Pergolide mesylate

Base Information

• Chemical Name: Pergolide mesylate
• CAS No.: 66104-23-2
• Molecular Formula: CH₄O₃S*C₁₉H₂₆N₂S
• Molecular Weight: 410.602
• Hs Code.: 2939690000
• European Community (EC) Number: 636-270-7
• NSC Number: 758442,319773
• UNII: 55B9HQY616
• DSSTox Substance ID: DTXSID6040583
• Wikidata: Q27107641
• NCI Thesaurus Code: C47665
• RXCUI: 8048
• ChEMBL ID: CHEMBL1275
• Mol file: 66104-23-2.mol

Synonyms:Celance;LY-127,809;LY-127809;LY127,809;LY127809;Mesylate, Pergolide;Parkotil;Pergolide;Pergolide Mesylate;Permax;Pharken

Chemical Property of Pergolide mesylate

Chemical Property:

• Appearance/Colour: White to off-white solid
• Melting Point: 252-254 °C
• Boiling Point: 491.3 °C at 760 mmHg
• PKA: pKa (66% DMF) 7.8(at 25℃)
• Flash Point: 250.9 °C
• PSA: 107.08000
• LogP: 4.79380
• Storage Temp.: −20°C
• Solubility.: ethanol: soluble2mg/mL
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 410.16978517
• Heavy Atom Count: 27
• Complexity: 480

Purity/Quality:

99% ^*data from raw suppliers

Pergolide Mesylate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T+
• Statements: 28
• Safety Statements: 28-36/37-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCN1CC(CC2C1CC3=CNC4=CC=CC2=C34)CSC.CS(=O)(=O)O
• Isomeric SMILES: CCCN1C[C@@H](C[C@H]2[C@H]1CC3=CNC4=CC=CC2=C34)CSC.CS(=O)(=O)O
• Recent EU Clinical Trials: Pharmakotherapie kognitiver Defizite bei schizophrenen St?rungen – Randomisierte placebokontrollierte Doppelblindstudie mit Pergolid versus Tolcapon
• Description: Pergolide 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. Pergolide 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).
• Uses: A dopaminergic agonist that also decrease plasma prolactin concentrations. An antiparkinsonian agent

Technology Process of Pergolide mesylate

There total 7 articles about Pergolide mesylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.7%

(8β)-8-(hydroxymethyl)-D-ergoline-6-carbonitrile (108895-69-8) → (8β)-D-ergoline-8-methanol (72821-81-9) + pergolide mesylate (66104-23-2)

Guidance literature:

With sodium hydroxide; In diethyl ether; water; ethylene glycol;

Reference yield:

pergolide (66104-22-1) → pergolide mesylate (66104-23-2)

Guidance literature:

With methanesulfonic acid; In methanol;

Reference yield:

D-6-propyl-8β-hydroxymethylergoline (63719-21-1) → pergolide mesylate (66104-23-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: pyridine / dichloromethane / 1 h / -5 °C / Inert atmosphere; Reflux; Large scale

1.2: 1 h / -5 °C / Inert atmosphere; Large scale

2.1: 1-methyl-pyrrolidin-2-one; dichloromethane / 20 °C / Inert atmosphere; Reflux; Large scale

2.2: 0 °C / Inert atmosphere; Large scale

3.1: methanol / 20 - 60 °C / Large scale

With pyridine; In 1-methyl-pyrrolidin-2-one; methanol; dichloromethane;

DOI:10.1021/op0501747

upstream raw materials:

pergolide

(8β)-8-(hydroxymethyl)-D-ergoline-6-carbonitrile

D-6-propyl-8β-hydroxymethylergoline

methanesulfonic acid

Refernces

• 1、 -. "Decyanation of pergolide intermediate". . . Retrieved 2008/06/13.