Human urinary metabolite pattern of a new synthetic cannabimimetic, methyl 2-(1-(cyclohexylmethyl)-1H-indole-3-carboxamido)-3,3-dimethylbutanoate

  title={Human urinary metabolite pattern of a new synthetic cannabimimetic, methyl 2-(1-(cyclohexylmethyl)-1H-indole-3-carboxamido)-3,3-dimethylbutanoate},
  author={Andrej Grigoryev and Pierce V Kavanagh and Alexandr Pechnikov},
  journal={Forensic Toxicology},
A number of metabolites of a new synthetic cannabimimetic, which is a derivative of 2-(1-(cyclohexylmethyl)-1H-indole-3-carboxamido)-3,3-dimethylbutanoic acid, were identified in human urine. The parent compound, a methyl ester of this acid, was identified in seizures in persons from the same city where analysis of drug-intoxication urine samples revealed the presence of the compound’s metabolites. This compound named ‘MDMB-CHMICA’ was reported to the European Monitoring Centre for Drugs and… 
Phase I metabolism of the carbazole-derived synthetic cannabinoids EG-018, EG-2201, and MDMB-CHMCZCA and detection in human urine samples.
A metabolite mono-hydroxylated at the cyclohexyl methyl tail is considered the most suitable compound-specific consumption marker while a biotransformation product of mono-Hydroxylation in combination with hydrolysis of the terminal methyl ester function provides best sensitivity due to its high abundance.
Detection of the recently emerged synthetic cannabinoid 5F-MDMB-PICA in 'legal high' products and human urine samples.
Exemplary analysis of one urine sample for 5F-MDMB-PICA phase II metabolites showed that two of the main phase I metabolites are subject to extensive glucuronidation prior to renal excretion, and conjugate cleavage is reasonable for enhancing sensitivity.
Phase I metabolism of the highly potent synthetic cannabinoid MDMB-CHMICA and detection in human urine samples.
In this study, the in vivo phase I metabolism of MDMB-CHMICA was investigated using liquid chromatography-electrospray ionization-tandem mass spectrometry (LC-ESI-MS/MS) techniques and intrinsic activity of MDMICA at the CB1 receptor was determined applying a cAMP accumulation assay and showed that the compound is a potent full agonist.
Detection of metabolites of two synthetic cannabimimetics, MDMB-FUBINACA and ADB-FUBINACA, in authentic human urine specimens by accurate mass LC–MS: a comparison of intersecting metabolic patterns
Based upon liquid chromatography–quadrupole time-of-flight-mass spectrometry analysis of urine and blood samples collected from patients who were admitted to hospital with suspected drug intoxications and from postmortem forensic investigations, 38 metabolites were tentatively identified.
Detection of a New Tert-Leucinate Synthetic Cannabinoid 5F-MDMB-PICA and Its Metabolites in Human Hair: Application to Authentic Cases
The validated UHPLC-MS/MS method was successfully applied to the identification and quantification of 5F-MDMB-PICA and its metabolites in hair from authentic forensic cases.
Structure-metabolism relationships of valine and tert-leucine-derived synthetic cannabinoid receptor agonists: a systematic comparison of the in vitro phase I metabolism using pooled human liver microsomes and high-resolution mass spectrometry
The presented pHLM approach proved to be an effective tool for systematic investigation of SMRs enabling in-depth understanding of their phase I biotransformation and facilitating the prediction of suitable analytical targets for urine analysis.
Identification of New Synthetic Cannabinoid ADB-CHMINACA (MAB-CHMINACA) Metabolites in Human Hepatocytes
Ten major metabolites of ADB-CHMINACA, a new synthetic cannabinoid with high potency and many reported adverse events and fatalities, are detected in hepatocyte incubations to identify its major metabolites and guide analytical standard manufacturers to better provide suitable references for further studies.
Post-mortem distribution of the synthetic cannabinoid MDMB-CHMICA and its metabolites in a case of combined drug intoxication
It was concluded from femoral blood analysis that the 27-year-old man found dead after falling from the 24th floor of a high-rise building was under the influence of the synthetic cannabinoid MDMB-CHMICA, THC, amphetamine and MDMA.


Study on the phase I metabolism of novel synthetic cannabinoids, APICA and its fluorinated analogue.
It was shown that for the detection of APICA abuse, the preferred metabolites are the di- and tri-hydroxylated species, while in case of 5F-APICA, a monohydroxy metabolite is a better target.
Pentylindole/Pentylindazole Synthetic Cannabinoids and Their 5-Fluoro Analogs Produce Different Primary Metabolites: Metabolite Profiling for AB-PINACA and 5F-AB-PINACA
This work determined metabolic stability and metabolites of N-(1-amino-3-methyl-1-oxobutan-2-yl)-1-pentyl-1H-indazole- 3-carboxamide (AB-PINACA) and 5-fluoro-AB- PINACA (5F-AB -PINACA), two new synthetic cannabinoids, and investigated if results were similar.
In vitro and in vivo human metabolism of the synthetic cannabinoid AB-CHMINACA.
Most of the in vitro metabolites of AB-CHMINACA were also present in urine obtained from an AB- CHMINACA user, therefore showing the reliability of the results obtained usingThe in vitro metabolism experiments conducted to predict AB-ChMINACA in vivo metabolism are investigated and can be used for routine analysis.
Metabolism of synthetic cannabinoids PB-22 and its 5-fluoro analog, 5F-PB-22, by human hepatocyte incubation and high-resolution mass spectrometry
Metabolism of synthetic cannabinoids PB-22 and 5F-PB-22 by human hepatocyte incubation and high-resolution mass spectrometry shows ester hydrolysis yielding a wide variety of (5-fluoro)pentylindole-3-carboxylic acid metabolites.
New Synthetic Cannabinoid – Methyl 2-{[1-(5-Fluoro-Pentyl)-3-Methyl-1H-Indol-3-Ylcarbonyl]-Amino}Butyrate – as a Designer Drug
Synthetic cannabinoids, which are being studied for the purpose of producing new pharmaceutical preparations [1, 2], have changed in recent years into a new form of designer drugs that are being
Four types of cannabimimetic indazole and indole derivatives, ADB-BINACA, AB-FUBICA, ADB-FUBICA, and AB-BICA, identified as new psychoactive substances
Four cannabimimetic indazole and indole derivatives in new illegal psychoactive substances seized from a clandestine laboratory in China are identified, the first report of their presence in illegal products.
Synthetic cannabimimetic agents metabolized by carboxylesterases.
The identified major metabolites of AB-PINACA and AB-FUBINACA are likely to be useful in documenting drug usage in forensic and clinical screening and improves knowledge in the emerging field of xenobiotic metabolism by esterases.
Detection and tentative identification of urinary phase I metabolites of phenylacetylindole cannabimimetics JWH-203 and JWH-251, by GC-MS and LC-MS/MS.
Chemical analysis of a benzofuran derivative, 2-(2-ethylaminopropyl)benzofuran (2-EAPB), eight synthetic cannabinoids, five cathinone derivatives, and five other designer drugs newly detected in illegal products
From November 2013 to May 2014, 19 newly distributed designer drugs were identified in 104 products in our ongoing survey of illegal products in Japan. The identified compounds included 8 synthetic