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| Formula | C25H36O3 |
| Molar mass | 384.560 g·mol−1 |
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THCP-O-acetate (THCP-O) is a semi-synthetic derivative of tetrahydrocannabiphorol (THCP) derived by acetylation of the OH group. It has been found as a component of grey-market cannabis products such as e-cigarette liquids and edible gummy lollies, and is allegedly a potent and long-lasting psychoactive cannabinoid. [1]
In 2022, researchers at Portland State University who screened for the presence of reacted ketene as N-benzylacetamide reported that Vitamin E acetate, CBD-acetate, CBN-acetate and THC-O-acetate may break down to release ketene gas when heated at 340 °C (644 °F). [2] [3]
Japan banned THCP-O-Acetate along with HHCP on December 26, 2023. [4]
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.
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.
Cannabidiol (CBD) is a phytocannabinoid, one of 113 identified cannabinoids in cannabis plants, along with tetrahydrocannabinol (THC), and accounts for up to 40% of the plant's extract. Medically, it is an anticonvulsant used to treat multiple forms of epilepsy. It was discovered in 1940 and, as of 2024 clinical research on CBD included studies related to the treatment of anxiety, addiction, psychosis, movement disorders, and pain, but there is insufficient high-quality evidence that CBD is effective for these conditions. CBD is sold as an herbal dietary supplement and promoted with yet unproven claims of particular therapeutic effects.
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.
Parahexyl, also known as synhexyl, is a synthetic homologue of tetrahydrocannabinol (THC) which was invented in 1941 during attempts to elucidate the structure of Δ9-THC, one of the active components of cannabis.
THC-O-acetate 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 bond placement on the cyclohexene ring.
Dimethylheptylpyran (DMHP) is a synthetic cannabinoid and analogue of tetrahydrocannabinol (THC). It 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.
Δ9-Tetrahydrocannabutol is a phytocannabinoid found in cannabis that is a homologue of tetrahydrocannabinol (THC), the main active component of Cannabis. Structurally, they are only different by the pentyl side chain being replaced by a butyl side chain. THCB was studied by Roger Adams as early as 1942
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.
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.
Tetrahydrocannabiphorol (THCP) is a potent phytocannabinoid, a CB1 and CB2 receptor agonist which was known as a synthetic homologue of tetrahydrocannabinol (THC), but for the first time in 2019 was isolated as a natural product in trace amounts from Cannabis sativa.
Δ-8-tetrahydrocannabinol is a psychoactive cannabinoid found in the cannabis plant. It is an isomer of delta-9-tetrahydrocannabinol, the compound commonly known as THC, with which it co-occurs in hemp; natural quantities of ∆8-THC found in hemp are low. Psychoactive effects are similar to that of Δ9-THC, with central effects occurring by binding to cannabinoid receptors found in various regions of the brain.
Hexahydrocannabinol (HHC) is a hydrogenated derivative of tetrahydrocannabinol (THC). It is a naturally occurring phytocannabinoid that has rarely been identified as a trace component in Cannabis sativa, but can also be produced synthetically by firstly acid cyclization of cannabidiol and then hydrogenation of tetrahydrocannabinol. The synthesis and bioactivity of HHC was first reported in 1940 by Roger Adams.
Cannabinoids are compounds found in the cannabis plant or synthetic compounds that can interact with the endocannabinoid system. The most notable cannabinoid is the phytocannabinoid tetrahydrocannabinol (THC) (Delta-9-THC), the primary intoxicating compound in cannabis. Cannabidiol (CBD) is another major constituent of some cannabis plants. Conversion of CBD to THC can occur when CBD is heated to temperatures between 250–300 °C, potentially leading to its partial transformation into THC.
JWH-138 (THC-Octyl, Δ8-THC-C8) is a synthetic cannabinoid first synthesized by Roger Adams and studied heavily by John W. Huffman, with a Ki of 8.5nM at the CB1 cannabinoid receptor. THC-Octyl and its hydrogenated analog HHC-Octyl was synthesized and studied by Roger Adams as early as 1942.
HHC-acetate is a semi-synthetic cannabinoid derivative which has been marketed since around 2022. It is believed to be made in a three step process from cannabidiol extracted from hemp. 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. On 1st of March 2024 HHC was banned on Czech Republic.
Hexahydrocannabiphorol is a semi-synthetic cannabinoid derivative which has been marketed since around 2021. It is believed to be made from the hydrogenation of tetrahydrocannabiphorol (THCP). THCP is only reported as a trace component of cannabis in 2019. HHCP was studied by Roger Adams as early as 1942.
Cannabidiol diacetate is a semi-synthetic derivative of cannabidiol derived by acetylation of the OH groups, which presumably acts as a prodrug for CBD. It has been found as a component of grey-market cannabis products such as e-cigarette liquids and edible gummy lollies.
HHCP-O-acetate is a semi-synthetic derivative of tetrahydrocannabiphorol (THCP) derived in several steps by hydrogenation to hexahydrocannabiphorol (HHCP) followed by acetylation of the OH group. It has been found as a component of grey-market cannabis products such as e-cigarette liquids and edible gumdrops, and is allegedly a potent and long-lasting psychoactive cannabinoid.
Isotetrahydrocannabinol (iso-THC) is a phytocannabinoid similar in structure to cannabicitran which has been identified as a trace component of Cannabis, but is more commonly found as an impurity in synthetic THC which has been made from cannabidiol. iso-THC is present with other isomers with the double bond in a different position and the saturated dihydro derivative. 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 as a trace impurity in commercially marketed Δ8-THC products.
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