3. The Fourth Schedule to the Misuse of Drugs Regulations is amended —| (a) | by deleting item (14) of paragraph 1 and substituting the following item:| “(14) | N,α-Dimethyl-3,4-(methylenedioxy)phenethylamine (also known as 3,4-Methylenedioxymethamphetamine or MDMA) and its acyloxy or sulphonyl derivatives at the nitrogen atom, and the following example of such a derivative:| (a) | tert-Butyl N-[1-(1,3-benzodioxol-5-yl)propan-2-yl]-N-methylcarbamate (also known as N‑tert-Butoxycarbonyl-MDMA or t-Boc-MDMA)”; |
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| | (b) | by deleting item (23) of paragraph 1 and substituting the following item:| “(23) | Lysergide and other compounds structurally derived from lysergamide by substitution of any of the hydrogen atoms, and the following examples of such a compound:| (a) | 1-Acetyl-N,N-diethyllysergamide (also known as N-acetyl-LSD or ALD-52) | | (b) | 6-Allyl-6-nor-lysergic acid diethylamide (also known as N-allyl-nor-LSD or AL-LAD) | | (c) | 6-Ethyl-6-nor-lysergic acid diethylamide (also known as ETH-LAD) | | (d) | 6-Propyl-6-nor-lysergic acid diethylamide (also known as PRO-LAD) | | (e) | Lysergic acid 2,4-dimethylazetidide (also known as LSZ) | | (f) | 1-Propionyl-N,N-diethyllysergamide (also known as 1-Propionyl-LSD or 1P-LSD) | | (g) | 1-Butanoyl-N,N-diethyllysergamide (also known as 1-Butanoyl-LSD or 1B-LSD)”; |
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| | (c) | by deleting paragraphs 7, 11, 13 and 14; | | (d) | by deleting items (1) to (2AAA), (2AAB) to (2K), (6F) to (6I), (8AC), (8AD), (14A), (19AAA) to (19ABE), (19A) to (20AA), (20B), (20C), (20D), (27AA), (27AB), (27DA), (27DB), (28A) to (28J), (29AA), (29A), (31A), (35A), (36A) to (38AB), (38AD) to (38C) and (40) of paragraph 17; and | | (e) | by inserting, immediately after paragraph 18, the following paragraphs:“19. Any compound structurally derived from indole-3-carboxaldehyde or indole-2-carboxaldehyde by substitution —| (a) | at the nitrogen atom of the indole ring with any of the following:| (i) | an alkyl group; | | (ii) | a cyanoalkyl group; | | (iii) | an alkenyl group; | | (iv) | a cycloalkylmethyl group; | | (v) | a cycloalkylethyl group; | | (vi) | a 1-(N-methyl-2-piperidinyl)methyl group; | | (vii) | a 2-(4-morpholinyl)ethyl group; | | (viii) | a 1-(N-methyl-2-pyrrolidinyl)methyl group; | | (ix) | a 1-(N-methyl-3-morpholinyl)methyl group; | | (x) | a tetrahydropyranylmethyl group; | | (xi) | an alkyl phenyl group; | | (xii) | a halogen, hydroxy and/or carboxylic acid derivative of any group mentioned in sub‑paragraphs (i) to (xi); and |
| | (b) | at the hydrogen atom of the carboxaldehyde with any of the following:| (i) | an alkyl group; | | (ii) | an alkenyl group; | | (iii) | an alkylamido group; | | (iv) | an alkylcarboxylic acid group; | | (v) | a phenyl group; | | (vi) | an alkyl phenyl group; | | (vii) | a cycloalkyl group; | | (viii) | a cycloalkylmethyl group; | | (ix) | a cycloalkylethyl group; | | (x) | an adamantyl group; | | (xi) | a naphthyl group; | | (xii) | a norbornyl group; | | (xiii) | a 1,2,3,4-tetrahydronaphthyl group; | | (xiv) | a heterocyclic analog of any group mentioned in sub-paragraphs (v) to (xiii), |
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| whether or not the compound is further modified in any of the following ways: |
| (c) | substitution of the indole ring with a nitrogen heterocyclic analog; | | (d) | substitution to the indole ring or its nitrogen heterocyclic analog to any extent; | | (e) | substitution to the group mentioned in sub‑paragraph (b) to any extent, |
| including any salt or stereoisomeric form of the compound or derivative of the compound, any preparation or product containing the compound or derivative of the compound, and the following examples of such a compound or derivative: |
| (1) | [1-(5-Bromopent-1-yl)-1H-indazol-3-yl](naphthalene-1-yl)methanone (also known as 5-Bromo-THJ-018) | | (2) | [1-(5-Bromopent-1-yl)-1H-indol-3-yl](2,2,3,3-tetramethylcyclopropyl)methanone (also known as 5‑Bromo-UR-144) | | (3) | [1-(5-Chloropent-1-yl)-1H-indazol-3-yl](naphthalen-1-yl)methanone (also known as 5-Chloro-THJ-018) | | (4) | [1-(5-Chloropent-1-yl)-1H-indol-3-yl](2,2,3,3-tetramethylcyclopropyl)methanone (also known as 5‑Chloro-UR-144) | | (5) | [1-(4-Fluorobenzyl)-1H-indol-3-yl](2,2,3,3-tetramethylcyclopropyl)methanone (also known as FUB‑144 or FUB-UR-144) | | (6) | [1-(5-Fluoropent-1-yl)-1H-benzimidazol-2-yl](naphthalen-1-yl)methanone (also known as FUBIMINA) | | (7) | [1-(5-Fluoropent-1-yl)-1H-indazol-3-yl](naphthalen-1-yl)methanone (also known as THJ-2201) | | (8) | [1-(5-Fluoropent-1-yl)-1H-indol-3-yl](2,2,3,3-tetramethylcyclopropyl)methanone (also known as XLR-11 or 5-Fluoro-UR-144) | | (9) | [1-(5-Hydroxypent-1-yl)-1H-indazol-3-yl](naphthalen-1-yl)methanone | | (10) | [1-(5-Hydroxypent-1-yl)-1H-indol-3-yl](2,2,3,3-tetramethylcyclopropyl)methanone | | (11) | [1-(5-Iodopent-1-yl)-1H-indazol-3-yl](naphthalen-1-yl)methanone (also known as 5-Iodo-THJ-018) | | (12) | Naphthalen-1-yl[1-(pent-1-yl)-1H-indazol-3-yl]methanone (also known as THJ-018) | | (13) | 5-[3-(1-Naphthoyl)-1H-indazol-1-yl]pentanoic acid | | (14) | 5-[3-(1-Naphthoyl)-1H-indol-1-yl]pentanenitrile (also known as AM-2232) | | (15) | (1-Pentyl-1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone (also known as UR-144) | | (16) | 5-[3-(2,2,3,3-Tetramethylcyclopropanecarbonyl)-1H-indol-1-yl]pentanoic acid | | (17) | (1-Butyl-1H-indol-3-yl)(naphthalen-1-yl)methanone (also known as JWH-073) | | (18) | (4-Chloronaphthalen-1-yl)(1-pentyl-1H-indol-3-yl)methanone (also known as JWH-398) | | (19) | [1-(4-Chloropent-1-yl)-1H-indol-3-yl](naphthalen-1-yl)methanone (also known as 4-Chloro-AM-2201) | | (20) | (4-Ethylnaphthalen-1-yl)(1-pentyl-1H-indol-3-yl)methanone (also known as JWH-210) | | (21) | [1-(5-Fluoropent-1-yl)-1H-indol-3-yl](4-methylnaphthalen-1-yl)methanone (also known as MAM-2201) | | (22) | [1-(5-Fluoropent-1-yl)-1H-indol-3-yl](naphthalen-1-yl)methanone (also known as AM-2201) | | (23) | [1-(4-Fluoropent-1-yl)-1H-indol-3-yl](naphthalen-1-yl)methanone (also known as 4-Fluoro-AM-2201) | | (24) | [1-(5-Fluoropent-1-yl)-6-nitro-1H-indol-3-yl](naphthalen-1-yl)methanone (also known as AM‑1235) | | (25) | [1-(Heptan-2-yl)-2-methyl-1H-indol-3-yl](naphthalen-1-yl)methanone (also known as JWH‑011) | | (26) | (1-Heptyl-1H-indol-3-yl)(naphthalen-1-yl)methanone (also known as JWH-020) | | (27) | (1-Hexyl-1H-indol-3-yl)(naphthalen-1-yl)methanone (also known as JWH-019) | | (28) | (4-Methoxynaphthalen-1-yl)(1-pentyl-1H-indol-3-yl)methanone (also known as JWH-081) | | (29) | (2-Methyl-1-propyl-1H-indol-3-yl)(naphthalen-1-yl)methanone (also known as JWH-015) | | (30) | (4-Methylnaphthalen-1-yl)(1-pentyl-1H-indol-3-yl)methanone (also known as JWH-122) | | (31) | {1-[(1-Methylpiperidin-2-yl)methyl]-1H-indol-3-yl}(naphthalen-1-yl)methanone (also known as AM‑1220) | | (32) | {1-[2-(Morpholin-4-yl)ethyl]-1H-indol-3-yl}(naphthalen-1-yl)methanone (also known as JWH‑200) | | (33) | Naphthalen-1-yl[1-(pent-4-en-1-yl)-1H-indol-3-yl]methanone (also known as JWH-022) | | (34) | Naphthalen-1-yl(1-pentyl-1H-indol-3-yl)methanone (also known as JWH-018) | | (35) | Naphthalen-1-yl(1-propyl-1H-indol-3-yl)methanone (also known as JWH-072) | | (36) | 2-(2-Chlorophenyl)-1-(1-pentyl-1H-indol-3-yl)ethanone (also known as JWH-203) | | (37) | 1-[1-(2-Cyclohexylethyl)-1H-indol-3-yl]-2-(2-methoxyphenyl)ethanone (also known as RCS-8) | | (38) | 2-(2-Methoxyphenyl)-1-{1-[(1-methylpiperidin-2-yl)methyl]-1H-indol-3-yl}ethanone (also known as cannabipiperidiethanone) | | (39) | 2-(2-Methoxyphenyl)-1-(1-pentyl-1H-indol-3-yl)ethanone (also known as JWH-250) | | (40) | 2-(3-Methoxyphenyl)-1-(1-pentyl-1H-indol-3-yl)ethanone (also known as JWH-302) | | (41) | 2-(4-Methoxyphenyl)-1-(1-pentyl-1H-indol-3-yl)ethanone (also known as JWH-201) | | (42) | 2-(2-Methylphenyl)-1-(1-pentyl-1H-indol-3-yl)ethanone (also known as JWH-251) | | (43) | [1-(5-Fluoropentyl)-1H-indol-3-yl](2-iodophenyl)methanone (also known as AM-694) | | (44) | (2-Iodo-5-nitrophenyl){1-[(1-methylpiperidin-2-yl)methyl]-1H-indol-3-yl}methanone (also known as AM-1241) | | (45) | (2-Iodophenyl){1-[(1-methylpiperidin-2-yl)methyl]-1H-indol-3-yl}methanone (also known as AM-2233) | | (46) | (2-Iodophenyl)(1-pentyl-1H-indol-3-yl)methanone (also known as AM-679) | | (47) | (4-Methoxyphenyl){2-methyl-1-[2-(morpholin-4-yl)ethyl]-1H-indol-3-yl}methanone (also known as pravadoline) | | (48) | (4-Methoxyphenyl)(1-pentyl-1H-indol-3-yl)methanone (also known as RCS-4) | | (49) | 1-Adamantyl{1-[(1-methylpiperidin-2-yl)methyl]-1H-indol-3-yl}methanone (also known as AM-1248) | | (50) | 1-Adamantyl(1-pentyl-1H-indol-3-yl)methanone (also known as AB-001) |
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20. Any compound structurally derived from indole-3-carboxamide or indole-2-carboxamide by substitution —| (a) | at the nitrogen atom of the indole ring with any of the following:| (i) | an alkyl group; | | (ii) | a cyanoalkyl group; | | (iii) | an alkenyl group; | | (iv) | a cycloalkylmethyl group; | | (v) | a cycloalkylethyl group; | | (vi) | a 1-(N-methyl-2-piperidinyl)methyl group; | | (vii) | a 2-(4-morpholinyl)ethyl group; | | (viii) | a 1-(N-methyl-2-pyrrolidinyl)methyl group; | | (ix) | a 1-(N-methyl-3-morpholinyl)methyl group; | | (x) | a tetrahydropyranylmethyl group; | | (xi) | an alkyl phenyl group; | | (xii) | a halogen, hydroxy and/or carboxylic acid derivative of any group mentioned in sub‑paragraphs (i) to (xi); and |
| | (b) | at any hydrogen atom of the carboxamide with any of the following:| (i) | an alkyl group; | | (ii) | an alkenyl group; | | (iii) | an alkylamido group; | | (iv) | an alkylcarboxylic acid group; | | (v) | a phenyl group; | | (vi) | an alkyl phenyl group; | | (vii) | a cycloalkyl group; | | (viii) | a cycloalkylmethyl group; | | (ix) | a cycloalkylethyl group; | | (x) | an adamantyl group; | | (xi) | a naphthyl group; | | (xii) | a norbornyl group; | | (xiii) | a 1,2,3,4-tetrahydronaphthyl group; | | (xiv) | a heterocyclic analog of any group mentioned in sub‑paragraphs (v) to (xiii), |
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| whether or not the compound is further modified in any of the following ways: |
| (c) | substitution of the indole ring with a nitrogen heterocyclic analog; | | (d) | substitution to the indole ring or its nitrogen heterocyclic analog to any extent; | | (e) | substitution to the group mentioned in sub‑paragraph (b) to any extent, |
| including any salt or stereoisomeric form of the compound or derivative of the compound, any preparation or product containing the compound or derivative of the compound, and the following examples of such a compound or derivative: |
| (1) | N-(1-Adamantyl)-1-(5-bromopentyl)-1H-indazole-3-carboxamide (also known as 5-Bromo-APINACA or 5‑Bromo-AKB48) | | (2) | N-(1-Adamantyl)-1-(5-chloropentyl)-1H-indazole-3-carboxamide (also known as 5-Chloro-APINACA or 5‑Chloro-AKB48) | | (3) | N-(1-Adamantyl)-1-(cyclohexylmethyl)-1H-indazole-3-carboxamide (also known as Adamantyl CHMINACA or SGT-37) | | (4) | N-(1-Adamantyl)-1-(5-hydroxypentyl)-1H-indazole-3-carboxamide | | (5) | N-(1-Adamantyl)-1-(4-fluorobenzyl)-1H-indazole-3-carboxamide (also known as FUB-APINACA or FUB‑AKB48) | | (6) | N-(1-Adamantyl)-1-(5-fluoropentyl)-1H-indazole-3-carboxamide (also known as 5-Fluoro-APINACA or 5F‑AKB48) | | (7) | N-(1-Adamantyl)-1-(5-fluoropentyl)-1H-indole-3-carboxamide (also known as 5-Fluoro-APICA or STS‑135) | | (8) | N-(1-Adamantyl)-1-pentyl-1H-indazole-3-carboxamide (also known as APINACA) | | (9) | N-(1-Adamantyl)-1-pentyl-1H-indole-3-carboxamide (also known as APICA) | | (10) | N-(1-Amino-3,3-dimethyl-1-oxobutan-2-yl)-1-(cyclohexylmethyl)-1H-indazole-3-carboxamide (also known as MAB-CHMINACA or ADB‑CHMINACA) | | (11) | N-(1-Amino-3,3-dimethyl-1-oxobutan-2-yl)-1-(4-fluorobenzyl)-1H-indazole-3-carboxamide (also known as N-(1-Amino-3,3-dimethyl-1-oxobutan-2-yl)-1-[(4-fluorophenyl)]methyl-1H-indazole-3-carboxamide or ADB-FUBINACA) | | (12) | N-(1-Amino-3,3-dimethyl-1-oxobutan-2-yl)-1-(5-fluoropentyl)-1H-indazole-3-carboxamide (also known as 5-Fluoro-ADB-PINACA) | | (13) | N-(1-Amino-3,3-dimethyl-1-oxobutan-2-yl)-1-(5-fluoropentyl)-1H-indole-3-carboxamide (also known as 5-Fluoro-ADBICA) | | (14) | N-(1-Amino-3,3-dimethyl-1-oxobutan-2-yl)-1-pentyl-1H-indazole-3-carboxamide (also known as ADB-PINACA) | | (15) | N-(1-Amino-3,3-dimethyl-1-oxobutan-2-yl)-1-pentyl-1H-indole-3-carboxamide (also known as ADBICA) | | (16) | N-(1-Amino-3-methyl-1-oxobutan-2-yl)-1-(5-chloropentyl)-1H-indazole-3-carboxamide (also known as 5-Chloro-AB-PINACA) | | (17) | N-(1-Amino-3-methyl-1-oxobutan-2-yl)-1-(cyclohexylmethyl)-1H-indazole-3-carboxamide (also known as AB-CHMINACA) | | (18) | N-(1-Amino-3-methyl-1-oxobutan-2-yl)-1-(4-fluorobenzyl)-1H-indazole-3-carboxamide (also known as N-[1-amino-3-methyl-1-oxobutan-2-yl]-1-[(4-fluorophenyl)methyl]-1H-indazole-3-carboxamide or AB‑FUBINACA) | | (19) | N-(1-Amino-3-methyl-1-oxobutan-2-yl)-1-(4-fluorobenzyl)-1H-indole-3-carboxamide (also known as AB-FUBICA) | | (20) | N-(1-Amino-3-methyl-1-oxobutan-2-yl)-1-(5-fluoropentyl)-1H-indazole-3-carboxamide (also known as 5-Fluoro-AB-PINACA) | | (21) | N-(1-Amino-3-methyl-1-oxobutan-2-yl)-1-pentyl-1H-indazole-3-carboxamide (also known as AB‑PINACA) | | (22) | N-(1-Amino-1-oxo-3-phenylpropan-2-yl)-1-(cyclohexylmethyl)-1H-indazole-3-carboxamide (also known as PX-3 or APP-CHMINACA) | | (23) | N-(1-Amino-1-oxo-3-phenylpropan-2-yl)-1-(5-fluoropentyl)-1H-indazole-3-carboxamide (also known as PX-2 or 5-Fluoro-APP-PINACA) | | (24) | N-(1-Amino-1-oxo-3-phenylpropan-2-yl)-1-(5-fluoropentyl)-1H-indole-3-carboxamide (also known as PX-1 or 5-Fluoro-APP-PICA) | | (25) | Ethyl 2-[1-(4-fluorobenzyl)-1H-indazole-3-carboxamido]-3-methylbutanoate (also known as EMB-FUBINACA or AEB-FUBINACA or FUB-AEB) | | (26) | Ethyl 2-[1-(5-fluoropentyl)-1H-indazole-3-carboxamido]-3,3-dimethylbutanoate (also known as 5-Fluoro-EDMB-PINACA) | | (27) | Ethyl 2-[1-(5-fluoropentyl)-1H-indazole-3-carboxamido]-3-methylbutanoate (also known as 5‑Fluoro-AEB or 5‑Fluoro-EMB-PINACA) | | (28) | 2-[1-(4-Fluorobenzyl)-1H-indazole-3-carboxamido]-3,3-dimethylbutanoic acid | | (29) | 2-[1-(4-Fluorobenzyl)-1H-indazole-3-carboxamido]-3-methylbutanoic acid | | (30) | 2-[1-(4-Fluorobenzyl)-1H-indole-3-carboxamido]-3-methylbutanoic acid | | (31) | 2-[1-(4-Fluorobutyl)-1H-indazole-3-carboxamido]-3,3-dimethylbutanoic acid | | (32) | 5-Fluoropent-1-yl-N-naphthalen-1-yl-1H-indole-3-carboxamide (also known as CBM-2201, 5-Fluoro-NNEI, 5F-NNEI or MN-24F) | | (33) | 1-(5-Fluoropentyl)-N-(2-phenylpropan-2-yl)-1H-indole-3-carboxamide (also known as 5-Fluoro-cumyl-PICA) | | (34) | 2-[1-(5-Fluoropentyl)-1H-indazole-3-carboxamido]-3,3-dimethylbutanoic acid | | (35) | 2-[1-(5-Fluoropentyl)-1H-indole-3-carboxamido]-3,3-dimethylbutanoic acid | | (36) | 2-[1-(5-Fluoropentyl)-1H-indazole-3-carboxamido]-3-methylbutanoic acid | | (37) | Methyl 2-[1-(cyclohexylmethyl)-1H-indazole-3-carboxamido]-3,3-dimethylbutanoate (also known as MDMB-CHMINACA) | | (38) | Methyl 2-[1-(cyclohexylmethyl)-1H-indazole-3-carboxamido]-3-methylbutanoate (also known as MA‑CHMINACA) | | (39) | Methyl 2-[1-(cyclohexylmethyl)-1H-indole-3-carboxamido]-3,3-dimethylbutanoate (also known as Methyl N-{[1-(cyclohexylmethyl)-1H-indol-3-yl]carbonyl}-3-methyl-L-valinate or MDMB-CHMICA) | | (40) | Methyl 2-[1-(cyclohexylmethyl)-1H-indole-3-carboxamido]-3-methylbutanoate (also known as MMB‑CHMICA) | | (41) | Methyl 3,3-dimethyl-2-[1-(pent-4-en-1-yl)-1H-indazole-3-carboxamido]butanoate (also known as MDMB-4en-PINACA or MDMB-PINACA N1-pentyl-4-en isomer or MDMB(N)-022) | | (42) | Methyl 2-[1-(4-fluorobenzyl)-1H-indazole-3-carboxamido]-3,3-dimethylbutanoate (also known as MDMB-FUBINACA) | | (43) | Methyl 2-[1-(4-fluorobenzyl)-1H-indazole-3-carboxamido]-3-methylbutanoate (also known as Methyl 2-({1-[(4-fluorophenyl)methyl]-1H-indazole-3-carbonyl}amino)-3-methylbutanoate or MMB-FUBINACA or AMB-FUBINACA or FUB-AMB) | | (44) | Methyl 2-[1-(4-fluorobenzyl)-1H-indole-3-carboxamido]-3-methylbutanoate (also known as MMB-FUBICA or AMB-FUBICA) | | (45) | Methyl 2-[1-(4-fluorobutyl)-1H-indazole-3-carboxamido]-3,3-dimethylbutanoate (also known as Methyl 2-{[1-(4-fluorobutyl)-1H-indazole-3-carbonyl]amino}-3,3-dimethylbutanoate, 4F-MDMB-BINACA, 4F-MDMB-BUTINACA or 4‑Fluoro-MDMB-BINACA) | | (46) | Methyl 2-[1-(5-fluoropentyl)-1H-indazole-3-carboxamido]-3,3-dimethylbutanoate (also known as 5‑Fluoro-MDMB-PINACA or 5-Fluoro-ADB) | | (47) | Methyl 2-[1-(5-fluoropentyl)-1H-indazole-3-carboxamido]-3-methylbutanoate (also known as Methyl 2-{[1-(5-fluoropentyl)-1H-indazole-3-carbonyl]amino}-3-methylbutanoate, 5F-AMP, 5‑Fluoro-AMP, 5F-MMB-PINACA, 5F-AMB-PINACA, 5-Fluoro-AMB or 5-Fluoro-MMB-PINACA) | | (48) | Methyl 2-[1-(5-fluoropentyl)-1H-indole-3-carboxamido]-3,3-dimethylbutanoate (also known as Methyl 2-{[1-(5-fluoropentyl)-1H-indole-3-carbonyl]amino}-3,3-dimethylbutanoate, 5F-MDMB-PICA, 5F-MDMB-2201, 5-Fluoro-MDMB-2201 or 5-Fluoro-MDMB-PICA) | | (49) | Methyl 2-[1-(5-fluoropentyl)-1H-indole-3-carboxamido]-3-phenylpropanoate (also known as 5-Fluoro-MPP-PICA or 5-Fluoro-MPhP-PICA or MPHP-2201) | | (50) | Methyl 2-[1-(4-hydroxybutyl)-1H-indazole-3-carboxamido]-3,3-dimethylbutanoate | | (51) | Methyl 2-[1-(5-hydroxypentyl)-1H-indazole-3-carboxamido]-3,3-dimethylbutanoate | | (52) | N-(1-Methyl-1-phenylethyl)-1-(4-cyanobutyl)-1H-indazole-3-carboxamide (also known as 1-(4-Cyanobutyl)-N-(2-phenylpropan-2-yl)-1H-indazole-3-carboxamide or Cumyl-4CN-BINACA or 4-Cyano cumyl-butinaca or SGT-78) | | (53) | N-(1-Amino-3,3-dimethyl-1-oxobutan-2-yl)-1-butyl-1H-indazole-3-carboxamide (also known as 2-[(1-Butyl-1H-indazol-3-yl)formamido]-3,3-dimethylbutanamide or ADB-BUTINACA) | | (54) | 1-Pentyl-N-(2-phenylpropan-2-yl)-1H-indole-3-carboxamide (also known as Cumyl-PICA) | | (55) | 5-{3-[(1-Adamantyl)carbamoyl]-1H-indazole-1-yl}pentanoic acid | | (56) | 5-{3-[(1-Amino-3,3-dimethyl-1-oxobutan-2-yl)carbamoyl]-1H-indazole-1-yl}pentanoic acid | | (57) | 5-{3-[(1-Amino-3,3-dimethyl-1-oxobutan-2-yl)carbamoyl]-1H-indole-1-yl}pentanoic acid | | (58) | 5-{3-[(1-Amino-3-methyl-1-oxobutan-2-yl)carbamoyl]-1H-indazole-1-yl}pentanoic acid | | (59) | 4-{3-[(2-Phenylprop-2-yl)carbamoyl]-1H-indazole-1-yl}butanoic acid | | (60) | 2-[1-(Pent-4-en-1-yl)-1H-indazole-3-carboxamido]-3,3-dimethylbutanoic acid | | (61) | 2-[1-(4,5-Dihydroxypentyl)-1H-indazole-3-carboxamido]-3,3-dimethylbutanoic acid | | (62) | 2-(1-Butyl-1H-indazole-3-carboxamido)-3,3-dimethylbutanoic acid | | (63) | N-(1-Amino-3,3-dimethyl-1-oxobutan-2-yl)-1-(4-hydroxybutyl)-1H-indazole-3-carboxamide | | (64) | 5-{3-[(2-Phenylpropan-2-yl)carbamoyl]-1H-indol-1-yl}pentanoic acid | | (65) | 1-(5-Fluoropentyl)-N-(2-phenylpropan-2-yl)-1H-indazole-3-carboxamide (also known as 5-Fluoro-cumyl-PINACA) | | (66) | Ethyl 2-[1-(5-fluoropentyl)-1H-indole-3-carboxamido]-3-methylbutanoate (also known as 5‑Fluoro-EMB-PICA or EMB-2201) | | (67) | Methyl 2-[1-(4-fluorobutyl)-1H-indole-3-carboxamido]-3,3-dimethylbutanoate (also known as Methyl 2-{[1-(4-fluorobutyl)-1H-indole-3-carbonyl]amino}-3,3-dimethylbutanoate, 4F-MDMB-BICA, 4F-MDMB-BUTICA or 4-Fluoro-MDMB-BUTICA) |
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21. Any compound structurally derived from indole-3-carboxylic acid or indole-2-carboxylic acid by substitution —| (a) | at the nitrogen atom of the indole ring with any of the following:| (i) | an alkyl group; | | (ii) | a cyanoalkyl group; | | (iii) | an alkenyl group; | | (iv) | a cycloalkylmethyl group; | | (v) | a cycloalkylethyl group; | | (vi) | a 1-(N-methyl-2-piperidinyl)methyl group; | | (vii) | a 2-(4-morpholinyl)ethyl group; | | (viii) | a 1-(N-methyl-2-pyrrolidinyl)methyl group; | | (ix) | a 1-(N-methyl-3-morpholinyl)methyl group; | | (x) | a tetrahydropyranylmethyl group; | | (xi) | an alkyl phenyl group; | | (xii) | a halogen, hydroxy and/or carboxylic acid derivative of any group mentioned in sub‑paragraphs (i) to (xi); and |
| | (b) | at the hydrogen atom of the carboxylic acid with any of the following:| (i) | an alkyl group; | | (ii) | an alkenyl group; | | (iii) | an alkylamido group; | | (iv) | an alkylcarboxylic acid group; | | (v) | a phenyl group; | | (vi) | an alkyl phenyl group; | | (vii) | a cycloalkyl group; | | (viii) | a cycloalkylmethyl group; | | (ix) | a cycloalkylethyl group; | | (x) | an adamantyl group; | | (xi) | a naphthyl group; | | (xii) | a norbornyl group; | | (xiii) | a 1,2,3,4-tetrahydronaphthyl group; | | (xiv) | a heterocyclic analog of any group mentioned in sub‑paragraphs (v) to (xiii), |
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| whether or not the compound is further modified in any of the following ways: |
| (c) | substitution of the indole ring with a nitrogen heterocyclic analog; | | (d) | substitution to the indole ring or its nitrogen heterocyclic analog to any extent; | | (e) | substitution to the group mentioned in sub‑paragraph (b) to any extent, |
| including any salt or stereoisomeric form of the compound or derivative of the compound, any preparation or product containing the compound or derivative of the compound, and the following examples of such a compound or derivative: |
| (1) | Naphthalen-1-yl 1-(5-fluoropentyl)-1H-indazole-3-carboxylate (also known as 5-Fluoro-SDB-005) | | (2) | Naphthalen-1-yl 1-(5-fluoropentyl)-1H-indole-3-carboxylate (also known as NM-2201 or CBL-2201) | | (3) | Naphthalen-1-yl 1-pentyl-1H-indazole-3-carboxylate (also known as SDB-005) | | (4) | Quinolin-8-yl 1-(cyclohexylmethyl)-1H-indole-3-carboxylate (also known as BB-22 or QUCHIC) | | (5) | Quinolin-8-yl 1-(5-fluoropentyl)-1H-indole-3-carboxylate (also known as 5-Fluoro-PB-22 or 5-Fluoro-QUPIC) | | (6) | Quinolin-8-yl 1-pentyl-1H-indole-3-carboxylate (also known as PB-22 or QUPIC)”. |
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