86891-15-8

Basic information

• Product Name: Ergoline-8-carboxylic acid, 6-(2-propenyl)-, (8-alpha)-
• Synonyms: Ergoline-8-carboxylic acid, 6-(2-propenyl)-, (8-alpha)-;6-Allyldihydronorisolysergic Acid
• CAS NO: 86891-15-8
• Molecular Formula: C₁₈H₂₀N₂O₂
• Molecular Weight: 296.36
• Mol File: 86891-15-8.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 530.4°C at 760 mmHg
• Flash Point: 274.6°C
• Appearance: /
• Density: 1.258g/cm³
• Vapor Pressure: 4.45E-12mmHg at 25°C
• Refractive Index: 1.65
• PKA: 3.77±0.20(Predicted)
• CAS DataBase Reference: Ergoline-8-carboxylic acid, 6-(2-propenyl)-, (8-alpha)-(CAS DataBase Reference)
• NIST Chemistry Reference: Ergoline-8-carboxylic acid, 6-(2-propenyl)-, (8-alpha)-(86891-15-8)
• EPA Substance Registry System: Ergoline-8-carboxylic acid, 6-(2-propenyl)-, (8-alpha)-(86891-15-8)

Safety Data

• Hazardous Substances Data: 86891-15-8(Hazardous Substances Data)

Usage

General Description

Ergoline-8-carboxylic acid, 6-(2-propenyl)-, (8-alpha)- is a chemical compound belonging to the ergoline alkaloid class. It is structurally related to the neurotransmitter serotonin and has been identified as a precursor in the biosynthesis of lysergic acid diethylamide (LSD). It is also known for its potential psychotropic effects and its ability to bind to serotonin receptors in the brain. Additionally, it has been investigated for its potential therapeutic applications, particularly in the treatment of migraines and cluster headaches. Due to its structural similarity to LSD, it is also regulated as a controlled substance in many countries.

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

• 5143-94-2 methyl (5R,8S,10R)-6-methyl-8-ergolinecarboxylate 
• 86891-09-0 (5R,8S,10R)-8-methoxycarbonylergoline 
• 86891-18-1 (5R,8S,10R)-6-cyano-8-methoxycarbonylergoline 
• 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 

Relevant articles and documents

(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.