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ECHA InfoCard | 100.201.022 |
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Formula | C25H38O3 |
Molar mass | 386.576 g·mol−1 |
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Dexanabinol (HU-211 or ETS2101 [1] ) is a synthetic cannabinoid derivative in development by e-Therapeutics plc. It is the "unnatural" enantiomer of the potent cannabinoid agonist HU-210. [2] Unlike other cannabinoid derivatives, HU-211 does not act as a cannabinoid receptor agonist, but instead as an NMDA antagonist. [3] It therefore does not produce cannabis-like effects, but is anticonvulsant and neuroprotective, and is widely used in scientific research as well as currently being studied for applications such as treating head injury, stroke, or cancer. [4] [5] [6] It was shown to be safe in clinical trials [7] and is currently undergoing Phase I trials for the treatment of brain cancer [8] and advanced solid tumors. [9]
Dexanabinol has been studied in IV administration and oral dosing. [10] e-Therapeutics is evaluating the compound in clinical trials for brain and solid cancers. [11] Phase II studies are planned based on the results of the current trials.
A phase 1b study for hepatocellular carcinoma and pancreatic cancer was started in 2015. [12]
HU-211 is not listed in the schedules set out by the United Nations' Single Convention on Narcotic Drugs from 1961 nor their Convention on Psychotropic Substances from 1971, [13] so the signatory countries to these international drug control treaties are not required by said treaties to control HU-211.
HU-211 is not listed in the list of scheduled controlled substances in the USA. [14] It is therefore not scheduled at the federal level in the United States, but it is possible that HU-211 could legally be considered an analog of Delta-8-THC (one of the THC isomers which is in Schedule I under the designation of "Tetrahydrocannabinols"), and therefore sales or possession could potentially be prosecuted under the Federal Analogue Act. [15]
HU-211 is a Schedule I controlled substance in Alabama. [16]
HU-211 is a Schedule I controlled substance in the state of Florida making it illegal to buy, sell, or possess in Florida. [17]
Effective January 1, 2016, HU-211 is a regulated drug in Vermont designated as a "Hallucinogenic Drug." [18]
Tetrahydrocannabinol (THC) is a cannabinoid found in cannabis. It is the principal psychoactive constituent of cannabis and one of at least 113 total cannabinoids identified on the plant. Although the chemical formula for THC (C21H30O2) describes multiple isomers, the term THC usually refers to the delta-9-THC isomer with chemical name (−)-trans-Δ9-tetrahydrocannabinol. It is a colorless oil.
Medical cannabis, medicinal cannabis or medical marijuana (MMJ) refers to cannabis products and cannabinoid molecules that are prescribed by physicians for their patients. The use of cannabis as medicine has a long history, but has not been as rigorously tested as other medicinal plants due to legal and governmental restrictions, resulting in limited clinical research to define the safety and efficacy of using cannabis to treat diseases.
Cannabinoids are several structural classes of compounds found in the cannabis plant primarily and most animal organisms or as synthetic compounds. The most notable cannabinoid is the phytocannabinoid tetrahydrocannabinol (THC) (delta-9-THC), the primary psychoactive compound in cannabis. Cannabidiol (CBD) is also a major constituent of temperate cannabis plants and a minor constituent in tropical varieties. At least 100 distinct phytocannabinoids have been isolated from cannabis, although only four have been demonstrated to have a biogenetic origin. It was reported in 2020 that phytocannabinoids can be found in other plants such as rhododendron, licorice and liverwort, and earlier in Echinacea.
Tetrahydrocannabivarin is a homologue of tetrahydrocannabinol (THC) having a propyl (3-carbon) side chain instead of pentyl (5-carbon), making it non-psychoactive in lower doses. It has been shown to exhibit neuroprotective activity, appetite suppression, glycemic control and reduced side effects compared to THC, making it a potential treatment for management of obesity and diabetes. THCV was studied by Roger Adams as early as 1942.
HU-210 is a synthetic cannabinoid that was first synthesized in 1988 from (1R,5S)-myrtenol by a group led by Raphael Mechoulam at the Hebrew University. HU-210 is 100 to 800 times more potent than natural THC from cannabis and has an extended duration of action. HU-210 has a binding affinity of 0.061 nM at CB1 receptors compared to 40.7 nM for Δ9-THC. The binding pose of HU-210 to the CB1 receptor is similar to other synthetic cannabinoids.
WIN 55,212-2 is a chemical described as an aminoalkylindole derivative, which produces effects similar to those of cannabinoids such as tetrahydrocannabinol (THC) but has an entirely different chemical structure.
Levonantradol (CP 50,556-1) is a synthetic cannabinoid analog of dronabinol (Marinol) developed by Pfizer in the 1980s. It is around 30 times more potent than THC, and exhibits antiemetic and analgesic effects via activation of CB1 and CB2 cannabinoid receptors. Levonantradol is not currently used in medicine as dronabinol or nabilone are felt to be more useful for most conditions, however it is widely used in research into the potential therapeutic applications of cannabinoids.
Cannabigerol (CBG) is a non-psychoactive cannabinoid and minor constituent of cannabis. It is one of more than 120 identified cannabinoids found in the plant genus Cannabis. The compound is the decarboxylated form of cannabigerolic acid (CBGA), the parent molecule from which other cannabinoids are biosynthesized.
JWH-073, a synthetic cannabinoid, is an analgesic chemical from the naphthoylindole family that acts as a full agonist at both the CB1 and CB2 cannabinoid receptors. It is somewhat selective for the CB1 subtype, with affinity at this subtype approximately 5× the affinity at CB2. The abbreviation JWH stands for John W. Huffman, one of the inventors of the compound.
Originally synthesized by chemist Wayne E. Kenney, BAY 38-7271 (KN 38-7271) is a drug which is a cannabinoid receptor agonist developed by Bayer AG. It has analgesic and neuroprotective effects and is used in scientific research, with proposed uses in the treatment of traumatic brain injury. It is a full agonist with around the same potency as CP 55,940 in animal studies, and has fairly high affinity for both CB1 and CB2 receptors, with Ki values of 2.91nM at CB1 and 4.24nM at CB2. It has been licensed to KeyNeurotek Pharmaceuticals for clinical development, and was in Phase II trials in 2008 but its development appears to have stopped.
JWH-200 (WIN 55,225) is an analgesic chemical from the aminoalkylindole family that acts as a cannabinoid receptor agonist. Its binding affinity, Ki at the CB1 receptor is 42 nM, around the same as that of THC, but its analgesic potency in vivo was higher than that of other analogues with stronger CB1 binding affinity in vitro, around 3 times that of THC but with less sedative effect, most likely reflecting favourable pharmacokinetic characteristics. It was discovered in 1991 by Sterling Drug as a potential analgesic following the earlier identification of related compounds such as pravadoline and WIN 55,212-2.
Synthetic cannabinoids are a class of designer drug molecules that bind to the same receptors to which cannabinoids in cannabis plants attach. These novel psychoactive substances should not be confused with synthetic phytocannabinoids or synthetic endocannabinoids from which they are in many aspects distinct.
Dronabinol, sold under the brand names Marinol and Syndros, is the generic name for the molecule of (−)-trans-Δ9-tetrahydrocannabinol (THC) in the pharmaceutical context. It has indications as an appetite stimulant, antiemetic, and sleep apnea reliever and is approved by the U.S. Food and Drug Administration (FDA) as safe and effective for HIV/AIDS-induced anorexia and chemotherapy-induced nausea and vomiting.
HU-243 (AM-4056) is a synthetic cannabinoid drug that is a single enantiomer of the hydrogenated derivative of the commonly used reference agonist HU-210. It is a methylene homologue of canbisol. It is a potent agonist at both the CB1 and CB2 receptors, with a binding affinity of 0.041 nM at the CB1 receptor, making it marginally more potent than HU-210, which had an affinity of 0.061 nM in the same assay.
AB-CHMINACA is an indazole-based synthetic cannabinoid. It is a potent agonist of the CB1 receptor (Ki = 0.78 nM) and CB2 receptor (Ki = 0.45 nM) and fully substitutes for Δ9-THC in rat discrimination studies, while being 16x more potent. Continuing the trend seen in other cannabinoids of this generation, such as AB-FUBINACA and AB-PINACA, it contains a valine amino acid amide residue as part of its structure, where older cannabinoids contained a naphthyl or adamantane residue.
'MDMB-CHMICAa' is an indole-based synthetic cannabinoid that is a potent agonist of the CB1 receptor and has been sold online as a designer drug. While MDMB-CHMICA was initially sold under the name "MMB-CHMINACA", the compound corresponding to this code name (i.e. the isopropyl instead of t-butyl analogue of MDMB-CHMINACA) has been identified on the designer drug market in 2015 as AMB-CHMINACA.
8,9-Dihydrocannabidiol is a synthetic cannabinoid that is closely related to cannabidiol (CBD) itself. that was first synthesized by Alexander R. Todd in 1940 derived from the catalytic hydrogenation of cannabidiol.
Synthetic drugs refer to substances that are artificially modified from naturally-occurring drugs and are capable of exhibiting both therapeutic and psychoactive effects.
EG-2201 is a synthetic cannabinoid belonging to the indole-3-carboxamide family. It has been identified as a designer drug and is structurally related to other synthetic cannabinoids, such as EG-018 and MDMB-CHMCZCA. It is primarily used illicitly due to its psychoactive effects, which mimic delta-9-tetrahydrocannabinol (THC), the active ingredient in cannabis.