In vitro metabolism of new synthetic cannabinoid SDB-006 in human hepatocytes by high-resolution mass spectrometry

@article{Diao2016InVM,
  title={In vitro metabolism of new synthetic cannabinoid SDB-006 in human hepatocytes by high-resolution mass spectrometry},
  author={Xingxing Diao and J{\'e}r{\'e}my Carlier and Karl B. Scheidweiler and Marilyn A. Huestis},
  journal={Forensic Toxicology},
  year={2016},
  volume={35},
  pages={252-262}
}
The drug abuse epidemic within the United States remains one of the nation’s most serious social challenges, especially among adolescents and young adults. Novel psychoactive substances continuously emerge into the illicit drugs-of-abuse market to evade legislation. In 2013, SDB-006 was detected as a novel synthetic cannabinoid (SC) with high binding affinity to CB1 (EC50 = 19 nM) and CB2 (EC50 = 134 nM). Unfortunately, no human metabolism data for SDB-006 are currently available, making it… 
7 Citations

Figures and Tables from this paper

Human Hepatocyte Metabolism of Novel Synthetic Cannabinoids MN-18 and Its 5-Fluoro Analog 5F-MN-18.
BACKGROUND In 2014, 2 novel synthetic cannabinoids, MN-18 and its 5-fluoro analog, 5F-MN-18, were first identified in an ongoing survey of novel psychoactive substances in Japan. In vitro
The chemistry and pharmacology of synthetic cannabinoid SDB-006 and its regioisomeric fluorinated and methoxylated analogs.
TLDR
All methoxy- and fluorine-substituted analogs showed reduced potency compared to SDB-006, although the 2-fluorinated analog was comparable to known synthetic cannabinoid RCS-4, suggesting lower potency than the recent synthetic cannabinoid AB-CHMINACA.
Kinetic and metabolic profiles of synthetic cannabinoids NNEI and MN-18.
TLDR
Interestingly, NNEI underwent a greater number of biotransformations, yet parent MN-18 was eliminated at a faster rate than NNEi in vivo, highlighting that even closely related synthetic cannabinoids can possess markedly distinct pharmacokinetic profiles, which can vary substantially between in vitro and in vivo models.
Pyrrolidinyl Synthetic Cathinones α-PHP and 4F-α-PVP Metabolite Profiling Using Human Hepatocyte Incubations
TLDR
The metabolite profile of two pyrrolidinyl SCs, α-PHP and 4F-α-PVP, were characterized to identify optimal intake markers and an additional major metabolite that might be crucial for documenting exposure to α- PHP is identified.
The Psychopharmacology of Novel Synthetic Cannabinoids
Synthetic cannabinoid (SC) designer drugs featuring bioisosteric fluorine substitution are identified by forensic chemists and toxicologists with increasing frequency. Although terminal fluorination
Exploring Stereochemical and Conformational Requirements at Cannabinoid Receptors for Synthetic Cannabinoids Related to SDB-006, 5F-SDB-006, CUMYL-PICA, and 5F-CUMYL-PICA.
TLDR
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.
Interpol review of toxicology 2016–2019

References

SHOWING 1-10 OF 40 REFERENCES
In vitro and in vivo human metabolism of a new synthetic cannabinoid NM-2201 (CBL-2201)
TLDR
The present study aims to recommend appropriate marker metabolites by investigating NM-2201 metabolism in human hepatocytes, and to confirm the results in authentic human urine specimens, and recommends M13 (5-fluoro PB-22 3-carboxyindole) as a suitable urinary marker metabolite for confirming NM- 2201 and/or 5F-PB-22 intake.
In Vitro Metabolite Profiling of ADB-FUBINACA, A New Synthetic Cannabinoid.
TLDR
This is the first ADB-FUBINACA in vitro metabolism study; in vivo experiments enabling pharmacokinetic and pharmacodynamics studies or urine from authentic clinical/forensic cases are needed to confirm the results.
High-Resolution Mass Spectrometry for Characterizing the Metabolism of Synthetic Cannabinoid THJ-018 and Its 5-Fluoro Analog THJ-2201 after Incubation in Human Hepatocytes.
TLDR
High-resolution mass spectrometry was used to identify optimal metabolite markers for laboratories to identify ThJ-018 and THJ-2201 intake and link observed adverse events to these new synthetic cannabinoids.
Identification of AB-FUBINACA metabolites in human hepatocytes and urine using high-resolution mass spectrometry
AB-FUBINACA, N-(1-amino-3-methyl-1-oxobutan-2-yl)-1-(4-fluorobenzyl)-1H-indazole-3-carboxamide, is an indazole synthetic cannabinoid identified in drug seizures around the world. Few metabolism data
25C-NBOMe and 25I-NBOMe metabolite studies in human hepatocytes, in vivo mouse and human urine with high-resolution mass spectrometry.
TLDR
The metabolic profile of 25C-NBOMe and 25I- NBOMe was investigated in human hepatocytes, an in vivo mouse model and authentic human urine samples from forensic cases to help clinical and forensic laboratories to develop analytical methods and to interpret results.
In Vitro and In Vivo Human Metabolism of Synthetic Cannabinoids FDU-PB-22 and FUB-PB-22
TLDR
The present study aims to identify appropriate analytical markers by investigating FDU- PB-22 and FUB-PB-22 metabolism in human hepatocytes and confirming the results in authentic urine specimens, and recommends M6 (hydroxylated FBI-COOH) and M7 (FBI-CooH) as suitable urinary markers for documenting FDU, PB,22 and/or FUB,PB- 22 intake.
Detection of urinary metabolites of AM-2201 and UR-144, two novel synthetic cannabinoids.
TLDR
In vitro and in vivo metabolism of AM-2201 and forensic urine samples were analyzed and it has been shown that for both cannabimimetics the recommended screening targets are the monohydroxylated metabolites.
Metabolic profiling of new synthetic cannabinoids AMB and 5F-AMB by human hepatocyte and liver microsome incubations and high-resolution mass spectrometry.
TLDR
The metabolism of AMB and 5F-AMB is investigated and appropriate markers to identify their intake in clinical or forensic cases are proposed, providing valuable data for identifying these two novel psychoactive substances.
Cytochrome P450-Mediated Oxidative Metabolism of Abused Synthetic Cannabinoids Found in K2/Spice: Identification of Novel Cannabinoid Receptor Ligands
TLDR
Test the hypothesis that JWH-018 and its fluorinated counterpart AM2201 are subject to cytochrome P450 (P450)-mediated oxidation, forming potent hydroxylated metabolites that retain significant affinity and activity at the cannabinoid 1 (CB1) receptor.
Strategies to distinguish new synthetic cannabinoid FUBIMINA (BIM-2201) intake from its isomer THJ-2201: metabolism of FUBIMINA in human hepatocytes
TLDR
Optimized chromatographic conditions to achieve different retention times and careful selection of specific product ion spectra enabled differentiation of isomeric metabolites, in this case FUBIMINA from THJ-2201.
...
1
2
3
4
...