18051-16-6

Basic information

• Product Name: 9,10-Dihydrolysergol
• Synonyms: LY 60722;6-Methylergoline-8b-methanol;6-Methyl-ergoline-8-methanol;8a,9-Dihydroelymoclavine;9,10-Dihydrolysergol;a-Dihydrolysergol;a-Dihydro-lysergol;Dihydrolysergol I
• CAS NO: 18051-16-6
• Molecular Formula: C₁₆H₂₀N₂O
• Molecular Weight: 256.34
• Product Categories: Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 18051-16-6.mol
• Article Data: 6

Chemical Properties

• Melting Point: >265°C (dec)
• Boiling Point: 444.8°Cat760mmHg
• Flash Point: 222.8°C
• Appearance: /
• Density: 1.205g/cm³
• Vapor Pressure: 1.08E-08mmHg at 25°C
• Refractive Index: 1.645
• Storage Temp.: -20?C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly), Pyridine (Slightly)
• PKA: 14.87±0.10(Predicted)
• CAS DataBase Reference: 9,10-Dihydrolysergol(CAS DataBase Reference)
• NIST Chemistry Reference: 9,10-Dihydrolysergol(18051-16-6)
• EPA Substance Registry System: 9,10-Dihydrolysergol(18051-16-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• Hazardous Substances Data: 18051-16-6(Hazardous Substances Data)

Usage

Description

9,10-Dihydrolysergol is an O-acylated derivative of Lysergol and Dehydrolysergol-I, characterized as a white to off-white solid. It functions as a partial agonist and antagonist at various receptors, including 5-HT2A, 5-HT2C, 5-HT1B, and α1-andrenergic receptors.

Uses

Used in Pharmaceutical Industry:
9,10-Dihydrolysergol is used as a pharmaceutical compound for its receptor modulating properties. It serves as a partial agonist and antagonist at 5-HT2A, 5-HT2C, and 5-HT1B receptors, as well as at α1-andrenergic receptors, making it a potential candidate for the development of drugs targeting these receptors.
Used in Research Applications:
In the field of scientific research, 9,10-Dihydrolysergol is utilized as a research tool to study the effects and interactions of various receptors, particularly those mentioned above. Its ability to act as both a partial agonist and antagonist allows researchers to gain insights into receptor function and potential therapeutic applications.

InChI:InChI=1/C16H20N2O/c1-18-8-10(9-19)5-13-12-3-2-4-14-16(12)11(7-17-14)6-15(13)18/h2-4,7,10,13,15,17,19H,5-6,8-9H2,1H3/t10-,13-,15-/m1/s1

Upstream product

• 25447-65-8 dihydroergocornine 
• 82-58-6 D-lysergic acid 
• 5878-43-3 9,10-dihydrolysergic acid 
• 602-85-7 lysergol 
• 548-43-6 elymoclavine 
• 3006-19-7 9,10-dihydrolysergic acid methyl ester 

Downstream Products

• 105579-54-2 1-(6-Methylergolin-8β-ylmethyl)-2-phenylimidazole 
• 105579-47-3 (5R,8R,10R)-6-methyl-8-(1,2,4-triazol-1-ylmethyl)ergoline 
• 105579-57-5 ethyl 5-methyl-1-(6-methylergolin-8β-ylmethyl)-4-imidazolecarboxylate 
• 160730-42-7 (6aR,9R,10aR)-9-[2-(4-Methoxy-phenyl)-imidazol-1-ylmethyl]-7-methyl-4,6,6a,7,8,9,10,10a-octahydro-indolo[4,3-fg]quinoline 
• 162070-31-7 1-((6aR,9R,10aR)-7-Methyl-4,6,6a,7,8,9,10,10a-octahydro-indolo[4,3-fg]quinolin-9-ylmethyl)-1H-imidazole-2-carboxylic acid ethyl ester 
• 115219-09-5 (6aR,9R,10aR)-7-Methyl-9-(5-methyl-3-phenyl-pyrazol-1-ylmethyl)-4,6,6a,7,8,9,10,10a-octahydro-indolo[4,3-fg]quinoline 
• 160730-46-1 (6aR,9R,10aR)-7-Methyl-9-(3-methyl-5-phenyl-pyrazol-1-ylmethyl)-4,6,6a,7,8,9,10,10a-octahydro-indolo[4,3-fg]quinoline 
• 160730-49-4 1-Methyl-3-(6-methylergolin-8β-ylmethyl)imidazolidin-2,4-dione 
• 160730-51-8 2-((6aR,9R,10aR)-7-Methyl-4,6,6a,7,8,9,10,10a-octahydro-indolo[4,3-fg]quinolin-9-ylmethyl)-isoindole-1,3-dione 
• 160730-43-8 (5R,8R,10R)-6-methyl-8-(4-phenyl-1-imidazolylmethyl)ergoline 
• 105579-52-0 2-Isopropyl-1-(6-methylergolin-8β-ylmethyl)imidazole 
• 105579-55-3 2-Ethyl-4-methyl-1-(6-methylergolin-8β-ylmethyl)imidazole 
• 105579-53-1 1-(6-Methylergolin-8β-ylmethyl)-2-propylimidazole 
• 105579-44-0 3-(6-Methylergolin-8β-ylmethyl)oxazolidin-2-one 

Relevant articles and documents

New and efficient process for the preperation of cabergoline and its intermediates

This invention relates to a new and efficient process for the production of dopamine agonists such as Cabergoline and the intermediates thereof.

Naturally occurring clavines: Antagonism/partial agonism at 5-HT(2A) receptors and antagonism at α1-adrenoceptors in blood vessels

The interaction of eight typical representatives of naturally occurring clavines (agroclavine, costaclavine, dihydrolysergol-I, elymoclavine, festuclavine, lysergene, lysergol, and pyroclavine) with 5-HT(2A) receptors and α1-adrenoceptors was studied in rat tail artery and aorta, respectively. Clavines antagonized 5-HT-induced contractions with calculated pK(B) values (pK(p) values for partial agonists) of 4.84 - 7.81 and (R)-phenylephrine-induced contractions with calculated pK(B) values of 5.34 - 7.09. Specificity of clavines at 5-HT(2A) receptors relative to α1-adrenoceptors was rather low. Low affinity for costaclavine at both 5-HT(2A) receptors (pK(p) = 4.84 ± 0.06) and α1-adrenoceptors (pK(B) = 5.34 ± 0.05) indicates that the trans-junction of ring C and D of the ergoline pharmacophore is crucial for the binding of ergolines to these sites. Lysergol, lysergene, and costaclavine produced non-parallel displacements of the 5-HT concentration-response curve in the rat tail artery and caused small contractions by themselves. Lysergol contracted the rat tail artery with a pEC50 of 6.36 ± 0.04 and an intrinsic activity of 0.18 ± 0.03 with respect to 5-HT. Lysergol-induced contractile responses were surmountably antagonized by ketanserin (10 nM) with a pK(B) of 9.1 which is consistent with an interaction of lysergol with 5-HT(2A) receptors. The pK(p) for the lysergol-5-HT(2A) receptor complex calculated from concentration-response curves to lysergol was 6.88 ± 0.07 and did not match the pK(p) of 7.66 ± 0.02 calculated from antagonism by lysergol of the contractile response to 5-HT. This suggests that lysergol and 5-HT possibly bind in two slightly different orientations at the 5-HT2(A) receptor. It is concluded that partial agonism and pure antagonism at 5-HT2(A) receptors on the one side and antagonism at α1-adrenoceptors on the other side may contribute to the noxious effects of naturally occurring clavines.

Diastereospecific formation of 6-N-oxide ergolines: A 1H NMR study of the configuration at nitrogen

The 6-N-oxides derivatives of a series of analogous ergoline/ene derivatives were prepared and their stereochemistry at nitrogen determined by 1H NMR analysis. The factors governing the outcome of the oxidation are discussed.