Cannabinoids

Cannabinoids are chemical compounds that occur naturally in the cannabis plant or can be produced synthetically, and they act in the human body primarily through the endocannabinoid system. They influence numerous physiological processes such as pain perception, mood, appetite, and inflammatory responses. The endocannabinoid system is an intrinsic regulatory network composed of receptors, endocannabinoids, and the enzymes that control their synthesis and breakdown. Plant-derived cannabinoids from the hemp plant can interact with this system and thereby elicit a wide range of different effects in the body.

Phytocannabinoids

Phytocannabinoids are the cannabinoids that occur naturally in plants. More than 100 different phytocannabinoids have now been identified, although most of them are present in the plant only in very small amounts. Nevertheless, in combination with one another and with terpenes (the plant’s aromatic compounds), they can contribute to the so-called entourage effect1. This effect describes the positive interaction of the components of cannabis, but it is still barely understood scientifically and difficult to investigate.

.

THC, Δ9-THC, d-9THC, Tetrahydrocannabinol, delta-9-THC, THC Struktur, THC analysis, THC Analyse

Δ9-THC – Tetrahydrocannabinol

THC, or delta-9-THC / tetrahydrocannabinol, is the best-known and most thoroughly studied cannabinoid and is primarily responsible for the psychoactive effects of cannabis. After inhalation or oral consumption, it is converted in the body into 11-hydroxy-THC, which is the compound that produces the actual effects. In most EU countries, industrial hemp in the form of CBD flowers or fiber hemp is permitted; however, specific national and EU-wide regulations apply regarding their THC content. Since January 2023, an EU-wide limit of 3 mg/kg of THC which corresponds to 0,3% is in effect for hemp.2 Specific rules also apply to the THC content of medical cannabis in the form of flowers. A medical cannabis flower may not deviate by more than 10% from the THC content stated on the label3. That’s why laboratory THC analysis is so important. THC testing for Cannabis Social Clubs (CSCs) is also mandated in the German cannabis law (§17 & §18 KCanG).4

THC-A, THCA, THC-Säure, Tetrahydrocannabinol-Säure, THC-Acid, Tetrahydrocannabinolic acid, THC-A structure, THCA-Struktur

THC-A – THC-Acid

THC acid (the “A” in THCA stands for acid) is the form of Δ9-THC produced by the cannabis plant. All cannabinoids are created in their acidic form in the plant by enzymes in the trichomes, and only through non-enzymatic processes such as exposure to light or heat are they converted into their neutral forms5. THC acid itself is not psychoactive and is usually converted into its neutral form during heating, either when inhaled or during processing. This process is called decarboxylation. Only at temperatures of 110 °C or higher does decarboxylation proceed efficiently enough for most of the THCA to be converted into THC6. When smoking, temperatures of over 600–800 °C are reached in the ember. Decarboxylation happens extremely quickly under these conditions—essentially within fractions of a second. However, not only is THCA converted to THC, but some of the THC is also thermally degraded due to the high temperatures. This is why a certain portion of the active compounds is lost during smoking, whereas vaporizing (at 160–180 °C) usually decarboxylates more efficiently and gently.

CBD, Cannabidiol, CBD Struktur, CBD structure, CBD Analyse, CBD analysis

CBD – Cannabidiol

CBD, or cannabidiol, is the second most abundant cannabinoid in the hemp plant after THC. Unlike THC, CBD binds very weakly to cannabinoid receptors and does not produce psychoactive effects. CBD is considered a potent anti-inflammatory compound7 and is attributed with a wide range of therapeutically beneficial effects. These include sleep-promoting, relaxing, anxiolytic, pain-relieving, and neuroprotective effects. Additionally, there are many user reports with highly variable outcomes, suggesting that CBD can affect different individuals in very different ways. Scientifically, the only well-established effect is its efficacy against epilepsy8. TDespite the widespread availability of CBD products, long-term studies are still lacking for many of the purported effects. Research has shown that only about one-third of over-the-counter CBD products actually contain the declared amount of active ingredient9 10 11. This makes independent scientific analyses of CBD flowers and products all the more important.

CBG, Cannabigerol, CBG Struktur, CBG structure

CBG – Cannabigerol

The acidic form of cannabigerol, CBGA, is synthesized in the trichomes from geranyl diphosphate and olivetolic acid. From cannabigerolic acid, the plant—through the action of specific enzymes—produces either CBDA or THCA, as well as other cannabinoids. CBG is therefore considered the “mother of all cannabinoids.” It does not bind to cannabinoid receptors in the brain and is not psychoactive. However, it is being studied for its pharmacological potential, as it exhibits anti-inflammatory, pain-relieving, and antibacterial effects12 13 14. Since CBG is never fully converted into THC or CBD, this cannabinoid is always present in natural cannabis flowers.

CBN, Cannabinol, CBN Struktur, CBN structure

CBN – Cannabinol

CBN is structurally very similar to Δ9-THC and is also mildly psychoactive. Its affinity for the CB1 receptor is only about half that of Δ9-THC. However, studies suggest that CBN may enhance the effects of Δ9-THC15. Plants do not have an enzymatic pathway to produce CBN directly. Instead, CBN forms as a degradation product through the oxidation of Δ9-THC16. The ratio of Δ9-THC to CBN can be used to estimate the approximate age of a cannabis flower17. CBN often forms due to friction during hash production, as well as during certain extraction methods.

CBC, Cannabirchromen, cannabichromene, CBC structure

CBC – Cannabichromene

Cannabichromene (CBC) is, alongside THC, CBD, and CBG, one of the four most common cannabinoids and is found in most cannabis flowers in small concentrations. It is also present in other plants and fungi. Pharmacologically, CBC shows little affinity for the classic cannabinoid receptors CB1 and CB2 and is not psychoactive. It inhibits the breakdown of endocannabinoids such as anandamide, thereby indirectly enhancing the activity of the endocannabinoid system18.In animal models, CBC has been shown to have pain-relieving effects and to reduce inflammation in the gut19. Additionally, there is evidence of antibacterial properties and regulation of sebum production, making CBC potentially interesting for the treatment of acne19.

THCV, Tetrahydrocannabivarin, THCV Struktur, THCV structure

THCV – Tetrahydrocannabivarin

Tetrahydrocannabivarin (THCV) is structurally similar to THC, but instead of a five-carbon side chain, it has a shorter three-carbon chain. THCV is often described as psychoactive; however, this is not the case21. It is believed that THCV attenuates the effects of THC. THCV acts as a competitive antagonist at the CB1 receptor. It binds to the same receptor but activates it much more weakly, effectively taking THC’s place and preventing it from exerting its full effect22. Nevertheless, THCV has several medically interesting properties. Two studies have shown that THCV intake in humans can influence blood sugar levels and appetite, suggesting potential use in the treatment of diabetes23 24.

CBDV, Cannabidivarin, CBDV Struktur, CBDV structure

CBDV – Cannabidivarin

Cannabidivarin (CBDV) is, analogous to THCV, a version of CBD with a shorter side chain. It has little effect on CB1 receptors, is not psychoactive, but does show activity at CB2 receptors. Animal studies and some early human trials indicate that CBDV may have anticonvulsant effects, meaning it can help reduce epileptic seizures25 26. Furthermore, CBDV is well tolerated, which is why its clinical efficacy is currently being investigated.

CBL, Cannabicyclol, CBL Struktur, CBL structure

CBL – Cannabicyclol

CBL is not a primary plant product but forms through light- or heat-induced conversion of cannabichromene. It was identified in cannabis samples very early on, but its chemical and biological properties remain largely unexplored. CBL has only a very weak effect on cannabinoid receptors, yet shows an unexpectedly strong effect on a serotonin receptor27. These receptors play a key role in mood regulation, anxiety, depression, and neuroprotection. Even at nanomolar concentrations, CBL significantly enhances the effects of serotonin27.

CBT, Cannabitriol, CBT Struktur, CBT structure

CBT – Cannabitriol

Cannabitriol is an oxidation product of THC and occurs only in extremely small amounts in very old cannabis samples. It has the same basic structure as THC but contains two additional hydroxyl (OH) groups and binds only weakly to the CB1 receptor29. It occurs in two different isomeric forms. Any psychoactive effect, if present, is very weak and has been scarcely studied.

CBE, Cannabielsoin, CBE Struktur, CBE structure

CBE – Cannabielsoin

Cannabielsoin (CBE) is produced in mammals, including humans, as a metabolic byproduct of CBD30 , and can also be detected in very small amounts in the cannabis plant. CBE and its isomers have been identified as the most commonly observed degradation products of CBD—both in plant material and in synthetic CBD e-liquids—and could serve as a marker for their decomposition.31.

Synthetic cannabinoids

Synthetic cannabinoids mimic the effects of natural cannabinoids but differ in that they are artificially produced in the laboratory and either do not occur in the cannabis plant at all or are present only in extremely small amounts. They are often conversion products derived from readily available cannabinoids such as CBD and closely resemble natural cannabinoids in their chemical structure. As a result, they frequently bind to the CB1 or CB2 receptors of the human endocannabinoid system and produce comparable effects. They are manufactured to circumvent existing legal regulations, which typically focus on specific chemical structures and ban them. Consequently, synthetic cannabinoids usually exist in a legal gray area and are marketed as a legal alternative to prohibited THC. Synthetic or semi-synthetic cannabinoids are also referred to as pseudocannabinoids.

Δ8-THC, d8-THC, delta-8-THC, Δ8-Tetrahydrocannabinol, delta-8-Tetrahydrocannabinol, d-8-THC

Δ8-THC – delta-8-Tetrahydrocannabinol

Delta-8-THC is an isomer of Δ9-THC and differs only in the position of a single double bond. This difference from Δ9-THC was sufficient for it to be considered legal in many U.S. states, as it was not explicitly banned like Δ9-THC, sparking a boom around 2021. Δ8-THC is somewhat less potent than delta-9-THC32. Δ8-THC is usually synthesized from readily available CBD33. The delta-8-THC boom declined starting in 2022, as more U.S. states restricted or banned its sale due to legal uncertainties and safety concerns, while regulated cannabis became more readily available. To date, there are only a few scientific studies on the substance, and much of the information about delta-8-THC remains purely anecdotal34.

THCP, Tetrahydrocannabiphorol, THCP Struktur

THCP – Tetrahydrocannabiphorol

Tetrahydrocannabiphorol (THCP) is a highly psychoactive cannabinoid. It has the same basic chemical structure as THC but features a seven-carbon side chain instead of five. Computational docking studies indicate that the longer side chain results in a 33-fold stronger binding affinity to the CB1 receptor35 which explains the higher potency. THCP also shows high affinity for the CB2 receptor, where CBD binds. It occurs in very small amounts (a few micrograms per gram) in some THC-dominant cannabis strains36. This could help explain the strong psychoactive effects of some strains, which cannot be accounted for by their THC content alone. However, THCP in cannabis products usually does not come from the flowers but is produced synthetically in the laboratory.

THCP-O, Tetrahydrocannabiphorolacetat

THCP-O – Tetrahydrocannabiphorol acetate

THCP‑O (THCP‑O‑Acetate) is a semi-synthetic derivative of THCP, produced by acetylating the hydroxyl (OH) group of THCP. This modification represents an attempt to make the otherwise controlled THCP available on the market as a substitute product. THCP‑O has effects comparable in strength to THCP; however, when acetates like THCP‑O are smoked or vaporized at temperatures around 340 °C, toxic ketene gases are produced37 that can cause harmful effects on the lungs.

HHC, Hexahydrocannabinol, HHC Struktur

HHC – Hexahydrocannabinol

Hexahydrocannabinol (HHC) acts similarly to Δ⁹-THC but is somewhat less potent. HHC is usually synthesized from CBD, with Δ⁹-THC often serving as an intermediate. The process produces a mixture of two different stereoisomers: 9S-HHC and 9R-HHC. 9R-HHC is primarily responsible for the psychoactive effects, as it binds much more strongly to the CB1 receptor than the minimally active S-form38. HHC is present in the cannabis plant only in trace amounts and, if at all, appears merely as an insignificant degradation product of Δ⁹-THC. Consumption of HHC can trigger a positive THC test, as its metabolites are similar.

HHCP, Hexahydrocannabiphorol, HHCP Struktur

HHCP- Hexahydrocannabiphorol

HHCP is sold as a legal, psychoactive alternative in countries where cannabis and its psychoactive component THC are regulated under narcotics laws. According to anecdotal consumer reports, HHCP is more potent and longer-lasting than HHC or THC. This is likely due to its higher binding affinity for the CB1 receptor, caused by its longer side chain, similar to THCP. Like HHC, HHCP can produce false-positive results in THC metabolite screening tests39.

H4CBD, hydriertes CBD

H4CBD

H4CBD, or “hydrogenated CBD,” unlike conventional CBD, shows a slight affinity for the CB1 receptor and can therefore produce mild psychoactive effects. Only a few peer-reviewed studies have specifically investigated the effects of H4CBD in humans. In animal studies, treatment with H4CBD led to weight reductions of up to 15% and a significantly improved glucose tolerance40. In this study, however, the dosage was relatively high at 200 mg/kg.

Andere Cannabinoide

THC-COOH

THC-COOH – 11-Nor-9-Carboxy-Δ9-Tetrahydrocannabinol

THC‑COOH is the inactive primary metabolite formed after cannabis consumption. This substance is commonly detected in drug screenings. THC‑COOH can also form in the body after taking CBD oils that contained no THC, potentially leading to a positive drug test41.

Perrottetinen, Perrottetinen

PET – Perrottetinen

Perrottetinen (PET) also belongs to the cannabinoid class, but it is not found in cannabis. Instead, it occurs in certain liverwort species, such as Radula marginata, in New Zealand. Structurally, PET is analogous to THC. Early studies showed that PET acts on cannabinoid receptors and exhibited psychoactive effects in mouse experiments42. Despite their similarity to the cannabinoids found in the cannabis plant, these substances are believed to have evolved independently43.

–
Do you have any questions? Get in touch with us via our contact form.

    References

    1. Ferber SG, Namdar D, Hen-Shoval D, Eger G, Koltai H, Shoval G, Shbiro L, Weller A. “The “Entourage Effect”: Terpenes Coupled with Cannabinoids for the Treatment of Mood Disorders and Anxiety Disorders.” Curr Neuropharmacol. 2020;18(2):87-96. https://doi.org/10.2174/1570159×17666190903103923 ↩︎
    2. https://eur-lex.europa.eu/legal-content/DE/TXT/PDF/?uri=CELEX:32022R1393 ↩︎
    3. https://gmpinsiders.com/cannabis-flower-ph-eur-monograph ↩︎
    4. https://www.gesetze-im-internet.de/kcang/BJNR06D0B0024.html ↩︎
    5. Grotenhermen F. “Pharmacokinetics and pharmacodynamics of cannabinoids.” Clin Pharmacokinet. 2003;42(4):327-60. https://doi.org/10.2165/00003088-200342040-00003 ↩︎
    6. Wang M, Wang YH, Avula B, Radwan MM, Wanas AS, van Antwerp J, Parcher JF, ElSohly MA, Khan IA. “Decarboxylation Study of Acidic Cannabinoids: A Novel Approach Using Ultra-High-Performance Supercritical Fluid Chromatography/Photodiode Array-Mass Spectrometry.” Cannabis Cannabinoid Res. 2016 Dec 1;1(1):262-271. https://doi.org/10.1089/can.2016.0020 ↩︎
    7. Burstein S. “Cannabidiol (CBD) and its analogs: a review of their effects on inflammation.” Bioorg Med Chem. 2015 Apr 1;23(7):1377-85. https://doi.org/10.1016/j.bmc.2015.01.059 ↩︎
    8. Peng J, Fan M, An C, Ni F, Huang W, Luo J. “A narrative review of molecular mechanism and therapeutic effect of cannabidiol (CBD).” Basic Clin Pharmacol Toxicol. 2022 Apr;130(4):439-456. https://doi.org/10.1016/j.bmc.2015.01.059 ↩︎
    9. Gidal BE, Vandrey R, Wallin C, Callan S, Sutton A, Saurer TB, Triemstra JL. “Product labeling accuracy and contamination analysis of commercially available cannabidiol product samples.” Front Pharmacol. 2024 Mar 18;15:1335441. https://doi.org/10.3389/fphar.2024.1335441 ↩︎
    10. Spindle TR, Sholler DJ, Cone EJ, Murphy TP, ElSohly M, Winecker RE, Flegel RR, Bonn-Miller MO, Vandrey R. “Cannabinoid Content and Label Accuracy of Hemp-Derived Topical Products Available Online and at National Retail Stores.” JAMA Netw Open. 2022 Jul 1;5(7):e2223019. https://doi.org/10.1001/jamanetworkopen.2022.23019 ↩︎
    11. Johnson E, Kilgore M, Babalonis S. Label accuracy of unregulated cannabidiol (CBD) products: measured concentration vs. label claim. J Cannabis Res. 2022 Jun 6;4(1):28. https://doi.org/10.1186/s42238-022-00140-1 ↩︎
    12. Li S, Li W, Malhi NK, Huang J, Li Q, Zhou Z, Wang R, Peng J, Yin T, Wang H. “Cannabigerol (CBG): A Comprehensive Review of Its Molecular Mechanisms and Therapeutic Potential.” Molecules. 2024; 29(22):5471. https://doi.org/10.3390/molecules29225471 ↩︎
    13. Jastrząb A, Jarocka-Karpowicz I, Skrzydlewska E. “The Origin and Biomedical Relevance of Cannabigerol.” International Journal of Molecular Sciences. 2022; 23(14):7929. https://doi.org/10.3390/ijms23147929 ↩︎
    14. Nachnani R, Raup-Konsavage WM, Vrana KE. “The Pharmacological Case for Cannabigerol.” The Journal of Pharmacology and Experimental Therapeutics. 2021; 376(2): 204-212. https://doi.org/10.1124/jpet.120.000340. ↩︎
    15. Karniol IG, Shirakawa I, Takahashi RN, Knobel E, Musty RE. “Effects of Δ9-Tetrahydrocannabinol and Cannabinol in Man.” Pharmacology 1 June 1975; 13 (6): 502–512. https://doi.org/10.1159/000136944 ↩︎
    16. Garrett ER, Gouyette AJ, Roseboom H. “Stability of Tetrahydrocannabinols II.” J. Pharm. Sci. 1978, 67, 27–32. https://doi.org/10.1002/jps.2600670108 ↩︎
    17. Ross SA, Elsohly MA. “CBN and D9-THC concentration ratio as an indicator of the age of stored marijuana samples.” United Nations Office on Drugs and Crime. 1999. https://www.unodc.org/unodc/en/data-and-analysis/bulletin/bulletin_1997-01-01_1_page008.html#fn ↩︎
    18. Pollastro F, Caprioglio D, Del Prete D, et al. “Cannabichromene.” Natural Product Communications. 2018;13(9). https://doi.org/10.1177/1934578X1801300922 ↩︎
    19. Sepulveda DE, Vrana KE, Kellogg JJ, Bisanz JE, Desai D, Graziane NM, Raup-Konsavage WM. “The Potential of Cannabichromene (CBC) as a Therapeutic Agent.” The Journal of Pharmacology and Experimental Therapeutics. 2024; 391(2): 206-213 https://doi.org/10.1124/jpet.124.002166 ↩︎
    20. Sepulveda DE, Vrana KE, Kellogg JJ, Bisanz JE, Desai D, Graziane NM, Raup-Konsavage WM. “The Potential of Cannabichromene (CBC) as a Therapeutic Agent.” The Journal of Pharmacology and Experimental Therapeutics. 2024; 391(2): 206-213 https://doi.org/10.1124/jpet.124.002166 ↩︎
    21. Haghdoost M, Peters EN, Roberts M, Bonn-Miller MO (2025) “Tetrahydrocannabivarin (THCV) is not tetrahydrocannabinol (THC).” Cannabis and Cannabinoid Research 10:1, 1–5 https://doi.org/10.1089/can.2024.0051 ↩︎
    22. Thomas A, Stevenson LA, Wease KN, Price MR, Baillie G, Ross RA, Pertwee RG. “Evidence that the plant cannabinoid Delta9-tetrahydrocannabivarin is a cannabinoid CB1 and CB2 receptor antagonist.” Br J Pharmacol. 2005 Dec;146(7):917-26. https://doi.org/10.1038/sj.bjp.0706414. ↩︎
    23. Jadoon KA, Ratcliffe SH, Barrett DA, Thomas EL, Stott C, Bell JD, O’Sullivan SE, Tan GD. “Efficacy and Safety of Cannabidiol and Tetrahydrocannabivarin on Glycemic and Lipid Parameters in Patients With Type 2 Diabetes: A Randomized, Double-Blind, Placebo-Controlled, Parallel Group Pilot Study.” Diabetes Care. 2016 Oct;39(10):1777-86. https://doi.org/10.2337/dc16-0650. ↩︎
    24. Tudge L, Williams C, Cowen PJ, McCabe C. “Neural effects of cannabinoid CB1 neutral antagonist tetrahydrocannabivarin on food reward and aversion in healthy volunteers.” Int J Neuropsychopharmacol. 2014 Dec 25;18(6):pyu094. https://doi.org/10.1093/ijnp/pyu094 ↩︎
    25. Zamberletti E, Rubino T, Parolaro D. “Therapeutic potential of cannabidivarin for epilepsy and autism spectrum disorder.” Pharmacology & Therapeutics. 2021; Volume 226,
      https://doi.org/10.1016/j.pharmthera.2021.107878. ↩︎
    26. Huizenga MN, Sepulveda-Rodriguez A, Forcelli PA. Preclinical safety and efficacy of cannabidivarin for early life seizures. Neuropharmacology. 2019 Apr;148:189-198. doi: 10.1016/j.neuropharm.2019.01.002. ↩︎
    27. Haghdoost M, DePorre Y, Figi M, Young S, Krebs C, Bonn-Miller MO. An Unexpected Activity of a Minor Cannabinoid: Cannabicyclol (CBL) Is a Potent Positive Allosteric Modulator of Serotonin 5-HT1A Receptor. J Nat Prod. 2025 Jan 24;88(1):58-66. https://doi.org/10.1021/acs.jnatprod.4c00977. ↩︎
    28. Haghdoost M, DePorre Y, Figi M, Young S, Krebs C, Bonn-Miller MO. An Unexpected Activity of a Minor Cannabinoid: Cannabicyclol (CBL) Is a Potent Positive Allosteric Modulator of Serotonin 5-HT1A Receptor. J Nat Prod. 2025 Jan 24;88(1):58-66. https://doi.org/10.1021/acs.jnatprod.4c00977. ↩︎
    29. Carbone, Marianna & Castelluccio, Francesco & Daniele, Antonella & Sutton, Alan & Ligresti, Alessia & Di Marzo, Vincenzo & Gavagnin, Margherita. (2010). “Chemical characterisation of oxidative degradation products of Δ 9THC.” Tetrahedron. 66. https://doi.org/10.1016/j.tet.2010.10.025 ↩︎
    30. Yamamoto I, Gohda H, Narimatsu S, Watanabe K, Yoshimura H. “Cannabielsoin as a new metabolite of cannabidiol in mammals.” Pharmacol Biochem Behav. 1991 Nov;40(3):541-6. https://doi.org/10.1016/0091-3057(91)90360-E ↩︎
    31. Schwarzenberg A, Carpenter H, Wright C. et al. “Characterizing the degradation of cannabidiol in an e-liquid formulation.” Sci Rep 12, 20058 (2022). https://doi.org/10.1038/s41598-022-23910-6 ↩︎
    32. Kruger JS, Kruger DJ. “Delta-8-THC: Delta-9-THC’s nicer younger sibling?”. J Cannabis Res 4, 4 (2022). https://doi.org/10.1186/s42238-021-00115-8 ↩︎
    33. Leas EC, Nobles AL, Yuyan Shi, Hendrickson E. “Public interest in ∆8-Tetrahydrocannabinol (delta-8-THC) increased in US states that restricted ∆9-Tetrahydrocannabinol (delta-9-THC) use.” International Journal of Drug Policy, Volume 101, 2022, 103557, https://doi.org/10.1016/j.drugpo.2021.103557. ↩︎
    34. LoParco CR, Rossheim ME, Walters ST, Zhou Z, Olsson S, Sussman SY. “Delta-8 tetrahydrocannabinol: a scoping review and commentary”. Addiction. 2023; 118(6): 1011–1028. https://doi.org/10.1111/add.16142 ↩︎
    35. Citti C, Linciano P, Russo F, Luongo L, Iannotta M, Maione S, Laganà A, Capriotti AL, Forni F, Vandelli MA, Gigli G, Cannazza G. “A novel phytocannabinoid isolated from Cannabis sativa L. with an in vivo cannabimimetic activity higher than Δ9-tetrahydrocannabinol: Δ9-Tetrahydrocannabiphorol.” Sci Rep. 2019 Dec 30;9(1):20335. https://doi.org/10.1038/s41598-019-56785-1. ↩︎
    36. Bueno J, Greenbaum EA. “(-)-trans-Δ9-Tetrahydrocannabiphorol Content of Cannabis sativa Inflorescence from Various Chemotypes.” J Nat Prod. 2021 Feb 26;84(2):531-536. https://doi.org/10.1021/acs.jnatprod.0c01034 ↩︎
    37. Munger KR, Jensen RP, Strongin RM. “Vaping Cannabinoid Acetates Leads to Ketene Formation.” Chem Res Toxicol. 2022 Jul 18;35(7):1202-1205. https://doi.org/10.1021/acs.chemrestox.2c00170 ↩︎
    38. Haghdoost M, López de Los Santos Y, Brunstetter M, Ferretti ML, Roberts M, Bonn-Miller MO. “Using In Silico Molecular Docking to Explain Differences in Receptor Binding Behavior of HHC and THCV Isomers: Revealing New Binding Modes”. Pharmaceuticals (Basel). 2024 May 15;17(5):637. https://doi.org/10.3390/ph17050637 ↩︎
    39. Helander A, Johansson M, Villén T, Andersson A. “Appearance of hexahydrocannabinols as recreational drugs and implications for cannabis drug testing – focus on HHC, HHC-P, HHC-O and HHC-H.” Scand J Clin Lab Invest. 2024 Apr;84(2):125-132. https://doi.org/10.1080/00365513.2024.2340039 ↩︎
    40. Wilson JN, Mendez DA, Dhoro F, Shevchenko N, Mascal M, Lund K, Fitzgerald R, DiPatrizio NV, Ortiz RM. “Pseudocannabinoid H4CBD improves glucose response during advanced metabolic syndrome in OLETF rats independent of increase in insulin signaling proteins.” Am J Physiol Regul Integr Comp Physiol. 2024 Feb 1;326(2):R100-R109. https://doi.org/10.1152/ajpregu.00125.2022 ↩︎
    41. Papoutsis I, Hatzidouka V, Ntoupa SP. et al. “Determination of Δ9-tetrahydrocannabinol, 11-nor-carboxy-Δ9-tetrahydrocannabinol and cannabidiol in human plasma and urine after a commercial cannabidiol oil product intake.” Forensic Toxicol 2024. 42, 191–201. https://doi.org/10.1007/s11419-024-00686-0 ↩︎
    42. Andre CM, Sansom CE, Plunkett BJ, Hamiaux C, Massey L, Chan A, Caddie M, Espley RV, Perry NB. “Unique bibenzyl cannabinoids in the liverwort Radula marginata: parallels with Cannabis chemistry.” New Phytol. 2025 Jun;246(6):2666-2682. https://doi.org/10.1111/nph.20349 ↩︎
    43. Hussain, T., Espley, R.V., Gertsch, J. et al. “Demystifying the liverwort Radula marginata, a critical review on its taxonomy, genetics, cannabinoid phytochemistry and pharmacology.” Phytochem Rev 18, 953–965 (2019). https://doi.org/10.1007/s11101-019-09638-8 ↩︎