478-95-5

Usage

Purification Methods

It crystallises from water as the dihydrate. The methyl ester has m 172-174o (from MeOH or *C6H6) and [] 20 +179o (c 0.5 CHCl3). [Smith & Timmis J Chem Soc 1440 1936, Craig et al. JBiochem 125 289 1938, Stenlake J Chem Soc 1626 1955, Leemann & Fabbri Helv Chim Acta 4 2696 1959, Beilstein 25 III/IV 935.]

InChI:InChI=1/C16H16N2O2/c1-18-8-10(16(19)20)5-12-11-3-2-4-13-15(11)9(7-17-13)6-14(12)18/h2-5,7,10,14,17H,6,8H2,1H3,(H,19,20)

Upstream product

• 88133-12-4 lysergic acid sulfate 
• 764710-82-9 N-[(7-methyl-6,6a,7,8-tetrahydro-4H-indolo[4,3-fg]quinolin-9-ylidene)-(toluene-4-sulfonyl)-methyl]-formamide 

Downstream Products

• 82-58-6 D-lysergic acid 
• 1268723-18-7 C₅₉H₈₁N₁₃O₁₁S 
• 1268723-30-3 C₆₂H₇₉FN₁₂O₁₀S 
• 1268723-11-0 C₅₇H₇₈N₁₂O₁₀S 
• 1268723-40-5 C₆₄H₈₂FN₁₃O₁₁S 
• 5256-60-0 (+/-)-isolysergic acid hydrazide 
• 3006-19-7 methyl (6aRS,9RS,10aSR)-7-methyl-4,6,6a,7,8,9,10,10a-octahydroindolo<4,3-fg>quinoline-9-carboxylate 
• 3006-19-7 methyl (6aRS,9SS,10aSR)-7-methyl-4,6,6a,7,8,9,10,10a-octahydroindolo<4,3-fg>quinoline-9-carboxylate 
• 2481-70-1 9,10-Dihydrolysergsaeure 
• 5878-43-3 9,10-dihydrolysergic acid 
• 2481-70-1 rac-9,10-dihydrolysergic acid 
• 1752-45-0 rac-6-methyl-ergoline-8β-carboxylic acid hydrazide 
• 1752-45-0 rac-6-methyl-ergoline-8α-carboxylic acid hydrazide 

Relevant academic research and scientific papers

PROCESS FOR THE MANUFACTURE OF LYSERGIC ACID

Lysergic acid is formed in high yields and high quality by isomerizing paspalic acid in a phase separated mixture formed by paspalic acid and a concentrated aqueous metal hydroxide solution.

Enantioefficient synthesis of α-ergocryptine: First direct synthesis of (+)-lysergic acid

The first direct synthesis of (+)-lysergic acid (2a) suitable for scale-up has been achieved by the following reaction sequence. Bromoketones 4d or 4g were allowed to react with amine 5 followed by deprotection, and the resulting diketone 6c was transformed into the unsaturated ketone (±)-7 by the LiBr/Et3N system. Resolution afforded (+)-7, which was further transformed by Schoellkopfs method into the mixture of esters 2e and 2f. Upon hydrolysis the latter mixture afforded (+)-2a. The peptide part of α-ergocryptine (1) was prepared according to the Sandoz method; the stereoefficiency, however, has been significantly improved by applying a new resolution method and recycling the undesired enantiomer. Coupling the peptide part with lysergic acid afforded 1. Having synthetic (+)-7 in hand, we can claim the total synthesis of all the alkaloids which were prepared earlier from (+)-7 that had been obtained through degradation of natural lysergic acid.