5878-43-3

Basic information

• Product Name: 6-methylergoline-8beta-carboxylic acid
• Synonyms: 6-methylergoline-8beta-carboxylic acid;DIHYDROLYSERGICACID(CONTROLLEDCHEMICAL);9,10-dihydrolysergic acid;9,10-Dihydro-D-lysergic acid;6-Methylergoline-8β-carboxylic acid;Dihydrolysergic Acid;Ergoline-8-carboxylicacid, 6-Methyl-, (8b)-;ORBSYPFBZQJNJE-MPKXVKKWSA-N
• CAS NO: 5878-43-3
• Molecular Formula: C₁₆H₁₈N₂O₂
• Molecular Weight: 270.32632
• EINECS: 227-551-1
• Product Categories: PP
• Mol File: 5878-43-3.mol
• Article Data: 9

Chemical Properties

• Melting Point: 300 °C
• Boiling Point: 517.3 °C at 760 mmHg
• Flash Point: 266.6 °C
• Appearance: /
• Density: 1.31 g/cm³
• PKA: 3.81±0.20(Predicted)
• CAS DataBase Reference: 6-methylergoline-8beta-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 6-methylergoline-8beta-carboxylic acid(5878-43-3)
• EPA Substance Registry System: 6-methylergoline-8beta-carboxylic acid(5878-43-3)

Safety Data

• Hazardous Substances Data: 5878-43-3(Hazardous Substances Data)

Usage

General Description

6-Methylergoline-8beta-carboxylic acid is a chemical compound that belongs to the class of organic compounds known as ergoline alkaloids. These alkaloids primarily occur in various species of the fungal genus Claviceps, which includes the infamous ergot fungus. Notably, this particular chemical is an ergoline derivative, which implies it shares a common structure with a variety of biologically active compounds, including some used as pharmaceutical drugs. Nonetheless, details about 6-methylergoline-8beta-carboxylic acid's specific properties or its potential applications in scientific or industrial contexts are less available in the literature.

Synthetic route

Dihydroergocryptine (25447-66-9) → 9,10-dihydrolysergic acid (5878-43-3)

Conditions	Yield
With sodium dithionite; sodium hydroxide In water for 4h; Reflux;	93%

9,10-dihydrolysergic acid methyl ester (3006-19-7, 5143-94-2, 35470-53-2, 77842-02-5, 87247-99-2, 96648-31-6, 96648-32-7) → 9,10-dihydrolysergic acid (5878-43-3)

Conditions	Yield
With sodium hydroxide In methanol; water for 3h;	71%
With sodium hydroxide In methanol; water for 3h;	71%
With sodium hydroxide In methanol Ambient temperature;

9,10-dihydroergocristine methanesulphonate → dihydrolysergyldehydrovaline azalactam (88299-13-2) + dihydrolysergyldehydrovaline methyl ester (88299-12-1) + (3S,8aS)-3-benzyloctahydropyrrolo[1,2-a]pyrazine-1,4-dione (5654-85-3, 14705-60-3, 26488-24-4, 32021-26-4, 43041-16-3, 43041-30-1, 3705-26-8) + 9,10-dihydrolysergic acid (5878-43-3)

Conditions	Yield
at 190℃; for 0.5h; Further byproducts given;	A 3.3% B 1.3% C 23% D 51%

D-lysergic acid (82-58-6) → ent-6-methyl-5α-ergoline-8β-carboxylic acid (2481-70-1) + 9,10-dihydrolysergic acid (5878-43-3)

Conditions	Yield
With acetic acid; platinum Hydrogenation;

D-lysergic acid (82-58-6) → 9,10-dihydrolysergic acid (5878-43-3)

Conditions	Yield
With ammonium hydroxide; nickel at 60 - 65℃; under 44130.5 - 47808 Torr; Hydrogenation;

6-methyl-8-methylen-ergolin-7-one (51867-15-3) → 9,10-dihydrolysergic acid (5878-43-3)

Conditions	Yield
With potassium hydroxide; 2-methyl-propan-1-ol

rac-9,10-dihydrolysergic acid (2481-70-1, 5878-43-3, 6838-23-9, 6871-64-3) → 9,10-dihydrolysergic acid (5878-43-3)

Conditions	Yield
With (1R,2S)-norephedrine Gewinnung aus rac-6-Methyl-ergolin-8β-carbonsaeure;

dihydroergocorninine-I → 9,10-dihydrolysergic acid (5878-43-3)

Conditions	Yield
With potassium hydroxide

dihydroergotamine → 9,10-dihydrolysergic acid (5878-43-3)

Conditions	Yield
With potassium hydroxide

i-Amyl alcohol (123-51-3) + 6-methyl-8-methylen-ergolin-7-one (51867-15-3) + KOH → 9,10-dihydrolysergic acid (5878-43-3)

Conditions	Yield
anschliessend Hydrolysieren;

methyl (5R,8S,10R)-6-methyl-8-ergolinecarboxylate (5143-94-2) + aqueous methanol.KOH → 6-methyl-ergoline-8α-carboxylic acid (6838-23-9) + 9,10-dihydrolysergic acid (5878-43-3)

C18H20N2O2 (955957-41-2) → 9,10-dihydrolysergic acid (5878-43-3)

Conditions	Yield
With silver(l) oxide In tetrahydrofuran; methanol; sodium hydroxide for 0.75h;

C16H18N2O3 → 9,10-dihydrolysergic acid (5878-43-3)

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol at 20℃; for 12h;

(+/-)-lysergic acid (82-58-6, 478-95-5, 6915-32-8, 23953-76-6, 68985-97-7, 68985-98-8) → 9,10-dihydrolysergic acid (5878-43-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium; butan-1-ol / Behandeln des Reaktionsprodukts mit methanol.HCl 2: N2H4 3: aq.-ethanolic KOH 4: (-)-norephedrine / Gewinnung aus rac-6-Methyl-ergolin-8β-carbonsaeure View Scheme

#rac-ergoline-8α-carboxylic acid methyl ester (30341-92-5, 86891-09-0) → 9,10-dihydrolysergic acid (5878-43-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: 220 °C / 0 Torr / Behandeln des Reaktionsprodukts mit methanol.HCl 2: N2H4 3: aq.-ethanolic KOH 4: (-)-norephedrine / Gewinnung aus rac-6-Methyl-ergolin-8β-carbonsaeure View Scheme

methyl (6aRS,9SS,10aSR)-7-methyl-4,6,6a,7,8,9,10,10a-octahydroindolo<4,3-fg>quinoline-9-carboxylate (3006-19-7, 5143-94-2, 35470-53-2, 77842-02-5, 87247-99-2, 96648-31-6, 96648-32-7) → 9,10-dihydrolysergic acid (5878-43-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: N2H4 2: aq.-ethanolic KOH 3: (-)-norephedrine / Gewinnung aus rac-6-Methyl-ergolin-8β-carbonsaeure View Scheme

rac-6-methyl-ergoline-8α-carboxylic acid hydrazide (1752-45-0, 1940-07-4, 2636-63-7, 41564-31-2) → 9,10-dihydrolysergic acid (5878-43-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: aq.-ethanolic KOH 2: (-)-norephedrine / Gewinnung aus rac-6-Methyl-ergolin-8β-carbonsaeure View Scheme

paspalic acid (5516-88-1) → 9,10-dihydrolysergic acid (5878-43-3)

Conditions	Yield
With hydrogen; palladium on activated charcoal

dihydroergotamine mesylate (6190-39-2) → 9,10-dihydrolysergic acid (5878-43-3)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydroxide / water; methanol / 72 h / Inert atmosphere 1.2: 48 h 2.1: sodium hydroxide / water; methanol / 3 h View Scheme
Multi-step reaction with 2 steps 1.1: sodium hydroxide; water / methanol / 72 h / Inert atmosphere 1.2: 48 h 2.1: sodium hydroxide / methanol; water / 3 h View Scheme

methanol (67-56-1) + 9,10-dihydrolysergic acid (5878-43-3) → 9,10-dihydrolysergic acid methyl ester (3006-19-7, 5143-94-2, 35470-53-2, 77842-02-5, 87247-99-2, 96648-31-6, 96648-32-7)

Conditions	Yield
With sulfuric acid	95%
With thionyl chloride for 1.5h; Heating;	90%
With sulfuric acid at 20℃; for 15h;	85%

cyclopentyl tosylate (3558-06-3) + 9,10-dihydrolysergic acid (5878-43-3) → (8β)-1-cyclopentyl-6-methylergoline-8-carboxylic acid (109839-87-4)

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide for 2h;	92.5%

9,10-dihydrolysergic acid (5878-43-3) + methyl iodide (74-88-4) → (5R,8R,10R)-1,6-dimethyl-8-ergolinecarboxylic acid (35470-52-1)

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 17℃;	88%

ethanol (64-17-5) + 9,10-dihydrolysergic acid (5878-43-3) → 6-methyl-ergoline-8-carboxylic acid ethyl ester (70625-23-9)

Conditions	Yield
With thionyl chloride for 1.5h; Heating;	82%

isopropyl alcohol (67-63-0) + 9,10-dihydrolysergic acid (5878-43-3) → (6aR,9R,10aR)-7-Methyl-4,6,6a,7,8,9,10,10a-octahydro-indolo[4,3-fg]quinoline-9-carboxylic acid isopropyl ester (87201-20-5)

Conditions	Yield
With thionyl chloride for 23h; Heating;	76%

1,3-di-tert-butylcarbodiimide (691-24-7) + 9,10-dihydrolysergic acid (5878-43-3) → N-t-butyl-N-<(t-butylamino)-carbonyl>-6-methylergoline-8β-carboxamide (81409-82-7)

Conditions	Yield
	75%

methanol (67-56-1) + acetone (67-64-1) + 9,10-dihydrolysergic acid (5878-43-3) → 2,2-bis(D-6-methyl-8-methoxycarbonylergolin-I-2-yl)propane (74569-81-6)

Conditions	Yield
With toluene-4-sulfonic acid for 16h; Heating;	67%

diisopropyl-carbodiimide (693-13-0) + 9,10-dihydrolysergic acid (5878-43-3) → N-isopropyl-N-<(isopropylamino)-carbonyl>-6-methylergoline-8β-carboxamide (81396-93-2)

Conditions	Yield
	65%

N,N'-dimethylcarbodiimide (4852-30-6) + 9,10-dihydrolysergic acid (5878-43-3) → N-methyl-N-<(methylamino)-carbonyl>-6-methylergoline-8β-carboxamide (81409-87-2)

Conditions	Yield
	62%

dicyclohexyl-carbodiimide (538-75-0) + 9,10-dihydrolysergic acid (5878-43-3) → N-cyclohexyl-N-<(cyclohexylamino)-carbonyl>-6-methylergoline-8β-carboxamide (81409-78-1)

Conditions	Yield
In tetrahydrofuran Heating;	61%

9,10-dihydrolysergic acid (5878-43-3) + butan-1-ol (71-36-3) → (6aR,9R,10aR)-7-Methyl-4,6,6a,7,8,9,10,10a-octahydro-indolo[4,3-fg]quinoline-9-carboxylic acid butyl ester (87201-21-6)

Conditions	Yield
With thionyl chloride at 100℃; for 1h;	57%

benzyl chloride (100-44-7) + 9,10-dihydrolysergic acid (5878-43-3) → (6aR,9R,10aR)-4-Benzyl-7-methyl-4,6,6a,7,8,9,10,10a-octahydro-indolo[4,3-fg]quinoline-9-carboxylic acid (2618-03-3)

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 17℃;	52%

ethyl iodide (75-03-6) + 9,10-dihydrolysergic acid (5878-43-3) → 1-ethyldihydrolysergic acid (41710-25-2)

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 17℃;	47%

propyl bromide (106-94-5) + 9,10-dihydrolysergic acid (5878-43-3) → (6aR,9R,10aR)-7-Methyl-4-propyl-4,6,6a,7,8,9,10,10a-octahydro-indolo[4,3-fg]quinoline-9-carboxylic acid (41710-26-3)

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 17℃;	35%

(L-Valyl)-L-phenylalanyl-L-prolin-lactam (78452-07-0) + 9,10-dihydrolysergic acid (5878-43-3) → (6aR,9R,10aR)-7-Methyl-4,6,6a,7,8,9,10,10a-octahydro-indolo[4,3-fg]quinoline-9-carboxylic acid [(S)-1-((S)-3-benzyl-1,4-dioxo-hexahydro-pyrrolo[1,2-a]pyrazine-2-carbonyl)-2-methyl-propyl]-amide; compound with (Z)-but-2-enedioic acid (81531-44-4)

Conditions	Yield
With 4-methyl-morpholine; benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran; dichloromethane for 20h; Ambient temperature;	20%

1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride (25952-53-8) + 9,10-dihydrolysergic acid (5878-43-3) → 6-Methylcabergoline

Conditions	Yield
With triethylamine In dichloromethane	13%
With triethylamine In dichloromethane	13%

diazomethane (186581-53-3, 908094-01-9) + 9,10-dihydrolysergic acid (5878-43-3) → 9,10-dihydrolysergic acid methyl ester (3006-19-7, 5143-94-2, 35470-53-2, 77842-02-5, 87247-99-2, 96648-31-6, 96648-32-7)

Conditions	Yield
With methanol; diethyl ether

acetic anhydride (108-24-7) + 9,10-dihydrolysergic acid (5878-43-3) → 6-methyl-8-methylen-ergolin-7-one (51867-15-3)

Conditions	Yield
at 160 - 170℃;

9,10-dihydrolysergic acid (5878-43-3) → 6-methyl-8-methylen-ergolin-7-one (51867-15-3)

Conditions	Yield
With acetic anhydride at 170℃;
at 350℃; under 25 Torr;

ethyl bromoacetate (105-36-2) + 9,10-dihydrolysergic acid (5878-43-3) → D-1-Carboxymethyl-8β-carboxy-6-methylergoline (81782-18-5)

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 17℃;

1,1'-carbonyldiimidazole (530-62-1) + 9,10-dihydrolysergic acid (5878-43-3) → 6-methyl-ergoline-8-carboxylic acid amide (2410-19-7)

Conditions	Yield
In dichloromethane for 1h;

2-iodo-propane (75-30-9) + 9,10-dihydrolysergic acid (5878-43-3) → (8β)-6-methyl-1-(1-methylethyl)ergoline-8-carboxylic acid (41710-27-4)

Conditions	Yield
With ammonia; sodium amide 1.) 30 min, 2.) 1 h; Yield given. Multistep reaction;

(R,R)-2,3-butandiol (24347-58-8) + 9,10-dihydrolysergic acid (5878-43-3) → (6aR,9R,10aR)-7-Methyl-4,6,6a,7,8,9,10,10a-octahydro-indolo[4,3-fg]quinoline-9-carboxylic acid (1R,2R)-2-hydroxy-1-methyl-propyl ester (109840-00-8, 148966-66-9)

Conditions	Yield
With toluene-4-sulfonic acid at 80℃;

Upstream product

• 82-58-6 (+/-)-lysergic acid 
• 51867-15-3 6-methyl-8-methylen-ergolin-7-one 
• 2481-70-1 rac-9,10-dihydrolysergic acid 
• 82-58-6 D-lysergic acid 
• 30341-92-5 #rac-ergoline-8α-carboxylic acid methyl ester 
• 1420013-09-7 N-(2-bromo-3-(2-methoxyvinyl)phenyl)acetamide 
• 3006-19-7 methyl (6aRS,9RS,10aSR)-7-methyl-4,6,6a,7,8,9,10,10a-octahydroindolo<4,3-fg>quinoline-9-carboxylate 
• 51867-06-2 1-benzoyl-1,2,2a,3-tetrahydrobenzindol-4-(5H)-one 
• 158479-05-1 4-hydroxy-1,3,4,5-tetrahydrobenzindole 
• 1420013-23-5 N-(2-bromo-3-(2-hydroxy-5-(trimethylsilyl)pent-4-yn-1-yl)phenyl)acetamide 
• 1420013-02-0 C₁₀H₁₀BrNO₂ 
• 3006-19-7 methyl (6aRS,9SS,10aSR)-7-methyl-4,6,6a,7,8,9,10,10a-octahydroindolo<4,3-fg>quinoline-9-carboxylate 

Downstream Products

• 3006-19-7 9,10-dihydrolysergic acid methyl ester 
• 2481-70-1 9,10-Dihydrolysergsaeure 
• 5143-94-2 methyl (5R,8S,10R)-6-methyl-8-ergolinecarboxylate 
• 3006-19-7 methyl (6aRS,9RS,10aSR)-7-methyl-4,6,6a,7,8,9,10,10a-octahydroindolo<4,3-fg>quinoline-9-carboxylate 
• 1016228-23-1 C₂₆H₂₉ClN₄O 
• 216377-84-3 C₂₆H₂₉N₅O₃ 
• 72821-79-5 methyl (6aR,9R,10aR)-7-allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate 
• 81409-74-7 (6aR,9R,10aR)-7-allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylic acid 
• 85329-86-8 (6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide 
• 126554-50-5 (6aR,9R,10aR)-7-allyl-N⁹-[3-(dimethylamino)propyl]-N⁴-ethyl-N⁹-(ethylcarbamoyl)-6a,7,8,9,10,10a-hexahydroindolo[4,3-fg]quinoline-4,9(6H)-dicarboxamide 
• 66104-23-2 pergolide mesylate 
• 66104-22-1 pergolide 
• 72821-83-1 D-6-propyl-8β-mesyloxymethylergoline 
• 63719-21-1 D-6-propyl-8β-hydroxymethylergoline 

Relevant articles and documents

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