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

Abstract

The invention relates to a method for producing an extract from cannabis plant matter, containing tetrahydrocannabinol, cannabidiol and optionally the carboxylic acids thereof. According to said method, the dried plant matter is ground and subjected to a CO.sub.2 extraction and the primary extract obtained is separated. The invention method permits Δ.sup.8 or Δ.sup.9 tetrahydrocannabinol to be selectively obtained both from industrial hemp and from drug-producing hemp, optionally after dissolving the primary extract in ethanol, separating undesirable waxes and removing the solvent under reduced pressure.

Claims

.[.1. A process for producing cannabidiol from a primary extract from industrial hemp plant material containing tetrahydrocannabinol and cannabidiol and optionally the carboxylic acids thereof, wherein said primary extract is obtained by a process comprising extracting dried comminuted industrial hemp plant material by means of CO.sub.2 (a) under supercritical pressure and temperature conditions at a temperature in a range of approx. 31° C. to 80° C. and at a pressure in a range of approx 75 bar or 500 bar, or (b) in liquefied form in the subcritical range at a temperature of approx. 20° C. to 30° C. and a supercritical pressure of approx. 100 bar to 350 bar; or (c) in liquefied form under subcritical pressure and temperature conditions; and separating the obtained primary extract out under subcritical conditions or under conditions subcritical in terms of pressure and supercritical in terms of temperature; and wherein said primary extract contains reduced proportions of at least monoterpene and sesquiterpene hydrocarbons, alkaloids, flavonoids and chlorophylls; and wherein process for producing cannabidiol from a primary extract comprises decarboxylating cannabidiolic acid and tetrahydrocannabidiolic acid in said primary extract into cannabidiol and tetrahydrocannabinol through increase in temperature; and dissolving the decarboxylated primary extract in the CO.sub.2 extracting agent used, and in this condition treating by means of a high-pressure vessel charged with a catalyst for anellation of cannabidiol into tetrahydrocannabinol and a water-binding agent, wherein cannabidiol is reacted to give tetrahydrocannabinol; and separating the product enriched in tetrahydrocannabinol at pressure and temperature conditions subcritical for CO.sub.2..].

.[.2. A process for producing cannabidiol from a primary extract from industrial hemp plant material containing tetrahydrocannabinol and cannabidiol and optionally the carboxylic acids thereof, wherein said primary extract is obtained by a process comprising extracting dried comminuted industrial hemp plant material by means of CO.sub.2 (a) under supercritical pressure and temperature conditions at a temperature in a range of approx. 31° C. to 80° C. and at a pressure in a range of approx. 75 bar or 500 bar, or (b) in the subcritical range at a temperature of approx. 20° C. to 30° C. and a supercritical pressure of approx. 100 bar to 350 bar; or (c) under subcritical pressure and temperature conditions; and separating the obtained primary extract out under subcritical conditions or under conditions subcritical in terms of pressure and supercritical in terms of temperature; and wherein said primary extract contains reduced proportions of at least monoterpene and sesquiterpene hydrocarbons, alkaloids, flavonoids and chlorophylls; and wherein process for producing cannabidiol from a primary extract comprises decarboxylating cannabidiolic acid and tetrahydrocannabidiolic acid in said primary extract into cannabidiol and tetrahydrocannabinol through increase in temperature; and subsequently separating the cannabidiol through column chromatography on silica gel or preparative high-pressure liquid chromatography..].

3. A process for producing an extract containing tetrahydrocannabinol, cannabidiol and optionally the carboxylic acids thereof from dried comminuted industrial hemp plant material, comprising (1) subjecting said plant material to a stream of CO.sub.2 .Iadd.in liquefied form in the subcritical range at a temperature of approx. 20° C. to 30° C. and a supercritical pressure of approx. 100 bar to 350 bar, to form an extract-loaded CO.sub.2;.Iaddend. .[.(1a) under supercritical pressure and temperature conditions at a temperature in a range of approx. 31° C. to 80° C. and at a pressure in a range of approx. 75 bar or 500 bar, or (1b) in liquefied form in the subcritical range at a temperature of approx. 20° C. to 30° C. and a supercritical pressure of approx. 100 bar to 350 bar; or (1c) in liquefied found under subcritical pressure and temperature conditions; to extract cannabinoid components;.]. (2) reducing the pressure and/or temperature of the .[.extract loaded.]. .Iadd.extract-loaded .Iaddend.CO.sub.2 in at least two steps, wherein (2a) in a first step pressure and/or temperature are reduced whereby monoterpenes and sesquiterpenes are separated from tetrahydrocannabinol and cannabidiol by differential solubility, .Iadd.and .Iaddend. (2b) in a subsequent step pressure is reduced to a pressure subcritical for CO.sub.2, whereby tetrahydrocannabinol and cannabidiol are separated from said CO.sub.2, .Iadd.and .Iaddend. .[.(2c).]. .Iadd.(3) .Iaddend.subjecting the CO.sub.2 extracted from step (2b) to increased pressure and temperature and recycling said CO.sub.2 to step (1).

.[.4. The process of claim 3, wherein step (2) further comprises exposure to adsorbent or absorbent to remove alkaloids, flavinoids, and chlorophylls..].

.Iadd.5. A process for producing an extract containing tetrahydrocannabinol, cannabidiol and optionally the carboxylic acids thereof from dried comminuted industrial hemp plant material, comprising: (1) subjecting the dried comminuted industrial hemp to a stream of CO.sub.2 under a supercritical pressure and temperature condition, wherein the CO.sub.2 has a temperature of approximately 31° C. to 80° C. and a pressure of approximately 75 bar to 500 bar to form an extract-loaded CO.sub.2; (2) reducing the pressure of the extract-loaded CO.sub.2 in at least two steps, comprising: (2a) first reducing the pressure to separate monoterpenes and sesquiterpenes from tetrahydrocannabinol and cannabidiol by differential solubility, and (2b) subsequently reducing the pressure within the subcritical range for CO.sub.2 to remove a remaining extract from the CO.sub.2 to produce a substantially extract-free CO.sub.2; and (3) subjecting the extract-free CO.sub.2 from step (2) to increased pressure and temperature and recycling said CO.sub.2 to step (1)..Iaddend.

.Iadd.6. The process of claim 5, wherein the CO.sub.2 in step (1) has a temperature of approximately 45° C. to 65° C. and a pressure of approximately 100 bar to 350 bar..Iaddend.

.Iadd.7. The process of claim 5, further comprising: dissolving a first extract created during step (2) in a cold solution comprising a solvent to precipitate waxes; separating the precipitated waxes by filtration; and removing the solvent from the solution to form a second extract..Iaddend.

.Iadd.8. The process of claim 7, wherein the solvent is ethanol..Iaddend.

.Iadd.9. The process according to claim 5, further comprising a step of decarboxylating the carboxylic acids of tetrahydrocannabinol and cannabidiol..Iaddend.

.Iadd.10. The process according to claim 5, wherein an entraining agent is added to the stream of CO.sub.2..Iaddend.

.Iadd.11. The process according to claim 10, wherein the entraining agent is propane, butane, ethanol or water. .Iaddend.

.Iadd.12. A process for producing an extract containing tetrahydrocannabinol, cannabidiol and optionally the carboxylic acids thereof from dried comminuted industrial hemp plant material, comprising: (1) subjecting the dried comminuted industrial hemp to a stream of CO.sub.2 in a liquified form under a supercritical pressure and subcritical temperature condition, wherein the CO.sub.2 has a temperature of approximately 20° C. to 30° C. and a pressure of approximately 100 bar to 350 bar to form an extract-loaded CO.sub.2; (2) reducing the pressure of the extract-loaded CO.sub.2 in at least two steps, comprising: (2a) first reducing the pressure to separate monoterpenes and sesquiterpenes from tetrahydrocannabinol and cannabidiol by differential solubility, and (2b) subsequently reducing the pressure within the subcritical range for CO.sub.2 to remove a remaining extract from the CO.sub.2 to produce a substantially extract-free CO.sub.2; and (3) subjecting the extract-free CO.sub.2 from step (2) to increased pressure and temperature and recycling said CO.sub.2 to step (1)..Iaddend.

.Iadd.13. The process of claim 12, further comprising: dissolving a first extract created during step (2) in a cold solution comprising a solvent to precipitate waxes; separating the precipitated waxes by filtration; and removing the solvent from the solution to form a second extract..Iaddend.

.Iadd.14. The process of claim 13, wherein the solvent is ethanol..Iaddend.

.Iadd.15. The process according to claim 12, further comprising a step of decarboxylating the carboxylic acids of tetrahydrocannabinol and cannabidiol..Iaddend.

.Iadd.16. The process according to claim 12, wherein an entraining agent is added to the stream of CO.sub.2..Iaddend.

.Iadd.17. The process according to claim 16, wherein the entraining agent is propane, butane, ethanol or water..Iaddend.

.Iadd.18. A process for producing an extract containing tetrahydrocannabinol, cannabidiol and optionally the carboxylic acids thereof from dried comminuted industrial hemp plant material, comprising: (1) subjecting the dried comminuted industrial hemp to a stream of CO.sub.2 in a liquefied form under a subcritical pressure and temperature condition to form an extract-loaded CO.sub.2; (2) reducing the pressure of the extract-loaded CO.sub.2 in at least two steps, comprising: (2a) first reducing the pressure to separate monoterpenes and sesquiterpenes from tetrahydrocannabinol and cannabidiol by differential solubility, and (2b) subsequently reducing the pressure within the subcritical range for CO.sub.2 to remove a remaining extract from the CO.sub.2 to produce a substantially extract-free CO.sub.2; and (3) subjecting the extract-free CO.sub.2 from step (2) to increased pressure and temperature and recycling said CO.sub.2 to step (1)..Iaddend.

.Iadd.19. The process of claim 18, further comprising: dissolving a first extract created during step (2) in a cold solution comprising a solvent to precipitate waxes; separating the precipitated waxes by filtration; and removing the solvent from the solution to form a second extract..Iaddend.

.Iadd.20. The process of claim 19, wherein the solvent is ethanol..Iaddend.

.Iadd.21. The process according to claim 18, further comprising a step of decarboxylating the carboxylic acids of tetrahydrocannabinol and cannabidiol..Iaddend.

.Iadd.22. The process according to claim 18, wherein an entraining agent is added to the stream of CO.sub.2..Iaddend.

.Iadd.23. The process according to claim 22, wherein the entraining agent is propane, butane, ethanol or water..Iaddend.

.Iadd.24. A process for producing an extract containing tetrahydrocannabinol, cannabidiol and optionally the carboxylic acids thereof from dried comminuted industrial hemp plant material, comprising: (1) subjecting the dried comminuted industrial hemp to a stream of CO.sub.2 in a liquified form under a supercritical pressure and subcritical temperature condition, wherein the CO.sub.2 has a temperature of approximately 20° C. to 30° C. and a pressure of approximately 100 bar to 350 bar to form an extract-loaded CO.sub.2; (2) reducing the pressure and/or temperature of the extract-loaded CO.sub.2 in at least two steps, comprising: (2a) first reducing the pressure and/or temperature to separate monoterpenes and sesquiterpenes from tetrahydrocannabinol and cannabidiol by differential solubility, and (2b) subsequently reducing the pressure within the subcritical range for CO.sub.2 to remove a remaining extract from the CO.sub.2 to produce a substantially extract-free CO.sub.2; and (3) subjecting the extract-free CO.sub.2 from step (2) to increased pressure and temperature and recycling said CO.sub.2 to step (1)..Iaddend.

.Iadd.25. A process for producing an extract containing tetrahydrocannabinol, cannabidiol and optionally the carboxylic acids thereof from dried comminuted industrial hemp plant material, comprising: (1) subjecting the dried comminuted industrial hemp to a stream of CO.sub.2 in a liquified form under a supercritical pressure and subcritical temperature condition, wherein the CO.sub.2 has a temperature of approximately 20° C. to 30° C. and a pressure of approximately 100 bar to 350 bar to form an extract-loaded CO.sub.2; (2) reducing the pressure of the extract-loaded CO.sub.2 in at least two steps, comprising: (2a) first reducing the pressure to separate monoterpenes and sesquiterpenes from tetrahydrocannabinol and cannabidiol by differential solubility, and (2b) subsequently reducing the pressure within the subcritical range for CO.sub.2 to remove a remaining extract from the CO.sub.2 to produce a substantially extract-free CO.sub.2; (3) subjecting the extract-free CO.sub.2 from step (2) to increased pressure and temperature and recycling said CO.sub.2 to step (1); (4) dissolving a first extract created during step (2) in a cold solution comprising a solvent to precipitate waxes; (5) separating the precipitated waxes by filtration; and (6) removing the solvent from the solution to form a second extract; and wherein the process further comprising a step of decarboxylating the carboxylic acids of tetrahydrocannabinol and cannabidiol..Iaddend.

.Iadd.26. The process of claim 3, further comprising: dissolving a first extract created during step (2) in a cold solution comprising a solvent to precipitate waxes; separating the precipitated waxes by filtration; and removing the solvent from the solution to form a second extract..Iaddend.

.Iadd.27. The process of claim 26, wherein the solvent is ethanol..Iaddend.

.Iadd.28. The process according to claim 3, further comprising a step of decarboxylating the carboxylic acids of tetrahydrocannabinol and cannabidiol..Iaddend.

Description

BRIEF DESCRIPTION OF THE DRAWINGS

(1) Further advantages and features of the present invention result from the description of practical examples and from the drawings, wherein:

(2) FIG. 1 is a schematic representation of a CO.sub.2 extraction plant for producing the primary extract of the invention;

(3) FIG. 2 is a schematic representation of a CO.sub.2 extraction plant for producing a secondary extract highly enriched in Δ.sup.8-THC and Δ.sup.9-THC; and

(4) FIG. 3 is a schematic representation of a CO.sub.2 extraction plant for separation of a primary and/or secondary extract in CBD, optionally Δ.sup.8-THC and Δ.sup.9-THC in a high-pressure column.

DETAILED DESCRIPTION OF THE INVENTION

(5) Ground Cannabis plant material comprised substantially of inflorescences and leaves is charged into extracting vessels 1-4. CO.sub.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 Δ.sup.9-tetrahydrocannabinol and cannabidiol as well as the carboxylic acids thereof. Suitably for extraction a flow rate of 50-150 kg of CO.sub.2/kg of starting material is used.

(6) At the upper end of extracting vessel 4, an extract enriched in the cannabinoids leaves the vessel via conduit 6a and arrives at the bottom of separating vessel 5a. The separating vessels 5a and 5b are in the exemplary case filled with various zeolitic molecular sieves and with diatomaceous earth as an adsorbent. In separating vessels 5a and 5b, the same pressure and temperature conditions prevail as in extracting vessels 1-4. The zeolitic molecular sieves placed in container 6a have an internal surface of approx. 800 m.sup.2/g, the zeolitic molecular sieves placed in container 6b have an internal surface of approx. 1200 m.sup.2/g.

(7) By charging containers 6a and 5b with molecular sieves—preferred, however not indispensable—alkaloids, flavonoids and chlorophylls are further separated from the CO.sub.2 loaded with extract. This CO.sub.2 extraction mixture thus purified exits from the head of vessel 5b via conduit 7, pressure regulation valve 8, with extraction pressure being reduced to less than 75 bar, in the exemplary case to approx. 60 bar. The CO.sub.2 extract mixture then arrives at heat exchanger 9 where it is heated to a temperature supercritical for CO.sub.2, preferably to 45° C.

(8) Under these pressure and temperature conditions, extraction of that extract portion takes place in the separating vessel 10 which essentially still contains undesirable monoterpenes and sesquiterpenes. The extract mixture consisting of CO.sub.2 and essentially of Δ.sup.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.

(9) With the aid of pressure regulation valve 12, the separation pressure in container 14 is set to pressure conditions subcricital for CO.sub.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.sub.2, in the exemplary case about 20° C. Under these conditions the pure CO.sub.2 is separated from the primary extract enriched in Δ.sup.9-THC and cannabidiol and the carboxylic acids thereof in separating vessel 14.

(10) The pure CO.sub.2 is conveyed via conduit 15 to liqufier 17 that is equipped with a condenser coil 16. From here the liquid CO.sub.2 is supplied via pressurizing pump 18 to heat exchanger 19, to be available for the following extraction cycle.

(11) For opening the extracting vessel, i.e. for charging and emptying the vessels with, or of, the starting material, the CO.sub.2 is either vented directly via conduit 21, or supplied via conduit 20 to recycling plant 22 which then pumps the liquid CO.sub.2 into the CO.sub.2 storage vessel 23.

(12) FIG. 2 shows a schematic representation of a CO.sub.2 extraction plant for producing a secondary extract highly enriched in Δ.sup.8-THC and Δ.sup.9-THC.

(13) For the reaction, in particular the decarboxylation, of the cannabinoid carboxylic acids contained in the primary extract into Δ.sup.9-THC and CBD, the primary extract in the exemplary case is treated during about 2 hours at 80° C.

(14) A mixture of decarboxylated primary extract, water-binding agent and catalyst is introduced into the extracting vessel 200. CO.sub.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.

(15) Following cyclization, the secondary extract highly enriched in Δ.sup.8-THC and Δ.sup.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. Through valve 206 the secondary extract thus obtained, which contains small amounts of CBD and is highly enriched in Δ.sup.8-THC and Δ.sup.9-THC, may be withdrawn from separating vessel 205.

(16) The pure CO.sub.2 is conveyed via conduit 207 to liquefier 208 which is equipped with a condenser coil 209. From there the liquid CO.sub.2 is supplied via pressurizing pump 210 to heat exchanger 211, to be available for the following extraction cycle.

(17) FIG. 3 shows a schematic representation of a CO.sub.2 extraction plant for separation of a primary and/or secondary extract CBD, optionally Δ.sup.8-THC and Δ.sup.9-THC, in a high-pressure column.

(18) Via extraction column 300 wherein an extraction pressure of 180 bar and a temperature of 55° C. prevail, consisting of bottom segment 301a, purification segment 301b (charged with silica gel) and head segment 301c, the extract mixture dissolved in CO.sub.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.

(19) Via duct 307, regulating valve 308 and heat exchanger 309 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 Δ.sup.8-THC takes place. Via valve 311 the obtained Δ.sup.8-THC may be withdrawn.

(20) The Δ.sup.9-THC still dissolved in CO.sub.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 Δ.sup.9-THC may be withdrawn.

(21) The pure CO.sub.2 is conveyed via conduit 317 to liquefier 318 which is equipped with a condenser coil 319. From here the liquid CO.sub.2 is supplied via pressurizing pump 320 to heat exchanger 321, to be available for the following extraction cycle.

(22) Modifications in the described plant systems are very well possible without the scope of the invention being restricted thereby.

(23) As industrial hemp of the fiber type, in the present exemplary case the French Cannabis sativa variety Fedora 19 is employed. The raw drug has an average content of approx. 0.25% of Δ.sup.9-THC and 1.54% of CBD.

(24) As a result, a primary extract having the properties indicated in Table 1 is obtained.

(25) TABLE-US-00001 TABLE 1 Primary extracts from industrial hemp with different solvents EtOH Hexane primary Inventive Measured primary extract* in accordance primary CO.sub.2 substance extract with WO00/25127 extract Chlorophyll 3.00% 2.85% 0.010% CBD 14.50%  12.40%  58.000%  Δ.sup.9-THC 2.30% 2.30% 9.500% Δ.sup.8-THC 0.00% 0.00% 0.000% CBN 0.50% 0.50% 0.100% Flavonoid 12.50%  8.50% 0.150% glycosides Alkaloids: 0.20% 0.35% 0.001% cannabisativin Monoterpenes: α-Pinene 0.02% 0.03% 0.001% β-Pinene 0.01% 0.02% 0.001% Myrcene 0.02% 0.02% 0.001% Sesquiterpenes: Caryophyllene 0.53% 0.45% 0.020% β-Humulene 0.18% 0.22% 0.008% Δ-Selinene 0.10% 0.15% 0.004% *This column relates to a test comparing the CO.sub.2 extracts in accordance with the present invention with the prior-art hexane extracts of WO00/25127 as discussed at the outset. An industrial hemp having the following raw drug data: water content: 11.2% (wt.); Δ.sup.9-THC 0.25% (wt.); and CBD: 1.54% were extracted with hexane in accordance with WO00/25127. To this end, 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.

(26) When one compares the data of the CO.sub.2 primary extract in accordance with the present invention as shown in Table 1 with the hexane extract in accordance with WO00/25127 and the ethanol extract, initially the relatively good coincidence of the primary extracts obtained by means of the organic solvents is conspicuous.

(27) Moreover in comparison with the CO.sub.2 primary extract of the present invention, there results a disadvantageously high chlorophyll content of 3.00% for the hexane extract and of 2.85% for the ethanol extract. For the extract of the invention, the chlorophyll content thus is lower by a factor of almost 300 than in the prior-art extracts.

(28) A low chlorophyll content is particularly advantageous because under certain circumstances, such as when a soft gelatin is used for encapsulation of the extract in the framework of galenic formulation, chlorophyll may involve cross-reticulations which may prevent the active principles contained in the extract from being released.

(29) The desired CBD content is in the inventive CO.sub.2 extract higher by a factor 4 to 5, and the Δ.sup.9-THC content also by a factor >4, in comparison with the prior-art solvent extracts.

(30) If one regards the overall cannabinoid content, essentially composed of CBD, Δ.sup.9-THC and CBN, it may be seen that even the inventive primary CO.sub.2 extract already is made up at more than two thirds of these constituents, whereas the prior-art extracts only contain an overall cannabinoid content of approx. 15 to 17%.

(31) Moreover what is conspicuous in comparison with the extract of the invention are the highly elevated (more than 80-fold) flavonoid glycoside contents of the ethanol and hexane extracts.

(32) The detected terpene and alkaloid quantities are also strongly elevated in comparison with the extracts according to the invention:

(33) The contents of undesirable monoterpenes listed in Table 1 are higher by a factor of 10-30 than in the two primary extracts obtained with ethanol and hexane than in the CO.sub.2 primary extract, and while the sesquiterpene content is higher by a factor 20 to 40 than in the inventive CO.sub.2 extracts.

(34) It is moreover noted that 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 Δ.sup.9-THC.

(35) In contrast, already the primary extracts of the invention without any further purification steps—as shown in Table 1—practically do not contain any more cannabisativin.

(36) Thus 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.sub.2 primary extract of the invention.

(37) Thus the CO.sub.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.

(38) What is particularly advantageous is the circumstance that the present invention starts out from a hemp having a THC proportion near Zero, which is not even the case in WO00/25127 as this reference starts out from higher THC concentrations in the raw drug inasmuch as drug hemp, not industrial hemp is extracted there.

(39) In view of this very fact it thus is already surprising that THC and cannabinoids may at all be enriched in technically useful amounts from readily available industrial hemp by means of CO.sub.2 extraction.

(40) Table 2 shows the components of a secondary extract after completed anellation.

(41) TABLE-US-00002 TABLE 2 Secondary extract following cyclization (FIG. 2) CO.sub.2 secondary extract P.sub.1 = 300 bar T.sub.1 = 70° C. P.sub.2 = 55 bar Measured substance T.sub.2 = 25° C. Chlorophyll 0.01% CBD 1.5% Δ.sup.9-THC 41.2% Δ.sup.8-THC 24.3% CBN 0.1%

(42) Table 3 shows the components of a primary extract purified by high-pressure column in accordance with FIG. 3.

(43) TABLE-US-00003 TABLE 3 Purified primary extract after chemical purification in a high-pressure column (FIG. 3) Purified primary extract P.sub.1 = 180 bar T.sub.1 = 55° C. P.sub.2 = 70 bar (separating vessel No. 5) T.sub.2 = 50° P.sub.3 = 60 bar (separating vessel No. 10) T.sub.3 = 30° C. P.sub.4 = 55 bar (separating vessel No. 15) Measured T.sub.4 = 25° C. substance Separator No. 5 Separator No. 10 Separator No. 15 Chlorophyll 0.01% 0.01% 0.01% CBD 85.0% 0.0% 1.5% Δ.sup.9-THC 2.0% 0.0% 87.0% Δ.sup.8-THC 0.0% 0.0% 0.0% CBN 0.1% 0.1% 0.1%

(44) Table 4 shows the components of a secondary extract which was purified in a high-pressure column.

(45) TABLE-US-00004 TABLE 4 Purified secondary extract following purification in a high-pressure column (FIG. 3) Purified secondary extract P.sub.1 = 180 bar T.sub.1 = 55° C. P.sub.2 = 70 bar (separating vessel No. 5) T.sub.2 = 50° C. P.sub.3 = 60 bar (separating vessel No. 10) T.sub.3 = 30° C. P.sub.4 = 55 bar (separating vessel No. 15) Measured T.sub.4 = 25° C. substance Separator No. 5 Separator No. 10 Separator No. 15 Chlorophyll 0.01% 0.01% 0.01% CBD 90.0% 0.1% 0.3% Δ.sup.9-THC 0.5% 1.0% 96.0% Δ.sup.8-THC 0.2% 85.0% 1.5% CBN 0.1% 0.1% 0.1%

(46) It is, of course, fundamentally also possible to use a drug hemp for carrying out the process of the invention.

(47) 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.

(48) Suitable application types are inhalation, oral, parenteral, as well as enteral application.