32,17(3)4)35-28(39)18-13-20-19-8-6-9-22-26(19)21(27(33)34-22)14-23(20)36(5)15-18;1-5(2,3)4/h6,8-9,13,16-18,23-25,34,42H,7,10-12,14-15H2,1-5H3,(H,35,39);1H3,(H,2,3,4)/t18?,23-,24+,25+,31-,32+;/m1./s1

InChI key

NOJMTMIRQRDZMT-NEKRQHSLSA-N

Gene Information

human ... DRD2(1813) , DRD3(1814) , PRL(5617)

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Application

2-Bromo-α-ergocryptine methanesulfonate salt has been used:
  • as D2 agonist in bird zebra finches
  • for Prl secretion inhibitor in mice
  • for the inhibition of motility in planaria worm

Biochem/physiol Actions

Bromocriptine is an ergot alkaloid and a dopamine D2 receptor agonist. It is prescribed for Parkinson′s disorder, hyperprolactinemia and galactorrhoea. It modulates β cells of the pancreas from insulin hypersecretion and improves the metabolic profile in type 2 diabetes patients with obesity. It also modulates glutamate release by glutamate transporter,GLT-1.

Pictograms

Exclamation markEnvironment
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H302,H410

Precautionary Statements

P273 - P301 + P312 + P330

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Prolactin and glucocorticoid signaling induces lactation-specific tight junctions concurrent with beta-casein expression in mammary epithelial cells.
Kobayashi K, et al.
Biochimica et Biophysica Acta - Molecular Cell Research, 1863(8), 2006-2016 (2016)
Bromocriptine, an ergot alkaloid, inhibits excitatory amino acid release mediated by glutamate transporter reversal.
Shirasaki Y, et al.
European Journal of Pharmacology, 643(1), 48-57 (2010)
Bromocriptine: old drug, new formulation and new indication.
Holt RI, et al.
Diabetes, obesity & metabolism, 12(12), 1048-1057 (2010)
The dopamine receptor D2 agonist bromocriptine inhibits glucose-stimulated insulin secretion by direct activation of the alpha2-adrenergic receptors in beta cells.
Van W, et al.
Biochemical Pharmacology, 79(12), 1827-1836 (2010)
Y Zhang et al.
Metabolism: clinical and experimental, 48(8), 1033-1040 (1999-08-25)
Our previous studies have shown that the dopaminergic D1 receptor agonist SKF38393 (SKF) plus the D2 receptor agonist bromocriptine (BC) act synergistically to reduce obesity in obese C57BL/6J (ob/ob) mice. The present study investigated the effects of this combination on
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