38542-83-5

Usage

Uses

Used in Pharmaceutical Industry:
(2α,5β,6α,18β)-Ibogamine-18-carboxylic acid methyl ester is used as a potential therapeutic agent for treating addiction and substance abuse due to its anti-addictive properties. It is being studied for its ability to modulate the central nervous system and its potential to alleviate withdrawal symptoms and cravings associated with addiction.
Used in Neuroprotective Applications:
In the field of neuroprotection, (2α,5β,6α,18β)-Ibogamine-18-carboxylic acid methyl ester is utilized for its neuroprotective properties, which may help in the treatment of neurodegenerative diseases and conditions affecting the central nervous system. Its potential to protect neurons and promote neuronal health is currently under investigation.
Used in Anti-inflammatory Applications:
(2α,5β,6α,18β)-Ibogamine-18-carboxylic acid methyl ester is also used as an anti-inflammatory agent, which can be beneficial in managing inflammation-related conditions and diseases. Its anti-inflammatory properties may contribute to reducing inflammation and alleviating symptoms associated with various inflammatory disorders.
Further research is required to explore additional applications and to fully understand the therapeutic potential and mechanisms of action of (2α,5β,6α,18β)-Ibogamine-18-carboxylic acid methyl ester in various industries.

Upstream product

• 139133-21-4 4-(1,3-dioxolan-2-yl)-1-hexanol 
• 77794-83-3 Δ⁵-catharanthine 
• 2468-21-5 catharinthine 
• 124096-76-0 (+)-(9R)-3-oxo-9-methoxycarbonylindolizino<8,7-b>indole 
• 139133-11-2 methyl (3aRS,4SR)-3-benzyl-2,3,3a,4,5,7-hexahydro-4-<2-ξ-(1,3-dioxolan-2-yl)-1-butyl>-1H-pyrrolo<2,3-d>carbazole-6-carboxylate 
• 139133-13-4 4-(1,3-dioxolan-2-yl)hexanal 
• 136851-17-7 methyl 4-(1,3-dioxolan-2-yl)hexanoate 
• 66757-48-0 methyl 4-formylhexanoate 
• 74627-73-9 3-(R/S)-ethoxycoronaridine 
• 56867-69-7 19-hydroxycoronaridine 
• 139133-15-6 methyl 3-benzyl-1,2,3,4,5,6,7,8-octahydro-5β-<2-ξ-(1,3-dioxolan-2-yl)-1-butyl>azonino<6,7-b>indole-7α-carboxylate 
• 139133-15-6 methyl 3-benzyl-1,2,3,4,5,6,7,8-octahydro-5β-<2-ξ-(1,3-dioxolan-2-yl)-1-butyl>azonino<6,7-b>indole-7β-carboxylate 
• 139133-14-5 11α/β-<4-ξ-(1,3-dioxolan-2-yl)-1-hexyl>-1,2,4,6-tetrahydro-3,10b-methanoazepino<4,5-b>indole-5-carboxylate 
• 139133-23-6 methyl 1,2,3,4,5,6,7,8-octahydro-5β-<2-ξ-(1,3-dioxolan-2-yl)-1-butyl>azonino<6,7-b>indole-7α-carboxylate 

Downstream Products

• 481-87-8 4-Epiibogamin 
• 39967-46-9 3-oxocoronaridine 
• 56867-69-7 19-hydroxycoronaridine 
• 3327-43-3 16S,20S-Carbomethoxydihydrocleavamin 
• 3327-43-3 18β-Carbomethoxy-14α-dihydrocleavamin 
• 28888-46-2 (+)-coronaridine hydrochloride 

Relevant academic research and scientific papers

Biopatterned Reorganization of Alkaloids Enabled by Ring-Opening Functionalization of Tertiary Amines

Biosynthetic processes often involve reorganization of one family of natural products to another. Chemical emulation of nature's rearrangement-based structural diversification strategy would enable the conversion of readily available natural products to other value-added secondary metabolites. However, the development of a chemical method that can be universally applied to structurally diverse natural products is nontrivial. Key to the successful reorganization of complex molecules is a versatile and mild bond-cleaving method that correctly places desired functionality, facilitating the target synthesis. Here, we report a ring-opening functionalization of a tertiary amine that can introduce desired functionalities in the context of alkaloids reorganization. The semistability of the difluoromethylated ammonium salt, accessed by the reaction of tertiary amine and in situ generated difluorocarbene, enabled the attack at the α-position by various external nucleophiles. The utility and generality of the method is highlighted by its applications in the transformation of securinega, iboga, and sarpagine alkaloids to neosecurinega, chippiine/dippinine, and vobasine-type bisindole alkaloids, respectively. During the course of these biosynthetically inspired reorganizations, we could explore chemical reactivities of biogenetically relevant precursors.

Synthetic noribogaine

Synthetic noribogaine preferably free of ibogaine and, optionally, one or more of other naturally occurring Tabernanth iboga alkaloids, is provided.

Enantioselective synthesis of: Iboga alkaloids and vinblastine via rearrangements of quaternary ammoniums

An efficient and novel strategy for the enantioselective syntheses of various iboga alkaloids has been developed. The salient features include a gold-catalyzed oxidation of a terminal alkyne followed by cyclization, a Stevens rearrangement and a tandem sequence that combines the gold-catalyzed oxidation, cyclization and [1,2]-shift. The catharanthine analogs provided by our approach were further converted to the vinca alkaloid vinblastine and its analogs, which confirmed the remarkable sensitivity of the cytotoxicity to the C20′ substituent of vinblastine.

Synthesis of (-)-pseudotabersonine, (-)-pseudovincadifformine, and (+)-coronaridine enabled by photoredox catalysis in flow

Natural product modification with photoredox catalysis allows for mild, chemoselective access to a wide array of related structures in complex areas of chemical space, providing the possibility for novel structural motifs as well as useful quantities of less abundant congeners. While amine additives have been used extensively as stoichiometric electron donors for photocatalysis, the controlled modification of amine substrates through single-electron oxidation is ideal for the synthesis and modification of alkaloids. Here, we report the conversion of the amine (+)-catharanthine into the natural products (-)-pseudotabersonine, (-)-pseudovincadifformine, and (+)-coronaridine utilizing visible light photoredox catalysis.

COMPOSES ANTITUMORAUX DU GROUPE DE LA VINBLASTINE: NOUVELLE METHODE DE PREPARATION

7'-Chloro-indolenines from several dimeric alkaloids of vinblastine type are useful intermediates in the preparation of antitumor derivatives belonging to seco-5',6' and nor-5'series.

19-ETHOXYCORONARIDINE, A NOVEL ALKALOID FROM TABERNAEMONTANA GLANDULOSA

Key Word Index - Tabernaemontana glandulosa; Apocynaceae; ibogamine alkaloids; 19-ethoxycoronaridine.