Method of preparing delta-9-tetrahydrocannabinol esters

A technology of pyridine and compound, which is applied in the field of preparation of δ-9-tetrahydrocannabinol ester, can solve the problems of lack of efficacy and high price of soft gelatin capsule preparations, etc.

Inactive Publication Date: 2002-01-16
UNIVERSITY OF MISSISSIPPI
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  • Summary
  • Abstract
  • Description
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Problems solved by technology

A major point made by medical cannabis proponents is the fact that current...

Method used

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Experimental program
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Effect test

Embodiment 1

[0012] To 1 gram of pure THC (about 95% pure) was added 1 g of succinic anhydride and 30 ml of pyridine and the reaction mixture was refluxed for 24 hours. The reaction mixture was poured into 100ml of ice water and extracted with diethyl ether (30ml×3), the diethyl ether extracts were combined, dried with anhydrous sodium sulfate and evaporated to dryness [TLC test using silica gel plates, developing solvent: hexane-diethyl ether (80 : 20), developer: fast blue solution, showing that its conversion rate is 30-40%]. The residue was mixed with 5 g of silica gel and 5 ml of ether, and the dried slurry was transferred to the top of a silica gel column (40 g of silica gel, size: 3×50 cm), and eluted with a mixture of hexane-ether in increasing polarity, mixed with hexane Alkane-diethyl ether (9:1) and diethyl ether were eluted and evaporated to give 0.442 g THC-HS (yield 33%).

Embodiment 2

[0014] To 1 g of THC (purity 95%) were added 0.5 g of anhydrous sodium carbonate, 1 g of succinic anhydride and 20 ml of dry benzene and the reaction mixture was refluxed for 24 hours. The reaction mixture was filtered and the filtrate was evaporated to dryness. Analysis by HPLC (C18 column, used methanol:water:acetic acid=80:20:0.01) showed that the THC-HS content of the residue was 17-20%.

Embodiment 3

[0016] To 1 g of THC (purity 95%) were added 0.5 g of succinic anhydride, 0.35 g of 4-pyrrolidinyl pyridine and 20 ml of benzene and the reaction mixture was kept at room temperature for 3 hours. TLC screen (Screening) showed that the content of THC-HS formed was about 20-30%, and the reaction mixture was allowed to stand overnight for about 24 hours before doing TLC test (the content of THC-HS was about 30-50%). Then the reaction mixture was refluxed for 4 hours (the content of THC-HS was 75.6%, HPLC analysis), after adding 0.30g 4-pyrrolidine pyridine, the reaction mixture was refluxed for 20 hours again, and the HPLC analysis showed that the content of THC-HS did not increase (about 75%).

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Abstract

An improved method of preparing delta-9-tetrahydrocannabinal esters involving use of a 4-amino-substituted pyridine.

Description

Background of the invention [0001] Delta-9-tetrahydrocannabinol (THC, also written as Dronabinol), the main bioactive component in the cannabis plant, has been shown by the U.S. Food and Drug Administration (FDA) to control nausea and vomiting associated with chemotherapy And can stimulate the appetite of AIDS patients suffering from wasting complications (recently). In addition, the drug exhibits other biological activities that may lead to its use in the treatment of, for example, glaucoma (1) ,Migraine (2、3) , spasm (4) ,anxiety (5) treatment and use as an analgesic (4) . It is these promising biological activities of THC that have drawn cannabis into public debate over its medicinal value. The balance between a drug's medical use and its potential for abuse is delicate. One of the main points raised by medical cannabis proponents is the fact that currently available softgel formulations are expensive and lack consistency in efficacy. The latter point above can be e...

Claims

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Application Information

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IPC IPC(8): A61K31/35C07D311/80
CPCC07D311/80
Inventor M·A·埃尔索利S·A·罗斯S·冯
Owner UNIVERSITY OF MISSISSIPPI
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