WO2020252277A1

WO2020252277A1 - Making delta 8 thc, delta 10 thc and/or cannabinol from cbd

Info

Publication number: WO2020252277A1
Application number: PCT/US2020/037456
Authority: WO
Inventors: Michael S. Hartman
Original assignee: Isomerz Inc
Current assignee: Isomerz Inc
Priority date: 2019-06-13
Filing date: 2020-06-12
Publication date: 2020-12-17
Anticipated expiration: 2021-12-13

Abstract

A method of making delta 8 tetrahydrocannabinol (Δ8 THC) or homologs thereof, delta 10 tetrahydrocannabinol (Δ10 THC) or homologs thereof and/or cannabinol (CBN) or homologs thereof, the method including: a) providing an extract or composition that comprises at least one of delta 9 tetrahydrocannabinol (Δ9 THC) or homologs thereof or a cannabidiol (CBD) or homologs thereof; b) heating the extract or composition; c) adding iodine to CBD or homologs thereof to the heated extract or composition; and d) continuing to heat while stirring, such that the (Δ9 THC or CBD or homologs thereof is converted into Δ8 THC, delta 10 tetrahydrocannabinol (Δ10 THC) and/or cannabinol (CBN) (including or homologs thereof of any of the preceding). In some cases, a catalyst is added to the heated extract. In some cases, a halogen or a free radical generator is added to the heated isolate.

Description

MAKING DELTA 8 THC, DELTA 10 THC AND/OR CANNABINOL FROM CBD RELATED APPLICATIONS

[0001] This application claims priority to U.S. Provisional Applications Ser. No. 62/860,986, filed June 13, 2019, Ser. No. 62/869,698, filed July 2, 2019, and Ser. No. 62/871,427, filed July 8, 2019, each of which are hereby incorporated by reference in their entireties. BACKGROUND

Field

[0002] The present application relates to methods of making of delta 8 tetrahydrocannabinol ( D⁸ THC), delta 10 tetrahydrocannabinol ( D¹⁰ THC) and/or cannabinol (CBN) with or without using a solvent. Description of the Related Art

[0003] Delta-8-THC (D⁸ THC) is an analog of tetrahydrocannabinol (THC) with antiemetic, anxiolytic, appetite-stimulating, analgesic, and neuroprotective properties.D⁸ THC binds to the cannabinoid G-protein coupled receptor CB1, located in the central nervous system. This agent exhibits a lower psychotropic potency than Delta-9-THC (D⁹ THC), the primary form of THC found in cannabis. D⁸ THC is chemically different fromD⁹ THC by only a few atomic bonds. While D⁸ THC only exists naturally in fractions of a percent, it may be used in a variety of applications, offering unique effects. D¹⁰ THC is a derivative and isomer of CBD and D⁹ THC. Cannabinol (CBN) is a mildly psychoactive cannabinoid found only in trace amounts in Cannabis, mostly in aged Cannabis. SUMMARY

[0004] Some embodiments relate to a method of making delta 8 tetrahydrocannabinol (D⁸ THC), delta 10 tetrahydrocannabinol (D¹⁰ THC) and/or cannabinol (CBN), the method including: a) providing an extract or composition that comprises at least one of delta 9 tetrahydrocannabinol (D9 THC) or a cannabidiol (CBD);

b) heating the extract or composition to at least 70 degrees centigrade to make a heated extract;

c) adding at least 0.0005:1 weight to weight of iodine to CBD to the heated extract or composition; and

d) continue heating for at least 20 minutes while stirring, such that the ( D9 THC or CBD is converted into D⁸ THC, delta 10 tetrahydrocannabinol ( D¹⁰ THC) and/or cannabinol (CBN).

[0005] In some examples, the extract or composition includes CBD.

[0006] In some examples, the CBD is converted to D⁸ THC.

[0007] In some examples, there is no significant amount of D⁹ THC in the product containing D⁸ THC.

[0008] In some examples, less than 0.3% w/w of D⁹ THC is present after the reaction.

[0009] In some examples, at least 50% of the CBD is converted to D⁸ THC.

[0010] In some examples, at least 99% of the CBD is converted to D⁸ THC.

[0011] In some examples, at least 90% of the CBD is converted to D⁸ THC.

[0012] In some examples, substantially all CBD is converted to D⁸ THC.

[0013] In some examples, the extract or composition is heated to at least 55 degrees centigrade.

[0014] In some examples, at least 1.0 g of iodine is employed.

[0015] In some examples, a ratio of 0.001:1 w/w of iodine to CBD is used.

[0016] In some examples, the method further includes the addition of calcium carbonate to the heated extract or composition.

[0017] In some examples, the method further includes the addition of sodium thiosulphate.

[0018] In some examples, the extract or composition is prepared by CO₂ extraction. [0019] In some examples, a ratio of 40 g of extract or composition is employed to 1.2g of elemental iodine.

[0020] In some examples, the extract or composition is first heated to at least 55 degrees centigrade for 20 minutes while stirring and then heated to at least 55 centigrade for at least 20 minutes.

[0021] In some examples, the extract or composition is first heated to 90 degrees centigrade.

[0022] In some examples, the method includes stirring and heating to at least 100 degrees centigrade.

[0023] In some examples, the process does not include the addition of a solvent.

[0024] In some examples, the process does not involve a use of a solvent between providing a extract or composition and production of D⁸ THC.

[0025] In some examples, no organic solvent is employed during a heating step b).

[0026] In some examples, no organic solvent is employed during d).

[0027] In some examples, no organic solvent is employed during a, b, c, or d.

[0028] In some examples, no organic solvent is employed during the process.

[0029] In some examples, the extract or composition is CO₂ extracted from hemp.

[0030] In some examples, the extract or composition is decarboxylated.

[0031] In some examples, the extract or composition is CO₂ extracted from hemp and the extract or composition is then decarboxlated in order to produce the extract or composition used as the starting material.

[0032] Some embodiments relate to a method of making D⁸ THC, the method including:

a) providing an extract or composition that comprises at least one of D9 THC or a CBD;

c) adding a catalyst to the heated extract or composition, wherein the extract or composition to catalyst is present in a ratio of about 1 : 0.0005 (grams of extract or composition to grams of catalyst) to about 1:1 (grams of extract or composition to grams of catalyst); and

d) continue heating for at least 20 minutes while stirring, such that the D9 THC or CBD is converted into D8 THC, D10 THC and/or CBN.

[0033] In some examples, the catalyst is a metallic catalyst.

[0034] In some examples, the catalyst is a non-metallic catalyst.

[0035] In some examples, the extract is a plant extract.

[0036] Some embodiments relate to a method of making D⁸ THC and/or CBN (and/or homologs thereof), the method including:

a) providing an isolate that comprises at least a CBD (or a homolog thereof); b) heating the isolate to between 55 and 800 degrees centigrade to make a heated isolate;

c) adding between: 0.0001:1 (w/w) of a halogen or a free radical generator to CBD (or a homolog thereof) to 10:1 (w/w) of halogen or a free radical generator to CBD (or a homolog thereof) to the heated isolate; and

d) continue heating for at least 30 minutes such that the CBD (or a homolog thereof) is converted into D8 THC and/or CBN (Cannabinol) (or a homolog thereof).

[0037] In some embodiments, the CBD homolog is cannabidivarin (CBDV).

[0038] In some examples, the reaction produces at least Tetrahydrocannabivarin (THCV).

[0039] In some examples, the isolate comprises between 20-95% CBD (or CBDV).

[0040] In some examples, the CBD is converted to D⁸ THC.

[0041] In some examples, the halogen or a free radical generator includes iodine. In some embodiments, any of the embodiments provided herein regarding a halogen or free radical generator can employ a halogen containing molecule.

[0042] In some examples, there is no significant amount of D⁹ THC remaining.

[0043] In some examples, less than 0.3% w/w of D⁹ THC is present after the reaction.

[0044] In some examples, at least 50% of the CBD is converted to D⁸ THC. [0045] In some examples, at least 99% of the CBD is converted to D⁸ THC.

[0046] In some examples, at least 90% of the CBD is converted to D⁸ THC.

[0047] In some examples, substantially all CBD is converted to D⁸ THC and CBN.

[0048] In some examples, substantially all CBDV is converted to D⁸ THCV and CBV.

[0049] In some examples, CBDV is converted to D⁸ THCV and CBV.

[0050] In some examples, the isolate is heated to at least 70 degrees centigrade.

[0051] In some examples, at least 1.0 g of iodine is employed.

[0052] In some examples, at least ratio of 0.001:1 w/w of iodine to CBD (or CBDV) isolate is used.

[0053] In some examples, less than a ratio of 10:1 w/w of iodine to CBD (or CBD) isolate is used.

[0054] In some examples, the CBD isolate (or CBDV isolate) is between 20 and 99% CBD and comprises at least one of propane or butane.

[0055] In some examples, the reaction is carried out between 1 torr and 3 million torr.

[0056] In some examples, the method further includes the addition of sodium thiosulphate as a quencher.

[0057] In some examples, the isolate is prepared by CO₂ extraction.

[0058] In some examples, the isolate is first heated to at least 55 degrees centigrade for 20 minutes while stirring and then heated to at least 55 centigrade for at least 20 minutes.

[0059] In some examples, the isolate is first heated to 90 degrees centigrade.

[0060] In some examples, the process does not comprise the addition of a solvent.

[0061] In some examples, the process is performed in a solvent.

[0062] In some examples, the isolate is decarboxylated.

[0063] Some embodiments relate to a method of making D⁸ THC and/or CBN or a homolog thereof, the method comprising:

a) providing an isolate that comprises a CBD or a homolog thereof; b) heating the isolate to at least 55 degrees centigrade to make a heated isolate;

c) adding a free radical generator to the heated isolate, wherein the isolate to free radical generator is present in a ratio of about 1:0.0001 (grams of isolate to grams of free radical generator) to about 1:10 (grams of isolate to grams of free radical generator); and

d) continue heating for at least 20 minutes while stirring, such that the CBD or homolog thereof is converted into D8 THC (or a homolog thereof) and/or CBN (or a homolog thereof).

[0064] In some examples, the isolate is from a plant.

[0065] In some examples, in lieu of the isolate, a plant extract is used instead. BRIEF DESCRIPTION OF THE DRAWINGS

[0066] FIG. 1 depicts some embodiments of a reaction scheme in which a“CBD homolog” (formula A) is converted to a“THC homolog” (including, for example, THCV) as in formula C and/or a“CBN homolog” (including, for example, CBV) as in formula D.

DETAILED DESCRIPTION

[0067] Provided herein are embodiments relating to the making of D⁸ THC, D¹⁰ THC and/or CBN via a solvent-less method. Some embodiments relate to using D⁹ THC or a CBD (cannabidiol) as a starting agent in the production of D⁸ THC, D¹⁰ THC and/or CBN via a solvent-less method.

[0068] In some embodiments, the methods involve heat and/or iodine (or any halogen or free radical generator as an alternative to iodine). In some embodiments, the method is applied to an isolate, which can include, for example, a hemp isolate. In some embodiments, the method is applied to any isolate, that has been isolated from, for example, hemp.

[0069] In some embodiments, the hemp isolate contains between 95 and 20% CBD in terms of purity. The isolate can also contain pentane and/or butane. [0070] As disclosed herein, in some embodiments, the reaction starts with CBD and produces D⁸ THC and/or CBN. The method can be applied to homologs thereof. In some embodiments, the reaction starts with CBDV to convert it to D⁹ THCV and then onto D⁸ THCV and CBV (cannabidivarin). Any of the embodiments (including those in the claims) provided herein with respect to one of these embodiments can be applied to the homolog embodiments as well.

[0071] In some embodiments, the reaction to produce D⁸ THC and/cannabinol from CBD can be quenched with sodium thiosulfate.

[0072] In some embodiments, the method involves an isolate of greater than 95% purity of CBD that can be converted into D⁸ THC and CBN with (and optionally solely) using iodine (or other options provided herein) and heat.

[0073] An exemplary reaction is shown in the reaction diagram below. In some embodiments, R1 can be 5 carbons long (pentyl) and R2 can be 1 carbon long (methyl) for CBD. Further, this same reaction can work for CBDV to D⁹ THCV then onto D⁸ THCV and CBV (R1=3 carbons, R2=1 carbon). This reaction scheme can work for a variety of CBD homologs and the resulting homolog products.

[0074] In some embodiments, the reaction comprises or consists of that outlined below (and in FIG.1):

wherein, R1 and R2 can be any alkyl group. In some embodiments, R1 and R2 are separately selected from any alkyl that is 1-20 carbon atoms in length. The term“alkyl,” alone or in combination, refers to a fully saturated aliphatic. In certain embodiments, alkyls are optionally substituted. In certain embodiments, an alkyl comprises 1 to 20 carbon atoms (whenever it appears herein, a numerical range, such as“1 to 20” or“C₁-C₂₀”, refers to each integer in the given range; e.g.,“C₁-C₂₀ alkyl” means that an alkyl group comprising only 1 carbon atom, 2 carbon atoms, 3 carbon atoms, etc., up to and including 20 carbon atoms). Examples of alkyls include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, tert-amyl, pentyl, hexyl, heptyl, octyl and the like.

[0075] In some embodiments, any of the compounds provided with respect to the options of R1 and R2 in the reaction diagram above can be applied in the context of any one of more of the embodiments and claims recited herein (simply by inserting the particular starting formula and following the reaction through, in place of the CBD embodiments provided in the claims below. The term“CBD homolog” denotes those options encompassed within formula A above. The term“THC homolog” (such as THCV) denotes those options encompassed within formula C above. The term“CBN homolog” (such as CBV) denotes those options encompassed within formula D above. For the CBD to THC conversion, R1 is 5 and R2 is one carbon. In some embodiments, one can use any of the relevant methods provided herein to convert a CBD homolog to one or both of a CBN homolog and/or a THC homolog, for example, as shown in FIG.1.

[0076] In some embodiments, the method in FIG.1 further comprises:

a) providing an isolate that comprises the compound A (various homologs);

b) heating the isolate to between 55 and 800 degrees centigrade to make a heated isolate;

c) adding between: 0.0001:1 (w/w) of a halogen or a free radical generator to A to 10:1 (w/w) of halogen or a free radical generator to A to the heated isolate; and d) continue heating for at least 30 minutes such that the A is converted into C and/or D (e.g., Cannabinol) (or a homolog thereof).

[0077] In some embodiments, the reaction comprises or consists of that outlined below:

[0078] Chemical structures of various compounds noted herein are as follows:

[0079] The numbering as used herein is that provided in the structure below:

[0080] As used herein, CBD or homologs thereof denotes both the general class of CBD:

as well as, for example, cannabidivarin (CBDV):

[0081] Cannabinol (CBN), denotes a compound with the following structure:

[0082] In some embodiments, the reaction is a generalized reaction in the presence of iodine, or another halogen, or a free radical generating species. In some embodiments, the reaction is one as outlined in FIG.1. In some embodiments, the reaction is a method to convert a CBD homolog to one or both of a CBN homolog and/or a THC homolog, for example, as shown in FIG.1.

[0083] In some embodiments, the reaction is carried out under atmospheric pressure. In some embodiments, the reaction is carried out between 1 torr and 3 million torr. In some embodiments, prior to adding the quencher, the reaction is allowed to continue for at least 30 minutes, for example, 0.5, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 24 hours or more, including 1, 2, 3, 4, 5, 6, 7 or more days, include 1, 2, or 3 or more months. In some embodiments, the reaction is one as outlined in FIG.1. In some embodiments, the reaction is a method to convert a CBD homolog to one or both of a CBN homolog and/or a THC homolog, for example, as shown in FIG.1.

[0084] In some embodiments, there is no base present during the conversion of CBD (or other homolog) to product. In some embodiments, the reaction is carried out under neutral or acidic conditions. In some embodiments, the reaction is one as outlined in FIG.1. In some embodiments, the reaction is a method to convert a CBD homolog to one or both of a CBN homolog and/or a THC homolog, for example, as shown in FIG.1.

[0085] In some embodiments, this is a one-pot process. In some embodiments, the reaction is one as outlined in FIG. 1. In some embodiments, the reaction is a method to convert a CBD homolog to one or both of a CBN homolog and/or a THC homolog, for example, as shown in FIG.1.

[0086] In some embodiments, unexpectedly, the oxane (tetrahydropyran) ring closure occurs (CBD to D9 THC) followed by an isomerization of the double bond around the 9^th carbon (THC carbon numbering shown below).

[0087] In some embodiments, this produces a more potent local analgesic isomer from CBD, delta 8 THC when topically applied reduces inflammation and pain.

[0088] In the case of when CBDV is used as a starting compound (as a CBD homolog), the reaction produces an isomer (THCV) that increases sensitivity to insulin as well as functions as an appetite suppressant in higher doses.

[0089] In some embodiments, a method of making delta 8 tetrahydrocannabinol ( D⁸ THC) is provided. The method comprises:

a) providing an extract or composition that comprises at least one of delta 9 tetrahydrocannabinol ( D⁹ THC) or a cannabidiol (CBD);

c) adding at least 0.0005:1 weight to weight of iodine to CBD to the heated extract or composition; and d) continue heating for at least 20 minutes while stirring, such that the ( D⁹ THC or CBD is converted into D⁸ THC, delta 10 tetrahydrocannabinol ( D¹⁰ THC) and/or cannabinol (CBN). In some embodiments, a-d can be applied to the homolog reaction process shown in FIG.1.

[0090] In some examples, the extract or composition is heated to 70°C, 71°C, 72°C, 73°C, 74°C, 75°C, 76°C, 77°C, 78°C, 79°C, 80°C, 81°C, 82°C, 83°C, 84°C, 85°C, 86°C, 87°C, 88°C, 89°C, 90°C, 91°C, 92°C, 93°C, 94°C, 95°C, 96°C, 97°C, 98°C, 99°C, 100°C, 101°C, 102°C, 103°C, 104°C, 105°C, 106°C, 107°C, 108°C, 109°C, 110°C, 115°C, 120°C, 125°C, 130°C, 135°C, 140°C, 145°C, 150°C, 155°C, 160°C, 165°C, 170°C, 175°C, 180°C, 185°C, 190°C, 195°C, 200°C, 250°C, 300°C, 350°C, 400°C, 450°C, 500°C, 550°C, 600°C, 650°C, 700°C, 750°C, 800°C or 850°C, including any range defined between any two of the preceding values. In some embodiments, the reaction is one as outlined in FIG. 1. In some embodiments, the reaction is a method to convert a CBD homolog to one or both of a CBN homolog and/or a THC homolog, for example, as shown in FIG.1.

[0091] In some examples, the w/w ratio of iodine to CBD to the heated extract or composition is 0.0005:1, 0.0010:1, 0.0015:1, 0.0020:1, 0.0025:1, 0.0030:1, 0.0035:1, 0.0040:1, 0.0045:1, 0.0050:1, 0.0055:1, 0.0060:1, 0.0065:1, 0.0070:1, 0.0075:1, 0.0080:1, 0.0085:1, 0.0090:1, 0.0095:1, 0.0100:1, 0.0150:1, 0.0200:1, 0.0250:1, 0.0300:1. In some embodiments, the reaction is one as outlined in FIG.1. In some embodiments, the reaction is a method to convert a CBD homolog to one or both of a CBN homolog and/or a THC homolog, for example, as shown in FIG.1.

[0092] In some examples, in step (d) the heating is continued for 20 min., 25 min., 30 min., 35 min., 40 min., 45 min., 50 min., 55 min., 1 hr., 1.5 hr, 2 hr., 2.5 hr, 3 hr., 3.5 hr, 4 hr., 4.5 hr., 5 hr., 5.5 hr, 6 hr., 6.5 hr, 7 hr., 7.5 hr, 8 hr., 8.5 hr, 9 hr., 9.5 hr,10 hr, 12 hr, 13hr, 14 hr, 15 hr, 16 hr, 17 hr, 18 hr, 19 hr, 20 hr, 21 hr, 22 hr, 23 hr, 24 hr, 48 hr or 72 hr, including any range defined between any two of the preceding values. In some embodiments, the reaction is one as outlined in FIG.1. In some embodiments, the reaction is a method to convert a CBD homolog to one or both of a CBN homolog and/or a THC homolog, for example, as shown in FIG.1.

[0093] In some examples, the extract or composition comprises CBD.

[0094] In some examples, the CBD is converted to D⁸ THC. [0095] In some examples, the amount of CBD converted to D⁸ THC is 1%, 2%, 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95%, 96%, 97%, 98%, 99%, 99.9%, 99.99%, 99.999%, or greater. In some embodiments, the reaction is one as outlined in FIG.1. In some embodiments, the reaction is a method to convert a CBD homolog to one or both of a CBN homolog and/or a THC homolog, for example, as shown in FIG.1.

[0096] In some examples, there is no significant amount of D⁹ THC in the product containing D⁸ THC.

[0097] In some examples, there is less than 0.3% w/w of D⁹ THC present after the reaction.

[0098] In some examples, there is less than 0.25%, 0.20%, 0.15%, 0.10%, 0.05%, 0.02%, 0.01%, 0.005%, 0.0025% or 0.0010% w/w of D⁹ THC present after the reaction.

[0099] In some examples, at least 50% of the CBD is converted to D⁸ THC.

[0100] In some examples, at least 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90% 95%, 96% 97%, 98%, 99%, 99.9%, 99.99%, 99.999%, or greater of the CBD is converted to D⁸ THC. In some examples, at least 99% of the CBD is converted to D⁸ THC. In some examples, at least 90% of the CBD is converted to D⁸ THC. In some examples, substantially all CBD is converted to D⁸ THC. In some examples, the extract or composition is heated to at least 55 degrees centigrade.

[0101] In some examples, the extract or composition is heated to 55°C, 56°C, 57°C, 58°C, 59°C, 60°C, 61°C, 62°C, 63°C, 64°C, 65°C, 66°C, 67°C, 68°C, 69°C, 70°C, 71°C, 72°C, 73°C, 74°C, 75°C, 76°C, 77°C, 78°C, 79°C, 80°C, 81°C, 82°C, 83°C, 84°C, 85°C, 86°C, 87°C, 88°C, 89°C, 90°C, 91°C, 92°C, 93°C, 94°C, 95°C, 96°C, 97°C, 98°C, 99°C, 100°C, 101°C, 102°C, 103°C, 104°C, 105°C, 106°C, 107°C, 108°C, 109°C, 110°C, 115°C, 120°C, 125°C, 130°C, 135°C, 140°C, 145°C, 150°C, 155°C, 160°C, 165°C, 170°C, 175°C, 180°C, 185°C, 190°C, 195°C or 200°C, including any range defined between any two of the preceding values

[0102] In some examples, at least 1.0 g of iodine is employed. In some examples, at least 0.1 g, 0.2 g, 0.3 g, 0.4 g, 0.5 g, 0.6 g, 0.7 g, 0.8 g, 0.9 g, 1.0 g. 1.5 g, 2.0 g, 2.5 g, 3.0 g, 3.5 g, 4.0 g, 4.5 g, 5.0 g or 10 g of iodine is employed. [0103] In some examples, a ratio of 0.001:1 w/w of iodine to CBD is used. In some examples, the w/w ratio of iodine to CBD to the heated extract or composition is 0.0001:1, 0.0005:1, 0.0010:1, 0.0015:1, 0.0020:1, 0.0025:1, 0.0030:1, 0.0035:1, 0.0040:1, 0.0045:1, 0.0050:1, 0.0055:1, 0.0060:1, 0.0065:1, 0.0070:1, 0.0075:1, 0.0080:1, 0.0085:1, 0.0090:1, 0.0095:1, 0.0100:1, 0.0150:1, 0.0200:1, 0.0250:1, 0.0300:1, 0.0500:1, 0.1000:1, 0.5000:1, 1:1, 2:1, 3:1, 4:1, 5:1, 6:1, 7:1, 8:1, 9:1 or 10:1.

[0104] In some examples, the method further comprises the addition of calcium carbonate to the heated extract or composition.

[0105] In some examples, then method further comprises the addition of sodium thiosulphate.

[0106] In some examples, the extract or composition is prepared by CO₂ extraction.

[0107] Cannabis oil is usually extracted on a commercial scale either through the use of solvents such as hexane or butane, or through more modern supercritical/subcritical CO₂ (carbon dioxide) processes.

[0108] Carbon dioxide-based extraction is considered to be more environmentally friendly, considerably safer, cleaner, cheaper and less toxic than using fossil fuel-based extraction, and results in a consistent product that is more palatable.

[0109] At standard temperatures and pressure, carbon dioxide is a gas. At 60.4 psi it is a liquid and at -78°C, at standard pressure, it is a solid (dry ice).

[0110] When heated to above 31.10°C (critical temperature) and at 1,071 psi (critical pressure) or higher, it has the properties of both a gas and liquid. It becomes a supercritical liquid.

[0111] Supercritical liquids can pass through porous solids and also dissolve materials, making them ideal as a solvent. The“tunability” of supercritical CO₂ extraction enables targeting maximum outputs of cannabidiol depending on the type and quality of cannabis material being used; while keeping undesirable compounds such as chlorophyll out of the product.

[0112] The following is an example outline of a supercritical CO₂ extraction process: i. An extractor chamber is filled with ground cannabis/hemp material (called trim).

ii. A pump forces pressurized carbon dioxide gas at the optimum supercritical temperature (ScCO₂) into the extractor chamber.

iii. The supercritical carbon dioxide interacts with the cannabis, dissolving the cannabinoid compounds it contains.

iv. The supercritical CO₂ carries the cannabis oil particles past a pressure release valve to a cyclonic separator.

v. In the separator, the pressure is lower and the carbon dioxide and cannabis oil separates.

vi. The carbon dioxide rises and is routed back to the CO₂ tank for reuse in the case of a closed loop system.

vii. The cannabis oil, waxes and resins descend in the separator where they are captured by a collection vessel.

viii. The resulting substance is processed further into various products, such as CBD-rich“cannabis oil”, free of any solvents.

[0113] In some examples, a ratio of 40 g of extract or composition is employed to 1.2g of elemental iodine (i.e., a 33.33:1 ratio of extract/composition to elemental iodine).

[0114] In some embodiments, the ratio of extract/composition to elemental iodine is 5:1, 10:1, 15:1, 20:1, 25:1, 30:1, 35:1, 40:1, 45:1, 50:1, 55:1, 60:1, 65:1, 70:1, 75:1, 80:1, 85:1, 90:1, 95:1 or 100:1.

[0115] In some examples, the extract or composition is first heated to at least 55 degrees centigrade for 20 minutes while stirring and then heated to at least 55 centigrade for at least 20 minutes.

[0116] In some embodiments, the extract or composition is heated to 55°C, 56°C, 57°C, 58°C, 59°C, 60°C, 61°C, 62°C, 63°C, 64°C, 65°C, 66°C, 67°C, 68°C, 69°C, 70°C, 71°C, 72°C, 73°C, 74°C, 75°C, 76°C, 77°C, 78°C, 79°C, 80°C, 81°C, 82°C, 83°C, 84°C, 85°C, 86°C, 87°C, 88°C, 89°C, 90°C, 91°C, 92°C, 93°C, 94°C, 95°C, 96°C, 97°C, 98°C, 99°C, 100°C, 101°C, 102°C, 103°C, 104°C, 105°C, 106°C, 107°C, 108°C, 109°C, 110°C, 115°C, 120°C, 125°C, 130°C, 135°C, 140°C, 145°C, 150°C, 155°C, 160°C, 165°C, 170°C, 175°C, 180°C, 185°C, 190°C, 195°C or 200°C, including any range defined between any two of the preceding values

[0117] In some examples, the heating is continued for 20 min., 25 min., 30 min., 35 min., 40 min., 45 min., 50 min., 55 min., 1 hr., 1.5 hr, 2 hr., 2.5 hr, 3 hr., 3.5 hr, 4 hr., 4.5 hr., 5 hr., 5.5 hr, 6 hr., 6.5 hr, 7 hr., 7.5 hr, 8 hr., 8.5 hr, 9 hr., 9.5 hr or 10 hr, including any range defined between any two of the preceding values.

[0118] In some examples, the extract or composition is first heated to 90 degrees centigrade.

[0119] In some examples, the method comprises stirring and heating to at least 100 degrees centigrade.

[0120] In some examples, the process does not comprise the addition of a solvent, such as ethanol, butane, propane, isopropyl, or alcohol.

[0121] In some examples, the process does not involve a use of a solvent between providing an extract or composition and production of D⁸ THC.

[0122] In some examples, no organic solvent is employed during a heating step b).

[0123] In some examples, no organic solvent is employed during d).

[0124] In some examples, no organic solvent is employed during a, b, c, or d.

[0125] In some examples, no organic solvent is employed during the process.

[0126] In some examples, the extract or composition is CO₂ extracted from hemp.

[0127] In some examples, the extract or composition is CO₂ extracted from a plant. Non-limiting examples of plants that are extracted are marijuana (cannabis) and hemp. D⁹ THC levels in hemp are significantly lower than those in marijuana. The D⁹ THC levels of hemp can rise if the plant becomes stressed by dry conditions, wind or other weather events.

[0128] In some examples, the extract or composition is decarboxylated.

[0129] Tetrahydrocannabinolic acid (THCA) is the precursor to THC, which is found in the trichomes of living hemp and cannabis plants. THCA contains an additional carboxyl group which makes for a different chemical structure compared to THC. THCA is the precursor to THC and it is converted to THC as it is exposed to heat and oxygen over time. This process is known as decarboxylation. After a cannabis plant is harvested and begins the drying process, THCA begins to convert to THC. Once dry, while there are trace amounts of THC in the plant, heating over time further converts THCA into THC.

[0130] In some examples, the extract or composition is CO₂ extracted from hemp and the extract or composition is then decarboxylated in order to produce the extract or composition used as the starting material.

[0131] Some embodiments relate to a method of making D⁸ THC, the method comprises:

a) providing an extract or composition that comprises at least one of D⁹ THC or a CBD;

d) continue heating for at least 20 minutes while stirring, such that the D⁹ THC or CBD is converted into D⁸ THC, D¹⁰ THC and/or CBN.

[0132] In some examples, the extract or composition is heated to 70°C, 71°C, 72°C, 73°C, 74°C, 75°C, 76°C, 77°C, 78°C, 79°C, 80°C, 81°C, 82°C, 83°C, 84°C, 85°C, 86°C, 87°C, 88°C, 89°C, 90°C, 91°C, 92°C, 93°C, 94°C, 95°C, 96°C, 97°C, 98°C, 99°C, 100°C, 101°C, 102°C, 103°C, 104°C, 105°C, 106°C, 107°C, 108°C, 109°C, 110°C, 115°C, 120°C, 125°C, 130°C, 135°C, 140°C, 145°C, 150°C, 155°C, 160°C, 165°C, 170°C, 175°C, 180°C, 185°C, 190°C, 195°C or 200°C.

[0133] In some embodiments, the catalyst is a metallic catalyst.

[0134] In some examples, the metallic catalyst is selected from those known in the art of organic chemistry.

[0135] In some embodiments, the catalyst is a non-metal catalyst.

[0136] In some examples, the non-metal catalyst is selected from those known in the art of organic chemistry. [0137] In some examples, the extract/composition : metallic catalyst ratio is 1:0.00001; 1:00005, 1:00010, 1:00015, 1:00020, 1:00025, 1:00030, 1:00035, 1:00040, 1:00045, 1:00050, 1:0010, 1:0015, 1:0020, 1:0025, 1:0050, 1:0100 or 1:0200.

[0138] In some examples, the heating is continued for 20 min., 25 min., 30 min., 35 min., 40 min., 45 min., 50 min., 55 min., 1 hr., 1.5 hr, 2 hr., 2.5 hr, 3 hr., 3.5 hr, 4 hr., 4.5 hr., 5 hr., 5.5 hr, 6 hr., 6.5 hr, 7 hr., 7.5 hr, 8 hr., 8.5 hr, 9 hr., 9.5 hr or 10 hr.

[0139] In some examples, the extract is a plant extract.

[0140] Some embodiments relate to a method of making D⁸ THC and/or CBN (and/or homologs thereof), the method comprising:

c) adding between 0.0001:1 (w/w) of a halogen or a free radical generator to CBD (or a homolog thereof) to 10:1 (w/w) of halogen or a free radical generator to CBD (or a homolog thereof) to the heated isolate; and

d) continue heating for at least 30 minutes such that the CBD (or a homolog thereof) is converted into D⁸ THC and/or CBN (Cannabinol) (or a homolog thereof).

[0141] In some embodiments, the reaction is one as outlined in FIG. 1. In some embodiments, the reaction is a method to convert a CBD homolog to one or both of a CBN homolog and/or a THC homolog, for example, as shown in FIG.1.

[0142] CBD and numerous analogs thereof are well known (Morales et al. 2017 “An Overview on Medicinal Chemistry of Synthetic and Natural Derivatives of Cannabidiol” Frontiers in Pharmacology 8: 422).

[0143] In some examples, the extract or composition is heated to 70°C, 71°C, 72°C, 73°C, 74°C, 75°C, 76°C, 77°C, 78°C, 79°C, 80°C, 81°C, 82°C, 83°C, 84°C, 85°C, 86°C, 87°C, 88°C, 89°C, 90°C, 91°C, 92°C, 93°C, 94°C, 95°C, 96°C, 97°C, 98°C, 99°C, 100°C, 101°C, 102°C, 103°C, 104°C, 105°C, 106°C, 107°C, 108°C, 109°C, 110°C, 115°C, 120°C, 125°C, 130°C, 135°C, 140°C, 145°C, 150°C, 155°C, 160°C, 165°C, 170°C, 175°C, 180°C, 185°C, 190°C, 195°C, 200°C, 250°C, 300°C, 350°C, 400°C, 450°C, 500°C, 550°C, 600°C, 650°C, 700°C, 750°C, 800°C or 850°C. [0144] In some examples, the ratio of halogen or a free radical generator to CBD (or a homolog thereof) is 0.0001:1, 0.0002:1, 0.0003:1, 0.0004:1, 0.0005:1, 0.0010:1, 0.0010:1, 0.0020:1, 0.0025:1, 0.0030:1, 0.0040:1, 0.0050:1 or 0.01:1.

[0145] In some examples, the halogen or a free radical generator is selected from iodine, and those known in the art of organic chemistry.

[0146] In some examples, the CBD homolog is cannabidivarin (CBDV).

[0147] In some examples, the reaction produces at least Tetrahydrocannabivarin (THCV).

[0148] In some examples, the isolate comprises between 20-95% CBD (or CBDV).

[0149] In some examples, the isolate comprises 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90% or 95% CBD or an analog thereof, such as CBDV.

[0150] In some examples, the CBD is converted to D⁸ THC.

[0151] In some examples, the halogen or a free radical generator comprises iodine.

[0152] In some examples, there is no significant amount of D⁹ THC remaining.

[0153] In some examples, less than 0.3% w/w of D⁹ THC is present after the reaction.

[0154] In some examples, less than 0.001%, 0.005%, 0.010%, 0.020%, 0.030%, 0.040%, 0.050%, 0.100%, 0.150%, 0.200%, 0.250% or 0.300%, w/w of D⁹ THC is present after the reaction.

[0155] In some examples, at least 50% of the CBD is converted to D⁸ THC.

[0156] In some examples, at least 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95%, 96%, 97%, 98% or 99% of the CBD is converted to D⁸ THC.

[0157] In some examples, at least 99% of the CBD is converted to D⁸ THC. In some examples, at least 90% of the CBD is converted to D⁸ THC. In some examples, substantially all CBD is converted to D⁸ THC and CBN. In some examples, substantially all CBDV is converted to D⁸ THCV and CBV. In some examples, CBDV is converted to D⁸ THCV and CBV. [0158] In some examples, the isolate is heated to at least 70 degrees centigrade.

[0159] In some embodiments, the isolate is heated to at least 70°C, 71°C, 72°C, 73°C, 74°C, 75°C, 76°C, 77°C, 78°C, 79°C, 80°C, 81°C, 82°C, 83°C, 84°C, 85°C, 86°C, 87°C, 88°C, 89°C, 90°C, 91°C, 92°C, 93°C, 94°C, 95°C, 96°C, 97°C, 98°C, 99°C, 100°C, 101°C, 102°C, 103°C, 104°C, 105°C, 106°C, 107°C, 108°C, 109°C, 110°C, 115°C, 120°C, 125°C, 130°C, 135°C, 140°C, 145°C, 150°C, 155°C, 160°C, 165°C, 170°C, 175°C, 180°C, 185°C, 190°C, 195°C, 200°C, 250°C, 300°C, 350°C, 400°C, 450°C, 500°C, 550°C, 600°C, 650°C, 700°C, 750°C, 800°C or 850°C, including any range defined between any two of the preceding values

[0160] In some examples, at least 1.0 g of iodine is employed.

[0161] In some examples, at least 0.1 g, 0.2 g, 0.3 g, 0.4 g, 0.5 g, 0.6 g, 0.7 g, 0.8 g, 0.9 g, 1.0 g. 1.5 g, 2.0 g, 2.5 g, 3.0 g, 3.5 g, 4.0 g, 4.5 g, 5.0 g or 10 g of iodine is employed, including any range defined between any two of the preceding values

[0162] In some examples, at least ratio of 0.001:1 w/w of iodine to CBD (or CBDV) isolate is used.

[0163] In some examples, the w/w ratio of iodine to CBD (or CBDV) in the isolate is 0.0001:1, 0.0005:1, 0.0010:1, 0.0015:1, 0.0020:1, 0.0025:1, 0.0030:1, 0.0035:1, 0.0040:1, 0.0045:1, 0.0050:1, 0.0055:1, 0.0060:1, 0.0065:1, 0.0070:1, 0.0075:1, 0.0080:1, 0.0085:1, 0.0090:1, 0.0095:1, 0.0100:1, 0.0150:1, 0.0200:1, 0.0250:1, 0.0300:1, 0.0500:1, 0.1000:1, 0.5000:1, 1:1, 2:1, 3:1, 4:1, 5:1, 6:1, 7:1, 8:1, 9:1 or 10:1, including any range defined between any two of the preceding values

[0164] In some examples, less than a ratio of 10:1 w/w of iodine to CBD (or CBDV) isolate is used.

[0165] In some examples, the CBD isolate (or CBDV isolate) is between 20 and 99% CBD and comprises at least one of propane or butane.

[0166] In some examples, the CBD isolate (or CBDV isolate) is 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95%, 96%, 97%, 98% or 99%, including any range defined between any two of the preceding values

[0167] In some examples, the reaction is carried out between 1 torr and 3 million torr. [0168] In some examples, the reaction is carried out at a pressure of about 1 torr, 2 torr, 3 torr, 4 torr, 5 torr, 6 torr, 7 torr, 8 torr, 9 torr, 10 torr, 20 torr, 30 torr, 40 torr, 50 torr, 60 torr, 70 torr, 80 torr, 90 torr, 100 torr, 200 torr, 300 torr, 400 torr, 500 torr, 600 torr, 700 torr, 800 torr, 900 torr, 1 x 10³ torr, 5 x 10³ torr, 1 x 10⁴ torr, 5 x 10⁴ torr, 1 x 10⁵ torr, 5 x 10⁵ torr, 1 x 10⁶ torr, 2 x 10⁶ torr or 3 x 10⁶ torr, including any range defined between any two of the preceding values

[0169] In some examples, the method further comprises the addition of sodium thiosulphate as a quencher.

[0170] In some examples, the isolate is prepared by CO₂ extraction.

[0171] In some examples, the isolate is first heated to at least 55 degrees centigrade for 20 minutes while stirring and then heated to at least 55 centigrade for at least 20 minutes.

[0172] In some embodiments, the extract or composition is heated to 55°C, 56°C, 57°C, 58°C, 59°C, 60°C, 61°C, 62°C, 63°C, 64°C, 65°C, 66°C, 67°C, 68°C, 69°C, 70°C, 71°C, 72°C, 73°C, 74°C, 75°C, 76°C, 77°C, 78°C, 79°C, 80°C, 81°C, 82°C, 83°C, 84°C, 85°C, 86°C, 87°C, 88°C, 89°C, 90°C, 91°C, 92°C, 93°C, 94°C, 95°C, 96°C, 97°C, 98°C, 99°C, 100°C, 101°C, 102°C, 103°C, 104°C, 105°C, 106°C, 107°C, 108°C, 109°C, 110°C, 115°C, 120°C, 125°C, 130°C, 135°C, 140°C, 145°C, 150°C, 155°C, 160°C, 165°C, 170°C, 175°C, 180°C, 185°C, 190°C, 195°C or 200°C, including any range defined between any two of the preceding values

[0173] In some examples, the heating is continued for 20 min., 25 min., 30 min., 35 min., 40 min., 45 min., 50 min., 55 min., 1 hr., 1.5 hr, 2 hr., 2.5 hr, 3 hr., 3.5 hr, 4 hr., 4.5 hr., 5 hr., 5.5 hr, 6 hr., 6.5 hr, 7 hr., 7.5 hr, 8 hr., 8.5 hr, 9 hr., 9.5 hr or 10 hr, including any range defined between any two of the preceding values

[0174] In some examples, the isolate is first heated to 90 degrees centigrade.

[0175] In some examples, the process does not comprise the addition of a solvent.

[0176] In some examples, the process is performed in a solvent.

[0177] In some examples, the isolate is decarboxylated.

[0178] Some embodiments relate to a method of making D⁸ THC and/or CBN or a homolog thereof, the method comprising:

d) continue heating for at least 20 minutes while stirring, such that the CBD or homolog thereof is converted into D⁸ THC (or a homolog thereof) and/or CBN (or a homolog thereof).

[0179] In some embodiments, the extract or composition is heated to 55°C, 56°C, 57°C, 58°C, 59°C, 60°C, 61°C, 62°C, 63°C, 64°C, 65°C, 66°C, 67°C, 68°C, 69°C, 70°C, 71°C, 72°C, 73°C, 74°C, 75°C, 76°C, 77°C, 78°C, 79°C, 80°C, 81°C, 82°C, 83°C, 84°C, 85°C, 86°C, 87°C, 88°C, 89°C, 90°C, 91°C, 92°C, 93°C, 94°C, 95°C, 96°C, 97°C, 98°C, 99°C, 100°C, 101°C, 102°C, 103°C, 104°C, 105°C, 106°C, 107°C, 108°C, 109°C, 110°C, 115°C, 120°C, 125°C, 130°C, 135°C, 140°C, 145°C, 150°C, 155°C, 160°C, 165°C, 170°C, 175°C, 180°C, 185°C, 190°C, 195°C or 200°C.

[0180] In some examples, the heating is continued for 20 min., 25 min., 30 min., 35 min., 40 min., 45 min., 50 min., 55 min., 1 hr., 1.5 hr, 2 hr., 2.5 hr, 3 hr., 3.5 hr, 4 hr., 4.5 hr., 5 hr., 5.5 hr, 6 hr., 6.5 hr, 7 hr., 7.5 hr, 8 hr., 8.5 hr, 9 hr., 9.5 hr or 10 hr.

[0181] In some examples, the isolate is from a plant.

[0182] In some non-limiting examples, the plant is selected from marijuana (cannabis) and hemp.

[0183] In some examples, in lieu of the isolate, a plant extract is used instead. Example 1

Method of making delta 8 tetrahydrocannabinol ( D⁸ THC) delta 10 tetrahydrocannabinol ( D¹⁰ THC) and/or cannabinol (CBN)

[0184] 1. An extract is obtained that comprises at least one of delta 9 tetrahydrocannabinol ( D⁹ THC) or a cannabidiol (CBD).

[0185] 2. The extract is heated to at least 70 degrees centigrade to make a heated extract. [0186] 3. At least 0.0005:1 weight to weight of iodine to CBD is added to the heated extract.

[0187] 4. The heated extract is for at least 20 minutes while stirring, such that the ( D⁹ THC or CBD is converted into D8 THC, delta 10 tetrahydrocannabinol ( D¹⁰ THC) and/or cannabinol (CBN). Example 2

Method of making D⁸ THC, D⁸ THC and/or CBN

[0188] 1. An extract is obtained that comprises at least one of D⁹ THC or a CBD;

[0189] 2. The extract is heated to at least 70 degrees centigrade to make a heated extract.

[0190] 3. A catalyst is added to the heated extract or composition, wherein the extract or composition to catalyst is present in a ratio of about 1 : 0.0005 (grams of extract or composition to grams of catalyst) to about 1:1 (grams of extract or composition to grams of catalyst).

[0191] 4. The extract is heated for an additional at least 20 minutes while stirring, such that the D⁹ THC or CBD is converted into D⁸ THC, D¹⁰ THC and/or CBN. Example 3

Method of making D⁸ THC and/or CBN (and/or homologs thereof)

[0192] 1. An isolate is obtained that comprises at least a CBD (or a homolog thereof).

[0193] 2. The isolate is heated to between 55 and 800 degrees centigrade to make a heated isolate;

[0194] 3. Between: 0.0001:1 (w/w) of a halogen or a free radical generator to CBD (or a homolog thereof) to 10:1 (w/w) of halogen or a free radical generator to CBD (or a homolog thereof) is added to the heated isolate.

[0195] 4. The isolate is heated for an additional at least 30 minutes, such that the CBD (or a homolog thereof) is converted into D⁸ THC and/or CBN (Cannabinol) (or a homolog thereof). Example 4 Method of making D⁸ THC and/or CBN or a homolog thereof

[0196] 1. An isolate is obtained that comprises a CBD or a homolog thereof.

[0197] 2. The isolate is heated to at least 55 degrees centigrade to make a heated isolate.

[0198] 3. A free radical generator is added to the heated isolate, wherein the isolate to free radical generator is present in a ratio of about 1:0.0001 (grams of isolate to grams of free radical generator) to about 1:10 (grams of isolate to grams of free radical generator).

[0199] 4. the isolate is heated for an additional at least 20 minutes while stirring, such that the CBD or homolog thereof is converted into D8 THC (or a homolog thereof) and/or CBN (or a homolog thereof).

Example 5

[0200] Each one of Examples 1-4 can be employed for the reaction scheme noted above in the alternative. This allows for the conversion of a CBD homolog to one or both of a CBN homolog and/or a THC homolog (as shown in FIG.1). [0201] While various embodiments are provided herein in terms of an isolate, in some embodiments, any one of these embodiments can be modified and applied to an extract.

[0202] Although the present application has been described in detail above, it will be understood by one of ordinary skill in the art that various modifications can be made without departing from the spirit of the invention. Accordingly, the present application is limited only by the following claims. All cited patents, patent applications and publications referred to in this application are herein incorporated by reference in their entirety. In this application, the use of the singular can include the plural unless specifically stated otherwise or unless, as will be understood by one of skill in the art in light of the present disclosure, the singular is the only functional embodiment. Thus, for example, "a" can mean more than one, and "one embodiment" can mean that the description applies to multiple embodiments. Additionally, in this application, "and/or" denotes that both the inclusive meaning of "and" and, alternatively, the exclusive meaning of "or" applies to the list. Thus, the listing should be read to include all possible combinations of the items of the list and to also include each item, exclusively, from the other items. The addition of this term is not meant to denote any particular meaning to the use of the terms "and" or "or" alone. The meaning of such terms will be evident to one of skill in the art upon reading the particular disclosure. All references cited herein, including patents, patent applications, papers, text books, and the like, and the references cited therein, to the extent that they are not already, are hereby incorporated by reference in their entirety. In the event that one or more of the incorporated literature and similar materials differs from or contradicts this application, including but not limited to defined terms, term usage, described techniques, or the like, this application controls. The foregoing description details certain preferred embodiments of the invention and describes the best mode contemplated by the inventors. It will be appreciated, however, that no matter how detailed the foregoing may appear in text, the invention may be practiced in many ways and the invention should be construed in accordance with the appended claims and any equivalents thereof. As will be appreciated by one of skill in the art, while the present specification may simply use one of the terms "comprise," "consists," or "consists essentially of," this is simply a shorthand way of describing all three possibilities, unless otherwise specified or unless the term is used in the claim (in which case the terms will have their normally accepted meanings under claim interpretation). Thus, as the terms are used above, they designate all three possibilities, unless explicitly noted otherwise.

Claims

WHAT IS CLAIMED IS:

1. A method of making delta 8 tetrahydrocannabinol ( D⁸ THC), delta 10 tetrahydrocannabinol ( D¹⁰ THC) and/or cannabinol (CBN), the method comprising:

d) continue heating for at least 20 minutes while stirring, such that the ( D⁹ THC or CBD is converted into D⁸ THC, delta 10 tetrahydrocannabinol ( D¹⁰ THC) and/or cannabinol (CBN).

2. The method of claim 1, wherein the extract or composition comprises CBD.

3. The method of claim 2, wherein the CBD is converted to D⁸ THC.

4. The method of any one of claims 1-3, wherein there is no significant amount of D⁹ THC in the product containing D⁸ THC.

5. The method of any one of claims 1-3, wherein less than 0.3% w/w of D⁹ THC is present after the reaction.

6. The method of claim 1, wherein at least 50% of the CBD is converted to D⁸ THC.

7. The method of claim 2, wherein at least 99% of the CBD is converted to D⁸ THC.

8. The method of any one of claims 1-7, wherein at least 90% of the CBD is converted to D⁸ THC.

9. The method of any one of claims 1-8, wherein substantially all CBD is converted to D⁸ THC.

10. The method of any one of claims 1-9, wherein the extract or composition is heated to at least 55 degrees centigrade.

11. The method of any one of claims 1-10, wherein at least 1.0 g of iodine is employed.

12. The method of any one of claims 1-10, wherein a ratio of 0.001:1 w/w of iodine to CBD is used.

13. The method of any one of claims 1-12, further comprising the addition of calcium carbonate to the heated extract or composition.

14. The method of any one of claims 1-13, further comprising the addition of sodium thiosulphate.

15. The method of any one of claims 1-14, wherein the extract or composition is prepared by CO₂ extraction.

16. The method of any one of claims 1-15, wherein a ratio of 40 g of extract or composition is employed to 1.2g of elemental iodine.

17. The method of any one of claims 1-16, wherein the extract or composition is first heated to at least 55 degrees centigrade for 20 minutes while stirring and then heated to at least 55 centigrade for at least 20 minutes.

18. The method of any one of claims 1-17, wherein the extract or composition is first heated to 90 degrees centigrade.

19. The method of any one of claims 1-18, wherein the method comprises stirring and heating to at least 100 degrees centigrade.

20. The method of any one of claims 1-19, wherein the process does not comprise the addition of a solvent.

21. The method of any one of claims 1-19, wherein the process does not involve a use of a solvent between providing a extract or composition and production of D⁸ THC.

22. The method of any one of claims 1-21, wherein no organic solvent is employed during a heating step b).

23. The method of any one of claims 1-21, wherein no organic solvent is employed during d).

24. The method of any one of claims 1-21, wherein no organic solvent is employed during a, b, c, or d.

25. The method of any one of claims 1-24, wherein no organic solvent is employed during the process.

26. The method of any one of claims 1-25, wherein the extract or composition is CO₂ extracted from hemp.

27. The method of any one of claims 1-26, wherein the extract or composition is decarboxylated.

28. The method of any one of claims 1-25, wherein the extract or composition is CO₂ extracted from hemp and the extract or composition is then decarboxlated in order to produce the extract or composition used as the starting material.

29. A method of making D⁸ THC, the method comprising:

a) providing an extract or composition that comprises at least one of D⁹ THC or a CBD (or homologs of either);

d) continue heating for at least 20 minutes while stirring, such that the D⁹ THC or CBD (or homologs of either) is converted into D⁸ THC, D¹⁰ THC and/or CBN (or homologs of any of these).

30. The method of claim 29, wherein the catalyst is a metallic catalyst.

31. The method of claim 29, wherein the catalyst is a non-metallic catalyst.

32. The method of any one of claims 1-20, wherein the extract is a plant extract.

33. A method of making D⁸ THC and/or CBN (and/or homologs thereof), the method comprising:

34. The method of claim 33, wherein the CBD homolog is cannabidivarin (CBDV).

35. The method of claim 34, wherein the reaction produces at least Tetrahydrocannabivarin (THCV).

36. The method of claim 33, wherein the isolate comprises between 20-95% CBD (or CBDV).

37. The method of claim 34, wherein the CBD is converted to D⁸ THC.

38. The method of any one of claims 33-37, wherein the halogen or a free radical generator comprises iodine.

39. The method of any one of claims 33-38, wherein there is no significant amount of D⁹ THC remaining.

40. The method of any one of claims 33-39, wherein less than 0.3% w/w of D⁹ THC is present after the reaction.

41. The method of any one of claims 33-40, wherein at least 50% of the CBD is converted to D⁸ THC.

42. The method of any one of claims 33-40, wherein at least 99% of the CBD is converted to D⁸ THC.

43. The method of any one of claims 33-42, wherein at least 90% of the CBD is converted to D⁸ THC.

44. The method of any one of claims 33-43, wherein substantially all CBD is converted to D⁸ THC and CBN.

45. The method of any one of claims 33-43, wherein substantially all CBDV is converted to D⁸ THCV and CBV.

46. The method of any one of claims 33-43, wherein CBDV is converted to D⁸ THCV and CBV.

47. The method of any one of claims 33-46, wherein the isolate is heated to at least 70 degrees centigrade.

48. The method of any one of claims 33-47, wherein at least 1.0 g of iodine is employed.

49. The method of any one of claims 33-48, wherein at least ratio of 0.001:1 w/w of iodine to CBD (or CBDV) isolate is used.

50. The method of claim 49, wherein less than a ratio of 10:1 w/w of iodine to CBD (or CBD) isolate is used.

51. The method of any one of claims 33-50, wherein the CBD isolate (or CBDV isolate) is between 20 and 99% CBD and comprises at least one of propane or butane.

52. The method of any one of claims 33-51, wherein the reaction is carried out between 1 torr and 3 million torr.

53. The method of any one of claims 33-52, further comprising the addition of sodium thiosulphate as a quencher.

54. The method of any one of claims 33-53, wherein the isolate is prepared by CO₂ extraction.

55. The method of any one of claims 33-54, wherein the isolate is first heated to at least 55 degrees centigrade for 20 minutes while stirring and then heated to at least 55 centigrade for at least 20 minutes.

56. The method of any one of claims 33-50, wherein the isolate is first heated to 90 degrees centigrade.

57. The method of any one of claims 33-56, wherein the process does not comprise the addition of a solvent.

58. The method of any one of claims 33-56, wherein the process is performed in a solvent.

59. The method of any one of claims 33-58, wherein the isolate is decarboxylated.

60. A method of making D⁸ THC and/or CBN or a homolog thereof, the method comprising:

a) providing an isolate that comprises a CBD or a homolog thereof;

b) heating the isolate to at least 55 degrees centigrade to make a heated isolate;

c) adding a free radical generator to the heated isolate, wherein the isolate to free radical generator is present in a ratio of about 1:0.0001 (grams of isolate to grams of free radical generator) to about 1:10 (grams of isolate to grams of free radical generator); and d) continue heating for at least 20 minutes while stirring, such that the CBD or homolog thereof is converted into D⁸ THC (or a homolog thereof) and/or CBN (or a homolog thereof).

61. The method of any one of claims 33-60, wherein the isolate is from a plant.

62. The method of any one of claims 33-60, wherein, in lieu of the isolate, a plant extract is used instead.

63. A method of converting A to C, D, or C and D as denoted below:

wherein, R1 and R2 can be any alkyl group.

64. The method of claim 63, wherein R1 and R2 are separately selected from any alkyl that is 1-20 carbon atoms in length.

65. The method of claim 64, further comprising

a) providing an isolate that comprises the compound A (a CBD homolog);

c) adding between: 0.0001:1 (w/w) of a halogen or a free radical generator to A to 10:1 (w/w) of halogen or a free radical generator to A to the heated isolate; and d) continue heating for at least 30 minutes such that the A is converted into a CBN homolog and/or a THC homolog.

66. The method of any one of claims 63-65, wherein A is a CBD homolog that is converted to one of a CBN homolog or a THC homolog.

67. The method of any one of claims 63-65, wherein A is a CBD homolog that is converted to both of a CBN homolog and a THC homolog.