CUMYL-CH-MEGACLONE

Last updated
CUMYL-CH-MEGACLONE
CUMYL-CH-MEGACLONE structure.png
Legal status
Legal status
Identifiers
  • 2,5-Dihydro-2-(1-methyl-1-phenylethyl)-5-(cyclohexylmethyl)-1H-pyrido[4,3-b]indol-1-one
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
Formula C27H30N2O
Molar mass 398.550 g·mol−1
3D model (JSmol)
  • CC(C)(C1=CC=CC=C1)N2C=CC3=C(C2=O)C4=CC=CC=C4N3CC5CCCCC5
  • InChI=1S/C27H30N2O/c1-27(2,21-13-7-4-8-14-21)29-18-17-24-25(26(29)30)22-15-9-10-16-23(22)28(24)19-20-11-5-3-6-12-20/h4,7-10,13-18,20H,3,5-6,11-12,19H2,1-2H3
  • Key:CGHCGYCTOLWAPL-UHFFFAOYSA-N

CUMYL-CH-MEGACLONE (CUMYL-CHMGACLONE, SGT-270) is a gamma-carboline based synthetic cannabinoid receptor agonist that has been sold as a designer drug, first being identified in Hungary in December 2018. [1] [2] [3]

See also

Related Research Articles

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

'MDMB-CHMICAa' is an indole-based synthetic cannabinoid that is a potent agonist of the CB1 receptor and has been sold online as a designer drug. While MDMB-CHMICA was initially sold under the name "MMB-CHMINACA", the compound corresponding to this code name (i.e. the isopropyl instead of t-butyl analogue of MDMB-CHMINACA) has been identified on the designer drug market in 2015 as AMB-CHMINACA.

<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">NM-2201</span> Chemical compound

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.

<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">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">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">CUMYL-PEGACLONE</span> Chemical compound

CUMYL-PEGACLONE (SGT-151) is a gamma-carboline based synthetic cannabinoid that has been sold as a designer drug. The gamma-carboline core structure seen in CUMYL-PEGACLONE had not previously been encountered in a designer cannabinoid, though it is similar in structure to other gamma-carboline cannabinoids disclosed by Bristol-Myers Squibb in 2001.

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

5F-MDMB-PICA (MDMB-5F-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">MDMB-4en-PINACA</span> Chemical compound

MDMB-4en-PINACA is an indazole-based synthetic cannabinoid that has been sold online as a designer drug. MDMB-4en-PINACA was first identified in Europe in 2017. In 2021, MDMB-4en-PINACA was the most common synthetic cannabinoid identified by the Drug Enforcement Administration in the United States. MDMB-4en-PINACA differs from 5F-MDMB-PINACA due to replacement of 5-fluoropentyl with a pent-4-ene moiety (4-en).

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

4F-MDMB-BINACA (also known as MDMB-4F-BINACA, 4F-MDMB-BUTINACA or 4F-ADB) is an indazole-based synthetic cannabinoid from the indazole-3-carboxamide family. It should not be confused with the amantadine analogue 4F-ABINACA. 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.

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

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.

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

CUMYL-CBMINACA (SGT-277) is an indazole-3-carboxamide based synthetic cannabinoid receptor agonist that has been sold as a designer drug, first being identified in Germany in February 2020. It is illegal in Finland.

<span class="mw-page-title-main">CUMYL-CB-MEGACLONE</span> Designer drug

CUMYL-CB-MEGACLONE is a gamma-carboline based synthetic cannabinoid receptor agonist that has been sold as a designer drug, first being identified in Hungary in April 2020.

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

CUMYL-CBMICA (SGT-280) is an indole-3-carboxamide based synthetic cannabinoid receptor agonist which has been sold as a designer drug, first being identified in Germany in August 2019. Since the structure fell outside the German drug analogue law provisions at the time, an amendment was made to the law to expand the relevant definition, which came into effect in April 2020. It has been shown to act as a CB1 receptor agonist with an EC50 of 62.9nM.

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

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.

<span class="mw-page-title-main">CUMYL-BC-HPMEGACLONE-221</span> Chemical compound

Cumyl-BC-HpMeGaClone-221 is a gamma-carboline derivative which is a synthetic cannabinoid that has been sold as a designer drug. It was first identified in Germany in September 2020.

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

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.

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

ADB-BUTINACA (also known as ADMB-BINACA using EMCDDA naming standards) is a synthetic cannabinoid compound which has been sold as a designer drug. It is a potent CB1 agonist, with a binding affinity of 0.29nM for CB1 and 0.91nM for CB2, and an EC50 of 6.36 nM for CB1.

References

  1. Alam RM, Keating JJ (March 2020). "Adding more "spice" to the pot: A review of the chemistry and pharmacology of newly emerging heterocyclic synthetic cannabinoid receptor agonists". Drug Testing and Analysis. 12 (3): 297–315. doi:10.1002/dta.2752. PMID   31854124. S2CID   209417068.
  2. Haschimi B, Giorgetti A, Mogler L, Nagy TZ, Kramer S, Halter S, et al. (June 2020). "The Novel Psychoactive Substance Cumyl-CH-MEGACLONE: Human Phase-I Metabolism, Basic Pharmacological Characterization, and Comparison to Other Synthetic Cannabinoid Receptor Agonists with a γ-Carboline-1-one Core". Journal of Analytical Toxicology. 45 (3): 277–290. doi:10.1093/jat/bkaa065. PMID   32514544.
  3. Institóris L, Kovács K, Sija É, Berkecz R, Körmöczi T, Németh I, Elek I, Bakos Á, Urbán I, Pap C, Kereszty É (June 2021). "Clinical symptoms and blood concentration of new psychoactive substances (NPS) in intoxicated and hospitalized patients in the Budapest region of Hungary (2018-19)". Clinical Toxicology. 60 (1). Philadelphia, Pa.: 18–24. doi:10.1080/15563650.2021.1928162. PMID   34080493. S2CID   235321374.