Pharmacology and toxicology of the synthetic cannabinoid receptor agonists

Lovett, Caitlyn; Wood, David M.; Dargan, Paul I.

doi:10.1007/s13546-015-1104-4

Cited by 9 publications

(4 citation statements)

References 88 publications

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“…SC use is associated with serious adverse reactions, − and the most recent SCs appear to possess greater dependence liabilities − and toxicities − than earlier examples. AMB-FUBINACA was clinically confirmed in a case of rhabdomolysis, and fatal intoxications have been attributed to consumption of 5F-AMB, ,, 5F-ADB, and MDMB-CHMICA. − …”

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confidence: 99%

Pharmacology of Valinate and tert-Leucinate Synthetic Cannabinoids 5F-AMBICA, 5F-AMB, 5F-ADB, AMB-FUBINACA, MDMB-FUBINACA, MDMB-CHMICA, and Their Analogues

Banister

Longworth²,

Kevin³

et al. 2016

ACS Chem. Neurosci.

225

208

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Indole and indazole synthetic cannabinoids (SCs) featuring l-valinate or l-tert-leucinate pendant group have recently emerged as prevalent recreational drugs, and their use has been associated with serious adverse health effects. Due to the limited pharmacological data available for these compounds, 5F-AMBICA, 5F-AMB, 5F-ADB, AMB-FUBINACA, MDMB-FUBINACA, MDMB-CHMICA, and their analogues were synthesized and assessed for cannabimimetic activity in vitro and in vivo. All SCs acted as potent, highly efficacious agonists at CB1 (EC50 = 0.45-36 nM) and CB2 (EC50 = 4.6-128 nM) receptors in a fluorometric assay of membrane potential, with a general preference for CB1 activation. The cannabimimetic properties of two prevalent compounds with confirmed toxicity in humans, 5F-AMB and MDMB-FUBINACA, were demonstrated in vivo using biotelemetry in rats. Bradycardia and hypothermia were induced by 5F-AMB and MDMB-FUBINACA doses of 0.1-1 mg/kg (and 3 mg/kg for 5F-AMB), with MDMB-FUBINACA showing the most dramatic hypothermic response recorded in our laboratory for any SC (>3 °C at 0.3 mg/kg). Reversal of hypothermia by pretreatment with a CB1, but not CB2, antagonist was demonstrated for 5F-AMB and MDMB-FUBINACA, consistent with CB1-mediated effects in vivo. The in vitro and in vivo data indicate that these SCs act as highly efficacious CB receptor agonists with greater potency than Δ(9)-THC and earlier generations of SCs.

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confidence: 99%

Pharmacology of Valinate and tert-Leucinate Synthetic Cannabinoids 5F-AMBICA, 5F-AMB, 5F-ADB, AMB-FUBINACA, MDMB-FUBINACA, MDMB-CHMICA, and Their Analogues

Banister

Longworth²,

Kevin³

et al. 2016

ACS Chem. Neurosci.

225

208

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“…[83, 84]), cannabinoids (e.g. [85]), hallucinogens [86] and stimulants [87]. The same theme is reflected in the cited articles, which were mostly concerned with the toxicological findings from NPS use [33, 88, 43, 89, 90].…”

Section: Discussionmentioning

confidence: 99%

The Novel Psychoactive Substances Epidemic: a Scientometric Perspective

Neoh

Carollo

Lim

et al. 2022

Preprint

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The unprecedented proliferation of novel psychoactive substances (NPS) in the illicit drug market has been a public health concern since their emergence in the 2000s. Their consumption can pose a severe health risks as their mechanism of action is poorly understood and their level of toxicity is high mainly due to the diffusion of very potent synthetic cannabinoids and synthetic opioids. This study systemically analyses the evolution of the scientific literature on NPS to gain a better understanding of the areas of major research interests and how they interlink. Findings indicate that the published evidence covers clusters focused on classes of NPS that have received widespread media attention, such as mephedrone and fentanyl, and have largely been concerned with the pharmacological and the toxicological profiles of these substances. This scientometric perspective also provides greater insight into the knowledge gaps within this new and rapidly growing field of study and highlights the need for an interdisciplinary approach in tackling the NPS epidemic.

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“…Among these synthetic cannabinoids is a structural analogue of Δ 9 ‐THC: HU‐210 . However, after the discovery of WIN‐48098, usually called pravadoline, which does not resemble Δ 9 ‐THC, new molecules such as the potent CB1 agonist JWH‐018 (1‐pentyl‐3‐(1‐naphthoyl)indole) were discovered and used illicitly as replacements for Δ 9 ‐THC (Figure ) …”

Section: Introductionmentioning

confidence: 99%

Cannabinoid Type 1 Receptor (CB1) Ligands with Therapeutic Potential for Withdrawal Syndrome in Chemical Dependents of Cannabis sativa

et al. 2017

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Cannabis sativa withdrawal syndrome is characterized mainly by psychological symptoms. By using computational tools, the aim of this study was to propose drug candidates for treating withdrawal syndrome based on the natural ligands of the cannabinoid type 1 receptor (CB1). One compound in particular, 2‐n‐butyl‐5‐n‐pentylbenzene‐1,3‐diol (ZINC1730183, also known as stemphol), showed positive predictions as a human CB1 ligand and for facile synthetic accessibility. Therefore, ZINC1730183 is a favorable candidate scaffold for further research into pharmacotherapeutic alternatives to treat C. sativa withdrawal syndrome.

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Pharmacology and toxicology of the synthetic cannabinoid receptor agonists

Cited by 9 publications

References 88 publications

Pharmacology of Valinate and tert-Leucinate Synthetic Cannabinoids 5F-AMBICA, 5F-AMB, 5F-ADB, AMB-FUBINACA, MDMB-FUBINACA, MDMB-CHMICA, and Their Analogues

Pharmacology of Valinate and tert-Leucinate Synthetic Cannabinoids 5F-AMBICA, 5F-AMB, 5F-ADB, AMB-FUBINACA, MDMB-FUBINACA, MDMB-CHMICA, and Their Analogues

The Novel Psychoactive Substances Epidemic: a Scientometric Perspective

Cannabinoid Type 1 Receptor (CB1) Ligands with Therapeutic Potential for Withdrawal Syndrome in Chemical Dependents of Cannabis sativa

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