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Processes and compositions for the preparation of noribogaine from voacangine

A technology of voacangine and covalent binding, applied in organic chemistry and other directions, can solve the problem of incorrect chemical formula of ibogaine

Active Publication Date: 2016-03-30
DEMERX
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

US Patent No. 2,813,873 provides an incorrect chemical formula for noribogaine despite asserting that it is "12-O-desmethylibogaine"

Method used

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  • Processes and compositions for the preparation of noribogaine from voacangine
  • Processes and compositions for the preparation of noribogaine from voacangine
  • Processes and compositions for the preparation of noribogaine from voacangine

Examples

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preparation example Construction

[0061] Preparation and Purification of Noribogaine

[0062] Voacangine (methyl 12-methoxyibogamine-18-carboxylate) is an alkaloid found mainly in the root bark of the African Voacanga africana tree and in other plants such as ibogamia, African horseshoe Found in Tabernaemontana africana, Trachelospermum jasminoides and Ervatamia yunnanensis. Voacangine has previously been used as a semi-synthetic precursor for ibogaine (see US Patent No. 2,813,873).

[0063] This application covers a process for the preparation of noribogaine from voacangine without providing ibogaine as an intermediate. The method described is useful for a number of reasons. First, known methods for the preparation of noribogaine involve demethylation of ibogaine as a final step. This is unlikely to provide pure noribogaine, and since ibogaine is a Class 1 controlled substance and is known to induce severe hallucinations, ibogaine contamination is not expected. Second, ibogaine is isolated from the root of...

example

[0092] In the following examples, the following abbreviations have the following meanings. Where an abbreviation is not defined, it has its broadly accepted meaning.

example 1

[0093] Example 1 - Synthesis of Noribogaine from Voacangine

[0094] Example 1 illustrates a method for the synthesis and purification of noribogaine from voacangine, which follows Scheme 5 below.

[0095] Option 5

[0096]

[0097] Voacangine 1 can be taken up in dichloromethane / ethylene glycol solution and cooled to 0°C to -10°C (ice-salt bath). An excess (1-3 molar equivalents) of the appropriate Lewis acid (boron trichloride, boron tribromide or aluminum trichloride) is added in portions. The resulting mixture was stirred at 25°C to 50°C for 2 hours to 24 hours until sufficiently complete by TLC. The reaction mixture can then be diluted with fresh dichloromethane and washed with saturated NaHCO 3 The solution was washed, dried and evaporated under reduced pressure to provide the corresponding methyl 12-hydroxyibogamine-18-carboxylate 2, which could then be purified by silica gel column chromatography using a gradient of hexane and ethyl acetate or without Purificati...

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Abstract

Disclosed are methods and compositions for preparing and purifying the non-addictive alkaloid noribogaine.

Description

technical field [0001] The present invention generally relates to methods and compositions for the preparation and purification of the non-addictive alkaloid noribogaine. Background technique [0002] Noribogaine is a well-known member of the ibogaine alkaloid family and is sometimes referred to as 12-hydroxyibogaine. US Patent No. 2,813,873, although claiming that noribogaine is "12-O-desmethyl ibogaine", provides an incorrect chemical formula for ibogaine. The structure of noribogaine has now been thoroughly evaluated and found to combine features of tryptamine, tetrahydrohavaine and indolezapine. Noribogaine can be described by the following formula: [0003] [0004] Recently, noribogaine and its pharmaceutically acceptable salts have been accepted as non-addictive alkaloids for the treatment of drug dependence (US Pat. No. 6,348,456) and as potent analgesics (US Pat. No. 7,220,737). to obvious attention. [0005] Conventionally, noribogaine is prepared by demethy...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/22
Inventor 德博拉·C·马什理查德·D·格莱斯罗伯特·M·莫里亚蒂
Owner DEMERX
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