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Merck

B2134

Sigma-Aldrich

2-Bromo-α-ergocryptine methanesulfonate salt

solid

Sinónimos:

(+)-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

Fórmula empírica (notación de Hill):
C32H40BrN5O5 · CH4SO3
Número de CAS:
Peso molecular:
750.70
Beilstein/REAXYS Number:
4115238
EC Number:
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

form

solid

Quality Level

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

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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

signalword

Warning

hcodes

Hazard Classifications

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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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)
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)
S Perachon et al.
European journal of pharmacology, 366(2-3), 293-300 (1999-03-19)
We measured the affinities of bromocriptine, pramipexole, pergolide and ropinirole at human recombinant dopamine D1, D2 and D3 receptors in binding and functional tests. All four compounds bound with high affinity at the dopamine D3 receptor; bromocriptine and pergolide also
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
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)

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