APINACA (AKB48, N-(1-adamantyl)-1-pentyl-1H-indazole-3-carboxamide) is a drug that acts as a reasonably potent agonist for the cannabinoid receptors. It is a full agonist at CB1 with an EC50 of 142 nM and Ki of 3.24 nM (compared to the Ki of Δ9-THC at 28.35 nM and JWH-018 at 9.62 nM), while at CB2 it acts as a partial agonist with an EC50 of 141 nM and Ki of 1.68 nM (compared to the Ki of Δ9-THC at 37.82 nM and JWH-018 at 8.55 nM). Its pharmacological characterization has also been reported in a discontinued patent application. It had never previously been reported in the scientific or patent literature, and was first identified by laboratories in Japan in March 2012 as an ingredient in synthetic cannabis smoking blends, along with a related compound APICA. Structurally, it closely resembles cannabinoid compounds from a University of Connecticut patent, but with a simple pentyl chain on the indazole 1-position, and APINACA falls within the claims of this patent despite not being disclosed as an example.
APICA is an indole based drug that acts as a potent agonist for the cannabinoid receptors.
ADBICA (also known as ADB-PICA) is a designer drug identified in synthetic cannabis blends in Japan in 2013. ADBICA had not previously been reported in the scientific literature prior to its sale as a component of synthetic cannabis blends. ADBICA features a carboxamide group at the 3-indole position, like SDB-001 and STS-135. The stereochemistry of the tert-butyl side-chain in the product is unresolved, though in a large series of indazole derivatives structurally similar to ADBICA that are disclosed in Pfizer patent WO 2009/106980, activity resides exclusively in the (S) enantiomers. ADBICA is a potent agonist of the CB1 receptor and CB2 receptor with an EC50 value of 0.69 nM and 1.8 nM respectively.
ADB-FUBINACA (ADMB-FUBINACA) is a designer drug identified in synthetic cannabis blends in Japan in 2013. In 2018, it was the third-most common synthetic cannabinoid identified in drugs seized by the Drug Enforcement Administration.
SDB-006 is a drug that acts as a potent agonist for the cannabinoid receptors, with an EC50 of 19 nM for human CB2 receptors, and 134 nM for human CB1 receptors. It was discovered during research into the related compound SDB-001 which had been sold illicitly as "2NE1". SDB-006 metabolism has been described in literature.
5F-SDB-006 is a drug that acts as a potent agonist for the cannabinoid receptors, with an EC50 of 50 nM for human CB1 receptors, and 123 nM for human CB2 receptors. It was discovered during research into the related compound APICA which had been sold illicitly as "2NE1". 5F-SDB-006 is the terminally fluorinated analog of SDB-006, just as STS-135 is the terminally fluorinated analog of APICA. Given the known metabolic liberation (and presence as an impurity) of amantadine in the related compound APINACA, it is suspected that metabolic hydrolysis of the amide group of 5F-SDB-006 may release benzylamine.
5F-AB-PINACA is an indazole-based synthetic cannabinoid that is derived from a series of compounds originally developed by Pfizer in 2009 as an analgesic medication, and has been sold online as a designer drug.
CUMYL-PICA (SGT-56) is an indole-3-carboxamide based synthetic cannabinoid. It is the α,α-dimethylbenzyl analogue of SDB-006. It was briefly sold in New Zealand during 2013 as an ingredient of at the time legal synthetic cannabis products, but the product containing CUMYL-BICA and CUMYL-PICA was denied an interim licensing approval under the Psychoactive Substances regulatory scheme, due to reports of adverse events in consumers. CUMYL-PICA acts as an agonist for the cannabinoid receptors, with Ki values of 59.21 nM at CB1 and 136.38 nM at CB2 and EC50 values of 11.98 nM at CB1 and 16.2 nM at CB2.
NM-2201 (also known as CBL-2201 and NA-5F-PIC) is an indole-based synthetic cannabinoid that presumably has similar properties to the closely related 5F-PB-22 and NNE1, which are both full agonists and unselectively bind to CB1 and CB2 receptors with low nanomolar affinity.
5F-CUMYL-PINACA (also known as SGT-25 and sometimes sold in e-cigarette form as C-Liquid) is an indazole-3-carboxamide based synthetic cannabinoid. 5F-CUMYL-PINACA acts as a potent agonist for the cannabinoid receptors, with the original patent claiming approximately 4x selectivity for CB1, having an EC50 of <0.1 nM for human CB1 receptors and 0.37 nM for human CB2 receptors. In more recent assays using different techniques, 5F-CUMYL-PINACA was variously found to have an EC50 of 0.43 nM at CB1 and 11.3 nM at CB2, suggesting a somewhat higher CB1 selectivity of 26 times, or alternatively 15.1 nM at CB1 and 34.8 nM at CB2 with only 2.3 times selectivity, however these figures cannot be directly compared due to the different assay techniques used in each case.
CUMYL-THPINACA (also known as SGT-42) is an indazole-3-carboxamide based synthetic cannabinoid. CUMYL-THPINACA acts as a potent agonist for the cannabinoid receptors, with approximately 6x selectivity for CB1, having an EC50 of 0.1nM for human CB1 receptors and 0.59nM for human CB2 receptors.
MDMB-FUBINACA (also known as MDMB(N)-Bz-F and FUB-MDMB) is an indazole-based synthetic cannabinoid that is a potent agonist for the cannabinoid receptors, with Ki values of 1.14 nM at CB1 and 0.1228 nM at CB2 and EC50 values of 0.2668 nM at CB1 and 0.1411 nM at CB2, and has been sold online as a designer drug. Its benzyl analogue (instead of 4-fluorobenzyl) has been reported to be a potent agonist for the CB1 receptor (Ki = 0.14 nM, EC50 = 2.42 nM). The structure of MDMB-FUBINACA contains the amino acid, 3-methylvaline or tert-leucine methyl ester.
FUB-APINACA (also known as A-FUBINACA according to the EMCCDA framework for naming synthetic cannabinoids and FUB-AKB48) is an indazole-based synthetic cannabinoid that is presumed to be a potent agonist of the CB1 receptor and has been sold online as a designer drug. It is an analog of APINACA and 5F-APINACA where the pentyl chain has been replaced with fluorobenzyl.
5F-NNE1 (also known as 5F-NNEI and 5F-MN-24) is an indole-based synthetic cannabinoid that is presumed to be a potent agonist of the CB1 receptor and has been sold online as a designer drug. Given the known metabolic liberation (and presence as an impurity) of amantadine in the related compound APINACA, it is suspected that metabolic hydrolysis of the amide group of 5F-NNE1 may release 1-naphthylamine, a known carcinogen.
CUMYL-4CN-BINACA (also known as CUMYL-CYBINACA or SGT-78) is an indazole-3-carboxamide based synthetic cannabinoid that has been sold online as a designer drug. It is a potent agonist for cannabinoid receptors CB1 and CB2, with in vitro EC50 values of 0.58 nM and 6.12 nM, respectively. In mice, CUMYL-4CN-BINACA produces hypothermic and pro-convulsant effects via the CB1 receptor, and anecdotal reports suggest it has an active dose of around 0.1 mg in humans.
5F-CUMYL-P7AICA is a pyrrolo[2,3-b]pyridine-3-carboxamide based synthetic cannabinoid that has been sold as a designer drug. It was first identified by the EMCDDA in February 2015.
5F-CUMYL-PEGACLONE (5F-SGT-151, SGT-269) is a gamma-carboline based synthetic cannabinoid that has been sold as a designer drug, first being identified in Germany in 2017. It acts as a potent full agonist of the CB1 receptor. It appears to be more toxic than related compounds such as CUMYL-PEGACLONE, and has been linked to numerous serious adverse reactions, some fatal.
CUMYL-FUBINACA (SGT-149) is an indazole-3-carboxamide based synthetic cannabinoid receptor agonist, with an EC50 of 1.8nM for human CB1 receptors and 23.7nM for human CB2 receptors, giving it around 13x selectivity for CB1. It has been sold online as a designer drug.
ADB-BINACA (also known as ADMB-BZINACA using EMCDDA naming standards) is a cannabinoid designer drug that has been found as an ingredient in some synthetic cannabis products. It was originally developed by Pfizer as a potential analgesic, and is a potent agonist of the CB1 receptor with a binding affinity (Ki) of 0.33 nM and an EC50 of 14.7 nM.
