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Journal articles on the topic 'Tetrahydrocannabinol'

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Author: Grafiati

Published: 4 June 2021

Last updated: 31 January 2023

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1

Jairoun, Ammar Abdulrahman, Sabaa Saleh Al-Hemyari, Moyad Shahwan, Baharudin Ibrahim, Mohamed Azmi Hassali, and Sa’ed H. Zyoud. "Risk Assessment of Over-the-Counter Cannabinoid-Based Cosmetics: Legal and Regulatory Issues Governing the Safety of Cannabinoid-Based Cosmetics in the UAE." Cosmetics 8, no. 3 (June 23, 2021): 57. http://dx.doi.org/10.3390/cosmetics8030057.

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Purpose: The lack of scientific evidence of the safety and efficacy of over-the-counter topical cannabinoid-based cosmetics remains a concern. The current study attempted to assess the quality of cannabinoid-based cosmetic products available on the UAE market. In particular, the study attempted to quantify the presence of undeclared tetrahydrocannabinol, specifically delta-9-tetrahydrocannabinol (THC) and delta-9-tetrahydrocannabinolic acid (THCA), in these products. Methods: A total of 18 cannabinoid-based cosmetics were collected and analysed in this study. GC-MS analysis was used to determine the presence of total undeclared tetrahydrocannabinol. Results: The estimate for the average tetrahydrocannabinol content was 0.011% with a 95% CI (0.004−0.019). Leave-on cosmetics products are more likely to contain total tetrahydrocannabinol compared to rinse-off cosmetics (p = 0.041). Although there was no statistically significant difference in the total tetrahydrocannabinol according to cosmetic category, there was a tendency towards higher tetrahydrocannabinol content in the hand care products, baby products, and body care preparations. Conclusion: The current study reveals the need for producers of cannabinoid-based cosmetic products to issue quality certificates for each batch produced to inform users of the tested levels of tetrahydrocannabinol.

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2

Gul, Waseem, Shahbaz Gul, Suman Chandra, Hemant Lata, Elsayed Ibrahim, and Mahmoud ElSohly. "Detection and Quantification of Cannabinoids in Extracts of Cannabis sativa Roots Using LC-MS/MS." Planta Medica 84, no. 04 (January 22, 2018): 267–71. http://dx.doi.org/10.1055/s-0044-100798.

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AbstractA liquid chromatography-tandem mass spectrometry single-laboratory validation was performed for the detection and quantification of the 10 major cannabinoids of cannabis, namely, (−)-trans-Δ9-tetrahydrocannabinol, cannabidiol, cannabigerol, cannabichromene, tetrahydrocannabivarian, cannabinol, (−)-trans-Δ8-tetrahydrocannabinol, cannabidiolic acid, cannabigerolic acid, and Δ9-tetrahydrocannabinolic acid-A, in the root extract of Cannabis sativa. Acetonitrile : methanol (80 : 20, v/v) was used for extraction; d3-cannabidiol and d3- tetrahydrocannabinol were used as the internal standards. All 10 cannabinoids showed a good regression relationship with r 2 > 0.99. The validated method is simple, sensitive, and reproducible and is therefore suitable for the detection and quantification of these cannabinoids in extracts of cannabis roots. To our knowledge, this is the first report for the quantification of cannabinoids in cannabis roots.

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3

Basas-Jaumandreu, Josep, and F. Xavier C. de las Heras. "GC-MS Metabolite Profile and Identification of Unusual Homologous Cannabinoids in High Potency Cannabis sativa." Planta Medica 86, no. 05 (February 13, 2020): 338–47. http://dx.doi.org/10.1055/a-1110-1045.

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AbstractPhytochemical investigation of the lipids extracted from seeds of Cannabis sativa by GC-MS showed 43 cannabinoids, 16 of which are new. The extract is dominated by Δ9-tetrahydrocannabinolic acid (A) and its neutral derivative trans-Δ9-tetrahydrocannabinol-C5 (THC) Cis and trans-Δ9-tetrahydrocannabinol-C7 isomers with an ethyl-pentyl branched chain together with minor amounts of trans-Δ9-tetrahydrocannabinol with a methyl-pentyl C6 branched side chain were identified as new natural compounds. Four cannabichromene isomers with a C5 side chain are postulated to be derived from the double bond migration at the terminal isoprenyl unit. C7 cannabichromene together with the neutral and acidic forms of cannabinol-C7 were also detected. The mass spectrum of these homologues as trimethylsilyl (TMS) derivatives are presented, and the fragmentation patterns are discussed.

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4

Blebea, Nicoleta Mirela, Dan Rambu, Teodor Costache, and Simona Negreș. "Very Fast RP–UHPLC–PDA Method for Identification and Quantification of the Cannabinoids from Hemp Oil." Applied Sciences 11, no. 20 (October 11, 2021): 9414. http://dx.doi.org/10.3390/app11209414.

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In recent years, hemp oils have become ubiquitous in health products on the European market. As the trend continues to grow and more cannabinoids are researched for their therapeutic benefits, more academic and industrial interests are drawn to this direction. Cannabidiol, Δ9-tetrahydrocannabinol, and their acidic forms remain the most examined cannabinoids in hemp and cannabis oils, in the case of cannabidiol due to its proven health implications in numerous articles, and in the case of Δ9-tetrahydrocannabinol, due to the legislation in the European area. These oils sold on the internet contain a wide range of cannabinoids that could demonstrate their effects and benefits. As a result of these claims, we developed a robust and rapid method that can identify and quantify 10 of the most common cannabinoids found in hemp oils: cannabivarin, cannabidiolic acid, cannabigerolic acid, cannabigerol, cannabidiol, cannabinol, Δ9-tetrahydrocannabinol, Δ8-tetrahydrocannabinol, cannabichromene, and tetrahydrocannabinolic acid in less than 11 min, with reverse-phase–high-performance liquid chromatography–photodiode matrix system (RP–UHPLC–PDA) equipped with C18 column, eluting in a gradient using water and acetonitrile with formic acid as mobile phases. The quantification of 9 sample products presented in different matrixes was performed using a calibration curve obtained by analyzing standard solutions from a 10-cannabinoid-mix-certified reference standard. The developed method demonstrated the ability to identify and quantify the main cannabinoids in hemp oil and is a useful tool for pharmaceutical professionals.

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5

Skell, Jeffrey M., Michael Kahn, and Bruce M. Foxman. "Δ9-Tetrahydrocannabinolic acid A, the precursor to Δ9-tetrahydrocannabinol (THC)." Acta Crystallographica Section C Structural Chemistry 77, no. 2 (January 14, 2021): 84–89. http://dx.doi.org/10.1107/s2053229621000280.

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While Δ9-tetrahydrocannabinolic acid A (THCA-A) has been reported to be difficult to crystallize and/or amorphous, we have obtained THCA-A in a pure crystalline form by extraction of marijuana and selective fractionation with liquid CO2. THCA-A (systematic name: 1-hydroxy-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]isochromene-2-carboxylic acid, C22H30O4) crystallizes in the orthorhombic space group P212121, with Z = 8 and Z′ = 2. The two independent molecules are related by a pseudo-twofold axis centered between the two –CO2H groups, but the conformations of the two –C5H11 chains are quite different (tgt and ttg; t is trans and g is gauche). The carboxylate groups form an intermolecular R 2 2(8) hydrogen-bonded ring; the two C2O2 carboxylate planes are twisted out of the planes of the attached arene rings in opposite directions by 13.59 (8) and 18.92 (8)°, respectively, with a resultant interplanar angle of 28.89 (8)°. Each molecule also has an intramolecular S(6) hydrogen-bond motif between the ortho –OH group and the dihydropyran-ring O atom. Other conformational aspects of the two independent molecules are quite similar to those found in the previously determined structure of THCA-B. THCA-A has shown promise in a number of medical applications. Demonstration of the crystallinity and details of the crystal structure are expected to provide a standard point of departure for chemical and medical experiments.

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6

Trynda, Anna, and Anna Duszyńska. "Forensic examination of illicit cannabis plantations." Issues of Forensic Science 310 (2020): 50–57. http://dx.doi.org/10.34836/pk.2020.310.2.

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The aim of this article is to present selected aspects related to the sampling for the purposes of forensic examinations of plants from cannabis plantations suspected to be not of industrial hemp, and the methodology of plant material testing allowing to determine the total delta-9-tetrahydrocannabinol (9THC) and tetrahydrocannabinolic acid (9THCA) content. The result of the research allows to qualify the cultivation in terms of its legality using the percentage criterion of 0.2% defined in the Act on Counteracting Drug Addiction.

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7

Rymanowski, Maciej. "Konopie, przegląd zagadnień związanych z oznaczeniem sumarycznej zawartości delta-9-tetrahydrokannabinolu (Δ-9-THC) oraz kwasu delta-9-tetrahydrokannabinolowego (Δ-9-THCA-A)." Issues of Forensic Science 285 (2014): 50–67. http://dx.doi.org/10.34836/pk.2014.285.1.

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Cannabis analysis belongs to the most common types of analyses performed by forensic laboratories, owing to the spread of cannabis-originated drugs on illegal markets. Yet, this subject brings about numerous controversial analytical issues that spark heated debates among specialists in the field. The present work is a review of cannabis-related and analytical issues pertaining to the determination of the total content of delta-9-tetrahydrocannabinol (A-9-THC) and delta 9-tetrahydrocannabinolic acid (A-9-THCA-A) in herbal cannabis samples. Such analyses are currently typically performed by means of gas chromatography or to a lesser extent by liquid chromatography. In the case of gas chromatography, the total content is determined as the sum of delta-9-tetrahydrocannabinol (A-9-THC) that was originally present in the sample and delta-9- tetrahydrocannabinol (A-9-THC) formed as a result of decarboxylation of delta 9-tetrahydrocannabinolic acid (a-9-THCA-A). Liquid chromatography method is suitable for assaying both compounds in their natural form. Both methods have a number of advantages and disadvantages that require particular attention while performing analyses. One of the objectives of the present work was to carry out a comparative study of both methods of analysis, including their advantages and disadvantages. A review of the literature is presented - particularly, related to the subject addressed herein - published in recent years by police drug experts in “Problemy Kryminalistyki” quarterly. The first part contains the review of issues related to cannabis and their products - cannabinoids, cannabis subspecies, use and effect on the human body, legal issues related to cannabis, instrumental methods of assaying A-9-THC and a-9-THCA-A. The following part contains a discussion on factors influencing the assays’ results such as sampling, stability of cannabinoids in cannabis, plant age, extraction, sample humidity, derivatization, stability of standard solutions, decarboxylation of delta 9-tetrahydrocannabinolic acid (A-9-THCA-A), chromatography separation conditions and equipment. In view of the requirements of the Quality Management System that imposes the need for achieving accreditation of the test procedures, the author hopes that the present work will be helpful for analytical chemists working on developing cannabis assays and it will draw their attention to the factors that need to be considered when drafting budget and assessing total measurement uncertainty.

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8

Galettis, Peter, Michelle Williams, Rebecca Gordon, and Jennifer H. Martin. "A Simple Isocratic HPLC Method for the Quantitation of 17 Cannabinoids." Australian Journal of Chemistry 74, no. 6 (2021): 453. http://dx.doi.org/10.1071/ch20380.

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Although cannabis has been used for several thousand years, the exact composition of the cannabinoids patients are administered for different symptoms has remained largely unknown. While this absence of catalogued information may be accepted in some cultures, the use of cannabis as a human product in the registered medicines setting requires knowing its composition so that doses can be standardised between patients. This is particularly so in clinical trials that are currently under way to determine the efficacy of a product. Although the major cannabinoids of interest to prescribers are well known – tetrahydrocannabinol and cannabidiol and the corresponding acids tetrahydrocannabinolic acid and cannabidiolic acid, the cannabis plant contains many more phytocannabinoids. We have developed and validated a robust and fast (11min) isocratic HPLC method for the analysis of 17 phytocannabinoids. The method had an analytical range of 1–150μg mL−1 for tetrahydrocannabinolic acid and cannabidiolic acid, 0.5–75μg mL−1 for tetrahydrocannabinol and cannabidiol, and 0.5–20μg mL−1 for the remaining 13 cannabinoids. The method had excellent repeatability with a relative standard deviation of between 5 and 14% and a bias of between –8.6 and 6% for the 17 cannabinoids. The method was applied to the analysis of medicinal cannabis products, including both flos and oils with results matching the supplier’s certificate of analysis. This simple fast isocratic method with basic HPLC equipment can be easily transferred to any analytical laboratory interested in the identification and quantitation of cannabinoids.

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9

&NA;. "Moclobemide/amphetamines/tetrahydrocannabinol." Reactions Weekly &NA;, no. 1399 (April 2012): 23. http://dx.doi.org/10.2165/00128415-201213990-00080.

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10

Akhtar, Muhammad T., Khozirah Shaari, and Robert Verpoorte. "Biotransformation of Tetrahydrocannabinol." Phytochemistry Reviews 15, no. 5 (September 16, 2015): 921–34. http://dx.doi.org/10.1007/s11101-015-9438-9.

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11

Wianowska, D., A. L. Dawidowicz, and M. Kowalczyk. "Transformations of Tetrahydrocannabinol, Tetrahydrocannabinolic Acid and Cannabinol During Their Extraction fromCannabis SativaL." Журнал аналитической химии 70, no. 8 (2015): 805–10. http://dx.doi.org/10.7868/s0044450215080216.

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12

Shaw, Leslie M., Judith Edling-Owens, and Richard Mattes. "Ultrasensitive Measurement of Δ-9-tetrahydrocannabinol with a High Energy Dynode Detector and Electron-Capture Negative Chemical-Ionization Mass Spectrometry." Clinical Chemistry 37, no. 12 (December 1, 1991): 2062–68. http://dx.doi.org/10.1093/clinchem/37.12.2062.

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Abstract Plasma concentrations of Δ-9-tetrahydrocannabinol, the principal psychoactive cannabinoid in marijuana, decline to values substantially <1 μg/L within a few hours after a subject has smoked a marijuana cigarette. Using a single-quadrupole gas chromatograph-mass spectrometer (GC/MS) operated in the negative chemical-ionization mode and retrofitted with a High Energy Dynode detector system, we measured Δ-9-tetrahydrocannabinol and a primary metabolite, 11-nor-Δ-9-tetrahydrocannabinol-9-COOH. Using a trifluoroacetic anhydride derivatization procedure and the High Energy Dynode detector system, we improved by 6.25-fold the limit of detection for Δ-9-tetrahydrocannabinol in plasma over that obtained with the same GC/MS system without the new detector (80 vs 500 ng/L). The new detector system will thus permit further investigation of the post-distribution pharmacokinetics of Δ-9-tetrahydrocannabinol and detection of Δ-9-tetrahydrocannabinol in plasma for a longer time after ingestion of the drug in forensic cases. The High Energy Dynode detector system should be applicable to a wide variety of other GC/MS analyses that require significantly improved sensitivity.

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13

Rudroff, Thorsten, Craig D. Workman, Phillip E. Gander, Justin R. Deters, and Laura L. Boles Ponto. "Differences in Inhibitory Control and Resting Brain Metabolism between Older Chronic Users of Tetrahydrocannabinol (THC) or Cannabidiol (CBD)—A Pilot Study." Brain Sciences 12, no. 7 (June 23, 2022): 819. http://dx.doi.org/10.3390/brainsci12070819.

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Δ9-Tetrahydrocannabinol is the main psychoactive component of cannabis and cannabidiol is purportedly responsible for many of the medicinal benefits. The effects of Δ9-tetrahydrocannabinol and cannabidiol in younger populations have been well studied; however, motor function, cognitive function, and cerebral glucose metabolism in older adults have not been extensively researched. The purpose of this study was to assess differences in cognitive function, motor function, and cerebral glucose metabolism (assessed via [18F]-fluorodeoxyglucose positron emission tomography) in older adults chronically using Δ9-tetrahydrocannabinol, cannabidiol, and non-using controls. Eight Δ9-tetrahydrocannabinol users (59.3 ± 5.7 years), five cannabidiol users (54.6 ± 2.1 years), and 16 non-users (58.2 ± 16.9 years) participated. Subjects underwent resting scans and performed cognitive testing (reaction time, Flanker Inhibitory Control and Attention Test), motor testing (hand/arm function, gait), and balance testing. Δ9-tetrahydrocannabinol users performed worse than both cannabidiol users and non-users on the Flanker Test but were similar on all other cognitive and motor tasks. Δ9-tetrahydrocannabinol users also had lower global metabolism and relative hypermetabolism in the bilateral amygdala, cerebellum, and brainstem. Chronic use of Δ9-tetrahydrocannabinol in older adults might negatively influence inhibitory control and alter brain activity. Future longitudinal studies with larger sample sizes investigating multiple Δ9-tetrahydrocannabinol:cannabidiol ratios on functional outcomes and cerebral glucose metabolism in older adults are necessary.

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Polyakova, A. S. "Biochemical analysis and assessment of modern monogamous varieties of hemp Cannabis sativa L. by the content of cannabinoid substances." Faktori eksperimental'noi evolucii organizmiv 23 (September 9, 2018): 321–28. http://dx.doi.org/10.7124/feeo.v23.1035.

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Aim. Defining the peculiarities of forming the cannabinoid substances in modern monogamous varieties of hemp is of both theoretical and practical importance. Methods. Modern monogamous varieties of hemp bred in Hlukhiv, Zolotonosha and specimens receive from France; were used for the chromatographically analysis of «damp» and dried in the shadow plant samples was conducted by the method of thin layer chromatography (TLC). Results. It was founding, that in the initial phase of growth and development the Ukrainian hemp varieties with the practical absence of neutral compounds and the French varieties with the sufficient content of these substances formed only natural acids. During the generative phase of growth and development, the varieties from France formed not only natural acids but also neutral compounds. The Ukrainian varieties demonstrated only insufficient increase of natural acids. Conclusions. In the initial phase of growth and development, the investigated hemp varieties containing both large and insignificant amount of cannabinoid substances formed only natural acids. Separate plants demonstrated the decrease of natural acids up to their total absence, which proves their biological interconnections and possible forming cannabidiol, tetrahydrocannabinol and сannabinol by way of fermentative decarboxylation the respective acids. Keywords: Cannabinol (CBN), cannabidiol (CBD), tetrahydrocannabinol (THC), cannabidiolic acid (CBDA), tetrahydrocannabinolic acid (THCA).

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15

Watanabe, Kazuhito, Midori Matsuda, Yuji Tateoka, Toshiyuki Kimura, Tamihide Matsunaga, Hiroyuki Tanaka, Yukihiro Shoyama, and Ikuo Yamamoto. "Cross-Reactivity of Various Tetrahydrocannabinol Metabolites with a Monoclonal Antibody against Tetrahydrocannabinolic Acid." JOURNAL OF HEALTH SCIENCE 46, no. 4 (2000): 310–13. http://dx.doi.org/10.1248/jhs.46.310.

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16

Moldzio, Rudolf, Alexander Unterberger, Christopher Krewenka, Barbara Kranner, and Khaled Radad. "Neuroprotective Effects of Delta-9-Tetrahydrocannabinol against FeSO4- and H2O2-Induced Cell Damage on Dopaminergic Neurons in Primary Mesencephalic Cell Culture." Planta Medica International Open 8, no. 03 (August 11, 2021): e88-e95. http://dx.doi.org/10.1055/a-1516-4182.

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AbstractDelta-9-Tetrahydrocannabinol and other phytocannabinoids have been previously demonstrated to possess neuroprotective effects in murine mesencephalic cell culture models of Parkinson’s disease, in which increased levels of superoxide radicals led to the loss of dopaminergic neurons. In these models, delta-9-tetrahydrocannabinol did not scavenge these radicals but displayed antioxidative capacity by increasing glutathione levels. Based on these findings, in the present study, we investigated whether the neuroprotective effect of delta-9-tetrahydrocannabinol can also be detected in FeSO4- and H2O2-stressed cells. Mesencephalic cultures were concomitantly treated with FeSO4 (350 μM) or H2O2 (150 μM) and delta-9-tetrahydrocannabinol (0.01, 0.1, 1, 10 μM) on the 12th days in vitro for 48 h. On the 14th DIV, dopaminergic neurons were stained immunocytochemically by tyrosine hydroxylase, and fluorescently using crystal violet, Hoechst 33342, and JC-1. FeSO4 and H2O2 significantly reduced the number of dopaminergic neurons by 33 and 36%, respectively, and adversely affected the morphology of surviving neurons. Moreover, FeSO4, but not H2O2, significantly decreased the fluorescence intensity of crystal violet and Hoechst 33342, and reduced the red/green ratio of JC-1. Co-treatment with delta-9-tetrahydrocannabinol at the concentrations 0.01 and 0.1 μM significantly rescued dopaminergic neurons in FeSO4 and H2O2-treated cultures by 16 and 30%, respectively. delta-9-Tetrahydrocannabinol treatment also led to a higher fluorescence intensity of crystal violet and Hoechst 33342, and increased the red/green fluorescence ratio of JC-1 when concomitantly administered with FeSO4 but not H2O2. To conclude, delta-9-tetrahydrocannabinol rescues dopaminergic neurons against FeSO4- and H2O2-induced neurotoxicity. Using fluorescence dyes, this effect seems to be mediated partially by restoring mitochondrial integrity and decreasing cell death, particularly in FeSO4-treated cultures.

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17

Boggs, Douglas L., Jose A. Cortes-Briones, Toral Surti, Christina Luddy, Mohini Ranganathan, John D. Cahill, Andrew R. Sewell, Deepak C. D’Souza, and Patrick D. Skosnik. "The dose-dependent psychomotor effects of intravenous delta-9-tetrahydrocannabinol (Δ9-THC) in humans." Journal of Psychopharmacology 32, no. 12 (September 26, 2018): 1308–18. http://dx.doi.org/10.1177/0269881118799953.

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Background: Binding studies have demonstrated that levels of the cannabinoid receptor type-1 are highest in the basal ganglia and cerebellum, two areas critical for motor control. However, no studies have systematically examined the dose-related effects of intravenous delta-9-tetrahydrocannabinol, the primary cannabinoid receptor type-1 partial agonist in cannabis, on broad domains of psychomotor function in humans. Aims: Therefore, three domains of psychomotor function were assessed in former cannabis users (cannabis abstinent for a minimum of three months; n=23) in a three test-day, within-subject, double-blind, randomized, cross-over, and counterbalanced study during which they received intravenous delta-9-tetrahydrocannabinol (placebo, 0.015 mg/kg, and 0.03 mg/kg). Methods: Gross motor function was assessed via the Cambridge Neuropsychological Test Automated Battery Motor Screening Task, fine motor control via the Lafayette Instrument Grooved Pegboard task, and motor timing via a Paced Finger-Tapping Task. In addition, the Cambridge Neuropsychological Test Automated Battery Rapid Visual Processing Task was utilized to determine whether delta-9-tetrahydrocannabinol-induced motor deficits were confounded by disruptions in sustained attention. Results/outcomes: Delta-9-tetrahydrocannabinol resulted in robust dose-dependent deficits in fine motor control (Grooved Pegboard Task) and motor timing (Paced Finger-Tapping Task), while gross motor performance (Motor Screening Task) and sustained attention (Rapid Visual Processing Task) were unimpaired. Interestingly, despite the observed dose-dependent increases in motor impairment and blood levels of delta-9-tetrahydrocannabinol, subjects reported similar levels of intoxication in the two drug conditions. Conclusions/interpretation: These data suggest that while several domains of motor function are disrupted by delta-9-tetrahydrocannabinol, subjective feelings of intoxication are dissociable from cannabinoid-induced psychomotor effects. Results are discussed in terms of the potential neural mechanisms of delta-9-tetrahydrocannabinol in motor structures.

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18

Pabon, Elisa, and Harriet de Wit. "Developing a phone-based measure of impairment after acute oral ∆9-tetrahydrocannabinol." Journal of Psychopharmacology 33, no. 9 (August 13, 2019): 1160–69. http://dx.doi.org/10.1177/0269881119862533.

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Background: Acute consumption of cannabis or its primary psychoactive ingredient ∆9-tetrahydrocannabinol has been shown to impair memory, reaction time, time perception, and attention. However, it is difficult to measure these impairments in a brief test that can be used in a non-laboratory setting. Aims: We aim to develop and validate a prototype for a mobile phone application to measure ∆9-tetrahydrocannabinol-induced cognitive impairment. Methods: We conducted two double-blind, within-subjects studies examining impairments after oral doses of ∆9-tetrahydrocannabinol (0, 7.5, 15 mg) using both standardized computer-based tasks and our novel phone-based tasks. The tasks measured cognitive speed, reaction time, fine motor ability, and working memory and, in the second study, time perception. Study 1 ( n=24) provided initial data, and Study 2 ( n=24) was designed to refine the measures. In both studies, healthy non-daily cannabis users participated in three four-hour experimental sessions in which they received capsules containing ∆9-tetrahydrocannabinol (7.5, 15 mg) or placebo. Subjective and cardiovascular measures were obtained at regular intervals, and at the time of peak drug effect subjects completed both standardized, computer-based and brief, phone-based tasks. Results: ∆9-Tetrahydrocannabinol-induced impairment was detected on most of the computer tasks, but was not evident on most of the phone tasks. Conclusions: The phone tasks were brief, to facilitate use in a non-laboratory setting, but it is likely that this made them less sensitive to the impairing effects of ∆9-tetrahydrocannabinol. These findings confirm that ∆9-tetrahydrocannabinol impairs performance on several tasks at two recreationally relevant doses, but raises question about the feasibility of designing a phone application as a sensitive field sobriety test for cannabis.

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Fantegrossi, William E., Keith R. McCain, Jeffery H. Moran, and Robert S. Hoffman. "Not simply synthetic tetrahydrocannabinol." Journal of Pediatrics 163, no. 6 (December 2013): 1797–98. http://dx.doi.org/10.1016/j.jpeds.2013.09.017.

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20

Meyer, Logan, and Sathyaprasad Burjonrappa. "Tetrahydrocannabinol (THC) cartridge ingestion." Journal of Pediatric Surgery Case Reports 54 (March 2020): 101390. http://dx.doi.org/10.1016/j.epsc.2020.101390.

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21

Touitou, Elka, Boris Fabin, Sanda Dany, and Shlomo Almog. "Transdermal delivery of tetrahydrocannabinol." International Journal of Pharmaceutics 43, no. 1-2 (April 1988): 9–15. http://dx.doi.org/10.1016/0378-5173(88)90052-x.

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22

Lam, Y. W. Francis. "Macrolide antibiotics and tetrahydrocannabinol." Brown University Psychopharmacology Update 28, no. 9 (August 14, 2017): 2–3. http://dx.doi.org/10.1002/pu.30257.

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23

Bindesri, Shruti D., Ricardo Jebailey, Najwan Albarghouthi, Cory C. Pye, and Christa L. Brosseau. "Spectroelectrochemical and computational studies of tetrahydrocannabinol (THC) and carboxy-tetrahydrocannabinol (THC-COOH)." Analyst 145, no. 5 (2020): 1849–57. http://dx.doi.org/10.1039/c9an02173f.

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Electrochemical SERS allows for the rapid detection of both THC and THC-COOH in bodily fluid matrices without interferences from matrix species, paving the way to a point-of-need tool for cannabinoid detection.

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Gul, Waseem, Shahbaz W. Gul, Mohamed M. Radwan, Amira S. Wanas, Zlatko Mehmedic, Ikhlas I. Khan, Maged H. M. Sharaf, and Mahmoud A. ElSohly. "Determination of 11 Cannabinoids in Biomass and Extracts of Different Varieties of Cannabis Using High-Performance Liquid Chromatography." Journal of AOAC INTERNATIONAL 98, no. 6 (November 1, 2015): 1523–28. http://dx.doi.org/10.5740/jaoacint.15-095.

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Abstract An HPLC single-laboratory validation was performed for the detection and quantification of the 11 major cannabinoids in most cannabis varieties, namely, cannabidiolic acid (CBDA), cannabigerolic acid (CBGA), cannabigerol (CBG), cannabidiol (CBD), tetrahydrocannabivarin (THCV), cannabinol (CBN), Δ9-trans-tetrahydrocannabinol (Δ9-THC), Δ8- trans-tetrahydrocannabinol (Δ8-THC), cannabicyclol (CBL), cannabichromene (CBC), and Δ9-tetrahydrocannabinolic acid-A (THCAA). The analysis was carried out on the biomass and extracts of these varieties. Methanol–chloroform (9:1, v/v) was used for extraction, 4-androstene-3,17-dione was used as the internal standard, and separation was achieved in 22.2 min on a C18 column using a two- step gradient elution. The method was validated for the 11 cannabinoids. The concentration-response relationship of the method indicated a linear relationship between the concentration and peak area with r2 values of >0.99 for all 11 cannabinoids. Method accuracy was determined through a spike study, and recovery ranged from 89.7 to 105.5% with an RSD of 0.19 to 6.32% for CBDA, CBD, THCV, CBN, Δ9-THC, CBL, CBC, and THCAA; recovery was 84.7, 84.2, and 67.7% for the minor constituents, CBGA, CBG, and Δ8-THC, respectively, with an RSD of 2.58 to 4.96%. The validated method is simple, sensitive, and reproducible and is therefore suitable for the detection and quantification of these cannabinoids in different types of cannabis plant materials.

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Wang, Yan-Hong, Bharathi Avula, Mahmoud ElSohly, Mohamed Radwan, Mei Wang, Amira Wanas, Zlatko Mehmedic, and Ikhlas Khan. "Quantitative Determination of Δ9-THC, CBG, CBD, Their Acid Precursors and Five Other Neutral Cannabinoids by UHPLC-UV-MS." Planta Medica 84, no. 04 (December 20, 2017): 260–66. http://dx.doi.org/10.1055/s-0043-124873.

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AbstractCannabinoids are a group of terpenophenolic compounds in the medicinal plant Cannabis sativa (Cannabaceae family). Cannabigerolic acid, Δ9-tetrahydrocannabinolic acid A, cannabidiolic acid, Δ9-tetrahydrocannabinol, cannabigerol, cannabidiol, cannabichromene, and tetrahydrocannabivarin are major metabolites in the classification of different strains of C. sativa. Degradation or artifact cannabinoids cannabinol, cannabicyclol, and Δ8-tetrahydrocannabinol are formed under the influence of heat and light during processing and storage of the plant sample. An ultrahigh-performance liquid chromatographic method coupled with photodiode array and single quadruple mass spectrometry detectors was developed and validated for quantitative determination of 11 cannabinoids in different C. sativa samples. Compounds 1 – 11 were baseline separated with an acetonitrile (with 0.05% formic acid) and water (with 0.05% formic acid) gradient at a flow rate of 0.25 mL/min on a Waters Cortec UPLC C18 column (100 mm × 2.1 mm I. D., 1.6 µm). The limits of detection and limits of quantitation of the 11 cannabinoids were below 0.2 and 0.5 µg/mL, respectively. The relative standard deviation for the precision test was below 2.4%. A mixture of acetonitrile and methanol (80 : 20, v/v) was proven to be the best solvent system for the sample preparation. The recovery of all analytes was in the range of 97 – 105%. A total of 32 Cannabis samples including hashish, leaves, and flower buds were analyzed.

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Brown, N. K., and D. J. Harvey. "In vivo metabolism of the methyl homologues of delta-8-tetrahydrocannabinol, delta-9-tetrahydrocannabinol andabn-delta-8-tetrahydrocannabinol in the mouse." Biological Mass Spectrometry 15, no. 7 (April 1, 1988): 389–98. http://dx.doi.org/10.1002/bms.1200150706.

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Wianowska, D., A. L. Dawidowicz, and M. Kowalczyk. "Transformations of Tetrahydrocannabinol, tetrahydrocannabinolic acid and cannabinol during their extraction from Cannabis sativa L." Journal of Analytical Chemistry 70, no. 8 (July 25, 2015): 920–25. http://dx.doi.org/10.1134/s1061934815080183.

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Moore, Christine, Sumandeep Rana, and Cynthia Coulter. "Simultaneous identification of 2-carboxy-tetrahydrocannabinol, tetrahydrocannabinol, cannabinol and cannabidiol in oral fluid." Journal of Chromatography B 852, no. 1-2 (June 2007): 459–64. http://dx.doi.org/10.1016/j.jchromb.2007.02.016.

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Bala, Asis, Sunelle Rademan, Khorommbi Ndivhuwo Kevin, Vinesh Maharaj, and Motlalepula G. Matsabisa. "UPLC-MS Analysis of Cannabis sativa Using Tetrahydrocannabinol (THC), Cannabidiol (CBD), and Tetrahydrocannabinolic Acid (THCA) as Marker Compounds: Inhibition of Breast Cancer Cell Survival and Progression." Natural Product Communications 14, no. 8 (August 2019): 1934578X1987290. http://dx.doi.org/10.1177/1934578x19872907.

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Cannabis sativa L. extracts were characterized by ultra performance liquid chromatography-mass spectrometry (UPLC-MS) using tetrahydrocannabinol (THC), cannabidiol (CBD), and tetrahydrocannabinolic acid (THCA) as marker compounds. The inhibitory effects of various extracts were determined on the survival and progression of highly metastatic breast cancer cells. A higher amount of CBD was found in the dichloromethane extract, and this was found to be effective in inhibiting breast cancer cell growth in vitro and in angiogenesis. Collectively, it may be concluded that CBD, THC, and THCA in the African variety of C. sativa can be used as marker compounds in UPLC-MS analysis. The ability of the plant to inhibit breast cancer cell survival and progression may affirm the traditional use of the drug as an anticancer agent.

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Ibrahim, Elsayed, Waseem Gul, Shahbaz Gul, Brandon Stamper, Ghada Hadad, Randa Abdel Salam, Amany Ibrahim, et al. "Determination of Acid and Neutral Cannabinoids in Extracts of Different Strains of Cannabis sativa Using GC-FID." Planta Medica 84, no. 04 (December 13, 2017): 250–59. http://dx.doi.org/10.1055/s-0043-124088.

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AbstractCannabis (Cannabis sativa L.) is an annual herbaceous plant that belongs to the family Cannabaceae. Trans-Δ9-tetrahydrocannabinol (Δ9-THC) and cannabidiol (CBD) are the two major phytocannabinoids accounting for over 40% of the cannabis plant extracts, depending on the variety. At the University of Mississippi, different strains of C. sativa, with different concentration ratios of CBD and Δ9-THC, have been tissue cultured via micropropagation and cultivated. A GC-FID method has been developed and validated for the qualitative and quantitative analysis of acid and neutral cannabinoids in C. sativa extracts. The method involves trimethyl silyl derivatization of the extracts. These cannabinoids include tetrahydrocannabivarian, CBD, cannabichromene, trans-Δ8-tetrahydrocannabinol, Δ9-THC, cannabigerol, cannabinol, cannabidiolic acid, cannabigerolic acid, and Δ9-tetrahydrocannabinolic acid-A. The concentration-response relationship of the method indicated a linear relationship between the concentration and peak area ratio with R2 > 0.999 for all 10 cannabinoids. The precision and accuracy of the method were found to be ≤ 15% and ± 5%, respectively. The limit of detection range was 0.11 – 0.19 µg/mL, and the limit of quantitation was 0.34 – 0.56 µg/mL for all 10 cannabinoids. The developed method is simple, sensitive, reproducible, and suitable for the detection and quantitation of acidic and neutral cannabinoids in different extracts of cannabis varieties. The method was applied to the analysis of these cannabinoids in different parts of the micropropagated cannabis plants (buds, leaves, roots, and stems).

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Goodwin, Robert S., Richard A. Gustafson, Allan Barnes, Wesenyalsh Nebro, Eric T. Moolchan, and Marilyn A. Huestis. "??9-Tetrahydrocannabinol, 11-Hydroxy-??9-Tetrahydrocannabinol and 11-Nor-9-Carboxy-??9-Tetrahydrocannabinol in Human Plasma After Controlled Oral Administration of Cannabinoids." Therapeutic Drug Monitoring 28, no. 4 (August 2006): 545–51. http://dx.doi.org/10.1097/00007691-200608000-00010.

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Ray, Colleen L., Madison P. Bylo, Jonny Pescaglia, James A. Gawenis, and C. Michael Greenlief. "Delta-8 Tetrahydrocannabinol Product Impurities." Molecules 27, no. 20 (October 15, 2022): 6924. http://dx.doi.org/10.3390/molecules27206924.

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Due to increased concerns regarding unidentified impurities in delta-8 tetrahydrocannabinol (Δ-8 THC) consumer products, a study using Nuclear Magnetic Resonance (NMR), high performance liquid chromatography (HPLC), and mass spectrometry (MS) was conducted to further investigate these products. Ten Δ-8 THC products, including distillates and ready to use vaporizer cartridges, were analyzed. The results yield findings that the tested products contain several impurities in concentrations far beyond what is declared on certificates of analysis for these products. As Δ-8 THC is a synthetic product synthesized from cannabidiol (CBD), there are valid concerns regarding the presence of impurities in these products with unknown effects on the human body. Compounding this problem is apparent inadequate testing of these products by producers and independent laboratories.

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Trost, B., and K. Dogra. "Synthesis of (-)-Δ9-trans-Tetrahydrocannabinol." Synfacts 2007, no. 7 (July 2007): 0667. http://dx.doi.org/10.1055/s-2007-968596.

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Chan, Guy Chiu-Kai, Thomas R. Hinds, Soren Impey, and Daniel R. Storm. "Hippocampal Neurotoxicity of Δ9-Tetrahydrocannabinol." Journal of Neuroscience 18, no. 14 (July 15, 1998): 5322–32. http://dx.doi.org/10.1523/jneurosci.18-14-05322.1998.

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Elsner, F., L. Radbruch, and R. Sabatowski. "Tetrahydrocannabinol zur Therapie chronischer Schmerzen." Der Schmerz 15, no. 3 (June 5, 2001): 200–204. http://dx.doi.org/10.1007/s004820170024.

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Temple, Leslie Mendoza, and Jerrold B. Leikin. "Tetrahydrocannabinol – friend or foe? – Debate." Clinical Toxicology 58, no. 2 (May 7, 2019): 75–81. http://dx.doi.org/10.1080/15563650.2019.1610567.

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Lile, Joshua A., Thomas H. Kelly, David J. Pinsky, and Lon R. Hays. "Substitution profile of Δ9-tetrahydrocannabinol, triazolam, hydromorphone, and methylphenidate in humans discriminating Δ9-tetrahydrocannabinol." Psychopharmacology 203, no. 2 (November 19, 2008): 241–50. http://dx.doi.org/10.1007/s00213-008-1393-3.

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38

Lewis, Mark, Ethan Russo, and Kevin Smith. "Pharmacological Foundations of Cannabis Chemovars." Planta Medica 84, no. 04 (November 21, 2017): 225–33. http://dx.doi.org/10.1055/s-0043-122240.

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AbstractAn advanced Mendelian Cannabis breeding program has been developed utilizing chemical markers to maximize the yield of phytocannabinoids and terpenoids with the aim to improve therapeutic efficacy and safety. Cannabis is often divided into several categories based on cannabinoid content. Type I, Δ 9-tetrahydrocannabinol-predominant, is the prevalent offering in both medical and recreational marketplaces. In recent years, the therapeutic benefits of cannabidiol have been better recognized, leading to the promotion of additional chemovars: Type II, Cannabis that contains both Δ 9-tetrahydrocannabinol and cannabidiol, and cannabidiol-predominant Type III Cannabis. While high-Δ 9-tetrahydrocannabinol and high-myrcene chemovars dominate markets, these may not be optimal for patients who require distinct chemical profiles to achieve symptomatic relief. Type II Cannabis chemovars that display cannabidiol- and terpenoid-rich profiles have the potential to improve both efficacy and minimize adverse events associated with Δ 9-tetrahydrocannabinol exposure. Cannabis samples were analyzed for cannabinoid and terpenoid content, and analytical results are presented via PhytoFacts, a patent-pending method of graphically displaying phytocannabinoid and terpenoid content, as well as scent, taste, and subjective therapeutic effect data. Examples from the breeding program are highlighted and include Type I, II, and III Cannabis chemovars, those highly potent in terpenoids in general, or single components, for example, limonene, pinene, terpinolene, and linalool. Additionally, it is demonstrated how Type I – III chemovars have been developed with conserved terpenoid proportions. Specific chemovars may produce enhanced analgesia, anti-inflammatory, anticonvulsant, antidepressant, and anti-anxiety effects, while simultaneously reducing sequelae of Δ 9-tetrahydrocannabinol such as panic, toxic psychosis, and short-term memory impairment.

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Soltan, Keyvan, and Behnoush Dadkhah. "Studies of the Major Gene Expression and Related Metabolites in Cannabinoids Biosynthesis Pathway Influenced by Ascorbic Acid." Planta Medica International Open 9, no. 01 (May 30, 2022): e116-e122. http://dx.doi.org/10.1055/a-1809-7862.

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Abstract Cannabis sativa L. is an annual dioecious plant that belongs to the Cannabaceae family and is essential for different pharmaceutical and nutritional properties. The most important and prevalent cannabinoids in cannabis are cannabidiol and delta-9-tetrahydrocannabinol. The application of elicitors is an effective method to improve secondary metabolite production, leading to a whole spectrum of molecular, genetic, and physiological modifications. Therefore, the expression changes of four key genes (THCAS, CBDAS, PT, and OLS) of the cannabinoids pathway along with the delta-9-tetrahydrocannabinol and cannabidiol metabolites fluctuation were surveyed following the application of ascorbic acid as an elicitor. Cannabis was sprayed immediately before flowering with ascorbic acid. Treated and untreated (control) plants were sampled in different time courses for real-time PCR and HPLC experiments. Results showed significant increases in THCAS, CBDAS, PT, and OLS expression after ascorbic acid treatments. The results of metabolite quantification also indicated that secondary metabolites, especially delta-9-tetrahydrocannabinol and cannabidiol, increased after the ascorbic acid application. This study contributes to the growing body of knowledge of the functions of key genes in the cannabinoids pathway to the engineering of cannabis for improving the production of delta-9-tetrahydrocannabinol and cannabidiol metabolites in this plant.

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Pertwee, Roger G., Kevin Nash, and Paul Trayhurn. "Evidence that the hypothermic response of mice to Δ9-tetrahydrocannabinol is not mediated by changes in thermogenesis in brown adipose tissue." Canadian Journal of Physiology and Pharmacology 69, no. 6 (June 1, 1991): 767–70. http://dx.doi.org/10.1139/y91-114.

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Δ9-Tetrahydrocannabinol (20 mg/kg i.p.) and propranolol (20 and 50 mg/kg i.p.) produced marked falls in the rectal temperatures of mice kept at an ambient temperature of 22 °C. Propranolol (50 mg/kg i.p.) also decreased the thermogenic activity of brown fat, as measured by a decrease in the level of [3H]GDP binding to mitochondria obtained from mouse interscapular brown adipose tissue. In contrast, Δ9-tetrahydrocannabinol (20 mg/kg i.p.) did not affect mitochondrial GDP binding even though the dose used was one shown previously to depress heat production. GDP binding was also unaffected by this cannabinoid in brown adipose tissue taken from mice that had been kept at 13 °C instead of 22 °C. In mice kept at 34 °C, isoprenaline (0.25 and 1.0 mg/kg s.c.) induced a marked rise in rectal temperature and increased the level of GDP binding to brown fat mitochondria. Propranolol (50 mg/kg i.p.) prevented the hyperthermic response to isoprenaline, the mice becoming hypothermic instead. Δ9-Tetrahydrocannabinol (20 mg/kg i.p.) had no effect on isoprenaline-induced hyperthermia. We conclude from these data that there is no significant involvement of brown adipose tissue in the hypothermic response of mice to Δ9-tetrahydrocannabinol.Key words: Δ9-tetrahydrocannabinol, body temperature, brown adipose tissue, GDP binding, thermogenesis.

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Soraya, hiva, Ruohollah Seddigh, Fatemeh Hadi, and Mohammad Faramarzi. "Chemical cannabis; The New Trend of addiction in Iran." Iranian Journal of Psychiatry and Clinical Psychology 28, no. 1 (April 20, 2022): 10. http://dx.doi.org/10.32598/ijpcp.28.1.4010.1.

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Synthetic cannabinoids (SC) are a heterogeneous group of substances with a high affinity for cannabinoid receptors. Unlike Δ9-tetrahydrocannabinol (THC), synthetic cannabinoids are incredibly potent, highly productive, have more affinity for the Cannabinoid receptor type 1 (CB1), and Cannabinoid receptor type 2 (CB2), and are designed to accelerate the effects of tetrahydrocannabinol. Also, there is experimental evidence that SCs acts on non-cannabinoid receptors, such as the 5-HT2B receptor or dopaminergic receptors. (1, 2).

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Hassenberg, Christoph, Florian Clausen, Grete Hoffmann, Armido Studer, and Jennifer Schürenkamp. "Investigation of phase II metabolism of 11-hydroxy-Δ-9-tetrahydrocannabinol and metabolite verification by chemical synthesis of 11-hydroxy-Δ-9-tetrahydrocannabinol-glucuronide." International Journal of Legal Medicine 134, no. 6 (August 17, 2020): 2105–19. http://dx.doi.org/10.1007/s00414-020-02387-w.

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Abstract (−)-Δ-9-tetrahydrocannabinol ((−)-Δ-9-THC) is the main psychoactive constituent in cannabis. During phase I metabolism, it is metabolized to (−)-11-hydroxy-Δ-9-tetrahydrocannabinol ((−)-11-OH-Δ-9-THC), which is psychoactive, and to (−)-11-nor-9-carboxy-Δ-9-tetrahydrocannabinol ((−)-Δ-9-THC-COOH), which is psychoinactive. It is glucuronidated during phase II metabolism. The biotransformation of (−)-Δ-9-tetrahydrocannabinol-glucuronide ((−)-Δ-9-THC-Glc) and (−)-11-nor-9-carboxy-Δ-9-tetrahydrocannabinol-glucuronide ((−)-Δ-9-THC-COOH-Glc) is well understood, which is mainly due to the availability of commercial reference standards. Since such a standardized reference is not yet available for (−)-11-hydroxy-Δ-9-tetrahydrocannabinol-glucuronide ((−)-11-OH-Δ-9-THC-Glc), its biotransformation is harder to study and the nature of the glucuronide bonding—alcoholic and/or phenolic—remains unclear. Consequently, the aim of this study was to investigate the biotransformation of (−)-11-OH-Δ-9-THC-Glc in vitro as well as in vivo and to identify the glucuronide by chemically synthesis of a reference standard. For in vitro analysis, pooled human S9 liver fraction was incubated with (−)-Δ-9-THC. Resulting metabolites were detected by high-performance liquid chromatography system coupled to a high-resolution mass spectrometer (HPLC-HRMS) with heated electrospray ionization (HESI) in positive and negative full scan mode. Five different chromatographic peaks of OH-Δ-9-THC-Glc have been detected in HESI positive and negative mode, respectively. The experiment set up according to Wen et al. indicates the two main metabolites being an alcoholic and a phenolic glucuronide metabolite. In vivo analysis of urine (n = 10) and serum (n = 10) samples from cannabis users confirmed these two main metabolites. Thus, OH-Δ-9-THC is glucuronidated at either the phenolic or the alcoholic hydroxy group. A double glucuronidation was not observed. The alcoholic (−)-11-OH-Δ-9-THC-Glc was successfully chemically synthesized and identified the main alcoholic glucuronide in vitro and in vivo. (−)-11-OH-Δ-9-THC-Glc is the first reference standard for direct identification and quantification. This enables future research to answer the question whether phenolic or alcoholic glucuronidation forms the predominant way of metabolism.

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Qi, Longwu, Noboru Yamamoto, Michael M. Meijler, Laurence J. Altobell, George F. Koob, Peter Wirsching, and Kim D. Janda. "Δ9-Tetrahydrocannabinol Immunochemical Studies: Haptens, Monoclonal Antibodies, and a Convenient Synthesis of Radiolabeled Δ9-Tetrahydrocannabinol." Journal of Medicinal Chemistry 48, no. 23 (November 2005): 7389–99. http://dx.doi.org/10.1021/jm050442r.

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44

Gustafson, R. A., I. Kim, P. R. Stout, K. L. Klette, M. P. George, E. T. Moolchan, B. Levine, and M. A. Huestis. "Urinary Pharmacokinetics of 11-Nor-9-carboxy- 9-tetrahydrocannabinol after Controlled Oral 9-Tetrahydrocannabinol Administration." Journal of Analytical Toxicology 28, no. 3 (April 1, 2004): 160–67. http://dx.doi.org/10.1093/jat/28.3.160.

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45

da Silva, George E., Gina S. Morato, and Reinaldo N. Takahashi. "Rapid tolerance to Δ9-tetrahydrocannabinol and cross-tolerance between ethanol and Δ9-tetrahydrocannabinol in mice." European Journal of Pharmacology 431, no. 2 (November 2001): 201–7. http://dx.doi.org/10.1016/s0014-2999(01)01449-2.

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46

Wiley, Jenny L., Rita L. Barrett, Darrell T. Britt, Robert L. Balster, and Billy R. Martin. "Discriminative stimulus effects of Δ9-tetrahydrocannabinol and Δ9–11-tetrahydrocannabinol in rats and rhesus monkeys." Neuropharmacology 32, no. 4 (April 1993): 359–65. http://dx.doi.org/10.1016/0028-3908(93)90157-x.

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47

Takeda, Shuso, Rongrong Jiang, Hironori Aramaki, Masumi Imoto, Akihisa Toda, Reiko Eyanagi, Toshiaki Amamoto, Ikuo Yamamoto, and Kazuhito Watanabe. "Δ9-Tetrahydrocannabinol and Its Major Metabolite Δ9-Tetrahydrocannabinol-11-oic Acid as 15-Lipoxygenase Inhibitors." Journal of Pharmaceutical Sciences 100, no. 3 (March 2011): 1206–11. http://dx.doi.org/10.1002/jps.22354.

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48

Huestis, Marilyn A., Cristina Sempio, Matthew N. Newmeyer, Maria Andersson, Allan J. Barnes, Osama A. Abulseoud, Benjamin C. Blount, Jennifer Schroeder, and Michael L. Smith. "Free and Glucuronide Urine Cannabinoids after Controlled Smoked, Vaporized and Oral Cannabis Administration in Frequent and Occasional Cannabis Users." Journal of Analytical Toxicology 44, no. 7 (May 5, 2020): 651–60. http://dx.doi.org/10.1093/jat/bkaa046.

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Abstract Total urinary 11-nor-9-carboxy-tetrahydrocannabinol (THCCOOH) concentrations are generally reported following cannabis administration. Few data are available for glucuronide and minor cannabinoid metabolite concentrations. All urine specimens from 11 frequent and 9 occasional cannabis users were analyzed for 11 cannabinoids for ~85 h by liquid chromatography with tandem mass spectrometry following controlled smoked, vaporized or oral 50.6 mg Δ9-tetrahydrocannabinol (THC) in a randomized, placebo-controlled, within-subject dosing design. No cannabidiol, cannabinol, cannabigerol, tetrahydrocannabivarin (THCV), THC, 11-OH-THC and Δ9-tetrahydrocannabinolic acid were detected in urine. Median THCCOOH-glucuronide maximum concentrations (Cmax) following smoked, vaporized and oral routes were 68.0, 26.7 and 360 μg/L for occasional and 378, 248 and 485 μg/L for frequent users, respectively. Median time to specific gravity-normalized Cmax (Tmax) was 5.1–7.9 h for all routes and all users. Median Cmax for THCCOOH, THC-glucuronide and 11-nor-9-carboxy-Δ9-THCV (THCVCOOH) were <7.5% of THCCOOH-glucuronide Cmax concentrations. Only THC-glucuronide mean Tmax differed between routes and groups, and was often present only in occasional users’ first urine void. Multiple THCCOOH-glucuronide and THCCOOH peaks were observed. We also evaluated these urinary data with published models for determining recency of cannabis use. These urinary cannabinoid marker concentrations from occasional and frequent cannabis users following three routes of administration provide a scientific database to assess single urine concentrations in cannabis monitoring programs. New target analytes (CBD, CBN, CBG, THCV and phase II metabolites) were not found in urine. The results are important to officials in drug treatment, workplace and criminal justice drug monitoring programs, as well as policy makers with responsibility for cannabis regulations.

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Bloemendal, Victor R. L. J., Jan C. M. van Hest, and Floris P. J. T. Rutjes. "Synthetic pathways to tetrahydrocannabinol (THC): an overview." Organic & Biomolecular Chemistry 18, no. 17 (2020): 3203–15. http://dx.doi.org/10.1039/d0ob00464b.

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50

Brogan, Andrew P., Lisa M. Eubanks, George F. Koob, Tobin J. Dickerson, and Kim D. Janda. "Antibody-Catalyzed Oxidation of Δ9-Tetrahydrocannabinol." Journal of the American Chemical Society 129, no. 12 (March 2007): 3698–702. http://dx.doi.org/10.1021/ja070022m.

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