38542-83-5

Basic information

• Product Name: (2α,5β,6α,18β)-Ibogamine-18-carboxylic acid methyl ester
• Synonyms: (2α,5β,6α,18β)-Ibogamine-18-carboxylic acid methyl ester
• CAS NO: 38542-83-5
• Molecular Formula: C₂₁H₂₆N₂O₂
• Molecular Weight: 338.448
• Mol File: 38542-83-5.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2α,5β,6α,18β)-Ibogamine-18-carboxylic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2α,5β,6α,18β)-Ibogamine-18-carboxylic acid methyl ester(38542-83-5)
• EPA Substance Registry System: (2α,5β,6α,18β)-Ibogamine-18-carboxylic acid methyl ester(38542-83-5)

Safety Data

• Hazardous Substances Data: 38542-83-5(Hazardous Substances Data)

Usage

Description

(2α,5β,6α,18β)-Ibogamine-18-carboxylic acid methyl ester is a chemical compound belonging to the iboga alkaloids class. It is a methyl ester derivative of ibogamine-18-carboxylic acid, sourced from the plant Tabernanthe iboga. (2α,5β,6α,18β)-Ibogamine-18-carboxylic acid methyl ester has demonstrated various pharmacological activities, such as anti-addictive, anti-inflammatory, and neuroprotective properties, and is being studied for its potential in treating addiction and substance abuse, as well as its effects on the central nervous system. Further research is necessary to fully understand its therapeutic potential and mechanisms of action.

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

• 139133-16-7 16-(methoxycarbonyl)-Δ²⁰-cleavamine 
• 66757-48-0 methyl 4-formylhexanoate 
• 139133-21-4 4-(1,3-dioxolan-2-yl)-1-hexanol 
• 139133-13-4 4-(1,3-dioxolan-2-yl)hexanal 
• 136851-17-7 methyl 4-(1,3-dioxolan-2-yl)hexanoate 
• 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 
• 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 
• 139133-11-2 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 
• 139133-15-6 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 
• 139133-15-6 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 
• 56867-69-7 19-hydroxycoronaridine 
• 74627-73-9 3-(R/S)-ethoxycoronaridine 
• 77794-83-3 Δ⁵-catharanthine 
• 2468-21-5 catharinthine 

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 articles and documents

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.

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.

A common intermediate providing syntheses of ψ-tabersonine, coronaridine, iboxyphylline, ibophyllidine, vinamidine, and vinblastine

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