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Merck

B2134

2-Bromo-α-ergocryptine methanesulfonate salt

solid

Sinonimo/i:

(+)-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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Informazioni su questo articolo

Formula empirica (notazione di Hill):
C32H40BrN5O5 · CH4SO3
Numero CAS:
22260-51-1
Peso molecolare:
750.70
UNSPSC Code:
12352200
NACRES:
NA.77
PubChem Substance ID:
24277885
EC Number:
244-881-1
Beilstein/REAXYS Number:
4115238
MDL number:
MFCD00069218
Form:
solid

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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

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

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

Gene Information

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

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Questo articolo
1076501Y0000677SML1957
2-Bromo-α-ergocryptine methanesulfonate salt solid

Sigma-Aldrich

B2134

2-Bromo-α-ergocryptine methanesulfonate salt

Bromocriptine mesylate United States Pharmacopeia (USP) Reference Standard

USP

1076501

Bromocriptine mesylate

Bromocriptine mesilate for system suitability European Pharmacopoeia (EP) Reference Standard

Y0000677

Bromocriptine mesilate for system suitability

ML RR-S2 CDA sodium salt ≥95% (HPLC)

Sigma-Aldrich

SML1957

ML RR-S2 CDA sodium salt

form

solid

form

-

form

-

form

powder

Quality Level

100

Quality Level

-

Quality Level

-

Quality Level

100

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

−20°C

solubility

H2O: 0.8 mg/mL, ethanol: 23 mg/mL

solubility

-

solubility

-

solubility

-

color

white

color

-

color

-

color

white to beige

optical activity

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

optical activity

-

optical activity

-

optical activity

-

Application

2-Bromo-α-ergocryptine methanesulfonate salt has been used:
  • as D2 agonist in bird zebra finches[1]
  • for Prl secretion inhibitor in mice[2]
  • for the inhibition of motility in planaria worm[3]

Biochem/physiol Actions

Bromocriptine is an ergot alkaloid and a dopamine D2 receptor agonist. It is prescribed for Parkinson′s disorder, hyperprolactinemia and galactorrhoea.[4] It modulates β cells of the pancreas from insulin hypersecretion and improves the metabolic profile in type 2 diabetes patients with obesity.[5] It also modulates glutamate release by glutamate transporter,GLT-1.[6]

pictograms

Exclamation markEnvironment
GHS07,GHS09

signalword

Warning

hcodes

H302,H410

Hazard Classifications

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

Classe di stoccaggio

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificati d'analisi (COA)

Lot/Batch Number
BCBS5037V
BCBR1233V
BCBJ3892V
BCBK9866V
BCBG7646V

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Bromocriptine: old drug, new formulation and new indication.
Holt RI, et al.
Diabetes, obesity & metabolism, 12(12), 1048-1057 (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
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)
O J Ginther et al.
Theriogenology, 78(9), 1969-1976 (2012-11-01)
The luteotrophic effect of bromocriptine in heifers was studied to determine if the reported posttreatment increase in progesterone (P4) just before or at the beginning of luteolysis was attributable to loss of a luteolytic effect of prolactin (PRL) or to
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