Cannabitriol

Last updated

Cannabitriol
(+)-trans-cannabitriol.png
Clinical data
Other names(+)-CBT, (S,S)-9,10-Dihydroxy-Δ6a(10a)-THC
Identifiers
  • (9S,10S)-6,6,9-trimethyl-3-pentyl-8,10-dihydro-7H-benzo[c]chromene-1,9,10-triol
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C21H30O4
Molar mass 346.467 g·mol−1
3D model (JSmol)
  • CCCCCC1=CC(=C2C(=C1)OC(C3=C2[C@@H]([C@@](CC3)(C)O)O)(C)C)O
  • InChI=1S/C21H30O4/c1-5-6-7-8-13-11-15(22)18-16(12-13)25-20(2,3)14-9-10-21(4,24)19(23)17(14)18/h11-12,19,22-24H,5-10H2,1-4H3/t19-,21-/m0/s1
  • Key:ZLYNXDIDWUWASO-FPOVZHCZSA-N

Cannabitriol (CBT) is a phytocannabinoid first isolated in 1966, [1] [2] [3] an oxidation product of tetrahydrocannabinol (THC) which has been identified both as a trace component of cannabis and as a metabolite in cannabis users. [4] Its pharmacology has been little studied, though it has been found to act as an antiestrogen and aromatase inhibitor. [5] [6]

Contents

See also

Related Research Articles

<i>Cannabis</i> Genus of flowering plants

Cannabis is a genus of flowering plants in the family Cannabaceae. The number of species within the genus is disputed. Three species may be recognized: Cannabis sativa, C. indica, and C. ruderalis. Alternatively, C. ruderalis may be included within C. sativa, or all three may be treated as subspecies of C. sativa, or C. sativa may be accepted as a single undivided species. The genus is widely accepted as being indigenous to and originating from Asia.

<span class="mw-page-title-main">Tetrahydrocannabinol</span> Psychoactive component of cannabis

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 (−)-trans9-tetrahydrocannabinol. It is a colorless oil.

<span class="mw-page-title-main">Cannabinoid</span> Compounds found in cannabis

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.

<span class="mw-page-title-main">Cannabinol</span> Naturally-occurring cannabinoid

Cannabinol (CBN) is a mildly psychoactive phytocannabinoid that acts as a low affinity partial agonist at both CB1 and CB2 receptors. This activity at CB1 and CB2 receptors constitutes interaction of CBN with the endocannabinoid system (ECS).

<span class="mw-page-title-main">Cannabidiol</span> Phytocannabinoid discovered in 1940

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.

<span class="mw-page-title-main">Tetrahydrocannabivarin</span> Homologue of tetrahydrocannabinol

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.

α-Pinene Chemical compound

α-Pinene is an organic compound of the terpene class. It is one of the two isomers of pinene, the other being β-pinene. An alkene, it contains a reactive four-membered ring. It is found in the oils of many species of coniferous trees, notably Pinus and Picea species. It is also found in the essential oil of rosemary and Satureja myrtifolia. Both enantiomers are known in nature; (1S,5S)- or (−)-α-pinene is more common in European pines, whereas the (1R,5R)- or (+)-α-isomer is more common in North America. The enantiomers' racemic mixture is present in some oils such as eucalyptus oil and orange peel oil.

<span class="mw-page-title-main">11-Hydroxy-THC</span> Active metabolite of Δ9-THC

11-Hydroxy-Δ9-tetrahydrocannabinol, usually referred to as 11-hydroxy-THC is the main active metabolite of tetrahydrocannabinol (THC), which is formed in the body after Δ9-THC is consumed.

<span class="mw-page-title-main">Cannabigerol</span> Minor cannabinoid

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.

<span class="mw-page-title-main">Tetrahydrocannabutol</span> Chemical compound

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

<span class="mw-page-title-main">Dronabinol</span> Generic name of Δ9-THC in medicine

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.

<span class="mw-page-title-main">Tetrahydrocannabinolic acid</span> THC precursor

Tetrahydrocannabinolic acid is a precursor of tetrahydrocannabinol (THC), an active component of cannabis.

<span class="mw-page-title-main">Tetrahydrocannabinolic acid synthase</span> Enzyme

Tetrahydrocannabinolic acid (THCA) synthase is an enzyme responsible for catalyzing the formation of THCA from cannabigerolic acid (CBGA). THCA is the direct precursor of tetrahydrocannabinol (THC), the principal psychoactive component of cannabis, which is produced from various strains of Cannabis sativa. Therefore, THCA synthase is considered to be a key enzyme controlling cannabis psychoactivity. Polymorphisms of THCA synthase result in varying levels of THC in Cannabis plants, resulting in "drug-type" and "fiber-type" C. sativa varieties.

<span class="mw-page-title-main">8,9-Dihydrocannabidiol</span> Chemical compound

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.

<span class="mw-page-title-main">Cannflavin</span> Chemical compound

Cannflavins are a group of chemical compounds found in Cannabis sativa. Chemically, they are prenylflavonoids and are unrelated to THC and other cannabinoids. Cannflavins A and B were first identified in the 1980s and cannflavin C was identified in 2008.

<span class="mw-page-title-main">Tetrahydrocannabiphorol</span> Cannabinoid agonist compound

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.

<span class="mw-page-title-main">Δ-8-Tetrahydrocannabinol</span> Isomer of tetrahydrocannabinol

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.

<span class="mw-page-title-main">Δ-3-Tetrahydrocannabinol</span> Chemical compound

Δ-3-Tetrahydrocannabinol is a synthetic isomer of tetrahydrocannabinol (THC) developed during the original research in the 1940s to develop synthetic routes to the natural products Δ8-THC and Δ9-THC found in the cannabis. While the normal trans configuration of THC is in this case flattened by the double bond, it still has two enantiomers as the 9-methyl group can exist in an (R) or (S) conformation. The (S) enantiomer has similar effects to Δ9-THC though with several times lower potency, while the (R) enantiomer is many times less active or inactive, depending on the assay used. It has been identified as a component of vaping liquid products.

<span class="mw-page-title-main">Hexahydrocannabinol</span> Hydrogenated derivative of THC

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.

Chemical defenses in <i>Cannabis</i> Defense of Cannabis plant from pathogens

Cannabis (/ˈkænəbɪs/) is commonly known as marijuana or hemp and has two known strains: Cannabis sativa and Cannabis indica, both of which produce chemicals to deter herbivory. The chemical composition includes specialized terpenes and cannabinoids, mainly tetrahydrocannabinol (THC), and cannabidiol (CBD). These substances play a role in defending the plant from pathogens including insects, fungi, viruses and bacteria. THC and CBD are stored mostly in the trichomes of the plant, and can cause psychological and physical impairment in the user, via the endocannabinoid system and unique receptors. THC increases dopamine levels in the brain, which attributes to the euphoric and relaxed feelings cannabis provides. As THC is a secondary metabolite, it poses no known effects towards plant development, growth, and reproduction. However, some studies show secondary metabolites such as cannabinoids, flavonoids, and terpenes are used as defense mechanisms against biotic and abiotic environmental stressors.

References

  1. Obata Y, Ishikawa Y (June 1966). "Studies on the constituents of hemp plant (Cannabis sativa L.) Part III. Isolation of a gibbs-positive compound from Japanese hemp". Agricultural and Biological Chemistry. 30 (6): 619–620. doi:10.1080/00021369.1966.10858651.
  2. Chan WR, Magnus KE, Watson HA (March 1976). "The structure of cannabitriol". Experientia. 32 (3): 283–4. doi:10.1007/BF01940792. PMID   1253891. S2CID   2679030.
  3. Elsohly MA, El-Feraly FS, Turner CE (1977). "Isolation and characterization of (+)-cannabitriol and (-)-10-ethoxy-9-hydroxy-delta 6a[10a]-tetrahydrocannabinol: two new cannabinoids from Cannabis sativa L. extract". Lloydia. 40 (3): 275–80. PMID   895385.
  4. White RM (January 2018). "Instability and poor recovery of cannabinoids in urine, oral fluid, and hair". Forensic Science Review. 30 (1): 33–49. PMID   29273570.
  5. Baroi S, Saha A, Bachar R, Bachar SC (June 2020). "Cannabinoid as Potential Aromatase Inhibitor through Molecular Modeling and Screening for Anti-Cancer Activity". Dhaka University Journal of Pharmaceutical Sciences. 19 (1): 47–58. doi: 10.3329/dujps.v19i1.47818 . S2CID   225712476.
  6. Kikiowo B, Ogunleye AJ, Iwaloye O, Ijatuyi TT, Adelakun NS, Alashe WO (2021). "Induced Fit Docking and Automated QSAR Studies Reveal the ER-α Inhibitory Activity of Cannabis sativa in Breast Cancer". Recent Patents on Anti-Cancer Drug Discovery. 16 (2): 273–284. doi:10.2174/1574892816666210201115359. PMID   33563181. S2CID   231865568.