Cannabimimetic activities of cumyl carboxamide-type synthetic cannabinoids

  title={Cannabimimetic activities of cumyl carboxamide-type synthetic cannabinoids},
  author={Akiko Asada and Takahiro Doi and Takaomi Tagami and Akihiro Takeda and Yuka Satsuki and Masami Kawaguchi and Akihiko Nakamura and Yoshiyuki Sawabe},
  journal={Forensic Toxicology},
Abstract1-Pentyl-N-(2-phenylpropan-2-yl)-1H-indazole-3-carboxamide (CUMYL-PINACA) is a carboxamide-type synthetic cannabinoid comprising a cumylamine moiety. Recently, the detection of CUMYL-PINACA and some analogs in illicit drug products has been reported by the European Monitoring Centre for Drugs and Drug Addiction. In this study, we synthesized seven cumyl carboxamide-type synthetic cannabinoids (CUMYL-PINACA, CUMYL-5F-PINACA, CUMYL-PICA, CUMYL-5F-PICA, CUMYL-THPINACA, CUMYL-BICA, and… 

Pharmacology of Cumyl-Carboxamide Synthetic Cannabinoid New Psychoactive Substances (NPS) CUMYL-BICA, CUMYL-PICA, CUMYL-5F-PICA, CUMYL-5F-PINACA, and Their Analogues.

Hypothermia was reversed by pretreatment with a CB1, but not CB2, antagonist, confirming that cumyl-derived SCs are cannabimimetic in vivo.

Synthesis and pharmacology of new psychoactive substance 5F-CUMYL-P7AICA, a scaffold- hopping analog of synthetic cannabinoid receptor agonists 5F-CUMYL-PICA and 5F-CUMYL-PINACA.

Five scaffold-hopping SCRAs, including 5F-CUMYL-P7AICA, were synthesized and characterized and found to exert potent cannabimimetic effects in mice, inducing hypothermia through a CB1 -dependent mechanism.

CUMYL-4CN-BINACA Is an Efficacious and Potent Pro-Convulsant Synthetic Cannabinoid Receptor Agonist

It is reported here that CUMYL-4CN-BINACA is a potent CB1 receptor agonist that produces pro-convulsant effects in mice at a lower dose than reported for any SCRA to date, and may underpin the toxicity associated with this compound in humans.

Exploring Stereochemical and Conformational Requirements at Cannabinoid Receptors for Synthetic Cannabinoids Related to SDB-006, 5F-SDB-006, CUMYL-PICA, and 5F-CUMYL-PICA.

Molecular dynamics simulations provided a conformational basis for the observed differences in agonist potency at CB1 pending benzylic substitution, highlighting an enantiomeric bias for this series of SCRAs.

Synthesis and in Vitro Cannabinoid Receptor 1 Activity of Recently Detected Synthetic Cannabinoids 4F-MDMB-BICA, 5F-MPP-PICA, MMB-4en-PICA, CUMYL-CBMICA, ADB-BINACA, APP-BINACA, 4F-MDMB-BINACA, MDMB-4en-PINACA, A-CHMINACA, 5F-AB-P7AICA, 5F-MDMB-P7AICA, and 5F-AP7AICA.

This study confirms that recently detected SCRAs 4F-MDMB-BICA, 5F-MPP-PICA, MMB-4en-Pica, CUMYL-CBMICA, ADB-BINACA, APP-BinACA, 4F and 5F were all able to activate the CB1 receptor in vitro, albeit to different extents, and are potentially psychoactive in vivo.

Phase I In Vitro Metabolic Profiling of the Synthetic Cannabinoid Receptor Agonists CUMYL-THPINACA and ADAMANTYL-THPINACA

In vitro phase I metabolic profiling was conducted of the two indazole-3-carboxamide SCRAs, suggesting that ADAMANTYL-THPINACA might be more prone to metabolic drug−drug interactions than CUMYL- THPINACA, when co-administrated with strong CYP3A4 inhibitors.

Toxic by design? Formation of thermal degradants and cyanide from carboxamide-type synthetic cannabinoids CUMYL-PICA, 5F-CUMYL-PICA, AMB-FUBINACA, MDMB-FUBINACA, NNEI, and MN-18 during exposure to high temperatures

People who smoke carboxamide-type synthetic cannabinoids are likely to be exposed to a range of potentially toxic thermal degradants, including cyanide, which could have significant health impacts in human users.

Comparison of in vitro and in vivo models for the elucidation of metabolic patterns of 7-azaindole-derived synthetic cannabinoids exemplified using cumyl-5F-P7AICA.

The pig model predicts best the human metabolic pattern of cumyl-5F-P7AICA, and besides the parent compound, the OF/carboxylated and monohydroxylated metabolites can be recommended as urinary targets.



The synthesis and pharmacological evaluation of adamantane-derived indoles: cannabimimetic drugs of abuse.

Which structural features of AB-001, AB-002, and their analogues govern the cannabimimetic potency of these chemotypes in vitro and in vivo are elucidated.

Isomeric discrimination of synthetic cannabinoids by GC-EI-MS: 1-adamantyl and 2-adamantyl isomers of N-adamantyl carboxamides.

1-adamantyl carboxamides can be clearly discriminated from their 2-adAmantyl isomers based on their different fragmentation patterns in the EI-MS spectra, and is expected to be of use for isomeric differentiation between other untested adamantyl car boxamide-type synthetic cannabinoids.

Identification of N,N-bis(1-pentylindol-3-yl-carboxy)naphthylamine (BiPICANA) found in an herbal blend product in the Tokyo metropolitan area and its cannabimimetic effects evaluated by in vitro [35S]GTPγS binding assays

During our careful survey of unregulated psychotropic drugs in June 2013 in the Tokyo metropolitan area, we found a new compound in a herbal product. It was identified as an analog of NNEI (MN-24)

Changes in the prevalence of synthetic cannabinoids and cathinone derivatives in Japan until early 2012

The changes in the prevalence of designer drugs and their legal status in Japan were investigated on the basis of the analyses of 686 different products containing synthetic cannabinoids and/or

Occupational transdermal poisoning with synthetic cannabinoid cumyl-PINACA

This case series highlights the possible transdermal exposure to synthetic cannabinoids oil resulting in prolonged cannabinoid syndrome.