Pergolide mesylate salt

Pergolide mesylate salt Basic information
Product Name:Pergolide mesylate salt
Synonyms:8BETA-[(METHYLTHIO)METHYL]-6-PROPYLERGOLINE MESYLATE SALT;8-BETA-[(METHYLTHIO)METHYL]-6-PROPYLERGOLINE MONOMETHANE SULFONATE;Pergolide mesylate EPIV;Pergolidemetylsulfonate;(8b)-8-[(Methylthio)methyl]-6-propylergoline Mesylate;Celance;Nopar;Permax
CAS:66104-23-2
MF:C20H30N2O3S2
MW:410.59
EINECS:
Product Categories:LOCOID;API;Intermediates & Fine Chemicals;Neurochemicals;Pharmaceuticals
Mol File:66104-23-2.mol
Pergolide mesylate salt Structure
Pergolide mesylate salt Chemical Properties
Melting point 252-254°C
alpha aD20 between -18.0° and -23.0° (c = 10 mg/ml in DMF)
storage temp. Inert atmosphere,Store in freezer, under -20°C
solubility ethanol: soluble2mg/mL
form solid
pkapKa (66% DMF) 7.8(at 25℃)
color white
optical activity[α]20/D 35°, c = 0.2 in pyridine(lit.)
InChIKeyUWCVGPLTGZWHGS-PLBOZXOQNA-N
SMILESC12=C3C=CC=C1[C@@]1([H])C[C@H](CN(CCC)[C@]1([H])CC2=CN3)CSC.S(=O)(=O)(O)C |&1:6,9,15,r|
CAS DataBase Reference66104-23-2(CAS DataBase Reference)
Safety Information
Hazard Codes T+
Risk Statements 28
Safety Statements 28-36/37-45
RIDADR UN 1544
WGK Germany 3
RTECS KE6345000
HS Code 2939690000
MSDS Information
Pergolide mesylate salt Usage And Synthesis
DescriptionPergolide mesylate is a potent, long-acting dopamine agonist useful in the treatment of Parkinson’s disease and hyperprolactinemia, Compared with lergotrile, pergolide mesylate has shown less toxicity and lower propensity for inducing psychosis.
DescriptionPergolide is a potent dopamine D1 and D2 receptor agonist (Kis = 111 and 0.495 nM, respectively, for rat striatal receptors). It depresses dopaminergic firing in paralyzed rats (ED50 = <20 μg/kg), an effect that can be reversed by the dopamine D2-selective antagonist spiperone or the dopamine D1-selective antagonist SCH 23390 . Pergolide (0.025 and 0.05 mg/kg) increases the volume threshold for inducing bladder contraction in a cynomolgus monkey model of Parkinson''s disease induced by MPTP. It also reduces carrageenan-induced paw edema in adrenalectomized rats (ED50 = 0.4 mg/kg).
Chemical PropertiesWhite to Off-White Solid
OriginatorLilly (USA)
UsesA dopaminergic agonist that also decrease plasma prolactin concentrations. An antiparkinsonian agent
Usesglucocorticoid, antiinflammatory
Usesdopamine receptor agonist, anti-Parkinson's agent
DefinitionChEBI: A methanesulfonate salt obtained from pergolide by mixing eqimolar amount of pergolide and methanesulfonic acid. A dopamine D2 receptor agonist which also has D1 and D2 agonist properties, it i used in the management of Parkinson's disease, although it was withdrawn from the U.S. and Canadian markets in 2007 due to an increased risk of cardiac valve dysfunction.
Manufacturing ProcessDimethyl disulfide (73.6 ml, 0.79 mol) and tri-n-butylphosphine (79.6 ml, 0.32 mol) were added to a solution of 9,10-dihydrolysergol in (8.1 g, 0.032 mol) in the 150 ml of anhydrous DMF and were stirred at room temperature for 6 hours under a nitrogen atmosphere. Dimethyl disulfide of the reaction mixture was removed under vacuo. A solution of the residue in ethyl acetate was extracted with 3.7% HCl (aq.). The aqueous layer was basified with ammonium hydroxide to a pH of 10 and then extracted with ethyl acetate. Removal of ethyl acetate followed by a silica gel column purification eluting with 10% MeOH/CH2Cl2 gave5.5.g of D-6-methyl-8β(methylthiomethyl)ergoline (60%).
A solution of D-6-methyl-8β-(methylthiomethyl)ergoline (0.4 g, 0.0014 mol) and NaI (0.63 g, 0.0042 mol) in 10 ml of propionic anhydride was refluxed for 40 hours. The reaction mixture was guenched with a 10% Na2CO3 solution and extracted by ethyl acetate. The combined organic layers were washed with a saturated brine solution, dried with magnesium sulfate and concentrated to produce oil. The oil was purified by silica gel column, eluting with 10% MeOH/CH2Cl2 to give 0.33 g of D-1,6-dipropionyl-8β(methylthiomethyl)ergoline.
LiAlH4 (0.6 g, 0.0156 mol) was slowly added to a solution of D-1,6dipropionyl-8β-(methylthiomethyl)ergoline in the 20 ml anhydrous THF at 0°C under nitrogene atmosphere. The mixture was stirred at 0°C for 30 min and then at room temperature for 4 hours. The reaction was cooled to 0°C and 0.6 ml of water was slowly added. The mixture was stirred at 0°C for 10 min and 1.8 ml of 15% NaOH (aq.) and 2.5 ml of water were added respectively. The mixture was stirred for 30 min at room temperature and then filtered. Excess of the solvent was removed under reduced pressure to give 150 mg of 8β-((methylthio)methyl)-6-propyl-ergoline or pergolide (yield: 68%). Ergoline,8-((methylthio)methyl)-6-propyl-, monomethanesulfonate, (8β)- may be prepared by mixing of components in solution.

Brand namePermax (Valeant).
Therapeutic FunctionDopamine agonist
Biochem/physiol ActionsDopaminergic agonist; suppresses pituitary secretion of prolactin; anti-Parkinsonian agent.
Pergolide mesylate salt Preparation Products And Raw materials
Preparation ProductsPergolide
Methylparaben alpha-methyl-1H-indole-3-ethylamine monomethanesulphonate Bensulfuron methyl 1H-INDOLE-4-ETHANAMINE Methanesulfonic acid Methyl cellulose N-BUTYL PERGOLIDE MESYLATE 1H-Indole, 4-(3-piperidinyl)-, (R)- ISOMETHIOZIN Kresoxim-methyl 3-PHENYLPIPERIDINE Methanol R)-3-PHENYL PIPERIDINE Gatifloxacin mesylate Methyl acrylate 8-CHLOROADENOSINE-3',5'-CYCLIC MONOPHOSPHOROTHIOATE, RP-ISOMER SODIUM SALT α-Ethyltryptamine Pergolide mesylate salt

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