Emerging drugs of abuse: current perspectives on synthetic cannabinoids

Figures & data

Table 1 Chemical structure of cannabinoid 3-indole derivatives

Note: “…” demonstrates that there is no substituant on the phenyl core in position R’ or R3.

Abbreviation: CAS, Chemical Abstracts Service.

Table 2 Chemical structure of other cannabinoid derivatives

Notes: “…” demonstrates that there is no substituant on the aromatic core in position R’ or R2. When there is no R3 or R4 in the basic structure the column was left blank. “H” has been included when the structure was not a phenyl or an aromatic core.

Abbreviation: CAS, Chemical Abstracts Service.

Figure 1 Chemical structure of indole derivatives.

Table 3 Gas chromatography mass spectrometry (GC-MS) identification of synthetic cannabinoids

Chemical class	Name	Molecular weight	GC-MS identification (electronic impact)		Reference
			Base peak	Other peaks
Benzoyl indoles	AM-694	435,27	232	435, 220, 380	^Citation30
			232	435, 220, 360	^Citation28
	RCS-4	321,41	312	284, 214, 135	^Citation30
			321	135, 264, 214,	^Citation27
			321	265, 135, 214	Personal data
	RCS-4-(N-Me)	265,31	158	265, 77, 264, 266	^Citation27
	WIN-48,098	378,46	100	135, 378	^Citation28
Naphthoyl indoles	JWH-018	341,45	341	284, 214, 127, 324	^Citation30
			341	284, 214, 127, 324	^Citation28
			341	325, 285, 215	Personal data
	JWH-019	355,47	355	284, 228, 127, 338	^Citation30
			355	338, 284, 228	Personal data
	JWH-073	327,42	327	200, 284, 127, 310	^Citation30
			327	200, 284, 310, 127	^Citation28
			327	310, 284, 200	Personal data
	JWH-081	371,47	371	354, 314, 214,185	^Citation30
			371	354, 370, 314, 214, 185	^Citation27
			371	354, 314, 214	Personal data
	JWH-122	355,47	355	338, 298, 215	^Citation30
			355	298, 214, 338	Personal data
	JWH-122-pentenyl	353,45	353	351, 335, 127, 284	^Citation31
	JWH-200	384,47	100	384, 339, 155, 127	Personal data
	JWH-210	369,50	369	352, 312, 214, 340	^Citation30
			369	352, 312, 214, 368, 340	^Citation27
	JWH-412	359,44	359	302, 145, 173, 214	^Citation29
	AM-1220	382,21	98	70, 127, 254, 284	^Citation31
			98	70, 127, 155, 254	^Citation32
	AM-1220- azepane	382,21	382	84, 127, 184, 57	^Citation31
			127	84, 57, 382, 98	^Citation32
	AM-2201	359,44	359	284, 232, 342, 358, 127	^Citation31
			359	127, 284, 232, 342	^Citation29
			359	127, 284, 232, 342	^Citation28
			359	284, 232, 342, 358	^Citation27
			359	284, 232, 127, 342	^Citation30
			355	338, 284, 228	Personal data
	AM-2201-pMe	373,46	373	298, 232, 356, 372	^Citation31
			373	298, 232, 356, 372	^Citation27
	AM-2232	352,43	352	351, 335, 225, 127	^Citation31
Phenylacetyl indoles	JWH-203	339,86	214	144, 116, 339	^Citation30
	JWH-250	335,44	214	144, 116, 335	^Citation30
			214	144, 335, 116	^Citation28
			214	144, 215, 335	Personal data
Alkoyl indoles	UR-144	311,2	214	144, 296, 215, 311	^Citation31
			215	296, 144, 311	Personal data
	XLR-11	329,2	232	144, 233, 329, 41	^Citation31
Carboxylate indoles	MN-27	396	109	252, 396	^Citation128
	NM-2201	375,16	232	144, 115	^Citation128
Carboxamide indoles	STS-135	382,2	232	382, 307, 144, 383	^Citation31
Naphtoyl pyrroles	JWH-147		381	155,127, 310, 296	^Citation30
	FUB-NPB-22	397,4	109	253, 397	^Citation128
Carboxylate indazoles	5-fluoro-NPB-22	377,4	233	145, 377	^Citation128
	5-fluoro-SDB-005	376	233	145, 213, 376	^Citation128
Dibenzopyranes	HU-210	386,57	303	387, 331, 285, 270	Personal data

Table 4 Liquid chromatography – tandem mass spectrometry identification of synthetic cannabinoids

Name	Molecular weight	Precursor ion	Product ions	Reference
Positive mode
AM-251	555.2	555.0	454.0; 472.0	^Citation39
AM-694	435.3	435.9	231,0; 309,2; 203,2	^Citation39
AM-2201	359.4	360.1	155.1; 127.2	^Citation11,Citation34,Citation37,Citation40
AM-1220	382.5	383,2	112,0; 98,1; 286,2	^Citation34,Citation36
AM-1241	503.3	504.1	98.0; 275.0	^Citation39
AM-2201	359.4	360.2	155.0; 232.0	^Citation39
AM-2233	458.3	459.1	112.1; 98.1; 230.0	^Citation33,Citation39
HU-210	386.6	387,2	243,2; 261,3; 85,0	^Citation36,Citation39
JWH-007	355.5	356.2	155.2; 127.2	^Citation33,Citation38,Citation39
JWH-011	383.5	384.2	155.0; 286.0	^Citation39
JWH-015	327.4	328.1	155.1; 200.1; 127.0	^Citation34,Citation36,Citation38
JWH-018	341.4	342.1	155.1; 214.2; 127.1	^Citation36^–^Citation38,Citation40
JWH-019	355.5	356.2	155.1; 126.9; 228.1	^Citation34,Citation36,Citation37
JWH-020	369.5	370.4	155.1; 242.1; 127.1	^Citation33,Citation36
JWH-022	339.4	340.2	155.0; 212.0	^Citation39
JWH-030	291.4	292.2	155.0; 168.0	^Citation39
JWH-073	327.4	328.1	155,0; 200,0; 127,0	^Citation34,Citation36^–^Citation38,Citation40
JWH-081	371.5	372.2	185.1; 157.1; 127.0	^Citation34,Citation36,Citation37
JWH-098	385.5	386.2	185.0; 198.0; 228.0	^Citation39
JWH-122	355.5	356.1	169.1; 214.2; 141.0	^Citation34,Citation36^–^Citation38,Citation40
JWH-182	383.5	384.2	197.0; 214.0; 144	^Citation38,Citation39
JWH-200	384.5	385.2	155.1; 114.0; 127.0	^Citation34,Citation36,Citation37
JWH-201	335.4	336.2	121.0; 135.0; 214.0	^Citation39
JWH-203	339.9	340,1	124.9; 188.1; 89.0	^Citation33,Citation36
JWH-210	369.5	370.1	183.1; 214.1; 153.1	^Citation36^–^Citation38
JWH-249	384.3	385	144	^Citation38
JWH-250	335.4	336.1	121.2; 91.1; 200.3	^Citation34,Citation36^–^Citation38
JWH-251	319.4	320,1	104,9; 214,1; 144,2	^Citation33,Citation34,Citation36,Citation37
JWH-302	335.4	336	144; 121	^Citation38
JWH-307	385.5	386,2	155,0; 127,1; 77,1	^Citation33,Citation34,Citation36
JWH-398	375.9	376.1	189; 161.1; 126.1	^Citation33,Citation36,Citation37
JWH-412	359.4	360.4	173.2; 145.1	^Citation33
JWH-424	420.3	422	144	^Citation38
MAM-2201	373.5	374.1	169.0; 115.0	^Citation37,Citation40
RCS-4	321.4	322,2	135,0; 77,0; 92,0	^Citation36,Citation37
RCS-8	375.5	376,2	121,0; 90,9; 143,9	^Citation36,Citation37
WIN-48,098	378.5	379,1	134,9; 114,0; 77,1	^Citation36
WIN 55,212-2	426.5	427,3	155,1; 127,0; 100,0	^Citation33,Citation36,Citation38
XRL-11	329.5	330.1	125.1; 232.0	^Citation37
Negative mode
CP-47,497-C7	318.5	317.1	245.1; 159.1	^Citation37
CP-47,497-C8	332.5	331.1	259.1; 159.0	^Citation37
HU-210	386.6	385.6	301.3; 281.1	^Citation37

Table 5 Affinities of much of synthetic cannabinoids

	CB1
	Ki < 1 nM	1 nM < Ki < 10 nM	10 nM < Ki < 100 nM	100 nM < Ki < 1000 nM	Ki > 1000 nM
CB2
Ki < 1 nM	JWH-210^Citation52*	JWH-149;^Citation52 AB-005;^Citation56 A-834,735;^Citation56 O-1871^Citation64	AM-1221^Citation54	A-836,339^Citation57
1 nM < Ki < 10 nM	AM-694;^Citation54 JWH-122;^Citation53 JWH-182;^Citation52 AM-2232^Citation54	AM-2233;^Citation58 JWH-007;^Citation7,Citation52 JWH-018;^Citation53 JWH-019;^Citation53 JWH-098;^Citation53 JWH-387;^Citation59 JWH-398;^Citation59 JWH-412;^Citation59 AM-220;^Citation57 JWH-203;^Citation55 JWH-250;^Citation55 NM-2201;^Citation54 JWH-307;^Citation52 JWH-370;^Citation52	JWH-424;^Citation61 UR-144;^Citation56 JWH-145;^Citation52 JWH-147;^Citation52 JWH-368^Citation52	A-796,260^Citation56
10 nM < Ki < 100 nM		JWH-073;^Citation53 JWH-081;^Citation53 AM-1235;^Citation54 JWH-249^Citation55	AM-679;^Citation54 Δ9-THC;^Citation52 JWH-204;^Citation55 JWH-253;^Citation55 JWH-302;^Citation55 JWH-311;^Citation55 JWH-176;^Citation63 JWH-220^Citation63	JWH-015;^Citation53
100 nM < Ki < 1000 nM			JWH-167;^Citation55 methanandamide^Citation60	JWH-206;^Citation55 JWH-208^Citation55	JWH-201;^Citation55 JWH-316^Citation55
Ki > 1000 nM				JWH-209^Citation55	JWH-071;^Citation53 JWH-207^Citation55

Notes:

* The number in exponent is the reference in the literature giving the Ki. The bold text represents the lead natural cannabinoid of Cannabis sativa.

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