δ9 tetrahydrocannabinol

Manufactured by Merck Group

Sourced in Italy, United States

Δ9-tetrahydrocannabinol is a chemical compound found in the Cannabis sativa plant. It is the primary psychoactive component of the plant. The product is used in research and laboratory settings to study the effects and properties of this compound.

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Lab products found in correlation

Cannabidiol, by Merck Group (8 mentions) Cannabinol, by Merck Group (5 mentions) Cannabigerol, by Merck Group (4 mentions) Cannabidiolic acid, by Merck Group (4 mentions) Cannabichromene, by Merck Group (4 mentions) Methanol, by Merck Group (4 mentions) Cannabidivarin, by Merck Group (3 mentions) δ8 tetrahydrocannabinol, by Merck Group (3 mentions) Acetonitrile, by Merck Group (3 mentions) Cannabivarin, by Cayman Chemical (2 mentions) Cannabichromene, by Cayman Chemical (2 mentions) Cisplatin, by Merck Group (2 mentions) Gemcitabine, by Merck Group (2 mentions) δ9 tetrahydrocannabinolic acid, by Merck Group (2 mentions) Gallic acid, by Merck Group (2 mentions) Potassium phosphate dibasic k2hpo4 2 2 azino bis 3 ethyl benzothiazoline 6 sulfonic acid diammonium salt abts 2 2 diphenyl 1 picrylhydrazyl dpph, by Merck Group (2 mentions) Gradient grade water, by Merck Group (2 mentions) 3 trimethylsilyl propionic 2 2 3 3 d4 acid sodium salt tsp, by Eurisotop (2 mentions) Folin ciocalteu reagent, by Merck Group (2 mentions) Chloroform, by Merck Group (2 mentions)

Spelling variants of this product

Δ9-tetrahydrocannabinol (THC) (3 citations) Δ9-Tetrahydrocannabinol solution (2 citations)

11 protocols using δ9 tetrahydrocannabinol

Phytochemical Compounds in Cannabis

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Gemcitabine, cisplatin, Δ⁹-tetrahydrocannabinol, cannabidiol, orientin, quercetin, silymarin, vitexin, isovitexin, and luteolin were obtained from Millipore-Sigma (Oakville ON, CA). Cannflavin A, kaempferol, apigenin, cannabichromene, and cannabivarin were obtained from Cayman Chemical (Ann Arbour MI, USA).

Tomko A.M., Whynot E.G, & Dupré D.J. (2022). Anti-cancer properties of cannflavin A and potential synergistic effects with gemcitabine, cisplatin, and cannabinoids in bladder cancer. Journal of Cannabis Research, 4, 41.

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Cannabinoid Combination Therapy Protocol

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Gemcitabine, cisplatin, Δ⁹-tetrahydrocannabinol, and cannabidiol were obtained from Millipore-Sigma. Cannabichromene, cannabivarin, rimonabant, SR 144,528, and A-967079 were obtained from Cayman Chemical.

Whynot E.G., Tomko A.M, & Dupré D.J. (2023). Anticancer properties of cannabidiol and Δ9-tetrahydrocannabinol and synergistic effects with gemcitabine and cisplatin in bladder cancer cell lines. Journal of Cannabis Research, 5, 7.

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Comprehensive Cannabinoid Analysis Protocol

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Gradient grade water, acetonitrile, chloroform, methanol, and formic acid were purchased from Merck Life Science (Milano, Italy). Cannabinoid reference standards dissolved in methanol, namely, cannabidivarin (CBDV, 1 mg/mL), cannabigerol (CBG, 1 mg/mL), cannabidiol (CBD, 1 mg/mL), cannabidiolic acid (CBDA, 1 mg/mL), cannabinol (CBN, 1 mg/mL), (–)-Δ9-tetrahydrocannabinol ((–)-Δ9-THC, 1 mg/mL), Δ9-tetrahydrocannabinolic acid ((–)-Δ9-THCA, 1 mg/mL), (–)-Δ8-tetrahydrocannabinol ((–)-Δ8-THC, 1 mg/mL), and cannabichromene (CBC, 1 mg/mL) with purity ≥ 99%, were purchased from Merck Life Science (Milano, Italy). Deuterated water (D₂O) 99.97 atom% of deuterium and 3-(trimethylsilyl)-propionic-2,2,3,3-d₄ acid sodium salt (TSP) were purchased from Euriso-Top (Saclay, France). Magnesium oxide (MgO), potassium phosphate monobasic (KH₂PO₄), and potassium phosphate dibasic (K₂HPO₄) 2,2-azino-bis (3-ethyl-benzothiazoline-6-sulfonic acid) diammonium salt (ABTS), 2,2-diphenyl-1-picrylhydrazyl (DPPH), Folin–Ciocalteu reagent, gallic acid (GA), and sodium carbonate (Na₂CO₃) were purchased from Merck Life Science (Milano, Italy).

Spano M., Di Matteo G., Ingallina C., Sobolev A.P., Giusti A.M., Vinci G., Cammarone S., Tortora C., Lamelza L., Prencipe S.A., Gobbi L., Botta B., Marini F., Campiglia E, & Mannina L. (2022). Industrial Hemp (Cannabis sativa L.) Inflorescences as Novel Food: The Effect of Different Agronomical Practices on Chemical Profile. Foods, 11(22), 3658.

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UHPLC Analysis of Cannabinoid Standards

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All solvents used for
UHPLC analyses were HPLC grade and were purchased from Merck Life
Science (Milan, Italy) and Carlo Erba Reagents (Milan, Italy). Cannabinoid
reference standards dissolved in methanol, namely, cannabidivarin
(CBDV, 1 mg/mL), cannabidiolic acid (CBDA, 1 mg/mL), cannabigerol
(CBG, 1 mg/mL), cannabidiol (CBD, 1 mg/mL), cannabinol (CBN, 1 mg/mL),
(−)-Δ⁹-tetrahydrocannabinol [(−)-Δ⁹-THC, 1 mg/mL], (−)-Δ⁸-tetrahydrocannabinol
[(−)-Δ⁸-THC, 1 mg/mL], cannabichromene (CBC,
1 mg/mL), and (−)-Δ⁹-tetrahydrocannabinolic
acid ((−)-Δ⁹-THCA, 1 mg/mL) with a purity
of ≥99%, were purchased from Merck Life Science (Milan, Italy).
Preparative TLC plates UV 254 nm (surface 20 × 20 cm, thickness
500 μm), used for the purification of CBC, were purchased from
Merck (Darmstadt, Germany).

Calcaterra A., Cianfoni G., Tortora C., Manetto S., Grassi G., Botta B., Gasparrini F., Mazzoccanti G, & Appendino G. (2023). Natural Cannabichromene (CBC) Shows Distinct Scalemicity Grades and Enantiomeric Dominance in Cannabis sativa Strains. Journal of Natural Products, 86(4), 909-914.

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Cannabinoid Analysis by NMR and Antioxidant Assays

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Gradient grade water, acetonitrile, chloroform, methanol, and formic acid were purchased from Merck Life Science (Milano, Italy). Cannabinoid reference standards dissolved in methanol, namely, cannabidivarin (CBDV, 1 mg/mL), cannabigerol (CBG, 1 mg/mL), cannabidiol (CBD, 1 mg/mL), cannabidiolic acid (CBDA, 1 mg/mL), cannabinol (CBN, 1 mg/mL), (–)-Δ9-tetrahydrocannabinol ((–)-Δ9-THC, 1 mg/mL), Δ9-tetrahydrocannabinolic acid ((–)-Δ9-THCA, 1 mg/mL), (–)-Δ8- tetrahydrocannabinol ((–)-Δ8-THC, 1 mg/mL), and cannabichromene (CBC, 1 mg/mL) with purity ≥ 99%, were purchased from Merck Life Science (Milano, Italy). Deuterated water (D₂O) 99.97 atom% of deuterium and 3-(trimethylsilyl)-propionic-2,2,3,3-d₄ acid sodium salt (TSP) were purchased from Euriso-Top (Saclay, France). Magnesium oxide (MgO), potassium phosphate monobasic (KH₂PO₄), and potassium phosphate dibasic (K₂HPO₄) 2,2-azino-bis (3-ethyl-benzothiazoline-6-sulfonic acid) diammonium salt (ABTS), 2,2-diphenyl-1-picrylhydrazyl (DPPH), Folin-Ciocalteu reagent, gallic acid (GA), and sodium carbonate (Na₂CO₃) were purchased from Merck Life Science (Milano, Italy).

Spano M., Di Matteo G., Ingallina C., Botta B., Quaglio D., Ghirga F., Balducci S., Cammarone S., Campiglia E., Giusti A.M., Vinci G., Rapa M., Ciano S., Mannina L, & Sobolev A.P. (2021). A Multimethodological Characterization of Cannabis sativa L. Inflorescences from Seven Dioecious Cultivars Grown in Italy: The Effect of Different Harvesting Stages. Molecules, 26(10), 2912.

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Modeling Migraine-like Pain in Rodents

Cited 2 times

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Allyl isothiocyanate (AITC; Sigma-Aldrich, Inc., St. Louis, MO, USA) was mixed in mineral oil at a concentration of 10% and injected into the periosteal space in a volume of 10 µl. Microinjection of 10% AITC onto the dura has previously been shown to mimic migraine-like pain in rodents (Edelmayer et al., 2012 (link); Kandasamy et al., 2017b (link)). Δ⁹-tetrahydrocannabinol (Sigma-Aldrich, Inc., St. Louis, MO, USA) was dissolved in vehicle (1:1:18; ethanol:cremophor:saline) and injected intraperitoneally at doses of 0.1, 0.32, and 1.0 mg/kg in a volume of 1 ml/kg. The CB₁ receptor antagonist SR141716A (1.0 mg/kg) and the CB₂ receptor antagonist SR144528 (3.2 mg/kg) (Tocris Bioscience, Minneapolis, MN, USA) were dissolved in the same vehicle as THC and injected intraperitoneally in a volume of 1 ml/kg. These drugs are highly selective for their target receptor (Rinaldi-Carmona et al., 1995 (link); 1998 (link)) and the doses used are known to block the antinociceptive effects of systemically administered THC in female rats(Craft et al., 2012 (link)).

Kandasamy R., Dawson C.T., Craft R.M, & Morgan M.M. (2017). Anti-migraine effect of Δ9-tetrahydrocannabinol in the female rat. European journal of pharmacology, 818, 271-277.

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Quantification of Drugs in Biological Samples

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Cotinine (COT), trans-3-hydroxycotinine (OH-COT), cotinine-d3 and trans-3-hydroxycotinine-d3 were obtained from LGC Standards (Molsheim, France). Caffeine, ibuprofen, methadone, morphine, pseudoephedrine, codeine, cocaine, clomipramine, propranolol and Δ-9-tetrahydrocannabinol analytical reference standards presented in Methanol were obtained from Cerilliant (Sigma-Aldrich, Saint-Quentin-Fallavier, France). Potassium dihydrogen phosphate and dipotassium hydrogen phosphate were obtained from Sigma-Aldrich (St Louis, MO, USA). Methanol, hexane, isopropanol were of analytical grade and were obtained from Merck (Darmstadt, Germany). Sterile water was obtained from Fresenius (Sevres, France). Ammonia solution 25% was purchased from VWR (Fontenay-sous-Bois, France). Hydrochloric acid 0.2 m was obtained from VWR (Fontenay-sous-Bois, France). Clean Screen SPE columns 200 mg were purchased from UCT (Bristol, PA, USA). The derivatizing agent utilized was bis(trimethylsilyl)trifluoroacetamide (BSTFA) + 1% trimethylchlorosilane (TMS) (Sigma-Aldrich, Saint-Quentin-Fallavier, France).

Chiadmi F, & Schlatter J. (2014). Simultaneous determination of cotinine and trans-3-hydroxycotinine in urine by automated solid-phase extraction using gas chromatography–mass spectrometry. Biomedical Chromatography, 28(4), 453-458.

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Cannabinoid Compounds Extraction and Analysis

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The cannabinoids studied, Δ⁹-tetrahydrocannabinol (THC) and cannabidiol (CBD), were obtained from Sigma-Aldrich (Rehovot, Israel).

Gorelick J., Assa-Glazer T., Zandani G., Altberg A., Sela N., Nyska A, & Madar Z. (2022). THC and CBD affect metabolic syndrome parameters including microbiome in mice fed high fat-cholesterol diet. Journal of Cannabis Research, 4, 27.

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Terpenoid and Cannabinoid Standards Catalogue

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The following terpenoid standards were purchased from Supelco: α-pinene, camphene, β-pinene, myrcene, 3-carene, α-terpinene, p-cymene, limonene, γ-terpinene, fenchone, terpinolene, linalool, camphor, isoborneol, borneol, menthol, α-terpineol, β-citronellol, neryl acetate, geranyl acetate, α-cedrene, β-caryophyllene, α-humulene, cis-nerolidol, geranyl isobutyrate, caryophyllene oxide, β-eudesmol, α-bisabolol, and phytol. Cannabinoid standards were purchased from Sigma Aldrich (1 mg/mL): cannabidiolic acid (CBD-A), cannabigerolic acid (CBG-A), cannabigerol (CBG), cannabidiol (CBD), cannabinol (CBN), Δ-9-tetrahydrocannabinol (Δ-9-THC), Δ-8-tetrahydrocannabinol (Δ-8-THC), cannabichromene (CBC), Δ-9-tetrahydrocannabinolic acid (Δ-9-THC-A), and cannabichromenic acid (CBC-A). Acid standards were dissolved in acetonitrile, and nonacid standards were dissolved in methanol. Hexane, ammonium format, and acetonitrile were purchased from Sigma Aldrich, methanol was purchased from J. T. Baker and formic acid was purchased from Scharlau. Chemical structures of essential oils and cannabinoids are presented in Supplementary Materials [37 ,38 ,39 ].

Eržen M., Košir I.J., Ocvirk M., Kreft S, & Čerenak A. (2021). Metabolomic Analysis of Cannabinoid and Essential Oil Profiles in Different Hemp (Cannabis sativa L.) Phenotypes. Plants, 10(5), 966.

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CBD and THC Extraction Protocol

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Cannabidiol (CBD) was purchased from Tocris Cookson (Bristol, UK). The medium for tissue cultures was purchased from Gibco-BRL (San Giuliano Milanese, MI, Italy), insert and Δ9-tetrahydrocannabinol (THC) were purchased from Sigma (St. Louis, MO, USA).

Landucci E., Mazzantini C., Lana D., Giovannini M.G, & Pellegrini-Giampietro D.E. (2022). Neuronal and Astrocytic Morphological Alterations Driven by Prolonged Exposure with Δ9-Tetrahydrocannabinol but Not Cannabidiol. Toxics, 10(2), 48.

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