2390-99-0

Basic information

• Product Name: chanoclavine
• Synonyms: (E)-2-Methyl-3-[(1,3,4,5-tetrahydro-4β-(methylamino)benz[cd]indol)-5α-yl]-2-propen-1-ol;(E)-2-Methyl-3-[(4R,5R)-1,3,4,5-tetrahydro-4-(methylamino)benz[cd]indol-5-yl]-2-propen-1-ol;Secaclavine
• CAS NO: 2390-99-0
• Molecular Formula: C₁₆H₂₀N₂O
• Molecular Weight: 256.3428
• Mol File: 2390-99-0.mol
• Article Data: 18

Chemical Properties

• Melting Point: 220-222°
• Boiling Point: 470.1°Cat760mmHg
• Flash Point: 238.1°C
• Appearance: /
• Density: 1.19g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.646
• CAS DataBase Reference: chanoclavine(CAS DataBase Reference)
• NIST Chemistry Reference: chanoclavine(2390-99-0)
• EPA Substance Registry System: chanoclavine(2390-99-0)

Safety Data

• Hazardous Substances Data: 2390-99-0(Hazardous Substances Data)

Usage

Description

Chanoclavine is a modified ergot alkaloid produced by fungus, known for its ability to stimulate dopamine receptors in the brain of rodents.

Uses

Used in Pharmaceutical Industry:
Chanoclavine is used as a pharmaceutical agent for its potential role in modulating dopamine receptors in the brain of rodents, which may have implications for the development of treatments for neurological disorders and conditions related to dopamine dysregulation.

InChI:InChI=1/C16H20N2O/c1-10(9-19)6-13-12-4-3-5-14-16(12)11(8-18-14)7-15(13)17-2/h3-6,8,13,15,17-19H,7,9H2,1-2H3/b10-6-/t13-,15-/m1/s1

Upstream product

• 16136-52-0 4-cyanoindole 
• 74059-91-9 3-(N,N-dimethylaminomethyl)-4-indolecarbaldehyde 
• 68156-97-8 (+/-)-5-epi-6,7-secoagroclavine 
• 76084-18-9 t-butyl cis-N(5-formyl-1,3,4,5-tetrahydrobenzindol-4-yl)N-methylcarbamate 
• 194346-18-4 (E)-2-Methyl-3-((4R,5R)-4-nitro-1,3,4,5-tetrahydro-benzo[cd]indol-5-yl)-prop-2-en-1-ol 
• 51743-69-2 (E)-3-((4R,5R)-4-Amino-1,3,4,5-tetrahydro-benzo[cd]indol-5-yl)-2-methyl-prop-2-en-1-ol 
• 111614-01-8 (-)-4,5-trans-5-(2-methyl-1-propen-1-yl)-4-nitro-1,3,4,5-tetrahydrobenzindole 
• 194346-28-6 [(4R,5R)-5-((E)-3-Hydroxy-2-methyl-propenyl)-1,3,4,5-tetrahydro-benzo[cd]indol-4-yl]-carbamic acid methyl ester 
• 109174-90-5 (E)-3-(4-indolyl)propenyl acetate 
• 76084-20-3 (E)-methyl 3-(1H-indol-4-yl)acrylate 
• 122045-23-2 (4R,5R)-4-nitro-5-vinyl-1,3,4,5-tetrahydrobenzindole 
• 1074-86-8 4-formyl indole 
• 158233-47-7 methyl-(E)-3<(4R,5R)-1-tert-butoxycarbonyl-4-(N-tert-butoxycarbonylamino)-1,3,4,5-tetrahydrobenzindol-5-yl>-2-methylpropenoate 
• 107343-13-5 4,5-cis-5-(2-methyl-1-propen-1-yl)-4-amino-1,3,4,5-tetrahydrobenz[cd]indole 

Downstream Products

• 478-89-7 Pyroclavin 
• 569-26-6 festuclavine 
• 548-42-5 (+/-)-Agroclavine 
• 95586-10-0 (+/-)-Agroclavine I 
• 77784-57-7 Acetic acid (E)-3-[(4S,5S)-4-(benzyloxycarbonyl-methyl-amino)-1,3,4,5-tetrahydro-benzo[cd]indol-5-yl]-2-methyl-allyl ester 
• 77784-56-6 Acetic acid 2-[(4S,5S)-4-(benzyloxycarbonyl-methyl-amino)-1,3,4,5-tetrahydro-benzo[cd]indol-5-ylmethyl]-allyl ester 

Relevant articles and documents

Catalase Involved in Oxidative Cyclization of the Tetracyclic Ergoline of Fungal Ergot Alkaloids

A dedicated enzyme for the formation of the central C ring in the tetracyclic ergoline of clinically important ergot alkaloids has never been found. Herein, we report a dual role catalase (EasC), unexpectedly using O2 as the oxidant, that catalyzes the oxidative cyclization of the central C ring from a 1,3-diene intermediate. Our study showcases how nature evolves the common catalase for enantioselective C-C bond construction of complex polycyclic scaffolds.

Total Synthesis of (-)-Chanoclavine i and an Oxygen-Substituted Ergoline Derivative

An efficient and direct route to ergot alkaloid (-)-chanoclavine I (3) is described using the inexpensive compound (2R)-(+)-phenyloxirane (15) as a chiral pool in 13 steps with 17% overall yield. Key features of the synthesis include a palladium-catalyzed intramolecular aminoalkynylation of terminal olefin and a rhodium-catalyzed intramolecular [3 + 2] annulation. An oxygen-substituted ergoline derivative (-)-25 was also achieved by using the same strategy.

Simple total syntheses of (-)-ergot alkaloids and their (+)-enantiomers by a common synthesis method utilizing optical resolution

The first and simple total syntheses of (-)-isochanoclavine-1 ((-)-1b), (-)-agroclavine ((-)-3), (-)-agroclavine-1 ((-)-4), and (-)-norchanoclavine-1 ((-)-5c) and their (+)-enantiomers are achieved from indole-3-carboxaldehyde (8) by a common synthesis method utilizing optical resolution. Absolute configuration of (-)-agroclavine-1 is determined to be 5R and 10S for the first time. Preparations of both enantiomers of chanoclavine-1 (1c) are also included.