Coloring agent, and detection method and detection kit for cannabinoids

Abstract

To provide a coloring agent capable of detecting cannabinoids, and a detection method and a detection kit for cannabinoids.SOLUTION: A coloring agent comprises a compound represented by formula (1) or formula (2). (In the formulas, R1 is a nitro group, cyano group, hydroxy group, alkoxy group, carboxy group, sulfo group, alkyl group, halogenated alkyl group, H, or the like; R2 and R4 are each a nitro group, cyano group, hydroxy group, alkoxy group, carboxy group, sulfo group, alkyl group, H, or the like; R3 and R5 are each an alkoxy group, alkyl group, alkenyl group, substituted or unsubstituted phenyl group, hydroxy group, or H; R6 and R7 are each an alkoxy group, alkyl group, or phenyl group; and X- and Y- are counter anions.)SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to a color former for detecting cannabinoids, a method for detecting cannabinoids, and a detection kit.

Background Art

[0002] Among the cannabinoids contained in cannabis, there are tetrahydrocannabinol (THC) and the like, which fall under the category of cannabis under the Cannabis Control Law of Japan and are illegal components, and cannabidiol (CBD), cannabinol (CBN), and the like, which do not fall under the category of cannabis under the Cannabis Control Law and are legal components. Legal components such as CBD and CBN can be imported, manufactured, and sold in Japan. For example, since CBD has a relaxation effect, products containing CBD are manufactured and sold in Japan. In the case of products containing legal components such as CBD and CBN, especially imported products, there is a concern that the illegal component THC may be mixed in during the manufacturing process. Therefore, it is obligatory to prove that THC is not contained. In addition, THC acts on the brain. When abused, it causes cannabis dependence, and there are many cases where users seek stronger stimulants and turn to drugs more toxic than cannabis. Therefore, THC is called a "gateway drug," and domestic laws prohibit its possession, transfer, import, export, and cultivation. On the other hand, different regulations may be in place overseas compared to Japan. For this reason, there is a need for a technology that can accurately, simply detect, and distinguish cannabinoids such as THC, CBN, and CBD.

[0003] As a technology for detecting such cannabinoids, a technology using Fast Blue BB or Fast Blue RR as a colorimetric reagent has been disclosed (for example, Non-Patent Document 1).

Prior Art Documents

Non-Patent Documents

[0004]

Non-Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0005] However, with conventionally used Fast Blue BB and Fast Blue RR in Non-Patent Document 1 and the like, the detection accuracy of cannabinoids may be insufficient. Therefore, it is desirable to be able to detect and distinguish cannabinoids such as THC, CBN, and CBD with higher accuracy than Fast Blue BB and Fast Blue RR.

[0006] The present invention has been made in view of the above problems, and an object thereof is to provide a color former capable of detecting cannabinoids, a method for detecting cannabinoids using the color former, and a detection kit using the color former.

Means for Solving the Problems

[0007] The present inventors have found that the above problems can be solved by a color former containing a compound represented by the following formula (1) or a compound represented by the following formula (2), and have completed the present invention. More specifically, the present invention provides the following.

[0008] [1] A color former for detecting cannabinoids, A color former containing a compound represented by the following formula (1) or a compound represented by the following formula (2).

Chemical formula

[0009] [2] The color former according to [1] above, which detects at least one selected from tetrahydrocannabinol, cannabidiol, cannabinol, cannabigerol, cannabidiolic acid, cannabinichrome, hexahydrocannabinol, hexahydrocannabinol - O - acetate and tetrahydrocannabinol - O - acetate.

[0010] [3] The color former according to [1] or [2] above, which detects at least one selected from tetrahydrocannabinol, cannabidiol and cannabinol.

[0011] [4] A method for detecting cannabinoids, a contacting step of contacting a sample that may contain the cannabinoids with a coloring solution containing the color former according to any one of [1] to [3] above, A detection method for cannabinoids, comprising a detection step of detecting the cannabinoids based on the color of a contact liquid obtained by contacting the sample with the coloring liquid in the contact step.

[0012] [5] The detection method for cannabinoids according to [4] above, comprising a conversion step of converting a compound represented by the following formula (i) or a compound represented by the following formula (ii), which is a precursor of the compound represented by the formula (1) or the compound represented by the formula (2), into the compound represented by the formula (1) or the compound represented by the formula (2).

Chemical formula

Chemical formula

[0013] [6] The detection method for cannabinoids according to [5] above, wherein the conversion step is performed before the contact step.

[0014] [7] The detection method for cannabinoids according to any one of [4] to [6] above, wherein the sample contains at least one selected from tetrahydrocannabinol, cannabidiol, cannabinol, cannabigerol, cannabinoid, cannabichromene, hexahydrocannabinol, hexahydrocannabinol - O - acetate, and tetrahydrocannabinol - O - acetate.

[0015] [8] The detection method of cannabinoids according to [7] above, wherein the sample contains at least one selected from tetrahydrocannabinol, cannabidiol, and cannabinol.

[0016] [9] The detection method of cannabinoids according to any one of [4] to [8] above, wherein the sample is a leachate or extract from at least one selected from plant pieces, foods, daily necessities, and luxury goods.

[0017]

[10] The detection method of cannabinoids according to any one of [4] to [9] above, wherein the sample is a substance derived from cannabis.

[0018]

[11] A detection kit for detecting cannabinoids, a coloring solution containing a coloring agent according to any one of [1] to [3] above, or a reagent solution containing a compound represented by the following formula (i) or a compound represented by the following formula (ii), which is a precursor of the compound represented by the formula (1) or the compound represented by the formula (2), and a detection kit including the coloring solution or the reagent solution and a container capable of contacting a sample that may contain the cannabinoids.

Chemical formula

Chemical formula

Advantages of the Invention

[0019] According to the present invention, it is possible to provide a color former that can accurately and simply detect cannabinoids, a method for detecting cannabinoids using the color former, and a detection kit using the color former.

Brief Description of the Drawings

[0020]

Figure 1

Figure 2

Modes for Carrying Out the Invention

[0021] ≪Color Former≫ The color former according to the present embodiment is a color former for detecting cannabinoids, and includes a compound represented by the following formula (1) or a compound represented by the following formula (2). The compound represented by the following formula (1) and the compound represented by the following formula (2) are diazonium salts as shown in each formula.

Chemical Formula

Chemical formula

[0022] Examples of cannabinoids include tetrahydrocannabinol (THC), cannabidiol (CBD), cannabinol (CBN), cannabigerol (CBG), cannabidiolic acid (CBDA), cannabichromene (CBC), hexahydrocannabinol (HHC), hexahydrocannabinol - O - acetate (HHC - O), and tetrahydrocannabinol - O - acetate (THC - O).

[0023] The color former according to this embodiment can detect at least one of cannabinoids. That is, the color former according to this embodiment can determine the presence or absence of at least one of cannabinoids (for example, at least one selected from THC, CBD, and CBN).

[0024] Also, depending on the types of the compound represented by the above formula (1) and the compound represented by the above formula (2) contained in the color former, THC, CBD, and CBN can also be discriminated (distinguished). For example, THC can be discriminated from at least one of CBD and CBN. Also, THC, CBD, and CBN can be discriminated from each other. Note that since the presence or absence is also determined during discrimination, in this specification, "detection" includes the concept of "discrimination". In Japan, THC is an illegal component (illegal drug), and CBD and CBN are legal components. Therefore, the ability to discriminate THC from at least one of CBD and CBN is particularly beneficial.

[0025] In addition, the detection of cannabinoids using a color former containing the compound represented by the above formula (1) or the compound represented by the above formula (2) is a simple method because it can be carried out visually.

[0026] In addition, the color development between the compound represented by the above formula (1) or the compound represented by the above formula (2) and cannabinoids can accurately identify cannabinoids because the color difference between different types of cannabinoids (for example, THC, CBD, and CBN) is large. By using a device capable of quantifying color such as a color difference meter, cannabinoids can be identified with higher accuracy. Because cannabinoids can be accurately identified, for example, with respect to THC, which is an illegal drug, false positives and mistaken arrests can be suppressed.

[0027] In formula (1), R 1 The number of carbon atoms of the alkoxy group as R is not particularly limited, but is preferably 1 or more and 8 or less carbon atoms, more preferably 1 or more and 4 or less carbon atoms. R 1 Examples of the alkoxy group as R include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butyloxy group, an isobutyloxy group, a sec-butyloxy group, a tert-butyloxy group, an n-pentyloxy group, an n-hexyloxy group, an n-heptyloxy group, an n-octyloxy group, and the like. R 1 The number of carbon atoms of the alkyl group as R is not particularly limited, but is preferably 1 or more and 8 or less carbon atoms, more preferably 1 or more and 4 or less carbon atoms. R 1 Examples of the alkyl group as R include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, and an n-octyl group. R 1 The number of carbon atoms of the halogenated alkyl group as R is not particularly limited, but is preferably 1 or more and 8 or less carbon atoms, more preferably 1 or more and 4 or less carbon atoms. R 1Examples of the alkyl halide group as such include groups in which some or all of the hydrogen atoms of the aforementioned alkyl group are substituted with halogen atoms such as fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms. Examples of the alkyl halide group include chloromethyl group, dichloromethyl group, trichloromethyl group, bromomethyl group, dibromomethyl group, tribromomethyl group, fluoromethyl group, difluoromethyl group, trifluoromethyl group, 1,1-difluoroethyl group, and 1,1,2,2,2-pentafluoroethyl group, etc. R 1 Examples of the substituent in the styryl group which may have a substituent as such include nitro group, etc. R 1 Examples of the halogen atom as such include fluorine atom, chlorine atom, bromine atom, iodine atom, etc.

[0028] In formula (1), R 2 and R 4 The number of carbon atoms of the alkoxy group as such is not particularly limited, but is preferably 1 or more and 8 or less, and more preferably 1 or more and 4 or less. R 2 and R 4 Examples of the alkoxy group as such include methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butyloxy group, isobutyloxy group, sec-butyloxy group, tert-butyloxy group, n-pentyloxy group, n-hexyloxy group, n-heptyloxy group, n-octyloxy group, etc. R 2 and R 4 The number of carbon atoms of the alkyl group as such is not particularly limited, but is preferably 1 or more and 8 or less, and more preferably 1 or more and 4 or less. R 2 and R 4 Examples of the alkyl group as such include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, and n-octyl group, etc. R 2 and R 4The number of carbon atoms of the alkenyl group as such is not particularly limited, but is preferably 2 or more and 8 or less, more preferably 2 or more and 4 or less. R 2 and R 4 Examples of the alkenyl group as such include a vinyl group, 1-propenyl group, 2-n-propenyl group (allyl group), 1-n-butenyl group, 2-n-butenyl group, and 3-n-butenyl group. R 2 and R 4 The number of carbon atoms of the alkyl halide group as such is not particularly limited, but is preferably 1 or more and 8 or less, more preferably 1 or more and 4 or less. R 1 Examples of the alkyl halide group as such include groups in which some or all of the hydrogen atoms of the aforementioned alkyl group are substituted with halogen atoms such as fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms. Examples of the alkyl halide group include chloromethyl group, dichloromethyl group, trichloromethyl group, bromomethyl group, dibromomethyl group, tribromomethyl group, fluoromethyl group, difluoromethyl group, trifluoromethyl group, 1,1-difluoroethyl group, and 1,1,2,2,2-pentafluoroethyl group. R 2 and R 4 Examples of the substituent in the styryl group which may have a substituent as such include a nitro group. R 2 and R 4 Examples of the halogen atom as such include fluorine atom, chlorine atom, bromine atom, iodine atom.

[0029] In formula (1), R 3 and R 5 The number of carbon atoms of the alkoxy group as such is not particularly limited, but is preferably 1 or more and 8 or less, more preferably 1 or more and 4 or less. R 3 and R 5Examples of the alkoxy group include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butyloxy group, an isobutyloxy group, a sec-butyloxy group, a tert-butyloxy group, an n-pentyloxy group, an n-hexyloxy group, an n-heptyloxy group, an n-octyloxy group and the like. R 3 and R 5 Although the number of carbon atoms of the alkyl group as R is not particularly limited, it is preferably 1 or more and 8 or less, more preferably 1 or more and 4 or less. R 3 and R 5 Examples of the alkyl group as R include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, and an n-octyl group and the like. R 3 and R 5 Although the number of carbon atoms of the alkenyl group as R is not particularly limited, it is preferably 2 or more and 8 or less, more preferably 2 or more and 4 or less. R 3 and R 5 Examples of the alkenyl group as R include a vinyl group, a 1-propenyl group, a 2-n-propenyl group (allyl group), a 1-n-butenyl group, a 2-n-butenyl group, and a 3-n-butenyl group and the like. R 3 and R 5 Examples of the substituent in the phenyl group which may have a substituent as R include an alkoxy group, a phenyl group and the like. Although the number of carbon atoms of the alkoxy group as the substituent is not particularly limited, it is preferably 1 or more and 8 or less, more preferably 1 or more and 4 or less. Examples of the alkoxy group as the substituent include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butyloxy group, an isobutyloxy group, a sec-butyloxy group, a tert-butyloxy group, an n-pentyloxy group, an n-hexyloxy group, an n-heptyloxy group, an n-octyloxy group and the like. X - Examples of the counter anion as X include Cl - , BF4 - and the like.

[0030] R 4 and R 5 form a ring by bonding to each other, R 4 and R 5 are such that R 4 and R 5 may form a naphthalene ring together with the benzene ring to which they are bonded.

[0031] Specific examples of the compound represented by formula (1) include compounds represented by the following formulas (1-1) to (1-25), and Cl in the compounds represented by the following formulas (1-1) to (1-25) - is BF4 - and the like. In the following formulas, R 8 represents an alkyl group having 1 to 4 carbon atoms.

Chemical formula

[0032]

Chemical formula

[0033] From the viewpoint that THC can be distinguished from CBD and CBN, in the compound represented by formula (1), R 1 is a nitro group, a cyano group, a hydroxy group, an alkoxy group, a carboxy group, an alkyl group, a halogenated alkyl group, a styryl group having no substituent, or a hydrogen atom, and R 2 and R 4 are each independently a nitro group, a cyano group, a hydroxy group, an alkoxy group, a carboxy group, an alkyl group, an alkenyl group, a halogenated alkyl group, or a styryl group having no substituent, or a hydrogen atom, and R 3 and R 5 are each independently an alkoxy group, an alkyl group, an alkenyl group, a phenyl group which may have a substituent, or a hydrogen atom, and R 1 R 2 and R 4 will not simultaneously become hydrogen atoms, R4 and R 5 may be bonded to each other to form a ring, and X - is preferably a compound that is a counteranion. Such compounds preferably include the compounds represented by the above formulas (1-1) to (1~17) and (1-25).

[0034] Also, from the viewpoint that THC, CBD, and CBN can each be identified, R 1 is a nitro group, a cyano group, a hydroxy group, an alkoxy group, a carboxy group, an alkyl group, a halogenated alkyl group, a styryl group having no substituent, or a hydrogen atom, and R 2 and R 4 are each independently a nitro group, a cyano group, a hydroxy group, a carboxy group, an alkyl group, an alkenyl group, a halogenated alkyl group, a styryl group having no substituent, or a hydrogen atom, and R 3 and R 5 are each independently an alkoxy group, an alkyl group, an alkenyl group, a phenyl group that may have a substituent, or a hydrogen atom, and R 1 , R 2 and R 4 do not simultaneously become hydrogen atoms, and R 4 and R 5 may be bonded to each other to form a ring, and X - is preferably a compound that is a counteranion. Such compounds preferably include the compounds represented by the above formulas (1-1) to (1~17).

[0035] In formula (2), the number of carbon atoms of the alkoxy group as R 6 and R 7 is not particularly limited, but is preferably 1 or more and 8 or less carbon atoms, and more preferably 1 or more and 4 or less carbon atoms. Examples of the alkoxy group as R 6 and R 7 include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butyloxy group, an isobutyloxy group, a sec-butyloxy group, a tert-butyloxy group, an n-pentyloxy group, an n-hexyloxy group, an n-heptyloxy group, an n-octyloxy group, and the like. R 6 and R 7 The number of carbon atoms of the alkyl group as R is not particularly limited, but is preferably 1 or more and 8 or less, and more preferably 1 or more and 4 or less. R 6 and R 7 Examples of the alkyl group as R and R include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, and an n-octyl group. Y - Examples of the counter anion as Y include Cl - , BF4 - and the like.

[0036] Specific examples of the compound represented by formula (2) include compounds represented by the following formulas (2-1) to (2-2), and Cl in the compounds represented by the following formulas (2-1) to (2-2) - is BF4 - and the like. In the following formulas, R 9 represents an alkyl group having 1 to 4 carbon atoms.

Chemical formula

[0037] From the viewpoint that THC, CBD, and CBN can be respectively identified, in the compound represented by formula (2), R 6 and R 7 are preferably compounds that are phenyl groups. As such a compound, the compound represented by the above formula (2-1) is preferred.

[0038] The color former preferably contains only one of the compound represented by formula (1) and the compound represented by formula (2).

[0039] The method for preparing the above color former is not particularly limited. For example, the compound represented by the following formula (i) or the compound represented by the following formula (ii), which is a precursor of the compound represented by the above formula (1) or the compound represented by the above formula (2), can be converted, that is, diazotized, to obtain the compound represented by the above formula (1) or the compound represented by the above formula (2).

Chemical formula

Chemical formula

[0040] As a method for diazotizing the compound represented by formula (i) or the compound represented by formula (ii), for example, a method of diazotizing the compound represented by formula (i) or the compound represented by formula (ii) in the presence of hydrochloric acid can be mentioned. Thereby, a compound represented by formula (i) or a compound represented by formula (ii) in which the counter ions X - , Y - are Cl - is obtained. Furthermore, by reacting with tetrafluoroboric acid, a compound represented by formula (i) or a compound represented by formula (ii) in which the counter ions X - , Y - are BF4 - is obtained.

[0041] The reaction conditions for diazotization are not particularly limited. The reaction temperature for diazotization is preferably 0°C or higher and 25°C or lower, more preferably 0°C or higher and 10°C or lower. Also, the reaction time for diazotization is preferably 10 minutes or longer and 2 hours or shorter.

[0042] Since diazonium salts are prone to decomposition when exposed to light or heat, the compounds represented by formula (i) or the compounds represented by formula (ii) can be prepared in advance and converted into diazonium salts (compounds represented by formula (1) or compounds represented by formula (2)) as needed for use. Aromatic amines can be easily converted into diazonium salts by reacting with nitrites.

[0043] The color former according to this embodiment preferably contains a solvent. The solvent is not particularly limited, and examples include aqueous solutions containing acids such as hydrochloric acid, nitric acid, and sulfuric acid. Also, the color former according to this embodiment may contain other components other than the compound represented by formula (1), the compound represented by formula (2), and the solvent.

[0044] When the color former according to this embodiment contains a solvent or other components, the color former can be produced by mixing the compound represented by formula (1) or the compound represented by formula (2) with the solvent and other components that are contained as needed.

[0045] ≪Method for Detecting Cannabinoids≫ The method for detecting cannabinoids according to this embodiment is a method for detecting cannabinoids that detects cannabinoids, a contacting step of contacting a sample that may contain cannabinoids with a coloring solution containing the above-described color former, and a detecting step of detecting cannabinoids based on the color of the contacting solution obtained in the contacting step, in which the sample and the coloring solution are in contact. The detection method of cannabinoids according to this embodiment may include a conversion step of converting a compound represented by the above formula (i) or a compound represented by the above formula (ii), which is a precursor of the compound represented by the above formula (1) or the compound represented by the above formula (2), into the compound represented by the above formula (1) or the compound represented by the above formula (2). Each step will be described below.

[0046] <Contact step> In the contact step, a sample (i.e., the test subject) that may contain cannabinoids is contacted with a coloring solution containing the above-described coloring agent. Thereby, a contact solution in which the sample and the coloring solution are in contact is obtained. Further, when the sample that may contain cannabinoids contains cannabinoids, a coloring reaction between the cannabinoids and the coloring agent occurs in the contact step.

[0047] Cannabinoids are as described in the above ≪Coloring agent≫. The sample that may contain cannabinoids is not particularly limited, and examples thereof include leachates or extracts from at least one selected from plant pieces, foods, daily necessities, and luxury goods. The leachate is, for example, a liquid that comes out of plant pieces, foods, daily necessities, luxury goods, etc., or their pulverized products. The extract is, for example, a liquid extracted with a solvent using plant pieces, foods, daily necessities, luxury goods, etc., their pulverized products, or their leachates as raw materials. Examples of the extraction solvent include alcohols such as methanol, ethanol, and propanol, and methanol etc. are preferable. Specific examples of the sample that may contain cannabinoids include cannabis-derived substances (for example, cannabis extracts) derived from cannabis plants. The coloring solution containing the coloring agent that is contacted with the sample that may contain cannabinoids may be a solution in which the coloring agent is dissolved in a solvent, or may be the coloring agent itself when the coloring agent contains a solvent.

[0048] The method of bringing a sample that may contain cannabinoids into contact with a coloring solution containing the above-described coloring agent is not particularly limited. For example, methods of mixing the sample and the coloring solution include adding the coloring solution to the sample or adding the sample to the coloring solution.

[0049] <Detection step> In the detection step, cannabinoids are detected based on the color of the contact solution obtained in the contact step, in which the sample and the coloring solution are in contact. The method of detecting cannabinoids based on the color of the contact solution is not particularly limited. For example, a method of comparing a sample of the color produced by the coloring reaction between each cannabinoid (e.g., THC, CBD, or CBN) and the coloring agent with the color of the contact solution obtained in the contact step can be mentioned. The comparison may be made visually or using a device having a comparison function. In particular, when the sample is colored, discrimination can be made by determining the difference between the color of the initial sample and the color after the coloring reaction. Also, using Carbons S manufactured by Agilent or QuEChERS, etc., impurities and the like that cause the coloring of the contact solution can be removed in advance before contacting the coloring solution.

[0050] Since the method for detecting cannabinoids according to this embodiment uses the above-described coloring agent containing the compound represented by the above formula (1) or the compound represented by the above formula (2), the detection of cannabinoids can be performed visually. Therefore, cannabinoids can be detected easily. In addition, the coloring reaction between the compound represented by the above formula (1) or the compound represented by the above formula (2) and cannabinoids has a large color difference among different types of cannabinoids (e.g., THC, CBD, and CBN). Therefore, cannabinoids can be discriminated with high accuracy.

[0051] <Conversion step> In the conversion step, the compound represented by the above formula (i) or the compound represented by the above formula (ii), which is a precursor of the compound represented by the above formula (1) or the compound represented by the above formula (2), is converted to obtain the compound represented by the above formula (1) or the compound represented by the above formula (2). The conversion step is preferably performed before the contact step. Further, the conversion step may be performed before the detection step or may be performed simultaneously with the detection step. The conversion, i.e., diazotization, is as described in the above-mentioned <<Color former>>.

[0052] In addition, by combining the detection method of cannabinoids according to this embodiment using a color former and the detection method of cannabinoids according to this embodiment using a color former different from the said color former, it is also possible to detect cannabinoids with higher accuracy.

[0053] <<Detection kit>> The detection kit according to this embodiment is a detection kit for detecting cannabinoids, a color developing solution containing the above-mentioned color former, or a reagent solution containing the compound represented by the above formula (i) or the compound represented by the above formula (ii), which is a precursor of the compound represented by the above formula (1) or the compound represented by the above formula (2), and a container capable of bringing the color developing solution or the reagent solution into contact with a sample that may contain cannabinoids.

[0054] Regarding cannabinoids, the color developing solution containing a color former, and a sample that may contain cannabinoids, they are as described in the above-mentioned <<Detection method of cannabinoids>>. The container capable of bringing the color developing solution or the reagent solution into contact with a sample that may contain cannabinoids is not particularly limited, but a transparent or translucent container is preferred. Examples of the container include a test tube and a bottle.

Examples

[0055] Hereinafter, the present invention will be described in detail with reference to examples, but the scope of the present invention is not limited to these examples.

[0056] [Synthesis of diazonium salt and preparation of color former] (Synthesis Example 1) Synthesis of the compound represented by the following formula (1-1-1) [Chemical formula]

[0057] The compound (2,6-dimethoxy-4-nitroaniline) (20 mg, 0.10 mmol) represented by the above formula (1-1-1a) that can be synthesized by the method described in J.Med.Chem.1983, 26, 1625 was added with a solution prepared by dissolving 12N HCl (250 μL) and sodium nitrite (6.9 mg, 0.10 mmol) in purified water (750 μL) under ice-cooling, and stirred for 30 minutes to obtain a solution (color former) containing the compound represented by the above formula (1-1-1).

[0058] (Synthesis Example 2) Synthesis of the compound represented by the following formula (1-2)

Chemical formula

[0059] First, the compound (2,6-dibromo-4-nitroaniline) represented by the above formula (1-2a-a) was synthesized. Specifically, 4-nitroaniline (1.0 g, 7.2 mmol) was dissolved in acetonitrile (36 mL), N-bromosuccinimide (2.7 g, 15 mmol) was added, and the mixture was stirred at room temperature for 4 hours under an argon atmosphere. Further, N-bromosuccinimide (1.7 g, 10 mmol) was added, and the mixture was stirred at room temperature for 14 hours under an argon atmosphere. After adding an aqueous sodium thiosulfate solution, the mixture was extracted with ethyl acetate, washed with saturated brine, and dried by adding sodium sulfate. The insoluble matter was filtered and concentrated, and recrystallized from ethyl acetate / hexane (40 mL / 5 mL) to obtain primary crystals (1.3 g, yield 61%). The remaining residue was recrystallized from ethyl acetate / hexane (20 mL / 2.5 mL) to obtain secondary crystals (0.31 g, yield 14%) (total 1.6 g, yield 75%). 1 H NMR (400 MHz, CDCl3); δ 5.29 (brs, 2H, NH2), 8.35 (s, 2H) ppm.

[0060] The obtained compound (2,6-dibromo-4-nitroaniline) (1.1 g, 3.8 mmol) represented by the formula (1-2a-a) was dissolved in toluene (19 mL) and purified water (19 mL), and phenylboronic acid (1.0 g, 8.3 mmol), palladium(II) acetate (44 mg, 0.20 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (155 mg, 0.378 mmol), and potassium phosphate (2.4 g, 11 mmol) were added. After degassing, the mixture was stirred under heating under reflux in an argon atmosphere for 19 hours. Palladium acetate was removed by filtration through celite, extracted with ethyl acetate, washed with saturated brine, and dried by adding sodium sulfate. The insoluble matter was filtered off and concentrated, and the crude product was purified by column chromatography (ethyl acetate / hexane = 1 / 4) to obtain the compound represented by the above formula (1-2a) as a powdery substance (1.1 g, yield 99%). 1 1H NMR (400 MHz, CDCl3); δ 4.58 (brs, 2H, NH2), 7.41 - 7.54 (m, 10H), 8.06 (s, 2H) ppm.

[0061] To the obtained compound (29 mg, 0.10 mmol) represented by the formula (1-2a), a solution prepared by dissolving 12N HCl (250 μL) and sodium nitrite (6.9 mg, 0.10 mmol) in purified water (750 μL) was added under ice cooling, and the mixture was stirred for 30 minutes to obtain a solution (color former) containing the compound represented by the above formula (1-2).

[0062] (Synthesis Example 3) Synthesis of the compound represented by the following formula (1-3-1)

Chemical formula

[0063] The compound (2,6-dibromo-4-nitroaniline) (1.3 g, 4.4 mmol) represented by the formula (1-2a-a) obtained in the same manner as above was dissolved in toluene (22 mL) and purified water (22 mL), and 4-methoxyphenylboronic acid (1.5 g, 9.7 mmol), palladium(II) acetate (50 mg, 0.22 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (182 mg, 0.443 mmol), and potassium phosphate (2.8 g, 13 mmol) were added. After degassing, the mixture was stirred under heating and reflux in an argon atmosphere for 19 hours. Palladium acetate was removed by filtration through celite, and the mixture was extracted with ethyl acetate, washed with saturated brine, and dried over sodium sulfate. The insoluble matter was filtered off and concentrated, and the crude product was purified by column chromatography (ethyl acetate / hexane = 1 / 4) to obtain the compound represented by the formula (1-3-1a) as a powdery substance (1.1 g, yield 73%). 1 H NMR (400 MHz, CDCl3): δ 3.87 (s, 6H), 4.56 (brs, 2H, NH2), 7.03 (d, J = 6.0 Hz, 4H), 7.40 (d, J = 6.0 Hz, 4H), 8.01 (s, 2H) ppm; 13 C NMR (100 MHz, CDCl3): δ 55.4, 114.7, 125.5, 126.4, 129.5, 130.3, 138.6, 147.8, 159.5 ppm; IR (ATR): 1246, 1488 (NO2), 1597 (NO2), 3389 (NH2), 3494 (NH2) cm -1 ; HRMS (ESI): m / z calcd for C 20 H 19 N2O4: 351.1339 (M + H) + , found: 351.1337.

[0064] To the obtained compound (35 mg, 0.10 mmol) represented by the formula (1-3-1a), a solution prepared by dissolving 12N HCl (250 μL) and sodium nitrite (6.9 mg, 0.10 mmol) in purified water (750 μL) was added under ice-cooling, and the mixture was stirred for 30 minutes to obtain a solution (color-forming agent) containing the compound represented by the above formula (1-3-1).

[0065] (Synthesis Example 4) Synthesis of the compound represented by the following formula (1-4-1) [Chemical formula]

[0066] 2,6-Dimethylaniline (0.50 mL, 4.0 mmol) was dissolved in ethanol (10 mL), 2,3,5,6-tetrabromo-4-methyl-4-nitro-2,5-cyclohexadien-1-one (1.9 g, 4.0 mmol) was added under ice-cooling, and the mixture was stirred for 1 hour under an argon atmosphere. After adding ice to the reaction solution, the mixture was extracted with dichloromethane, washed with saturated brine, and dried by adding sodium sulfate. The insoluble matter was filtered off and concentrated, and the crude product was purified by column chromatography (ethyl acetate / hexane = 1 / 10) to obtain the compound represented by the formula (1-4-1a) as a powdery substance (130 mg, yield 20%). 1 H NMR (400 MHz, CDCl3): δ 2.23 (s, 6H), 4.27 (brs, 2H, NH2), 7.91 (s, 2H) ppm.

[0067] To the obtained compound (17 mg, 0.10 mmol) represented by the formula (1-4-1a), a solution prepared by dissolving 12N HCl (250 μL) and sodium nitrite (6.9 mg, 0.10 mmol) in purified water (750 μL) was added under ice-cooling, and the mixture was stirred for 30 minutes to obtain a solution (color-forming agent) containing the compound represented by the above formula (1-4-1).

[0068] (Synthesis Example 5) Synthesis of the compound represented by the following formula (1-5-1) [Chemical formula] To 1-amino-4-methoxynaphthalene (the compound represented by the above formula (1-5-1a)) (17 mg, 0.10 mmol), a solution prepared by dissolving 12N HCl (250 μL) and sodium nitrite (6.9 mg, 0.10 mmol) in purified water (750 μL) was added under ice-cooling, and the mixture was stirred for 30 minutes to obtain a solution (color-forming agent) containing the compound represented by the above formula (1-5-1).

[0069] (Synthesis Example 6) Synthesis of the compound represented by the following formula (1-6)

Chemical formula

[0070] (Synthesis Example 7) Synthesis of the compound represented by the following formula (1-7)

Chemical formula

[0071] (Synthesis Example 8) Synthesis of the compound represented by the following formula (1-8-1)

Chemical formula

[0072] (Synthesis Example 9) Synthesis of the compound represented by the following formula (1-9) [Chemical formula] To 4-carboxyaniline (the compound represented by the above formula (1-9a)) (14 mg, 0.10 mmol), a solution prepared by dissolving 12N HCl (250 μL) and sodium nitrite (6.9 mg, 0.10 mmol) in purified water (750 μL) was added under ice-cooling, and the mixture was stirred for 30 minutes to obtain a solution (color former) containing the compound represented by the above formula (1-9).

[0073] (Synthesis Example 10) Synthesis of the compound represented by the following formula (1-10) [Chemical formula] To 4-(trifluoromethyl)aniline (the compound represented by the above formula (1-10a)) (16 mg, 0.10 mmol), a solution prepared by dissolving 12N HCl (250 μL) and sodium nitrite (6.9 mg, 0.10 mmol) in purified water (750 μL) was added under ice-cooling, and the mixture was stirred for 30 minutes to obtain a solution (color former) containing the compound represented by the above formula (1-10).

[0074] (Synthesis Example 11) Synthesis of the compound represented by the following formula (1-11) [Chemical formula] To 4-cyanoaniline (the compound represented by the above formula (1-11a)) (12 mg, 0.10 mmol), a solution prepared by dissolving 12N HCl (250 μL) and sodium nitrite (6.9 mg, 0.10 mmol) in purified water (750 μL) was added under ice-cooling, and the mixture was stirred for 30 minutes to obtain a solution (color former) containing the compound represented by the above formula (1-11).

[0075] (Synthesis Example 12) Synthesis of the compound represented by the following formula (1-12)

Chemical formula

[0076] (Synthesis Example 13) Synthesis of the compound represented by the following formula (1-13)

Chemical formula

[0077] (Synthesis Example 14) Synthesis of the compound represented by the following formula (1-14)

Chemical formula

[0078] (Synthesis Example 15) Synthesis of the compound represented by the following formula (1-15) [Chemical formula] To 3-cyanoaniline (the compound represented by the above formula (1-15a)) (12 mg, 0.10 mmol), a solution prepared by dissolving 12N HCl (250 μL) and sodium nitrite (6.9 mg, 0.10 mmol) in purified water (750 μL) was added under ice-cooling, and the mixture was stirred for 30 minutes to obtain a solution (color former) containing the compound represented by the above formula (1-15).

[0079] (Synthesis Example 16) Synthesis of the compound represented by the following formula (1-16) [Chemical formula] To 3-nitroaniline (the compound represented by the above formula (1-16a)) (14 mg, 0.10 mmol), a solution prepared by dissolving 12N HCl (250 μL) and sodium nitrite (6.9 mg, 0.10 mmol) in purified water (750 μL) was added under ice-cooling, and the mixture was stirred for 30 minutes to obtain a solution (color former) containing the compound represented by the above formula (1-16).

[0080] (Synthesis Example 17) Synthesis of the compound represented by the following formula (1-17) [Chemical formula] To 4-hydroxy-3-nitroaniline (the compound represented by the above formula (1-17a)) (15 mg, 0.10 mmol), a solution prepared by dissolving 12N HCl (250 μL) and sodium nitrite (6.9 mg, 0.10 mmol) in purified water (750 μL) was added under ice-cooling, and the mixture was stirred for 30 minutes to obtain a solution (color former) containing the compound represented by the above formula (1-17).

[0081] (Synthesis Example 18) Synthesis of the compound represented by the following formula (1-18) [Chemical formula] To the compound represented by the above formula (1-18a) (24 mg, 0.10 mmol), a solution prepared by dissolving 12N HCl (250 μL) and sodium nitrite (6.9 mg, 0.10 mmol) in purified water (750 μL) was added under ice-cooling, and the mixture was stirred for 30 minutes to obtain a solution (color former) containing the compound represented by the above formula (1-18).

[0082] (Synthesis Example 19) Synthesis of the compound represented by the following formula (1-19-1) [Chemical formula] To 4-methoxyaniline (the compound represented by the above formula (1-19-1a)) (12 mg, 0.10 mmol), a solution prepared by dissolving 12N HCl (250 μL) and sodium nitrite (6.9 mg, 0.10 mmol) in purified water (750 μL) was added under ice-cooling, and the mixture was stirred for 30 minutes to obtain a solution (color former) containing the compound represented by the above formula (1-19-1).

[0083] (Synthesis Example 20) Synthesis of the compound represented by the following formula (1-20) [Chemical formula] To aniline (the compound represented by the above formula (1-20a)) (10 mg, 0.10 mmol), a solution prepared by dissolving 12N HCl (250 μL) and sodium nitrite (6.9 mg, 0.10 mmol) in purified water (750 μL) was added under ice-cooling, and the mixture was stirred for 30 minutes to obtain a solution (color former) containing the compound represented by the above formula (1-20).

[0084] (Synthesis Example 21) Synthesis of the compound represented by the following formula (1-21)

Chemical formula

[0085] (Synthesis Example 22) Synthesis of the compound represented by the following formula (1-22)

Chemical formula

[0086] (Synthesis Example 23) Synthesis of the compound represented by the following formula (1-23)

Chemical formula

[0087] (Synthesis Example 24) Synthesis of the compound represented by the following formula (1-24)

Chemical formula

[0088] (Synthesis Example 25) Synthesis of the compound represented by the following formula (1-25-1)

Chemical formula

[0089] (Synthesis Example 26) Synthesis of the compound represented by the following formula (2-1)

Chemical formula

[0090] To the obtained compound (36 mg, 0.10 mmol) represented by the formula (2-1a), a solution prepared by dissolving 12N HCl (250 μL) and sodium nitrite (6.9 mg, 0.10 mmol) in purified water (750 μL) was added under ice-cooling, and the mixture was stirred for 30 minutes to obtain a solution (color-forming agent) containing the compound represented by the above formula (2-1).

[0091] (Synthesis Example 27) Synthesis of the compound represented by the following formula (2-2) [Chemical formula] First, the compound represented by the above formula (2-2-1a) was synthesized. Specifically, 2,6-dimethyl-4-nitroaniline (200 mg, 1.01 mmol) was dissolved in methanol (10 mL), 10% palladium carbon (107 mg, 0.101 mmol) was added and degassed, and the mixture was stirred at room temperature for 18 hours under a hydrogen atmosphere. Palladium carbon was removed by filtration through celite, and the concentrated crude product was dissolved in dichloromethane (5 mL). Benzoyl chloride (0.11 mL, 0.98 mmol) and diisopropylethylamine (0.50 mL, 2.9 mmol) were added, and the mixture was stirred at room temperature for 18 hours under an argon atmosphere. After adding water, the mixture was extracted with dichloromethane, washed with saturated brine, and dried over sodium sulfate. Insoluble matters were filtered off and concentrated, and the crude product was purified by column chromatography (ethyl acetate / hexane = 1 / 2) to obtain the compound represented by the above formula (2-2-1a) as a powdery substance (61 mg, yield 30%). 1 H NMR (400 MHz, CDCl3): δ 3.75 (brs, 2H, NH2), 3.88 (s, 6H), 6.91 (s, 2H), 7.47 - 7.55 (m, 3H), 7.66 (s, 1H, NH), 7.86 - 7.88 (m, 2H) ppm.

[0092] To the obtained compound (27 mg, 0.10 mmol) represented by the formula (2-2-1a), a solution prepared by dissolving 12N HCl (250 μL) and sodium nitrite (6.9 mg, 0.10 mmol) in purified water (750 μL) was added under ice-cooling, and the mixture was stirred for 30 minutes to obtain a solution (color former) containing the compound represented by the above formula (2-2-1).

[0093] (Synthesis Comparative Example 1) Synthesis of the compound represented by the following formula (2'-1) [Chemical formula] First, the compound represented by the above formula (2'-1a) was synthesized. Specifically, 2,5-dimethylaniline (600 mg, 3.92 mmol) was dissolved in dichloromethane (10 mL), 2-iodobenzoyl chloride (1.15 g, 4.31 mmol) and diisopropylethylamine (1.0 mL, 5.9 mmol) were added, and the mixture was stirred at room temperature for 22 hours under an argon atmosphere. After adding water, the mixture was extracted with dichloromethane, washed with saturated brine, dried over sodium sulfate, filtered to remove insolubles, and concentrated. The resulting crude product was dissolved in chloroform (9 mL), acetic acid (10 mL) and fuming nitric acid (1.4 mL) were added under ice-cooling, and the mixture was stirred for 1 hour under an air atmosphere. After adding ice to the reaction solution, the mixture was extracted with dichloromethane, washed with saturated brine, dried over sodium sulfate, filtered to remove insolubles, and concentrated to obtain a crude product of the nitro compound (1.47 g). The obtained crude product (0.97 g) was dissolved in ethanol (10 mL) and water (38 mL), iron (1.01 g, 18.1 mmol) and ammonium chloride (425 mg, 7.95 mmol) were added, and the mixture was heated to reflux for 2 hours under an argon atmosphere. Iron was removed by celite filtration, the mixture was extracted with ethyl acetate, washed with saturated brine, dried over sodium sulfate, filtered to remove insolubles, and concentrated. The resulting crude product was purified by column chromatography (ethyl acetate / hexane = 1 / 2) to obtain the compound represented by the above formula (2'-1a) as a powdery substance (432 mg). 1 H NMR (400 MHz, CDCl3): δ 3.79 (brs, 2H, NH2), 3.79 (s, 3H), 3.90 (s, 3H), 6.38 (s, 1H), 7.12 - 7.16 (m, 1H), 7.41 - 7.45 (m, 1H), 7.51 - 7.53 (m, 1H), 7.86 - 7.93 (m, 2H), 8.15 (s, 1H) ppm.

[0094] To the obtained compound represented by the formula (2'-1a) (40 mg, 0.10 mmol), a solution prepared by dissolving 12N HCl (250 μL) and sodium nitrite (6.9 mg, 0.10 mmol) in purified water (750 μL) was added under ice-cooling, and the mixture was stirred for 30 minutes to obtain a solution (color former) containing the compound represented by the above formula 2'-1).

[0095] (Synthesis Comparative Example 2) Synthesis of the compound represented by the following formula (2'-2)

Chemical formula

[0096] To the obtained compound represented by the formula (2'-2a) (42 mg, 0.10 mmol), a solution prepared by dissolving 12N HCl (250 μL) and sodium nitrite (6.9 mg, 0.10 mmol) in purified water (750 μL) was added under ice-cooling, and the mixture was stirred for 30 minutes to obtain a solution (color former) containing the compound represented by the above formula (2'-2).

[0097] (Synthesis Comparative Example 3) Synthesis of the compound represented by the following formula (1'-1)

Chemical formula

[0098] (Synthesis Comparative Example 4) Synthesis of the compound represented by the following formula (1'-2) [Chemical formula] To 1-aminonaphthalene (the compound represented by formula (1'-2a)) (14 mg, 0.10 mmol), a solution prepared by dissolving 12N HCl (250 μL) and sodium nitrite (6.9 mg, 0.10 mmol) in purified water (750 μL) was added under ice-cooling, and the mixture was stirred for 30 minutes to obtain a solution (color former) containing the compound represented by the above formula (1'-2).

[0099] (Reference Example 1) In Reference Example 1, an ethanol solution (color former) of the compound (Fast Blue RR salt) represented by the following formula (2'-3) was used [Chemical formula]

[0100] [Examples 1 to 27, Comparative Examples 1 to 4, and Reference Example] 50 μL of the solution (color former) containing each obtained diazonium salt was dispensed, and at room temperature (25 °C), a 100 mM ethanol solution (20 μL) of each cannabinoid (THC, CBD, or CBN) and ethanol (30 μL) were added to obtain a contact solution. The color of the obtained contact solution was visually observed. Table 1 shows the observed color and the results evaluated according to the following criteria. a: THC, CBD, and CBN could be distinguished from each other. b: THC could be distinguished from CBD and CBN. c: It was possible to distinguish CBD from THC and CBN. d: It was possible to distinguish CBN from THC and CBD. e: It was not possible to distinguish any of CBN, THC, and CBD.

[0101] Also, for Reference Example 1, after adding THC, CBD, and CBN respectively in the following manner, the absorption spectrum of the colored solution (contact solution) was measured using a spectrophotometer. In the following compounds, Me represents a methyl group. Similarly, for Example 12, the absorption spectra of the colored solutions after adding THC, CBD, and CBN respectively were also measured. Figure 1 is the absorption spectrum of Reference Example 1, and Figure 2 is the absorption spectrum of Example 12. The peaks in Figure 1 are CBD: 395 nm and 462 nm, CBN: 392 nm, THC: 392 nm. The peak around 330 nm on the left is a peak observed even with only the diazonium salt and is considered not to be derived from the colored substance. Also, the peaks in Figure 2 were CBD: 420 nm, CBN: 435 nm, THC: 438 nm.

[0102] (Isolation of the compound (the following compound) after adding CBD) [Chemical formula] Sodium hydroxide (44 mg, 1.1 mmol) was dissolved in ethanol (4.0 mL), CBD (63 mg, 0.20 mmol), and commercially available Fast Blue RR salt (78 mg, 0.20 mmol) were added, and the mixture was stirred at room temperature for 15 minutes. The reaction solution was concentrated to remove ethanol, water and 1N hydrochloric acid were added to the residue to adjust the pH to about 7, then extracted with ethyl acetate, washed with saturated brine, and dried by adding sodium sulfate. The insoluble matter was filtered and concentrated, and the crude product was purified by column chromatography (ethyl acetate / hexane = 4 / 96 → 35 / 65) to obtain the target compound as a powdery substance (72 mg, yield 60%). 11H NMR (400 MHz, CDCl3): δ 0.88 (t, J = 6.8 Hz, 3H), 1.34 - 1.41 (m, 4H), 1.66 - 1.71 (m, 2H), 1.75 (s, 3H), 1.80 (s, 3H), 1.80 - 1.85 (m, 2H), 2.08 - 2.13 (m, 1H), 2.20 - 2.30 (m, 1H), 2.40 - 2.48 (m, 1H), 2.84 - 2.91 (m, 1H), 2.97 - 3.04 (m, 1H), 3.96 (s, 3H), 4.04 (s, 3H), 4.16 - 4.22 (m, 1H), 4.46 (s, 1H), 4.53 (s, 1H), 5.58 (s, 1H), 6.31 (s, 1H), 6.53 (brs, 1H, OH), 7.47 (s, 1H), 7.51 - 7.61 (m, 3H), 7.91 - 7.93 (m, 2H), 8.52 (s, 1H), 8.74 (s, 1H, NH), 15.7 (s, 1H, OH) ppm; 13 13C NMR (100 MHz, CDCl3): δ 14.1, 18.9, 22.6, 23.7, 28.0, 30.3, 31.6, 32.0, 32.1, 34.6, 46.7, 56.0, 56.6, 97.5, 104.1, 110.4, 111.2, 115.2, 124.3, 127.0, 128.9, 129.6, 131.0, 132.0, 133.1, 134.8, 140.0, 142.9, 145.2, 147.4, 149.4, 158.5, 160.2, 165.2 ppm; IR (ATR): 1251, 1466, 1522, 1677 (C=O), 2924, 3416 (OH, HN) cm -1 ; HRMS (ESI): m / z calcd for C 36 H 44 N3O5: 598.3275 (M + H) + , found: 598.3275.

[0103] (Isolation of the compound (the following compound) after adding CBN)

Chemical formula

[0104] (Isolation of the compound (the following compound) after adding THC)

Chemical formula

[0105]

Table 1

[0106] As shown in Table 1, it can be seen that in Examples 1 to 27 using a color former containing the compound represented by the formula (1) or the compound represented by the formula (2), cannabinoids can be visually detected.

Claims

1. A color former for detecting cannabinoids, comprising a compound represented by the following formula (1) or a compound represented by the following formula (2).

2. 【Chemical 1】 (In formula (1), R １ represents a nitro group, a cyano group, a hydroxy group, an alkoxy group, a carboxy group, a sulfo group, an alkyl group, a halogenated alkyl group, a styryl group which may have a substituent, a halogen atom, or a hydrogen atom, and R ２ and R ４ each independently represents a nitro group, a cyano group, a hydroxy group, an alkoxy group, a carboxy group, a sulfo group, an alkyl group, an alkenyl group, a halogenated alkyl group, a styryl group which may have a substituent, a halogen atom, or a hydrogen atom, R ３ and R ５ each independently represents an alkoxy group, an alkyl group, an alkenyl group, a phenyl group which may have a substituent, a hydroxy group, or a hydrogen atom, R ４ and R ５ may be bonded to each other to form a ring, X － represents a counter anion.) 【Chemical 2】 (In formula (2), R ６ and R ７ each independently represents an alkoxy group, an alkyl group or a phenyl group, Y － represents a counter anion.) The color former according to claim 1, which detects at least one selected from the group consisting of tetrahydrocannabinol, cannabidiol, cannabinol, cannabigerol, cannabidiolic acid, cannabichromene, hexahydrocannabinol, hexahydrocannabinol - O - acetate, and tetrahydrocannabinol - O - acetate.

3. The color former according to claim 2, which detects at least one selected from the group consisting of tetrahydrocannabinol, cannabidiol, and cannabinol.

4. A method for detecting cannabinoids, comprising: a contacting step of contacting a sample that may contain the cannabinoids with a coloring solution containing the color former according to any one of claims 1 to 3; and a detecting step of detecting the cannabinoids based on the color of the contacting solution obtained in the contacting step, in which the sample and the coloring solution are in contact with each other.

5. The method for detecting cannabinoids according to claim 4, further comprising a converting step of converting a compound represented by the following formula (i) or a compound represented by the following formula (ii), which is a precursor of the compound represented by the formula (1) or the compound represented by the formula (2), into the compound represented by the formula (1) or the compound represented by the formula (2).

6. [Chemical Formula 3] (In formula (i), R １ , R ２ , R ３ , R ４ , and R ５ are each the same as R １ , R ２ , R ３ , R ４ , and R ５ in formula (1).) 【Chemical Formula 4】 (In formula (ii), R ６ and R ７ are respectively the same as R ６ and R ７ in formula (2).) The method for detecting cannabinoids according to claim 5, wherein the converting step is performed before the contacting step.

7. The method for detecting cannabinoids according to claim 4, wherein the sample contains at least one selected from the group consisting of tetrahydrocannabinol, cannabidiol, cannabinol, cannabigerol, cannabinoid, cannabichromene, hexahydrocannabinol, hexahydrocannabinol - O - acetate, and tetrahydrocannabinol - O - acetate.

8. The method for detecting cannabinoids according to claim 7, wherein the sample contains at least one selected from the group consisting of tetrahydrocannabinol, cannabidiol, and cannabinol.

9. The method for detecting cannabinoids according to claim 4, wherein the sample is an extract or an infusion from at least one selected from the group consisting of plant pieces, foods, daily necessities, and luxury goods.

10. ​ The detection method of cannabinoids according to claim 4, wherein the sample is derived from cannabis.

11. A detection kit for detecting cannabinoids, comprising: a color developing solution containing the color developing agent according to any one of claims 1 to 3, or a reagent solution containing a compound represented by the following formula (i) or a compound represented by the following formula (ii), which is a precursor of the compound represented by the formula (1) or the compound represented by the formula (2); A detection kit comprising a container capable of bringing the color developing solution or the reagent solution into contact with a sample that may contain the cannabinoids. [Chemical Formula 5] (In formula (i), R １ , R ２ , R ３ , R ４ , and R ５ are each the same as R １ , R ２ , R ３ , R ４ , and R ５ in formula (1). ) 【Chemical Formula 6】 (In formula (ii), R ６ and R ７ are the same as R ６ and R ７ in formula (2), respectively.)

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