Ajulemic acid (CT3): a potent analog of the acid metabolites of THC.

Abstract

“The acid metabolites of THC were discovered almost 30 years ago and were later shown to posses modest analgesic and anti-inflammatory activity in a variety of models. Ajulemic acid (CT3) is a more potent analog of THC-11-oic acid in which a dimethylheptyl side chain is substituted for the pentyl side chain of the naturally occurring metabolite. It produces analgesia in the mouse hot plate, the PPQ writhing, the formalin and the tail clip assays. In the latter, it was equipotent to morphine; however, it showed a much greater duration of action. In the paw edema, subcutaneous air pouch and rat adjuvant-induced arthritis models of inflammation; it showed significant therapeutic activity at a dose of 0.2 mg/kg p.o. In the arthritis model it greatly reduced permanent damage to joints when compared to an indomethacin control as evidenced by an improved joint score over vehicle controls and by histopathological examination. In contrast to the NSAIDs, it was totally nonulcerogenic at therapeutically relevant doses. Moreover, it does not depress respiration, exhibit dependence, induce body weight loss or cause mutagenesis. It shows none of the typical actions in models of the psychotropic actions of cannabinoids suggesting that a good separation of desirable from undesirable effects was achieved. Studies on its mechanism of action are currently underway. The data thus far suggest the existence of a novel receptor for ajulemic acid with possible downstream effects on eicosanoid production, cytokine synthesis and metalloprotease activity. There is also circumstantial evidence for a putative endogenous ajulemic acid, namely, arachidonylglycine.”

http://www.ncbi.nlm.nih.gov/pubmed/10903396

1′,1′-Dimethylheptyl-Δ-8-tetrahydrocannabinol-11-oic Acid: A Novel, Orally Effective Cannabinoid with Analgesic and Anti-inflammatory Properties

  “1′,1′-Dimethylheptyl-Δ-8-tetrahydrocannabinol-11-oic acid (CT-3) is a novel cannabinoid that is under development by Atlantic Pharmaceuticals as an anti-inflammatory and analgesic drug. The objective of the study was to investigate the effects of CT-3 on overt symptom complex (Irwin’s test), nociception, gastrointestinal (GI) ulceration, and pharmacological availability after intragastric (i.g.) and intraperitoneal (i.p.) administration… .The evidence indicates that CT-3 exhibits a large dissociation between its anti-inflammatory/analgesic effects and its ulcerogenic actions. CT-3 warrants clinical development as a novel anti-inflammatory and analgesic drug.”

“1′,1′-Dimethylheptyl-Δ-8-tetrahydrocannabinol-11-oic acid (CT-3) is a novel cannabinoid with analgesic and anti-inflammatory activities. CT-3 is chemically similar to Δ-9-tetrahydrocannabinol (THC, dronabilone) and nabilone.”

“Analgesia is one of the most profound effects of THC in most species after its parenteral administration, and THC had shown equivalent potency to morphine in rats and mice in a variety of analgesic tests, including the tail-flick latency measurements. Several synthetic cannabinoids have also shown analgesic activities in animal models selective for detecting opiate analgesics.”

“The analgesic action of CT-3 is well confirmed in rats and in mice. Available evidence indicates that CT-3 exhibits two distinct pharmacological properties: an anti-inflammatory property occurring at a very low dose (ED50 = ∼0.1 mg/kg i.g.; and an analgesic property occurring at a higher dose (ED50 = ∼5 mg/kg i.g. and i.p.). The present results indicate that CT-3 is an orally effective analgesic drug, and acceptable pharmaceutical formulation of CT-3 would not require the adjuvant use of permeability enhancers to promote its bioavailability. CT-3 clearly warrants clinical development as an analgesic and anti-inflammatory drug.”

http://jpet.aspetjournals.org/content/291/1/31.long

Marijuana, inflammation, and CT-3 (DMH-11C): cannabis leads to new class of antiinflammatory drugs.

Abstract:

“CT-3, a synthetic derivative of a metabolite of marijuana, is being tested by arthritis researchers as a possible new anti-inflammatory drug. Early studies show that CT-3 may be effective without the gastric side effects of steroids and psychoactive effects of marijuana. The processes of inflammation may be important in the pathogenesis of HIV disease. Obtaining the medical benefits without the psychoactive effects of marijuana is also important, as the high associated with cannabis use can be debilitating. The drug is currently in early pre-clinical animal testing.”

http://www.ncbi.nlm.nih.gov/pubmed/11365002

Inhibitory effect of cannabichromene, a major non-psychotropic cannabinoid extracted from Cannabis sativa, on inflammation-induced hypermotility in mice.

“BACKGROUND AND PURPOSE:

Cannabichromene (CBC) is a major non-psychotropic phytocannabinoid that inhibits endocannabinoid inactivation and activates the transient receptor potential ankyrin-1 (TRPA1). Both endocannabinoids and TRPA1 may modulate gastrointestinal motility. Here, we investigated the effect of CBC on mouse intestinal motility in physiological and pathological states.”

“CONCLUSION AND IMPLICATIONS:

CBC selectively reduces inflammation-induced hypermotility in vivo in a manner that is not dependent on cannabinoid receptors or TRPA1.”

http://www.ncbi.nlm.nih.gov/pubmed/22300105

Cannabinoid receptor type 2 activation induces a microglial anti-inflammatory phenotype and reduces migration via MKP induction and ERK dephosphorylation

“Cannabinoid receptor type 2 (CBR2) inhibits microglial reactivity through a molecular mechanism yet to be elucidated. We hypothesized that CBR2 activation induces an anti-inflammatory phenotype in microglia by inhibiting extracellular signal-regulated kinase (ERK) pathway, via mitogen-activated protein kinase-phosphatase (MKP) induction. MKPs regulate mitogen activated protein kinases, but their role in the modulation of microglial phenotype is not fully understood.”

“Our results uncover a cellular microglial pathway triggered by CBR2 activation. These data suggest that the reduction of pro-inflammatory factors and microglial migration via MKP-3 induction is part of the mechanism of action of CBR2 agonists. These findings may have clinical implications for further drug development.”

“In summary, our current results uncovered a cellular mechanism of action of CBR2 agonists that produces a microglial anti-inflammatory phenotype, which may modulate microglial motility in vivo. We identified MKP-3 and microglial migration as potential new targets for drug development. The clinical utility of CBR2 agonists is supported by their analgesic efficacy and their lack of neurological side effects in animal models of postoperative or neuropathic pain.”

http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2704199/

Cannabinoid-like anti-inflammatory compounds from flax fiber.

Abstract

“Flax is a valuable source of fibers, linseed and oil. The compounds of the latter two products have already been widely examined and have been proven to possess many health-beneficial properties. In the course of analysis of fibers extract from previously generated transgenic plants overproducing phenylpropanoids a new terpenoid compound was discovered.The UV spectra and the retention time in UPLC analysis of this new compound reveal similarity to a cannabinoid-like compound, probably cannabidiol (CBD). This was confirmed by finding two ions at m/z 174.1 and 231.2 in mass spectra analysis. Further confirmation of the nature of the compound was based on a biological activity assay. It was found that the compound affects the expression of genes involved in inflammatory processes in mouse and human fibroblasts and likely the CBD from Cannabis sativa activates the specific peripheral cannabinoid receptor 2 (CB2) gene expression. Besides fibers, the compound was also found in all other flax tissues. It should be pointed out that the industrial process of fabric production does not affect CBD activity.The presented data suggest for the first time that flax products can be a source of biologically active cannabinoid-like compounds that are able to influence the cell immunological response. These findings might open up many new applications for medical flax products, especially for the fabric as a material for wound dressing with anti-inflammatory properties.”

http://www.ncbi.nlm.nih.gov/pubmed/22706678

Analgesic and antiinflammatory activity of constituents of Cannabis sativa L.

Abstract

“Two extracts of Cannabis sativa herb, one being cannabinoid-free (ethanol) and the other containing the cannabinoids (petroleum), were shown to inhibit PBQ-induced writhing in mouse when given orally and also to antagonize tetradecanoylphorbol acetate (TPA)-induced erythema of mouse skin when applied topically. With the exception of cannabinol (CBN) and delta 1-tetrahydrocannabinol (delta 1-THC), the cannabinoids and olivetol (their biosynthetic precursor) demonstrated activity in the PBQ test exhibiting their maximal effect at doses of about 100 micrograms/kg. delta 1-THC only became maximally effective in doses of 10 mg/kg. This higher dose corresponded to that which induced catalepsy and is indicative of a central action. CNB demonstrated little activity and even at doses in excess of 10 mg/kg could only produce a 40% inhibition of PBQ-induced writhing. Cannabinoid (CBD) was the most effective of the cannabinoids at doses of 100 micrograms/kg. Doses of cannabinoids that were effective in the analgesic test orally were used topically to antagonize TPA-induced erythema of skin. The fact that delta 1-THC and CBN were the least effective in this test suggests a structural relationship between analgesic activity and antiinflammatory activity among the cannabinoids related to their peripheral actions and separate from the central effects of delta 1-THC.”

http://www.ncbi.nlm.nih.gov/pubmed/3169967

A peripheral cannabinoid mechanism suppresses spinal fos protein expression and pain behavior in a rat model of inflammation.

  “The present studies were conducted to test the hypothesis that systemically inactive doses of cannabinoids suppress inflammation-evoked neuronal activity in vivo via a peripheral mechanism…

…These data provide direct evidence that a peripheral cannabinoid mechanism suppresses the development of inflammation-evoked neuronal activity at the level of the spinal dorsal horn and implicate a role for CB(2) and CB(1) in peripheral cannabinoid modulation of inflammatory nociception.”

http://www.ncbi.nlm.nih.gov/pubmed/12617970

Selective activation of cannabinoid CB(2) receptors suppresses spinal fos protein expression and pain behavior in a rat model of inflammation.

“Activation of cannabinoid CB(2) receptors attenuates thermal nociception in untreated animals while failing to produce centrally mediated effects such as hypothermia and catalepsy. The present study was conducted to test the hypothesis that activation of CB(2) in the periphery suppresses the development of inflammatory pain as well as inflammation-evoked neuronal activity at the level of the CNS…”

“These data provide evidence that actions at cannabinoid CB(2) receptors are sufficient to suppress inflammation-evoked neuronal activity at rostral levels of processing in the spinal dorsal horn…”

http://www.ncbi.nlm.nih.gov/pubmed/12809695