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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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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
M Geurts et al.
Brain research, 841(1-2), 135-142 (1999-11-05)
The role of dopamine receptor-G protein coupling in the development of striatal dopamine receptor supersensitivity was studied in rats with a 6-hydroxydopamine (6-OHDA)-induced unilateral lesion of the nigrostriatal pathway. This coupling was assessed by the measurement of dopamine agonist-induced guanosine
M Velasco et al.
American journal of therapeutics, 5(1), 37-43 (1999-03-31)
Dopamine is a biogenic amine synthesized in the hypothalamus, in the arcuate nucleus, the caudad, and various areas of the central and peripheral nervous system. It has been widely established that dopamine and its agonists play an important role in
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)
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
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