CUMYL-FUBINACA

Last updated
CUMYL-FUBINACA
CUMYL-FUBINACA structure.png
Legal status
Legal status
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class B
Identifiers
  • 1-[(4-fluorophenyl)methyl]-N-(2-phenylpropan-2-yl)indazole-3-carboxamide
PubChem CID
UNII
Chemical and physical data
Formula C24H22FN3O
Molar mass 387.458 g·mol−1
3D model (JSmol)
  • CC(C)(C1=CC=CC=C1)NC(=O)C2=NN(C3=CC=CC=C32)CC4=CC=C(C=C4)F
  • InChI=1S/C24H22FN3O/c1-24(2,18-8-4-3-5-9-18)26-23(29)22-20-10-6-7-11-21(20)28(27-22)16-17-12-14-19(25)15-13-17/h3-15H,16H2,1-2H3,(H,26,29)
  • Key:ABBDMPBQHOHMJZ-UHFFFAOYSA-N

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. [1] [2] [3] [4] It has been sold online as a designer drug. [5]

See also

Related Research Articles

<span class="mw-page-title-main">APICA (synthetic cannabinoid drug)</span> Chemical compound

APICA is an indole based drug that acts as a potent agonist for the cannabinoid receptors.

<span class="mw-page-title-main">AB-PINACA</span> Chemical compound

AB-PINACA is a compound that was first identified as a component of synthetic cannabis products in Japan in 2012.

<span class="mw-page-title-main">ADBICA</span> Group of stereoisomers

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.

<span class="mw-page-title-main">ADB-FUBINACA</span> Chemical compound

ADB-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.

<span class="mw-page-title-main">SDB-006</span> Chemical compound

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.

<span class="mw-page-title-main">5F-SDB-006</span> Chemical compound

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.

<span class="mw-page-title-main">CUMYL-PICA</span> Chemical compound

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.

<span class="mw-page-title-main">5F-CUMYL-PINACA</span> Chemical compound

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.

<span class="mw-page-title-main">MDMB-FUBINACA</span> Chemical compound

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.

<span class="mw-page-title-main">AB-FUBICA</span> Chemical compound

AB-FUBICA is a drug that acts as a potent agonist for the cannabinoid receptors, with EC50 values of 21 nM at CB1 and 15 nM at CB2.

<span class="mw-page-title-main">ADB-FUBICA</span> Chemical compound

ADB-FUBICA is a drug that acts as a potent agonist for the cannabinoid receptors, with EC50 values of 2.6 nM at CB1 and 3.0 nM at CB2.

<span class="mw-page-title-main">AB-PICA</span> Chemical compound

AB-PICA is a potent agonist for the CB1 receptor (EC50 = 12 nM) and CB2 receptor (EC50 = 12 nM).

<span class="mw-page-title-main">5F-ADBICA</span> Chemical compound

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.

<span class="mw-page-title-main">AMB-FUBINACA</span> Chemical compound

AMB-FUBINACA (also known as FUB-AMB and MMB-FUBINACA) is an indazole-based synthetic cannabinoid that is a potent agonist for the cannabinoid receptors, with Ki values of 10.04 nM at CB1 and 0.786 nM at CB2 and EC50 values of 0.5433 nM at CB1 and 0.1278 nM at CB2, and has been sold online as a designer drug. It was originally developed by Pfizer which described the compound in a patent in 2009, but was later abandoned and never tested on humans. AMB-FUBINACA was the most common synthetic cannabinoid identified in drug seizures by the Drug Enforcement Administration in 2017 and the first half of 2018.

<span class="mw-page-title-main">FUB-APINACA</span> Chemical compound

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.

<span class="mw-page-title-main">CUMYL-4CN-BINACA</span> Chemical compound

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.

<span class="mw-page-title-main">5F-CUMYL-P7AICA</span> Chemical compound

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.

<span class="mw-page-title-main">5F-MDMB-PICA</span> Chemical compound

5F-MDMB-PICA is a designer drug and synthetic cannabinoid. In 2018, it was the fifth-most common synthetic cannabinoid identified in drugs seized by the Drug Enforcement Administration.

<span class="mw-page-title-main">4F-MDMB-BINACA</span> Chemical compound

4F-MDMB-BINACA (also known as 4F-MDMB-BUTINACA or 4F-ADB) is an indazole-based synthetic cannabinoid from the indazole-3-carboxamide family. It has been used as an active ingredient in synthetic cannabis products and sold as a designer drug since late 2018. 4F-MDMB-BINACA is an agonist of the CB1 receptor (EC50 = 7.39 nM), though it is unclear whether it is selective for this target. In December 2019, the UNODC announced scheduling recommendations placing 4F-MDMB-BINACA into Schedule II throughout the world.

References

  1. WO 2014167530,Bowden MW, Williamson PB,"Cannabinoid compounds",published 11 April 2013
  2. Longworth M, Banister SD, Boyd R, Kevin RC, Connor M, McGregor IS, Kassiou M (October 2017). "Pharmacology of Cumyl-Carboxamide Synthetic Cannabinoid New Psychoactive Substances (NPS) CUMYL-BICA, CUMYL-PICA, CUMYL-5F-PICA, CUMYL-5F-PINACA, and Their Analogues". ACS Chemical Neuroscience. 8 (10): 2159–2167. doi:10.1021/acschemneuro.7b00267. PMID   28792725.
  3. Banister SD, Connor M (2018). "The Chemistry and Pharmacology of Synthetic Cannabinoid Receptor Agonist New Psychoactive Substances: Evolution". New Psychoactive Substances. Handbook of Experimental Pharmacology. Vol. 252. pp. 191–226. doi:10.1007/164_2018_144. ISBN   978-3-030-10560-0. PMID   30105473.
  4. Krishna Kumar K, Shalev-Benami M, Robertson MJ, Hu H, Banister SD, Hollingsworth SA, et al. (January 2019). "Structure of a Signaling Cannabinoid Receptor 1-G Protein Complex". Cell. 176 (3): 448–458.e12. doi: 10.1016/j.cell.2018.11.040 . PMC   6461403 . PMID   30639101.
  5. Thornton SL, Darracq MA, Gugelmann HM, Armenian P (2019). "Surface internet marketplace presence and availability of NPS sold as research chemicals: a snapshot study". Toxicology Communications. 3 (1): 67–74. doi: 10.1080/24734306.2019.1648067 . S2CID   202372196.