Tetrahydrocannabinol (THC) is a terpenoid found in cannabis. It is the principal psychoactive constituent of cannabis and one of at least 113 total cannabinoids identified on the plant. Its chemical formula C21H30O2 includes compounds, the term THC usually refers to the delta-9-THC isomer with chemical name (−)-trans-Δ9-tetrahydrocannabinol. It is a colorless oil.
Medical cannabis, or medical marijuana (MMJ), is cannabis and cannabinoids that are prescribed by physicians for their patients. The use of cannabis as medicine has not been rigorously tested due to production 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 113 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.
Nabilone, sold under the brand name Cesamet among others, is a synthetic cannabinoid with therapeutic use as an antiemetic and as an adjunct analgesic for neuropathic pain. It mimics tetrahydrocannabinol (THC), the primary psychoactive compound found naturally occurring in Cannabis.
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.
Dimethylheptylpyran is a synthetic analog of THC, which was invented in 1949 during attempts to elucidate the structure of Δ9-THC, one of the active components of Cannabis. DMHP is a pale yellow, viscous oil which is insoluble in water but dissolves in alcohol or non-polar solvents.
O-2545 is an analgesic cannabinoid derivative created by Organix Inc. for use in scientific research. Unlike most cannabinoids discovered to date, it is water-soluble, which gives it considerable advantages over many related cannabinoids. It has high affinity for both CB1 and CB2 receptors, with Ki values of 1.5 nM at CB1 and 0.32 nM at CB2.
O-1057 is an analgesic cannabinoid derivative created by Organix Inc., Newburyport, Massachusetts, for use in scientific research. Unlike most cannabinoids discovered to date, it is water-soluble, which gives it considerable advantages over many related cannabinoids. It has moderate affinity for both CB1 and CB2 receptors, with Ki values of 8.36 nM at CB1 and 7.95 nM at CB2
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.
CP 47,497 or (C7)-CP 47,497 is a cannabinoid receptor agonist drug, developed by Pfizer in the 1980s. It has analgesic effects and is used in scientific research. It is a potent CB1 agonist with a Kd of 2.1 nM.
AMG-3 (part of the AM cannabinoid series) is an analgesic drug which is a cannabinoid agonist. It is a derivative of Δ8-THC substituted with a dithiolane group on the 3-position side chain. AMG-3 is a potent agonist at both CB1 and CB2 receptors with a Ki of 0.32 nM at CB1 and 0.52 nM at CB2, and its particularly high binding affinity has led to it being used as a template for further structural development of novel cannabinoid drugs. It has sedative and analgesic effects, with analgesia lasting for up to 36 hours after administration.
AMG-41 (part of the AM cannabinoid series) is an analgesic drug which is a cannabinoid agonist. It is a derivative of Δ8-THC substituted with a cyclopropyl group on the C1'-position of the C3-alkyl side chain. AMG-41 is a potent agonist at both CB1 and CB2, with a Ki of 0.44 nM at CB1 vs 0.86 nM at CB2.
AMG-1 (part of the AM cannabinoid series) is an analgesic drug which is a cannabinoid agonist. It is a derivative of Δ8-THC with a rigidified and extended 3-position side chain. AMG-1 is a potent agonist at both CB1 and CB2 with moderate selectivity for CB1, with a Ki of 0.6 nM at CB1 vs 3.1 nM at CB2.
Abnormal cannabidiol (Abn-CBD) is a synthetic regioisomer of cannabidiol, which unlike most other cannabinoids produces vasodilator effects, lowers blood pressure, and induces cell migration, cell proliferation and mitogen-activated protein kinase activation in microglia, but without producing any psychoactive effects.
Dronabinol (INN), also known under the trade names Marinol and Syndros, is a generic name for the molecule of delta-9-tetrahydrocannabinol in the pharmaceutical context. It has indications as an appetite stimulant, antiemetic, and sleep apnea reliever and is approved by the FDA as safe and effective for HIV/AIDS-induced anorexia and chemotherapy-induced nausea and vomiting only.
A-40174 (SP-1) is an analgesic drug which acts as a potent cannabinoid receptor agonist, and was developed by Abbott Laboratories in the 1970s. It's a structural analog of dronabinol and dimethylheptylpyran.
O-774 is a classical cannabinoid derivative which acts as a potent agonist for the cannabinoid receptors, with a Ki of 0.6 nM at CB1, and very potent cannabinoid effects in animal studies.
Cannabidiol-dimethylheptyl (CBD-DMH or DMH-CBD) is a synthetic homologue of cannabidiol where the pentyl chain has been replaced by a dimethylheptyl chain. Several isomers of this compound are known. The most commonly used isomer in research is (−)-CBD-DMH, which has the same stereochemistry as natural cannabidiol, and a 1,1-dimethylheptyl side chain. This compound is not psychoactive and acts primarily as an anandamide reuptake inhibitor, but is more potent than cannabidiol as an anticonvulsant and has around the same potency as an antiinflammatory. Unexpectedly the “unnatural” enantiomer (+)-CBD-DMH, which has reversed stereochemistry from cannabidiol, was found to be a directly acting cannabinoid receptor agonist with a Ki of 17.4nM at CB1 and 211nM at CB2, and produces typical cannabinoid effects in animal studies, as does its 7-OH derivative.
Medical cannabis research includes any medical research on using cannabis. Different countries conduct and respond to medical cannabis research in different ways.
O-1656 is a cannabinoid agonist which was invented by Billy R Martin and Raj K Razdan at Organix Inc in 2002. It is moderately selective for the CB2 receptor with a CB1 receptor affinity of 18 nM and a CB2 receptor affinity of 2 nM. Since it has a cycloheptyl ring attached to the phenol core, it falls outside the definition of a "cyclohexylphenol derivative", but may still be controlled by generic legislation in some jurisdictions.
