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| Formula | C23H27N3O2 |
| Molar mass | 377.488 g·mol−1 |
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CUMYL-THPINACA (also known as SGT-42) is an indazole-3-carboxamide based synthetic cannabinoid. [1] [2] 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. [3]
Sweden's public health agency suggested to classify CUMYL-THPINACA as hazardous substance on November 10, 2014. [4]
As of October 2015 CUMYL-THPINACA is a controlled substance in China. [5]
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, with a Ki of 304.5nM and an EC50 of 585nM at CB1. 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 (WO 2003/035005), 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.
STS-135 (N-(adamantan-1-yl)-1-(5-fluoropentyl)-1H-indole-3-carboxamide, also called 5F-APICA) is a designer drug offered by online vendors as a cannabimimetic agent. The structure of STS-135 appears to use an understanding of structure-activity relationships within the indole class of cannabimimetics, although its design origins are unclear. STS-135 is the terminally-fluorinated analogue of SDB-001, just as AM-2201 is the terminally-fluorinated analogue of JWH-018, and XLR-11 is the terminally-fluorinated analogue of UR-144. STS-135 acts a potent cannabinoid receptor agonist in vitro, with an EC50 of 51 nM for human CB2 receptors, and 13 nM for human CB1 receptors. STS-135 produces bradycardia and hypothermia in rats at doses of 1–10 mg/kg, suggesting cannabinoid-like activity.
AB-PINACA is a compound that was first identified as a component of synthetic cannabis products in Japan in 2012.
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.
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.
AB-CHMINACA is an indazole-based synthetic cannabinoid. It is a potent agonist of the CB1 receptor (Ki = 0.78 nM) and CB2 receptor (Ki = 0.45 nM) and fully substitutes for Δ9-THC in rat discrimination studies, while being 16x more potent. Continuing the trend seen in other cannabinoids of this generation, such as AB-FUBINACA and AB-PINACA, it contains a valine amino acid amide residue as part of its structure, where older cannabinoids contained a naphthyl or adamantane residue.
ADB-PINACA is a cannabinoid designer drug that is an ingredient in some synthetic cannabis products. It is a potent agonist of the CB1 receptor and CB2 receptor with EC50 values of 0.52 nM and 0.88 nM respectively. Like MDMB-FUBINACA, this compound contains an amino acid residue of tert-leucine.
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.
5F-APINACA is an indazole-based synthetic cannabinoid that has been sold online as a designer drug. Structurally it closely resembles cannabinoid compounds from patent WO 2003/035005 but with a 5-fluoropentyl chain on the indazole 1-position, and 5F-APINACA falls within the claims of this patent, as despite not being disclosed as an example, it is very similar to the corresponding pentanenitrile and 4-chlorobutyl compounds which are claimed as examples 3 and 4.
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.
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-PINACA (also known as SGT-24) is an indazole-3-carboxamide based synthetic cannabinoid. CUMYL-PINACA acts as a potent agonist for the cannabinoid receptors, with approximately 3x selectivity for CB1, having an EC50 of 0.15nM for human CB1 receptors and 0.41nM 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.
5F-ADBICA (also known as 5F-ADB-PICA) is an indole-based synthetic cannabinoid that is a potent agonist at CB1 receptors and CB2 receptors with EC50 values of 0.77 nM and 1.2 nM respectively.
FUB-APINACA (also known as AFUBINACA 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.
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.
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.
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