THC-methylcarbonate
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THC-methylcarbonate
THC methylcarbonate (Δ9-THC-methylcarbonate) is a semi-synthetic derivative of tetrahydrocannabinol, first reported as a designer drug in August 2024 when it was identified in a seized shipment by customs in Sweden. Coincidentally, it was the 1000th new psychoactive substance identified by the EU Early Warning System on New Psychoactive Substances, first established in 1997. Related THC carbonates and carbamates have been described as THC prodrugs in the patent literature. See also * Cod-THC * THC-O-acetate THC-O-acetate (THC acetate ester, O-acetyl-THC, THC-O, AcO-THC) is the acetate ester of THC. The term ''THC-O-acetate'' and its variations are commonly used for two types of the substance, dependent on which cannabinoid it is synthesized from. ... * THC hemisuccinate * THC morpholinylbutyrate References Cannabinoids Oxygen heterocycles Heterocyclic compounds with 3 rings Carbonate esters Methyl esters {{cannabinoid-stub ...
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Cod-THC
Cod-THC (Codeine Δ9-tetrahydrocannabinol carbonate) is a synthetic codrug formed by linking tetrahydrocannabinol with codeine via a carbonate bridge. It is well absorbed orally and shows superior analgesic effects in animal studies compared to a simple mixture of the two drugs. See also * Benorilate * Codeine-6-glucuronide * Fenethylline Fenethylline (British Approved Name, BAN, United States Adopted Name, USAN) or fenetylline (International Nonproprietary Name, INN) is a codrug of amphetamine and theophylline and so a mutual prodrug of both. It is also spelled phenethylline; ... * THC-methylcarbonate * THC-O-acetate * THC-VHS References Benzochromenes Cannabinoids Carbonate esters Heterocyclic compounds with 5 rings Methoxy compounds Nitrogen heterocycles Codrugs {{cannabinoid-stub ...
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Tetrahydrocannabinol
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 uses THC, referred to as dronabinol in the pharmaceutical context, is approved in the United States as a capsule or solution to relieve chemotherapy-induced nausea and vomiting and HIV/AIDS-induced anorexia. THC is an active ingredient in nabiximols, a specific extract of ''Cannabis'' that was approved as a botanical drug in the United Kingdom in 2010 as a mouth spray for people with multiple sclerosis to alleviate neuropathic pain, spasticity, overactive bladder, and other symptoms. Nabiximols (as Sativex) is available as a prescription drug in Canada. In 20 ...
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Designer Drug
A designer drug is a structural or functional analog of a controlled substance that has been designed to mimic the pharmacological effects of the original drug, while avoiding classification as illegal and/or detection in standard drug tests. Designer drugs include psychoactive substances that have been designated by the European Union, Australia, and New Zealand, as new psychoactive substances (NPS) as well as analogs of performance-enhancing drugs such as designer steroids. Some of these designer drugs were originally synthesized by academic or industrial researchers in an effort to discover more potent derivatives with fewer side effects and shorter duration (and possibly also because it is easier to apply for patents for new molecules) and were later co-opted for recreational use. Other designer drugs were prepared for the first time in clandestine laboratories. Because the efficacy and safety of these substances have not been thoroughly evaluated in animal and human tr ...
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Prodrug
A prodrug is a pharmacologically inactive medication or compound that, after intake, is metabolized (i.e., converted within the body) into a pharmacologically active drug. Instead of administering a drug directly, a corresponding prodrug can be used to improve how the drug is absorbed, distributed, metabolized, and excreted (ADME). Prodrugs are often designed to improve bioavailability when a drug itself is poorly absorbed from the gastrointestinal tract. A prodrug may be used to improve how selectively the drug interacts with cells or processes that are not its intended target. This reduces adverse or unintended effects of a drug, especially important in treatments like chemotherapy, which can have severe unintended and undesirable side effects. History Many herbal extracts historically used in medicine contain glycosides (sugar derivatives) of the active agent, which are hydrolyzed in the intestines to release the active and more bioavailable aglycone. For example, sal ...
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THC-O-acetate
THC-O-acetate (THC acetate ester, O-acetyl-THC, THC-O, AcO-THC) is the acetate ester of THC. The term ''THC-O-acetate'' and its variations are commonly used for two types of the substance, dependent on which cannabinoid it is synthesized from. The difference between Δ8-THC and Δ9-THC is the location of the double bond within the cyclohexene ring system. Physical data, chemistry, and properties THC acetate ester (THC-O or THCOA) can be synthesized from THC, or from THCA. The acetylation of THC does not change the properties of the compound to the same extent as with other acetate esters, as the parent compound (THC) is already highly lipophilic, but potency is nonetheless increased to some extent. While the acetate ester of Δ9-THC is the best studied, the acetate esters of other isomers, especially Δ8-THC but also Δ10-THC are also known, as are other esters such as THC-O-propionate, THC-O-phosphate, THC hemisuccinate, THC hemiglutarate, THC morpholinylbutyrate, THC ...
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THC Hemisuccinate
THC hemisuccinate (Δ9-THC-O-hemisuccinate, Dronabinol hemisuccinate) is a synthetic derivative of tetrahydrocannabinol, developed in the 1990s. It is a water-soluble prodrug ester which is converted into THC inside the body, and was developed to overcome the poor bioavailability of THC when taken by non-inhaled routes of administration. In medical applications it has mainly been formulated as rectal suppositories. See also * THC methylcarbonate * THC-O-acetate * THC-O-phosphate * THC-VHS THC valine hemisuccinate (THC-VHS, NB-1111, SBI-100) is a synthetic prodrug of tetrahydrocannabinol, developed at the University of Mississippi as a stabilised formulation for ophthalmic administration, for use in the treatment of glaucoma and ... * SP-111 References Benzochromenes Cannabinoids {{cannabinoid-stub ...
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THC Morpholinylbutyrate
THC morpholinylbutyrate (SP-111, Δ9-THC-O- -(morpholin-4-yl)butyrate'') is a synthetic derivative of tetrahydrocannabinol, developed in the 1970s. It is a prodrug which is converted into THC inside the body, and was one of the first derivatives of THC that is able to form water-soluble salts, giving it a significant advantage over THC for some applications. However, it is less potent than THC and the metabolic conversion to THC is relatively slow and variable, giving it unpredictable pharmacokinetics which has limited its research applications. See also * THC-O-acetate * THC-O-phosphate * THC hemisuccinate * THC methylcarbonate * THC-VHS THC valine hemisuccinate (THC-VHS, NB-1111, SBI-100) is a synthetic prodrug of tetrahydrocannabinol, developed at the University of Mississippi as a stabilised formulation for ophthalmic administration, for use in the treatment of glaucoma and ... * Nabitan * O-1057 References Benzochromenes Cannabinoids Prodrugs 4-Morpholi ...
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Cannabinoids
Cannabinoids () are several structural classes of compounds found primarily in the ''Cannabis'' plant 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 (i.e., THCA, CBDA, CBCA and their common precursor CBGA) 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. Phytocannabinoids are multi-ring phenolic compounds structurally related to THC, but endocannabinoids are fatty acid derivatives. Nonclassical synthetic cannabinoids (cannabimimetics) include aminoalkylindoles, 1,5-diarylpyrazoles, quinolines, a ...
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Oxygen Heterocycles
Oxygen is a chemical element; it has symbol O and atomic number 8. It is a member of the chalcogen group in the periodic table, a highly reactive nonmetal, and a potent oxidizing agent that readily forms oxides with most elements as well as with other compounds. Oxygen is the most abundant element in Earth's crust, making up almost half of the Earth's crust in the form of various oxides such as water, carbon dioxide, iron oxides and silicates.Atkins, P.; Jones, L.; Laverman, L. (2016).''Chemical Principles'', 7th edition. Freeman. It is the third-most abundant element in the universe after hydrogen and helium. At standard temperature and pressure, two oxygen atoms will bind covalently to form dioxygen, a colorless and odorless diatomic gas with the chemical formula . Dioxygen gas currently constitutes approximately 20.95% molar fraction of the Earth's atmosphere, though this has changed considerably over long periods of time in Earth's history. A much rarer triat ...
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Heterocyclic Compounds With 3 Rings
A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different chemical element, elements as members of its ring(s). Heterocyclic organic chemistry is the branch of organic chemistry dealing with the synthesis, properties, and applications of organic heterocycles. Examples of heterocyclic compounds include all of the nucleic acids, the majority of drugs, most biomass (cellulose and related materials), and many natural and synthetic dyes. More than half of known compounds are heterocycles. 59% of US FDA-approved drugs contain nitrogen heterocycles. Classification The study of organic heterocyclic chemistry focuses especially on organic unsaturated derivatives, and the preponderance of work and applications involves unstrained organic 5- and 6-membered rings. Included are pyridine, thiophene, pyrrole, and furan. Another large class of organic heterocycles refers to those fused to benzene rings. For example, the fused benzene deriv ...
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Carbonate Esters
In organic chemistry, a carbonate ester (organic carbonate or organocarbonate) is an ester of carbonic acid. This functional group consists of a carbonyl group flanked by two alkoxy groups. The general structure of these carbonates is and they are related to esters (), ethers () and also to the inorganic carbonates. Monomers of polycarbonate (e.g. Makrolon or Lexan) are linked by carbonate groups. These polycarbonates are used in eyeglass lenses, compact discs, and bulletproof glass. Small carbonate esters like dimethyl carbonate, ethylene carbonate, propylene carbonate are used as solvents, dimethyl carbonate is also a mild methylating agent. Structures Carbonate esters have planar OC(OC)2 cores, which confers rigidity. The unique O=C bond is short (1.173 Å in the depicted example), while the C–O bonds are more ether-like (the bond distances of 1.326 Å for the example depicted). Carbonate esters can be divided into three structural classes: acyclic, cyclic, and ...
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