86891-15-8

Usage

Uses

Used in Pharmaceutical Industry:
Ergoline-8-carboxylic acid, 6-(2-propenyl)-, (8-alpha)is used as a precursor in the synthesis of various ergot alkaloids, which have significant applications in the pharmaceutical industry. These alkaloids are known for their therapeutic effects, particularly in the treatment of migraines and cluster headaches.
Used in Research Applications:
Ergoline-8-carboxylic acid, 6-(2-propenyl)-, (8-alpha)is used in research settings to study the effects of ergoline alkaloids on the central nervous system and their potential applications in the treatment of various neurological disorders. Its ability to bind to serotonin receptors makes it a valuable tool for understanding the role of serotonin in the brain and developing new therapeutic agents.
Used in Controlled Substance Regulation:
Due to its structural similarity to LSD, Ergoline-8-carboxylic acid, 6-(2-propenyl)-, (8-alpha)is regulated as a controlled substance in many countries. This regulation is important to prevent its misuse and ensure that it is used only for legitimate scientific and medical purposes.

InChI:InChI=1/C18H20N2O2/c1-2-6-20-10-12(18(21)22)7-14-13-4-3-5-15-17(13)11(9-19-15)8-16(14)20/h2-5,9,12,14,16,19H,1,6-8,10H2,(H,21,22)/t12-,14?,16+/m0/s1

Synthetic route

(6aR,9S,10aR)-7-Allyl-4,6,6a,7,8,9,10,10a-octahydro-indolo[4,3-fg]quinoline-9-carboxylic acid methyl ester (86891-16-9) → (6aR,9S,10aR)-7-Allyl-4,6,6a,7,8,9,10,10a-octahydro-indolo[4,3-fg]quinoline-9-carboxylic acid (86891-15-8)

Conditions	Yield
With sodium hydroxide In methanol at 60 - 65℃; for 22h;	91%

(5R,8S,10R)-6-cyano-8-methoxycarbonylergoline (86891-18-1) → (6aR,9S,10aR)-7-Allyl-4,6,6a,7,8,9,10,10a-octahydro-indolo[4,3-fg]quinoline-9-carboxylic acid (86891-15-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 70 percent / hydrogen / Raney nickel / dimethylformamide / 130 h / 30 Torr / Ambient temperature 2: 91 percent / anhydrous potassium carbonate / dimethylformamide / 8 h / Ambient temperature 3: 91 percent / 0.2M NaOH / methanol / 22 h / 60 - 65 °C View Scheme

(5R,8S,10R)-8-methoxycarbonylergoline (86891-09-0) → (6aR,9S,10aR)-7-Allyl-4,6,6a,7,8,9,10,10a-octahydro-indolo[4,3-fg]quinoline-9-carboxylic acid (86891-15-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 91 percent / anhydrous potassium carbonate / dimethylformamide / 8 h / Ambient temperature 2: 91 percent / 0.2M NaOH / methanol / 22 h / 60 - 65 °C View Scheme

methyl (5R,8S,10R)-6-methyl-8-ergolinecarboxylate (5143-94-2) → (6aR,9S,10aR)-7-Allyl-4,6,6a,7,8,9,10,10a-octahydro-indolo[4,3-fg]quinoline-9-carboxylic acid (86891-15-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: 86 percent / CH2Cl2 / 5 h / 20 °C 2: 70 percent / hydrogen / Raney nickel / dimethylformamide / 130 h / 30 Torr / Ambient temperature 3: 91 percent / anhydrous potassium carbonate / dimethylformamide / 8 h / Ambient temperature 4: 91 percent / 0.2M NaOH / methanol / 22 h / 60 - 65 °C View Scheme

Upstream product

• 86891-16-9 (6aR,9S,10aR)-7-Allyl-4,6,6a,7,8,9,10,10a-octahydro-indolo[4,3-fg]quinoline-9-carboxylic acid methyl ester 
• 86891-18-1 (5R,8S,10R)-6-cyano-8-methoxycarbonylergoline 
• 86891-09-0 (5R,8S,10R)-8-methoxycarbonylergoline 
• 5143-94-2 methyl (5R,8S,10R)-6-methyl-8-ergolinecarboxylate 

Relevant academic research and scientific papers

(5R, 8S, 10R)-6-ALKYL-8-ERGOLINECARBOXYLIC ACIDS AND SOME OF THEIR DERIVATIVES

(5R, 8S, 10R)-6-methyl-8-methoxycarbonylergoline (VIIb) was converted via Ib and IIb into its 6-analogues IIIb-VIb, which, in turn, were converted into acids IIIa-VIa and hydrazides IIIc-VIc.Some of the esters prepared, mainly IVb, had inhibitory effects on the secretion of prolactin in rats.