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Abeo-HHC Acetate
Abeo-HHC acetate is a semi-synthetic derivative of tetrahydrocannabinol, first described in the 1980s. It is synthesised from delta-11-tetrahydrocannabinol, which can be made to undergo a ring expansion reaction via a hydrazone intermediate. It is structurally similar to HHC-acetate except that the methylated cyclohexyl ring has been replaced by a cycloheptane. See also * Cis-THC * Cycloheptyl CP 55,940 * Hexahydrocannabinol * Iso-THC * O-1656 * 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. ... References Cannabinoids Oxygen heterocycles Heterocyclic compounds with 3 rings Acetate esters {{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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Hydrazone
Hydrazones are a class of organic compounds with the structure . They are related to ketones and aldehydes by the replacement of the oxygen =O with the = functional group. They are formed usually by the action of hydrazine on ketones or aldehydes. Synthesis Hydrazine, organohydrazines, and 1,1-diorganohydrazines react with aldehydes and ketones to give hydrazones. : Phenylhydrazine reacts with reducing sugars to form hydrazones known as osazones, which was developed by German chemist Emil Fischer as a test to differentiate monosaccharides. Uses image:Pigment Yellow 97.svg, left, Pigment Yellow 97, a popular yellow colorant, is a hydrazone., 160px Hydrazones are the basis for various analyses of ketones and aldehydes. For example, dinitrophenylhydrazine coated onto a silica sorbent is the basis of an adsorption cartridge. The hydrazones are then eluted and analyzed by high-performance liquid chromatography (HPLC) using a ultraviolet, UV detector. The compound carbonyl cyanide-p-t ...
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HHC-acetate
HHC-acetate (Hexahydrocannabinol-O-acetate, HHC-O) is a semi-synthetic cannabinoid derivative which has been marketed since around 2022. Synthesis and chemistry It is believed to be made in a three step process from cannabidiol extracted from industrial hemp by synthesis of Delta-8-THC from CBD, then hydrogenation of Delta-8-THC to Hexahydrocannabinol, then finally acetylation of HHC. Legality The legal status of hexahydrocannabinol and derivatives such as HHC-O varies between countries leading to widespread sale in some jurisdictions in Europe and the US, but in France HHC and HHC-O were banned in 2023, and HHC is already banned in several other countries. This molecule has also been banned in the Czech Republic. See also * Abeo-HHC acetate * Cannabidiol diacetate * THC-O-acetate * THCP-O-acetate * Hexahydrocannabiphorol Hexahydrocannabiphorol (HHCP, sometimes mistakenly referred to as ''hexahydroxycannabiphorol'') is a semi-synthetic cannabinoid derivative which ...
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Methylcyclohexane
Methylcyclohexane (cyclohexylmethane) is an organic compound with the molecular formula is CH3C6H11. Classified as saturated hydrocarbon, it is a colourless liquid with a faint odor. Methylcyclohexane is used as a solvent. It is mainly converted in naphtha reformers to toluene.M. Larry Campbell. "Cyclohexane" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2012. A special use is in PF-1 priming fluid in cruise missiles to aid engine start-up when they run on special nonvolatile jet fuel like JP-10. Methylcyclohexane is also used in some correction fluids (such as White-Out) as a solvent. History While researching hydrogenation of arenes with hydroiodic acid in 1876 as part of his doctoral dissertation, first prepared the hydrocarbon from toluene. He determined its boiling point to be 97°C, its density at 20°C to by 0.76 g/cc and named it hexahydrotoluene. It was soon identified in oil from Baku and obtained by other synthetic methods. Production ...
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Cycloheptane
Cycloheptane, also known as Suberane, is an Chemical compound, organic compound, which belongs to the group of cycloalkanes. The compound can occur in different Rotamer, conformers. Production Cycloheptane occurs naturally in petroleum and can be extracted from it. It is synthesized by a Clemmensen reduction from cycloheptanone. Properties Cycloheptane is a colorless liquid with a mild, aromatic odor. The boiling point at normal pressure is 119°C. The molar enthalpy of vaporization is 38.5 kJ mol−1. According to the Antoine equation, the vapor pressure function is given by log10(''P'') = ''A''−(''B''/(''T''+''C'')) (''P'' in bar, ''T'' in kelvins) with ''A'' = 3.97710, ''B'' = 1330.402 and ''C'' = −56.946 in the temperature range from 341.3 K to 432.2 K. In the solid phase, cycloheptane occurs in four Crystal polymorphism, polymorphic forms. The transformation temperatures for the conversion from form IV to form III are −138°C, from form III to form II −75°C and f ...
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Cis-THC
''cis''-Delta-9-Tetrahydrocannabinol ((-)-''cis''-Δ9-THC) is an isomer of tetrahydrocannabinol found in the ''Cannabis'' plant but in lower quantities than the more well-known ''trans'' isomer. Formation of cis-THC could take place in process of epimerization associated with acid-catalyzed cyclization of CBD to THC. It has similar psychoactive effects to ''trans''-Δ9-THC in tests on mice, but with only around 1/5th the potency. The equivalent Δ8 isomer is also known as a synthetic compound, but has not been isolated from ''Cannabis'' plant material. All four cis/trans isomers are known, though only the (6aR,10aR) and (6aS,10aR) enantiomers are psychoactive, while the others retain activity at targets such as GPR18 and GPR55. See also * Abeo-HHC acetate * Abn-CBD * CBD-DMH * Exo-THC * Iso-THC * HU-211 * Perrottetinene Perrottetinene is a naturally occurring cannabinoid compound found in liverworts from the family Radulaceae native to Japan, New Zealand and Costa Ri ...
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Cycloheptyl CP 55,940
Cycloheptyl CP 55,940 is a synthetic cannabinoid related to CP 55,940 but is a ring-expanded homologue with a cycloheptyl ring in place of the cyclohexyl ring. It was first synthesized by Pfizer in the 1980s. It falls outside the definition of a " cyclohexylphenol derivative" since it does not have a cyclohexyl ring. Cycloheptyl CP 55,940 has similar potency to CP 55,940 itself, with an ED50 of 0.06 mg/kg in animal studies. See also * Abeo-HHC acetate * CP 47,497 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 ''K''d of 2.1 nM. Homologue On the 19th of ... * O-1656 References Cannabinoids Seven-membered rings Phenols Diols Drugs developed by Pfizer {{cannabinoid-stub ...
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Hexahydrocannabinol
Hexahydrocannabinol (HHC) is a phytocannabinoid that has been reported as a trace component of ''Cannabis sativa''. It can also be synthesized by hydrogenation of tetrahydrocannabinol (THC). The synthesis and bioactivity of HHC was first reported in 1940 by Roger Adams. HHC is a psychoactive substance with effects reportedly similar to those of THC. HHC vaporizers have been openly sold at head shops and convenience stores since at least the early 2020s in North America and Europe. Pharmacology HHC has 2 diastereomers that only differ by the orientation of the 9-methyl group, unlike D9-THC and D8-THC which have the double bond position next to the 9-methyl group that prevents this. The 9-methyl group orientation is believed to be important for cannabinoid binding affinity. Research has found 9R-HHC to have a binding affinity of 15nM ± 0.8nM at CB1 and 13nM ± 0.4nM at CB2, while 9S-HHC has a binding affinity of 176nM ± 3.3nM at CB1 and 105nM ± 26nM at CB2. The same study ...
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Iso-THC
Isotetrahydrocannabinol (iso-THC or Δ8-Isotetrahydrocannabinol) is a phytocannabinoid commonly found as a component in synthetic THC which has been made from acid-catalyzed cyclization of cannabidiol. iso-THC can be described as the upper cyclization product of CBD, while THC is the lower cyclization product of CBD. Its pharmacology has not been studied, though it is commonly found in commercially marketed Δ8-THC products. Via a migration of the exocyclic double bond iso-THC can easily rearrange to delta-4(8)-iso-THC, which can also be found in Δ8 THC products. Iso-THC can be found as an impurity in pharmaceutical Dronabinol. See also * Abeo-HHC acetate * Cannabicyclol * Cannabielsoin * Cis-THC ''cis''-Delta-9-Tetrahydrocannabinol ((-)-''cis''-Δ9-THC) is an isomer of tetrahydrocannabinol found in the ''Cannabis'' plant but in lower quantities than the more well-known ''trans'' isomer. Formation of cis-THC could take place in process o ... * Exo-THC References ...
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O-1656
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. See also * Abeo-HHC acetate * CBD-DMH * CP 55,940 * Cannabidiol * Cannabicyclohexanol * Cycloheptyl CP 55,940 Cycloheptyl CP 55,940 is a synthetic cannabinoid related to CP 55,940 but is a ring-expanded homologue with a cycloheptyl ring in place of the cyclohexyl ring. It was first synthesized by Pfizer in the 1980s. It falls outside the definition of ... * O-1871 References {{cannabinoid-stub Cannabinoids Diols ...
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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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