USRE49434E1 - Process for producing an extract containing tetrahydrocannabinol and cannabidiol from cannabis plant material, and cannabis extracts - Google Patents

Process for producing an extract containing tetrahydrocannabinol and cannabidiol from cannabis plant material, and cannabis extracts Download PDF

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USRE49434E1
USRE49434E1 US17/219,170 US200117219170A USRE49434E US RE49434 E1 USRE49434 E1 US RE49434E1 US 200117219170 A US200117219170 A US 200117219170A US RE49434 E USRE49434 E US RE49434E
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cannabidiol
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Adam Mueller
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Canopy Growth Corp
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/78—Ring systems having three or more relevant rings
    • C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/26—Psychostimulants, e.g. nicotine, cocaine
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids

Definitions

  • the present invention relates to a process for producing an extract containing tetra-hydrocannabinol, cannabidiol, and optionally the carboxylic acids thereof from cannabis plant material in accordance with the preamble of claim 1 , a primary extract from cannabis plant material in accordance with claim 8 , and a process for producing tetrahydrocannabinol in accordance with claim 13 and a process for producing cannabidiol in accordance with claim 14 .
  • hops for the botanical and chemotaxonomical differentiation of the genus Cannabis there are two different concepts. One differentiates between three species, Cannabis sativa Linnaeus, Cannabis indica LAM., and Cannabis ruderalis, while a different theory only sees the existence of the one collective species Cannabis sativa L. made up of the subspecies Cannabis sativa ssp. sativa and ssp. indica.
  • the cannabis plant is differentiated into a drug type and a fiber type, with differentiation being performed on the basis of the quantity ratio of the main cannabinoids, cannabidiol (CBD) and ⁇ 9 -tetrahydrocannabinol ( ⁇ 9 -THC).
  • CBD cannabidiol
  • ⁇ 9 -THC ⁇ 9 -tetrahydrocannabinol
  • the ratio of ⁇ 9 -THC to CBD in fiber hemp is mostly less than 1.5.
  • the varieties rich in ⁇ 9 -THC may reach a ratio of 2:1 to 7:1.
  • Cannabis sativa L. occurs worldwide in all warm and moderate zones with the exception of the humid tropical rain forests. It is an annual to biennial, anemogamous herb which may attain a height of up to 8 m.
  • the dioecous, rarely monoecious inflorescences contain the active cannabinoids in the resin which is mainly secreted by the numerous glandular bracts in the leaf axils.
  • all the plant parts of Cannabis sativa L. with the exception of the seeds may contain cannabinoids.
  • the highest cannabinoid concentrations are found in the floral bracts and fruit stalks.
  • the leaves have a low content of cannabinoids as a function of leaf age, while the stalk and particularly the root exhibit clearly lower cannabinoid contents.
  • the known cannabis preparations having a hallucinogenic effect, marijuana and hashish are subject to the regulations of the Narcotics Act as non-trafficable narcotics like opium, morphine, heroin, cocaine and LSD.
  • Cannabis sativa L. contains more than 420 different components, with 61 compounds of these belonging to the class of cannabinoids. These are lipophilic, nitrogen-free, mostly phenolic compounds.
  • the neutral cannabinoids are biogenetically derived from a monoterpene and a phenol, the acidic cannabinoids from a monoterpene and a phenolic acid, and present a C 21 parent substance.
  • two different numbering systems for cannabinoids are found. The older numbering system is based on the monoterpene skeleton, whereas the more recent IUPAC designation which is exclusively employed in the present application, relates to the dibenzopyrane skeleton.
  • the associated carboxylic acids thereof are moreover found in the raw drug as well as in the plant products.
  • the carboxylic acids have the function of a biosynthetic precursor.
  • the tetrahydrocannabinols ⁇ 9 - and ⁇ 8 -THC and CBD are generated in vivo from the THC carboxylic acids by decarboxylation from the associated cannabidiol carboxylic acids.
  • ⁇ 8 -THC may, for instance, also form upon cyclization of CBD. Another possibility is that ⁇ 8 -THC may be generated under certain conditions. for instance acidity, by double bond isomerism from ⁇ 9 -THC or its carboxylic acid, respectively.
  • tetrahydrocannabinol or “THC”—where not otherwise specified—is to encompass any isomers, in particular double bond isomers.
  • cannabis has been a traditional drug and a remedy.
  • cannabis was employed for the most variegated ailments—from asthma to migraine.
  • Restrictive legislation against cannabis on the part of the USA brought about its complete disappearance from the pharmacopoeia and from physicians' repertories of treatment.
  • DE 41 00 441 A1 discloses a process for producing 6,12-dihydro-6-hydroxy-cannabidiol and its use for producing trans- ⁇ 9 -tetrahydrocannabinol.
  • DE 41 00 441 A1 describes the manufacture of 6,12-dihydro-6-hydroxy-cannabidiol, which is obtained by reacting olivetol and cis-p-menth-2-ene-1,8-diol, and its further reaction to trans- ⁇ 9 -tetrahydrocannabinol by using suitable catalysts.
  • solvent extraction e.g. with the aid of ethanol, and steam distillation of cannabis constituents
  • a hashish oil also referred to as Oil, Red Oil or Indian Oil
  • Oil, Red Oil or Indian Oil is known, which is produced with the aid of solvent extraction or distillation from cannabis herb or cannabis resin and which is a dark brown, viscous and sticky oil.
  • the oil thus obtained is subsequently mostly diluted with edible oil for improved handling and contains up to 65% of the hallucinogenic agent ⁇ 9 -THC (Kleiber/Kovar: specialized des Cannabiskonsums: Neue Expertise zu pharmakêtellen and psycho book compact, Stuttgart: Wiss. Verl.-Ges. 1998).
  • Dronabinol, ⁇ 9 -THC has meanwhile been approved in the USA in accordance with USP [United States Pharmacopeia] 24, pp. 613, 614 as a medicament—also in capsule form—.
  • dronabinol contains no less than 95% of ⁇ 9 -THC and no more than 2% of ⁇ 8 -THC.
  • dronabinol may be prescribed as an anaesthetic in Germany.
  • WO 00/25127 A1 moreover relates to the extraction of hemp for the isolation of tetrahydrocannabinol from the natural cannabis plant. What is described in particular is an extraction process with an apolar organic solvent, followed by fractional distillation under reduced pressure in order to produce distillates having high tetrahydrocannabinol contents.
  • apolar solvents lower alkanes such as, e.g., hexane, heptane or isooctane are named in WO 00/25127 A1.
  • Such primary hexane extracts in accordance with WO 00/25127 A1 contain 28.76% (Example 2) up to a maximum of 41.2% (Example 3) of tetrahydrocannabinol.
  • WO 00/25127 A1 does not disclose any further constituents of the hexane primary extract.
  • a primary extract containing tetrahydrocannabinol, cannabidiol, and optionally the carboxylic acids thereof is obtained from cannabis plant material in that the dried plant material is comminuted, the plant material is extracted with the aid of CO 2 under super-critical pressure and temperature conditions at a temperature in the range of approx. 31° C. to 80° C. and at a pressure in the range of approx. 75 bar to 500 bar, or in the subcricital range at a temperature of approx. 20° C. to 30° C. and a supercritical pressure of approx. 100 bar to 350 bar; or extracted under subcricital pressure and temperature conditions; and the obtained primary extract is separated under subcricital conditions, or under conditions that are subcricital in terms of pressure and supercritical in terms of temperature.
  • the primary extract of the invention contains high proportions of cannabidiol carboxylic acid (CBDS), cannabidiol (CBD), and ⁇ 9 -tetra-hydrocannabinol carboxylic acid ( ⁇ 9 -THCS), and ⁇ 9 -THC (when drug hemp is used).
  • CBDDS cannabidiol carboxylic acid
  • CBD cannabidiol
  • ⁇ 9 -THCS ⁇ 9 -tetra-hydrocannabinol carboxylic acid
  • ⁇ 9 -THC when drug hemp is used
  • CO 2 extracts The production of CO 2 extracts is known in principle.
  • DE 198 00 330 A1 discloses the production of a pharmaceutically active extract from Tanacetum parthenium through CO 2 extraction with the aid of an extraction plant as used in the present invention.
  • Cannabis sativa L. in particular hemp of the fiber type, i.e. so-called industrial hemp, is used.
  • industrial hemp species of the fiber type may contain 0.3% of ⁇ 9 -THC at maximum in the Federal Republic of Germany; for Switzerland an upper limit of 0.5% ⁇ 9 -THC applies, based on the dry plant mass in either case.
  • the like industrial hemp varieties may be cultivated both in the Federal Republic of Germany and in Switzerland, for example, while requiring neither any complicated cultivating permission nor any complicated safety installations during storage.
  • cannabis plant material of the fiber type may be used for the production of primary extracts containing ⁇ 9 -THC and CBD, for it is possible to employ such starting material having a low ⁇ 9 -THC content for the inventive process without any further operating and handling permissions as are required in the case of drug hemp types.
  • the ⁇ 9 -THC content in the primary extract is higher than in one produced of fiber hemp.
  • the addition to the CO 2 of an entraining agent selected from the group consisting of: propane, butane, ethanol and water, has the advantage that hereby the yields for ⁇ 9 -THC and CBD may be increased without involving the drawbacks as with an extract produced, e.g., with ethanol or ethanol/water or methanol/chloroform or with other chlorinated hydrocarbons.
  • the entraining agent concentrations are in the range of 1-10% based on the employed quantity of CO 2 .
  • the extraction process of the invention preferably operates in the supercritical range at a temperature of approx. 31° C. to 80° C. and a pressure of approx. 75 bar to 500 bar, in particular at a temperature of approx. 45° C. to 65° C. and a pressure of approx. 100 bar to 350 bar, preferably at a temperature of approx. 60° C. and a pressure of approx. 250 bar.
  • a temperature of approx. 20° C. to 30° C. and a supercritical pressure of approx. 100 bar to 350 bar are used.
  • the measure of arranging a layer of adsorbent on the material to be extracted downstream relative to the CO 2 flow has the advantage that monoterpenes and sesquiterpenes as well as alkaloids, flavonoids and chlorophylls may be separated out, so that the inventive primary extracts are even the more superior to the ethanol extracts known in the prior art and to the extracts prepared with the aid of chlorinated hydrocarbons, for the latter in any case are fairly high in mono- and sesquiterpenes as well as chlorophylls, flavonoids and alkaloids.
  • the CO 2 laden with THC and CBD as well as with proportions of reduced mono- and sesquiterpenes, flavonoids, chlorophylls and alkaloids may also be passed over adsorbers charged with adsorbents or separators ( FIG. 1 ).
  • Preferred adsorbents are those selected from the group comprised of: silica gel, diatomaceous earth, bentonites, bleaching earth, activated carbons, in particular magnesium oxide and alumina, as well as mixtures thereof.
  • extraction it is preferred to repeat extraction at least once, with extraction preferably being repeated with diatomaceous earth and/or some other adsorbent.
  • the inventive primary extracts from Cannabis plant material containing ⁇ 9 -THC and cannabidiol are substantially free from monoterpenes and sesquiterpenes and moreover free from alkaloids and flavonoids, and contain practically no chlorophylls.
  • ⁇ 9 -THC is the main constituent of the primary extract, and CBD the second highest proportion.
  • hemp of the fiber type is used as a starting material, which is being preferred, CBD and in a given case the carboxylic acids thereof are found as the main constituents of the primary extract.
  • the primary extract of the invention contains at least reduced proportions of monoterpene and sesquiterpene hydrocarbons, alkaloids. flavonoids and chlorophylls, and is preferably already free from these components, in particular from alkaloids, flavonoids and chlorophylls.
  • the cannabidiol carboxylic acids and ⁇ 9 -tetrahydrocannabinol carboxylic acids contained in the primary extract are decarboxylated into cannabidiol and ⁇ 9 -tetrahydrocannabinol through increase in temperature.
  • the CBD may be reacted into ⁇ 9 -THC through catalyzed cyclization.
  • ⁇ 8 -THC may form depending on process conditions, which in itself also possesses interesting pharmacological properties.
  • ⁇ 8 -THC may, for example, be employed as an antiemetic in pediatric oncology.
  • the decarboxylated primary extract is mixed with a water-binding agent and a catalyst defined more closely hereinbelow.
  • the mixture is treated in a high-pressure extraction plant ( FIG. 2 ) with supercritical CO 2 , preferably at 300 bar and 70° C.
  • supercritical CO 2 preferably at 300 bar and 70° C.
  • the obtained extract is separated out under pressure and temperature conditions subcricital for CO 2 , preferably at approx. 55 bar and approx. 25° C.
  • zeolitic molecular sieves having a pore size of 3-10 ⁇ , preferably 5 ⁇ may be used, and useful catalysts are metal-containing halogen salts containing the metals tin, zinc, iron or titanium, preferably zinc chloride.
  • the secondary extract thus obtained only contains very little CBD and is highly enriched in ⁇ 8 -THC and ⁇ 9 -THC.
  • a treatment in a high-pressure apparatus with supercritical CO 2 is performed as described in the following ( FIG. 3 ).
  • a high-pressure column ( FIG. 3 ) subdivided into segments, comprising a bottom segment for dissolving the primary extract in supercritical CO 2 , a purification segment filled, e.g., with silica gel (mean particle size of 0.02 mm to 0.2 mm, preferably 0.1 mm), a head segment for discharging the mixture dissolved in supercritical CO 2 of CBD, ⁇ 8 -THC and ⁇ 9 -THC into three separating vessels for separate separation of the purified CBD and the purified ⁇ 8 -THC and ⁇ 9 -THC.
  • a high-pressure column FIG. 3 subdivided into segments, comprising a bottom segment for dissolving the primary extract in supercritical CO 2 , a purification segment filled, e.g., with silica gel (mean particle size of 0.02 mm to 0.2 mm, preferably 0.1 mm), a head segment for discharging the mixture dissolved in supercritical CO 2 of CBD, ⁇ 8 -THC
  • the extraction conditions prevailing for purification in the column are supercritical for CO 2 , preferably 180 bar and 55° C., in the first separating vessel where CBD is separated out for CO 2 subcricital conditions in terms of pressure and supercritical conditions in terms of temperature, preferably 70 bar and 50° C.
  • the second and third separating vessels where ⁇ 8 -THC and ⁇ 9 -THC are separated out, conditions subcricital for CO 2 in terms of pressure and temperature are to prevail, in the second separating vessel preferably 60 bar and 30° C., in the third separating vessel preferably 55 bar and 25° C.
  • fiber hemp it may possibly be necessary to further purify the tetrahydrocannabinol products ⁇ 8 -THC and ⁇ 9 -THC thus obtained with the aid of additional processes such as preparative chromatography or HPLC.
  • ⁇ 8 -THC is an isomer of ⁇ 9 -THC and forms substantially during the cyclization of CBD zu to ⁇ 9 -THC as well as in the presence of acids.
  • ⁇ 8 -THC, ⁇ 9 -THC and CBD thus obtained to be purified by further processes such as preparative chromatography or HPLC.
  • ⁇ 9 -THC may under the action of acids isomerize to ⁇ 8 -THC.
  • cannabidiol taken for itself has interesting pharmacological properties while furthermore lacking the psychotropic hallucinogenic effect of ⁇ 9 -THC, cannabidiol itself is also of interest for practical application because it may be used, e.g., as an anti-epileptic.
  • Cannabidiol may be obtained in accordance with the inventive process of claim 15 .
  • ⁇ 8 -THC by itself also has substantially lower psychotropic hallucinogenic effects than ⁇ 9 -THC and may be obtained in accordance with claim 14 .
  • FIG. 1 is a schematic representation of a CO 2 extraction plant for producing the primary extract of the invention
  • FIG. 2 is a schematic representation of a CO 2 extraction plant for producing a secondary extract highly enriched in ⁇ 8 -THC and ⁇ 9 -THC;
  • FIG. 3 is a schematic representation of a CO 2 extraction plant for separation of a primary and/or secondary extract in CBD, optionally ⁇ 8 -THC and ⁇ 9 -THC in a high-pressure column.
  • Ground Cannabis plant material comprised substantially of inflorescences and leaves is charged into extracting vessels 1 - 4 .
  • CO 2 having been brought to a temperature of approx. 60° C. and to a pressure of approx. 250 bar, enters into contact with the material to be extracted in the extracting vessels 1 - 4 and extracts the desired cannabinoid components, in particular comprising ⁇ 9 -tetrahydrocannabinol and cannabidiol as well as the carboxylic acids thereof.
  • a flow rate of 50-150 kg of CO 2 /kg of starting material is used for extraction.
  • an extract enriched in the cannabinoids leaves the vessel via conduit 6 a and arrives at the bottom of separating vessel 5 a.
  • the separating vessels 5 a and 5 b are in the exemplary case filled with various zeolitic molecular sieves and with diatomaceous earth as an adsorbent. In separating vessels 5 a and 5 b, the same pressure and temperature conditions prevail as in extracting vessels 1 - 4 .
  • the zeolitic molecular sieves placed in container 6 a have an internal surface of approx. 800 m 2 /g
  • the zeolitic molecular sieves placed in container 6 b have an internal surface of approx. 1200 m 2 /g.
  • the extract mixture consisting of CO 2 and essentially of ⁇ 9 -THC and cannabidiol as well as the carboxylic acids thereof, exits from separating vessel 10 via conduit 11 , pressure regulation valve 12 , heat exchanger 13 , and finally is conveyed into separating vessel 14 .
  • the separation pressure in container 14 is set to pressure conditions subcricital for CO 2 , in the exemplary case 50 bar.
  • the separation temperature in vessel 14 is controlled by heat exchanger 13 to a temperature subcricital for CO 2 , in the exemplary case about 20° C. Under these conditions the pure CO 2 is separated from the primary extract enriched in ⁇ 9 -THC and cannabidiol and the carboxylic acids thereof in separating vessel 14 .
  • the pure CO 2 is conveyed via conduit 15 to liqufier 17 that is equipped with a condenser coil 16 . From here the liquid CO 2 is supplied via pressurizing pump 18 to heat exchanger 19 , to be available for the following extraction cycle.
  • the CO 2 is either vented directly via conduit 21 , or supplied via conduit 20 to recycling plant 22 which then pumps the liquid CO 2 into the CO 2 storage vessel 23 .
  • FIG. 2 shows a schematic representation of a CO 2 extraction plant for producing a secondary extract highly enriched in ⁇ 8 -THC and ⁇ 9 -THC.
  • the primary extract in the exemplary case is treated during about 2 hours at 80° C.
  • a mixture of decarboxylated primary extract, water-binding agent and catalyst is introduced into the extracting vessel 200 .
  • CO 2 at a temperature of 70° C. and a pressure of 300 bar enters into contact with the material to be extracted and extracts the desired components.
  • the secondary extract highly enriched in ⁇ 8 -THC and ⁇ 9 -THC exits from vessel 200 at the top end of extracting vessel 200 via conduit 202 and arrives in separating vessel 205 via regulating valve 203 —wherein pressure is reduced to 60 bar or 55 bar, respectively—and heat exchanger 204 , the temperature being 30° C. or 25° C., respectively.
  • valve 206 the secondary extract thus obtained, which contains small amounts of CBD and is highly enriched in ⁇ 8 -THC and ⁇ 9 -THC, may be withdrawn from separating vessel 205 .
  • the pure CO 2 is conveyed via conduit 207 to liquefier 208 which is equipped with a condenser coil 209 . From there the liquid CO 2 is supplied via pressurizing pump 210 to heat exchanger 211 , to be available for the following extraction cycle.
  • FIG. 3 shows a schematic representation of a CO 2 extraction plant for separation of a primary and/or secondary extract CBD, optionally ⁇ 8 -THC and ⁇ 9 -THC, in a high-pressure column.
  • the extract mixture dissolved in CO 2 arrives via duct 302 , regulating valve 303 and heat exchanger 304 in separating vessel 305 , where preferably a pressure of 70 bar and a temperature of 50° C. are to prevail. It is here that the CBD is obtained.
  • the extraction mixture arrives in the second separating vessel 310 , preferably with a pressure of 60 bar and a temperature of 30° C. prevailing. It is here that the separation of ⁇ 8 -THC takes place. Via valve 311 the obtained ⁇ 8 -THC may be withdrawn.
  • ⁇ 9 -THC still dissolved in CO 2 is transferred into separating vessel 315 via duct 312 , regulating valve 313 and heat exchanger 314 . There it is separated out under a pressure of preferably 55 bar and a temperature of preferably 25° C. Via valve 316 the obtained ⁇ 9 -THC may be withdrawn.
  • the pure CO 2 is conveyed via conduit 317 to liquefier 318 which is equipped with a condenser coil 319 . From here the liquid CO 2 is supplied via pressurizing pump 320 to heat exchanger 321 , to be available for the following extraction cycle.
  • the French Cannabis sativa variety Fedora 19 is employed as industrial hemp of the fiber type.
  • the raw drug has an average content of approx. 0.25% of ⁇ 9 -THC and 1.54% of CBD.
  • An industrial hemp having the following raw drug data: water content: 11.2% (wt.); ⁇ 9 -THC 0.25% (wt.); and CBD: 1.54% were extracted with hexane in accordance with WO00/25127.
  • 100 g of air-dried, pulverized industrial hemp was extracted for 24 hours in 4 l of hexane in accordance with the Soxhlet method. The solvent was removed under reduced pressure, and the obtained extract was analyzed with a view to the parameters indicated in Table 1.
  • chlorophyll may involve cross-reticulations which may prevent the active principles contained in the extract from being released.
  • the desired CBD content is in the inventive CO 2 extract higher by a factor 4 to 5, and the ⁇ 9 -THC content also by a factor >4, in comparison with the prior-art solvent extracts.
  • the primary extracts obtained with the aid of lipophilic solvents contain the alkaloids that are readily soluble in these solvents, such as, e.g., cannabisativin which is highly cytotoxic.
  • This alkaloid contamination may very well also still occur in an extract prepared in accordance with WO00/25127 from the primary extract described there, following additional purification and enrichment steps in accordance with WO00/25127 which extract is said to have a 98% content of ⁇ 9 -THC.
  • the ethanol extract contains about 200 times more toxic alkaloids, in particular the highly cytotoxic cannabisativin, and the hexane extract in accordance with WO00/25127 even about 350 times more than the CO 2 primary extract of the invention.
  • CO 2 extracts of the present invention are superior both to the hexane extracts in accordance with WO00/25127 and to the customary ethanol extracts, because of their high cannabinoid contents and the fact that they are largely free from alkaloids, flavonoid glycosides, mono- and sesquiterpenes.
  • THC and cannabinoids may at all be enriched in technically useful amounts from readily available industrial hemp by means of CO 2 extraction.
  • Table 2 shows the components of a secondary extract after completed anellation.
  • Table 3 shows the components of a primary extract purified by high-pressure column in accordance with FIG. 3 .
  • Table 4 shows the components of a secondary extract which was purified in a high-pressure column.
  • the above mentioned primary extract is treated further in accordance with the description in FIG. 2 and FIG. 3 and is suited as an active principle for the production of a medicament for the indications described at the outset.
  • Suitable application types are inhalation, oral, parenteral, as well as enteral application.

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DE10051427.8 2000-10-17
DE10051427A DE10051427C1 (de) 2000-10-17 2000-10-17 Verfahren zur Herstellung eines Tetrahydrocannabinol- und Cannabidiol-haltigen Extraktes aus Cannabis-Pflanzenmaterial sowie Cannabis-Extrakte
US17/219,170 USRE49434E1 (en) 2000-10-17 2001-10-16 Process for producing an extract containing tetrahydrocannabinol and cannabidiol from cannabis plant material, and cannabis extracts
US10/399,362 US8895078B2 (en) 2000-10-17 2001-10-16 Method for producing an extract from cannabis plant matter, containing a tetrahydrocannabinol and a cannabidiol and cannabis extracts
PCT/EP2001/011967 WO2002032420A1 (de) 2000-10-17 2001-10-16 Verfahren zur herstellung eines tetrahydrocannabinol- und cannabidiol-haltigen extraktes aus cannabis-pflanzenmaterial sowie cannabis-extrakte

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