Cannabidiol-2’,6’-dimethyl ether stimulates body weight gain in apolipoprotein E-deficient BALB/c. KOR/Stm Slc-&lt;i&gt;Apoe&lt;/i&gt;&lt;i&gt;&lt;sup&gt;shl&lt;/sup&gt;&lt;/i&gt; mice

Takeda, Shuso; Hirota, Rena; Teradaira, Sari; Takeda-Imoto, Masumi; Watanabe, Kazuhito; Toda, Akihisa; Aramaki, Hironori

doi:10.2131/jts.40.739

Cited by 8 publications

(4 citation statements)

References 19 publications

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“…By methylation of the two phenolic −OH moieties of CBD, cannabidiol is converted to CBDD, a non-biogenic cannabinoid that has been shown to stimulate weight gain in apolipoprotein E (ApoE)-deficient BALB/c. KOR/Stm Slc- Apoe shl mice . CBDD contains no phenolic −OH groups, and thus, direct comparison to CBD can elucidate the importance of free phenolic −OH functional groups on cannabinoid recovery rates.…”

Section: Resultsmentioning

confidence: 99%

Investigation of Chocolate Matrix Interference on Cannabinoid Analytes

Dawson¹,

Martin²

2020

J. Agric. Food Chem.

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The first known findings of chocolate matrix interference on cannabinoid analytes is reported. Stock solutions of four biogenic cannabinoids (Δ 9 -tetrahydrocannabinol, cannabidiol, cannabinol, and cannabigerol) and one synthetic cannabinoid (cannabidiol dimethyl ether) are subjected to milk chocolate, dark chocolate, and cocoa powder. A clear trend of matrix interference is observed, which correlates to several chemical factors. The amount of chocolate present is directly proportional to the degree of matrix interference, which yields lower percent recovery rates for the cannabinoid analyte. Structural features on the cannabinoid analytes are shown to affect matrix interference, because cannabinoids with fewer phenolic −OH groups suffer from increased signal suppression. Additionally, aromatization of the p-menthyl moiety appears to correlate with enhanced matrix effects from chocolate products high in cocoa solids. These findings represent the first known documentation of chocolate matrix interference in cannabinoid analysis, which potentially has broad implications for complex matrix testing in the legal Cannabis industry.

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Section: Resultsmentioning

confidence: 99%

Investigation of Chocolate Matrix Interference on Cannabinoid Analytes

Dawson¹,

Martin²

2020

J. Agric. Food Chem.

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“…Así, los derivados monometilado (23) y dimetilado (24) (Figura 7) revelaron una mayor potencia y selectividad como inhibidores de la 15-lipoxigenasa en comparación con el CBD (Takeda, 2009). Otros estudios, sugirieron que el compuesto 24, más conocido como CBDD, no sólo demostró ser un potencial prototipo para el tratamiento de la aterosclerosis, sino también una herramienta farmacológica para el estudio de los mecanismos de regulación del peso corporal (Takeda, 2015). Por otra parte, se ha descripto la obtención del O-propil y O-pentil CBD, así como su caracterización estructural (Malingré, 1975), aunque sus características farmacológicas aún no han sido descriptas.…”

Section: Análogos De Resorcinolunclassified

Diversidad y bioactividad de análogos semisintéticos de cannabidiol

Musso

2023

Educación Química

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La especie vegetal Cannabis sativa (Cannabaceae) posee importantes propiedades medicinales gracias a los componentes bioactivos que posee. El fitoestrógeno CBD se puede encontrar en la planta y debido a las características terapéuticas y estructurales de la molécula, lo convierte en un interesante andamio susceptible a numerosas modificaciones sintéticas, con el fin de mejorar su eficacia y potencia terapéutica. Este trabajo proporciona información sobre los distintos análogos sintéticos de CBD descubiertos en los últimos años (2010 - 2021). La búsqueda bibliográfica se realizó en distintas bases de datos, con distintas palabras clave. Dicha búsqueda se limitó a los años 2010 - 2021, y se consideraron revisiones, micro revisiones y meta-análisis de mayor impacto. Se recopilaron alrededor de 40 nuevos análogos sintéticos de CBD y fueron clasificados según el blanco estructural modificado. Estos compuestos poseen una importante bioactividad e incluso, muchos conservan la actividad de su precursor. Sin embargo, en muchos casos, el conocimiento de su mecanismo de acción aún se encuentra en estudio por lo que se necesitan numerosas investigaciones farmacológicas y medicinales.

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“…Finally, one group studied cannabidiol-2',6'-dimethyl ether (CBDD), a dimethyl ether derivative of cannabidiol and its effect on body weight. Using ApoE-deficient mice with compromised lipid metabolism capabilities, CBDD increased body weight gain to a greater extent than vehicle-treated ApoE-deficient mice [87]. Other cannabis-related agonistic compounds such as ∆ 9 -tetrahydrocannabinolic acid-A (THCA-A) have recently been studied in preclinical models and have shown promise in modulating weight; however, this is beyond the scope of this review as it is not a CB1 receptor ligand [173].…”

Section: Other Cb1 Agonistsmentioning

confidence: 99%

Targeting the Endocannabinoid CB1 Receptor to Treat Body Weight Disorders: A Preclinical and Clinical Review of the Therapeutic Potential of Past and Present CB1 Drugs

Murphy

Foll

2020

Biomolecules

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Obesity rates are increasing worldwide and there is a need for novel therapeutic treatment options. The endocannabinoid system has been linked to homeostatic processes, including metabolism, food intake, and the regulation of body weight. Rimonabant, an inverse agonist for the cannabinoid CB1 receptor, was effective at producing weight loss in obese subjects. However, due to adverse psychiatric side effects, rimonabant was removed from the market. More recently, we reported an inverse relationship between cannabis use and BMI, which has now been duplicated by several groups. As those results may appear contradictory, we review here preclinical and clinical studies that have studied the impact on body weight of various cannabinoid CB1 drugs. Notably, we will review the impact of CB1 inverse agonists, agonists, partial agonists, and neutral antagonists. Those findings clearly point out the cannabinoid CB1 as a potential effective target for the treatment of obesity. Recent preclinical studies suggest that ligands targeting the CB1 may retain the therapeutic potential of rimonabant without the negative side effect profile. Such approaches should be tested in clinical trials for validation.

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Cannabidiol-2’,6’-dimethyl ether stimulates body weight gain in apolipoprotein E-deficient BALB/c. KOR/Stm Slc-<i>Apoe</i><i><sup>shl</sup></i> mice

Cited by 8 publications

References 19 publications

Investigation of Chocolate Matrix Interference on Cannabinoid Analytes

Investigation of Chocolate Matrix Interference on Cannabinoid Analytes

Diversidad y bioactividad de análogos semisintéticos de cannabidiol

Targeting the Endocannabinoid CB1 Receptor to Treat Body Weight Disorders: A Preclinical and Clinical Review of the Therapeutic Potential of Past and Present CB1 Drugs

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