1349-51-5

Basic information

• Product Name: (2E)-2-methyl-3-[(4R,5R)-4-(methylamino)-1,3,4,5-tetrahydrobenzo[cd]indol-5-yl]prop-2-en-1-ol
• Synonyms: (E)-8,9-Didehydro-6-methyl-6,7-secoergoline-8-methanol; (2Z)-2-methyl-3-[(4R,5R)-4-(methylamino)-1,3,4,5-tetrahydrobenzo[cd]indol-5-yl]prop-2-en-1-ol
• CAS NO: 1349-51-5
• Molecular Formula: C₁₆H₂₀N₂O
• Molecular Weight: 256.3428
• Mol File: 1349-51-5.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 470.144°C at 760 mmHg
• Flash Point: 238.135°C
• Density: 1.192g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.646
• CAS DataBase Reference: (2E)-2-methyl-3-[(4R,5R)-4-(methylamino)-1,3,4,5-tetrahydrobenzo[cd]indol-5-yl]prop-2-en-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-2-methyl-3-[(4R,5R)-4-(methylamino)-1,3,4,5-tetrahydrobenzo[cd]indol-5-yl]prop-2-en-1-ol(1349-51-5)
• EPA Substance Registry System: (2E)-2-methyl-3-[(4R,5R)-4-(methylamino)-1,3,4,5-tetrahydrobenzo[cd]indol-5-yl]prop-2-en-1-ol(1349-51-5)

Safety Data

• Hazardous Substances Data: 1349-51-5(Hazardous Substances Data)

Upstream product

• 142923-93-1 (5R,10R)-6-methyl-(8S)-acetoxymethyl-ergoline 
• 3006-19-7 9,10-dihydrolysergic acid methyl ester 
• 602-85-7 lysergol 
• 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 
• 82-58-6 D-lysergic acid 
• 5878-43-3 9,10-dihydrolysergic acid 
• 548-43-6 elymoclavine 
• 25447-65-8 dihydroergocornine 
• 5143-94-2 methyl (5R,8S,10R)-6-methyl-8-ergolinecarboxylate 

Downstream Products

• 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 
• 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 
• 95688-34-9 FCE 22716 
• 18051-18-8 D-8β-Cyanomethyl-6-methylergoline 
• 63719-21-1 D-6-propyl-8β-hydroxymethylergoline 
• 66104-22-1 pergolide 

Relevant articles and documents

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.

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Total synthesis of dihydrolysergic acid and dihydrolysergol: development of a divergent synthetic strategy applicable to rapid assembly of D-ring analogs

Abstract The total syntheses of dihydrolysergic acid and dihydrolysergol are detailed based on a Pd(0)-catalyzed intramolecular Larock indole cyclization for the preparation of the embedded tricyclic indole (ABC ring system) and a subsequent powerful inverse electron demand Diels-Alder reaction of 5-carbomethoxy-1,2,3-triazine with a ketone-derived enamine for the introduction of a functionalized pyridine, serving as the precursor for a remarkably diastereoselective reduction to the N-methylpiperidine D-ring. By design, the use of the same ketone-derived enamine and a set of related complementary heterocyclic azadiene [4+2] cycloaddition reactions permitted the late stage divergent preparation of a series of alternative heterocyclic derivatives not readily accessible by more conventional approaches.

Serotonergic ergoline derivatives

Novel classes of 13- and 14-tertbutyl-ergoline derivatives were prepared, and characterised in vitro for their affinity for adrenergic, dopaminergic and serotonergic binding sites. This study particularly examines the importance of the presence and the position of the tert-butyl group in conferring either significant 5-HT(1A) or 5-HT2 affinity and selectivity respectively.