63719-21-1

Basic information

• Product Name: PERGOLIDE MESYLATE INTERMEDIATE
• Synonyms: PERGOLIDE MESYLATE INTERMEDIATE
• CAS NO: 63719-21-1
• Molecular Formula: C₁₈H₂₄N₂O
• Molecular Weight: 284.4
• Mol File: 63719-21-1.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: PERGOLIDE MESYLATE INTERMEDIATE(CAS DataBase Reference)
• NIST Chemistry Reference: PERGOLIDE MESYLATE INTERMEDIATE(63719-21-1)
• EPA Substance Registry System: PERGOLIDE MESYLATE INTERMEDIATE(63719-21-1)

Safety Data

• Hazardous Substances Data: 63719-21-1(Hazardous Substances Data)

Upstream product

• 30341-92-5 methyl (6aR,9R,10aR)-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate 
• 51260-62-9 D-6-cyano-8β-methoxycarbonylergoline 
• 3006-19-7 9,10-dihydrolysergic acid methyl ester 
• 107-08-4 1-iodo-propane 
• 5878-43-3 9,10-dihydrolysergic acid 
• 63719-09-5 6-nor-6-n-propyl-9,10-dihydrolysergic acid methyl ester 
• 18051-16-6 9,10-dihydrolysergol 

Downstream Products

• 79675-18-6 Toluene-4-sulfonic acid (6aR,9R,10aR)-7-propyl-4,6,6a,7,8,9,10,10a-octahydro-indolo[4,3-fg]quinolin-9-ylmethyl ester 
• 72821-83-1 D-6-propyl-8β-mesyloxymethylergoline 
• 66104-23-2 pergolide mesylate 
• 66104-22-1 pergolide 

Relevant articles and documents

Simple and selective one-pot replacement of the N-methyl group of tertiary amines by quaternization and demethylation with sodium sulfide or potassium thioacetate: An application to the synthesis of pergolide

The paper describes a mild, selective, and rapid replacement of an N-methyl group of tertiary amines with other alkyl groups via a simple one-pot procedure. This transformation is easily achieved by preparation of the appropriate quaternary ammonium salt in sulfolane and in situ treatment with sodium sulfide or potassium thioacetate. The protocol is successfully applied to the transformation of dihydrolysergol, dextromethorphan and laudanosine (as models of ergot and opium N-methyl alkaloids) into various N-alkyl congeners.

Synthesis and structure-activity relationships of new (5R,8R,10R)-ergoline derivatives with antihypertensive or dopaminergic activity

A series of new (5R,8R,10R)-ergoline derivatives was synthesized, and their antihypertensive and dopaminergic activities were tested in conscious spontaneously hypertensive rats and in rats with unilateral 6- hydroxydopamine-induced lesions of the substantia nigra. (5R,8R,10R)-6- Alkyl-8-ergolinemethanols, prepared from the corresponding ergolinecarboxylates, were converted to the tosylates, which were treated with various five-membered heterocycles containing nitrogen atoms to afford the new ergolines. (5R,8R,10R)-8-(1,2,4-Triazol-1-ylmethyl)-6-methylergoline (4s, maleate: BAM-1110) exhibited potent dopaminergic activity, about 18- fold greater than that of bromocriptine mesylate. (5R,8R,10R)-8-(1,2,4- Triazol-1-ylmethyl)-6-propylergoline (8b, fumarate: BAM-1602) showed extremely potent dopaminergic activity, being about 220 and 1.15 times more active than bromocriptine mesylate and pergolide mesylate, respectively. Several compounds exhibited potent antihypertensive activity. Structure- activity relationships for antihypertensive and dopaminergic activities are discussed.

6-N-Propyl-8-methoxymethyl or methylmercaptomethylergolines and related compounds

6-n-Propyl (ethyl or allyl)-8β-methoxy-(methylsulfinyl, methylsulfonyl, or methylmercapto) methylergolines, 8-ergolenes or 9-ergolenes, useful as prolactin inhibitors and in the treatment of Parkinsonism.