Cited by 409Cannabis and Cannabinoid ResearchForensic Toxicology and Drug AnalysisPharmacogenetics and Drug Metabolism

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Pharmacokinetics and metabolism of delta 1-tetrahydrocannabinol and other cannabinoids with emphasis on man.

Agurell, S, Halldin, M, Lindgren, J E, Ohlsson, A, Widman, M, Gillespie, H, Hollister, L·1986·Pharmacological Reviews

DOI 10.1016/s0031-6997(25)06861-9

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Identification and quantification of 11-nor-Δ9-tetrahydrocannabinol-9-carboxylic acid glucuronide (THC-COOH-glu) in hair by ultra-performance liquid chromatography tandem mass spectrometry as a potential hair biomarker of cannabis use
Pichini, S., Marchei, E., Martello, S., et al. (2015) · Forensic Science International · doi:10.1016/j.forsciint.2015.01.011 · Cited by 27
“Cannabinoids are rapidly and extensively metabolized by hepatic enzymes [5].”
Background
“Herbal incense”: Designer drug blends as cannabimimetics and their assessment by drug discrimination and other in vivo bioassays
Järbe, T. U. C., & Gifford, R. S. (2013) · Life Sciences · doi:10.1016/j.lfs.2013.07.011 · Cited by 27
“These efforts set the stage for the initial scientific efforts to better understand the pharmacology of cannabis, including pharmacokinetics and bio-distribution (Agurell et al., 1986; Pertwee, 2006).”
Background
Naltrexone does not attenuate the effects of intravenous Δ9-tetrahydrocannabinol in healthy humans
Ranganathan, M., Carbuto, M., Braley, G., Elander, J., Perry, E. B., Pittman, B. P., Radhakrishnan, R., Sewell, R. A., & D’Souza, D. C. (2012) · The International Journal of Neuropsychopharmacology · doi:10.1017/s1461145711001830 · Cited by 27
“6% purity was dissolved in 95% ethanol (Agurell et al. 1986) to yield a concentration of 2 mg/ml stock solution, which was then passed through a 0.”
Method
Barriers to the wider adoption of medicinal Cannabis
Alexander, S. P. H. (2020) · British Journal of Pain · doi:10.1177/2049463720922884 · Cited by 28
Repurposing Cannabidiol as a Potential Drug Candidate for Anti-Tumor Therapies
Wang, F., & Multhoff, G. (2021) · Biomolecules · doi:10.3390/biom11040582 · Cited by 28
“The metabolism of CBD starts with a hydroxylation on position C-7, which results in (−)-7-hydroxy-CBD, followed by (−)-7-carboxy-CBD after a further oxidation step [30].”
Background
Preparation and Characterization of Inclusion Complexes of a Hemisuccinate Ester Prodrug of Δ9-Tetrahydrocannabinol with Modified Beta-Cyclodextrins
Upadhye, S. B., Kulkarni, S. J., Majumdar, S., Avery, M. A., Gul, W., ElSohly, M. A., & Repka, M. A. (2010) · AAPS PharmSciTech · doi:10.1208/s12249-010-9401-4 · Cited by 27
Identification of cannabielsoin, a new metabolite of cannabidiol formed by guinea-pig hepatic microsomal enzymes, and its pharmacological activity in mice.
Yamamoto, I., GOHDA, H., Narimatsu, S., et al. (1988) · Journal of Pharmacobio-Dynamics · doi:10.1248/bpb1978.11.833 · Cited by 27
Marijuana Misadventures in Children
Heizer, J. W., Borgelt, L. M., Bashqoy, F., Wang, G. S., & Reiter, P. D. (2016) · Pediatric Emergency Care · doi:10.1097/pec.0000000000000770 · Cited by 25
Prediction of regioselectivity and preferred order of metabolisms on CYP1A2-mediated reactions. Part 1. Focusing on polycyclic arenes and the related chemicals
Yamazoe, Y., Ito, K., Yamamura, Y., Iwama, R., & Yoshinari, K. (2016) · Drug Metabolism and Pharmacokinetics · doi:10.1016/j.dmpk.2016.07.005 · Cited by 25
“2A)[11, 12] and an ethyl group of laquinimod (Supplement Fig.”
Background
Adverse effects of Δ9-tetrahydrocannabinol on neuronal bioenergetics during postnatal development
Beiersdorf, J., Hevesi, Z., Calvigioni, D., Pyszkowski, J., Romanov, R. A., Szodorai, E., Lübec, G., Shirran, S. L., Botting, C. H., Kasper, S. F., et al. (2020) · JCI Insight · doi:10.1172/jci.insight.135418 · Cited by 27
“Our choice of these wash-out periods was two-fold: i) to ensure that bioactive THC metabolites are no longer present (70) with complete clearance reported at >72h upon chronic administration (71-73), and ii) that biologically meaningful and persistently-altered targets are captured.”
Harm reduction-the cannabis paradox
Melamede, R. J. (2005) · Harm Reduction Journal · doi:10.1186/1477-7517-2-17 · Cited by 26
“Cannabinoids Affect Drug Metabolism Another important cannabis and harm reduction topic that must be considered is that of how the use of cannabis impacts on the pharmacokinetics of other drugs [99].”
Background
1′,1′-Dimethylheptyl-Δ-8-tetrahydrocannabinol-11-oic Acid: A Novel, Orally Effective Cannabinoid with Analgesic and Anti-inflammatory Properties
Dajani, E. Z., Larsen, K. R., Taylor, J., Dajani, N. E., Shahwan, T. G., Neeleman, S. D., Taylor, M. S., Dayton, M. T., & Mir, G. (1999) · Journal of Pharmacology and Experimental Therapeutics · doi:10.1016/s0022-3565(24)35067-0 · Cited by 25
Brain microsomal oxidation of Δ8- and Δ9-tetrahydrocannabinol
Watanabe, K., Tanaka, T., Yamamoto, I., & Yoshimura, H. (1988) · Biochemical and Biophysical Research Communications · doi:10.1016/s0006-291x(88)80013-5 · Cited by 20
CYP2C9, CYP3A and CYP2C19 metabolize Δ9-tetrahydrocannabinol to multiple metabolites but metabolism is affected by human liver fatty acid binding protein (FABP1)
Yabut, K. C. B., Wen, Y. W., Simon, K. T., et al. (2024) · Biochemical Pharmacology · doi:10.1016/j.bcp.2024.116191 · Cited by 24
“The primary circulating metabolite of THC found in humans is 11-hydroxy-THC (11-OH-THC), but several dozen different metabolites of THC have been identified [3–5].”
Background
Analysis of the Medical Use of Marijuana and its Societal Implications
Taylor, H. G. (1998) · Journal of the American Pharmaceutical Association (1996) · doi:10.1016/s1086-5802(16)30318-7 · Cited by 24
Short‐Term Cannabidiol with Δ‐9‐Tetrahydrocannabinol in Parkinson's Disease: A Randomized Trial
Liu, Y., Bainbridge, J. L., Sillau, S., Rajkovic, S. N., Adkins, M., Domen, C. H., Thompson, J. A., Seawalt, T., Klawitter, J., Sempio, C., et al. (2024) · Movement Disorders · doi:10.1002/mds.29768 · Cited by 23
“17 To facilitate interpretation of effects, cannabinoid plasma levels were documented at the ﬁ nal dose visit.”
Background
Delay- and Dose-Dependent Effects of Δ9-Tetrahydrocannabinol Administration on Spatial and Object Working Memory Tasks in Adolescent Rhesus Monkeys
Verrico, C. D., Liu, S., Bitler, E. J., Gu, H., Sampson, A. R., Bradberry, C. W., & Lewis, D. A. (2012) · Neuropsychopharmacology · doi:10.1038/npp.2011.321 · Cited by 23
“…in male rhesus monkeys (Slikker et al, 1991; Paule et al, 1987; Schulze et al, 1989), the pharmacodynamics of THC associated with the clinical ‘high’ (Agurell et al, 1986; Lindgren et al, 1981; Ohlsson et al, 1980), and the time course of THC-induced cognitive impairments in humans following…”
Influential
Chemistry and Biological Activity of Tetrahydrocannabinol and its Derivatives
Flemming, T., Muntendam, R., Steup, C., & Kayser, O. (2007) · Topics in heterocyclic chemistry · doi:10.1007/7081_2007_084 · Cited by 24
Cannabis: The never-ending, nefarious nepenthe of the 21st century: What should the clinician know?
Greydanus, D. E., Kaplan, G., Baxter, L. E., Patel, D. R., & Feucht, C. L. (2015) · Disease-a-Month · doi:10.1016/j.disamonth.2015.01.004 · Cited by 22
“Occasional inhalation use, extensive first-pass metabolism, and erratic absorption produce lower bioavailability compared to heavy inhalation use.(126,129) THC is extensively distributed to tissues, especially fat, where it accumulates and is stored.”
BackgroundInfluential
Cannabinoids in the Treatment of Back Pain
Kim, T. E., Townsend, R. K., Branch, C. L., Romero-Sandoval, E. A., & Hsu, W. (2020) · Neurosurgery · doi:10.1093/neuros/nyz573 · Cited by 21
A Cannabinoid Ligand, Anandamide, Exacerbates Endotoxin-Induced Uveitis in Rabbits
Altinsoy, A., Dileköz, E., Kul, O., İlhan, S. Ö., Tunçcan, Ö. G., Seven, I., Bağrıaçık, E. Ü., Sarıoğlu, Y., Or, M., & Ercan, Z. S. (2011) · Journal of Ocular Pharmacology and Therapeutics · doi:10.1089/jop.2011.0049 · Cited by 22
“8 9–11 Many of these effects are due to activation of speciﬁc cannabinoid receptors, but some are related to receptor-independent mechanisms.”
Freie und glucuronidierte Cannabinoide im Urin - Untersuchungen zur Einschätzung des Konsumverhaltens
Skopp, G., Pötsch, L., Ganßmann, B., et al. (1999) · Rechtsmedizin · doi:10.1007/s001940050125 · Cited by 21
The endocannabinoid system: Novel targets for treating cancer induced bone pain
Sun, J., Zhou, Y., Chen, S., Wang, X., Xu, B., Li, D., Tian, Y., & Ye, D. (2019) · Biomedicine & Pharmacotherapy · doi:10.1016/j.biopha.2019.109504 · Cited by 19
Cannabinoids lead to enhanced virulence of the smallpox vaccine (vaccinia) virus
Huemer, H. P., Lassnig, C., Bernhard, D., Sturm, S., Nowotny, N. R., Kitchen, M., & Pavlic, M. (2010) · Immunobiology · doi:10.1016/j.imbio.2010.11.001 · Cited by 20
Cannabis: Time for Scientific Evaluation of This Ancient Remedy?
Sharpe, P., & Smith, G. (2000) · Anesthesia & Analgesia · doi:10.1097/00000539-200002000-00001 · Cited by 21
“rienced with serum concentrations around 3 ng/mL (4),”
Background
Clinical Pharmacokinetics of Cannabinoids and Potential Drug-Drug Interactions
Vázquez, M., García‐Carnelli, C., Maldonado, C., & Fagiolino, P. L. (2021) · Advances in experimental medicine and biology · doi:10.1007/978-3-030-61663-2_3 · Cited by 24
Unintentional cannabis poisoning in toddlers: A one year study in Marseille
Mehamha, H., Doudka, N., Minodier, P., Néant, N., Lacarelle, B., Solas, C., & Fabresse, N. (2021) · Forensic Science International · doi:10.1016/j.forsciint.2021.110858 · Cited by 17
An Ultra-Low Dose of ∆9-Tetrahydrocannabinol Alleviates Alzheimer’s Disease-Related Cognitive Impairments and Modulates TrkB Receptor Expression in a 5XFAD Mouse Model
Nitzan, K., Ellenbogen, L., Bentulila, Z., David, D., Franko, M., Break, E. P., Zoharetz, M., Shamir, A., Sarne, Y., & Doron, R. (2022) · International Journal of Molecular Sciences · doi:10.3390/ijms23169449 · Cited by 19
“As THC is largely fat-soluble, THC and its metabolites accumulate in fat tissue and slowly leak back into the circulation; thus, complete elimination from the body takes several days [26].”
Background
Dosing medical marijuana: rational guidelines on trial in Washington State.
Aggarwal, S. K., Kyashna-Tocha, M., & Carter, G. T. (2007) · PubMed · Cited by 19
Human Cannabinoid Pharmacokinetics and Interpretation of Cannabinoid Concentrations in Biological Fluids and Tissues
Huestis, M. A., & Smith, M. L. (2007) · Humana Press eBooks · doi:10.1007/978-1-59259-947-9_9 · Cited by 19
Cannabinoids induce incomplete maturation of cultured human leukemia cells.
Murison, G. L., Chubb, C., Maeda, S., et al. (1987) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.84.15.5414 · Cited by 19
Synthesis, pharmacology, and molecular modeling of novel 4-alkyloxy indole derivatives related to cannabimimetic aminoalkyl indoles (AAIs)
Dutta, A. K., Ryan, W. J., Thomas, B. F., et al. (1997) · Bioorganic & Medicinal Chemistry · doi:10.1016/s0968-0896(97)00111-9 · Cited by 19
Development of agonists, partial agonists and antagonists in the Δ8-Tetrahydrocannabinol series
Crocker, P. J., Saha, B., Ryan, W. J., et al. (1999) · Tetrahedron · doi:10.1016/s0040-4020(99)00849-2 · Cited by 19
Nasal Accumulation and Metabolism of Δ9-Tetrahydrocannabinol Following Aerosol (‘Vaping’) Administration in Adolescent Rats
Torrens, A., Ruiz, C., Martinez, M. X., Tagne, A. M., Roy, P., Grimes, D., Ahmed, F., Lallai, V., Inshishian, V., Bautista, M., et al. (2022) · Pharmacological Research · doi:10.1016/j.phrs.2022.106600 · Cited by 14
Novel, potent THC/anandamide (hybrid) analogs
Bourne, C., Roy, S., Wiley, J. L., et al. (2007) · Bioorganic & Medicinal Chemistry · doi:10.1016/j.bmc.2007.08.039 · Cited by 18
Chemical stabilization of a Δ9-tetrahydrocannabinol prodrug in polymeric matrix systems produced by a hot-melt method: Role of microenvironment pH
Munjal, M. K., ElSohly, M. A., & Repka, M. A. (2006) · AAPS PharmSciTech · doi:10.1208/pt070371 · Cited by 18
Amyotrophic Lateral Sclerosis and Pain: A Narrative Review from Pain Assessment to Therapy
Pota, V., Sansone, P., Sarno, S. D., Aurilio, C., Coppolino, F., Barbarisi, M., Barbato, F., Fiore, M., Cosenza, G., Passavanti, M. B., et al. (2024) · Behavioural Neurology · doi:10.1155/2024/1228194 · Cited by 19
“Unfortunately, with this method of administration, it is di ﬃ cult to determine the e ﬀ ective concentration of the active component [292, 293].”
The effect of cannabis edibles on driving and blood THC
Zhao, S., Brands, B., Kaduri, P., et al. (2024) · Journal of Cannabis Research · doi:10.1186/s42238-024-00234-y · Cited by 17
Mother of Berries, ACDC, or Chocolope: Examination of the Strains Used by Medical Cannabis Patients in New England
Piper, B. J. (2017) · Journal of Psychoactive Drugs · doi:10.1080/02791072.2017.1390179 · Cited by 17
“perceived “high” appears only moderate (Agurell et al. 1986).”
Background
Δ9-tetrahydrocannabinol (THC) is present in the body between smoking sessions in occasional non-daily cannabis users
Mørland, J. G., & Bramness, J. G. (2020) · Forensic Science International · doi:10.1016/j.forsciint.2020.110188 · Cited by 17
Cannabis and Bioactive Cannabinoids
Messina, F., Rosati, O., Curini, M., & Marcotullio, M. C. (2015) · Studies in natural products chemistry · doi:10.1016/b978-0-444-63473-3.00002-2 · Cited by 18
Potential Interventions for HIV/AIDS Wasting: An Overview
Abrams, D. I. (2000) · JAIDS Journal of Acquired Immune Deficiency Syndromes · doi:10.1097/00042560-200010001-00012 · Cited by 17
Human Urinary Excretion Profile after Smoking and Oral Administration of [14C]Δ1-Tetrahydrocannabinol*
Johansson, E., Gillespie, H. K., & Halldin, M. M. (1990) · Journal of Analytical Toxicology · doi:10.1093/jat/14.3.176 · Cited by 17
Self-citation
Einige praxisrelevante Aspekte der Pharmakokinetik von THC
Grotenhermen, F. (1999) · Complementary Medicine Research · doi:10.1159/000057155 · Cited by 17
Evidence of 11-Hydroxy-hexahydrocannabinol and 11-Nor-9-carboxy-hexahydrocannabinol as Novel Human Metabolites of Δ9-Tetrahydrocannabinol
Jørgensen, C. F., Rasmussen, B. S., Línnet, K., & Thomsen, R. (2023) · Metabolites · doi:10.3390/metabo13121169 · Cited by 16
“…with the glucuronide of THC-COOH being the major metabolite excreted in urine [8]. includes glucuronide, glutathione and fa tt y acid conjugations [2], with the glucuronide of THC-COOH being the major metabolite Metabolites 2023 , 13 , x FOR PEER REVIEW 2 of 13 include the 8-position, which…”
BackgroundInfluential
Disposition of oral delta-9 tetrahydrocannabinol (THC) in children receiving cannabis extracts for epilepsy
Wang, G. S., Bourne, D. W. A., Klawitter, J., et al. (2019) · Clinical Toxicology · doi:10.1080/15563650.2019.1616093 · Cited by 16
11-OH-THC in hair as marker of active cannabis consumption: Estimating a reliable cut-off by evaluation of 672 THC-positive hair samples
Casati, S., Angeli, I., Ravelli, A., FABBRO, M. D., Minoli, M., & Orioli, M. (2019) · Forensic Science International · doi:10.1016/j.forsciint.2019.109951 · Cited by 16
“Cannabinoids are rapidly and extensively metabolized by hepatic enzymes [2].”
Background
Increased brain metabolism after acute administration of the synthetic cannabinoid HU210: A small animal PET imaging study with 18F-FDG
Nguyen, V. H., Verdurand, M., Dedeurwaerdere, S., et al. (2011) · Brain Research Bulletin · doi:10.1016/j.brainresbull.2011.11.011 · Cited by 16
Disposition of Oral Cannabidiol-Rich Cannabis Extracts in Children with Epilepsy
Wang, G. S., Bourne, D. W. A., Klawitter, J., et al. (2020) · Clinical Pharmacokinetics · doi:10.1007/s40262-020-00869-z · Cited by 16
Marijuana (Cannabis) as Medicine
Hollister, L. E. (2001) · Journal of Cannabis Therapeutics · doi:10.1300/j175v01n01_02 · Cited by 16
“Smoked marijuana produces a THC concentration that mimics the pattern of intravenously administered THC (Agurell et al. 1986).”
BackgroundSelf-citation
An approach to the medical marijuana controversy
Hollister, L. E. (2000) · Drug and Alcohol Dependence · doi:10.1016/s0376-8716(99)00076-9 · Cited by 16
Self-citation
Cannabis: Time for Scientific Evaluation of This Ancient Remedy?
Sharpe, P. T., & Smith, G. (2000) · Anesthesia & Analgesia · doi:10.1213/00000539-200002000-00001 · Cited by 16
Gas chromatographic—mass spectrometric methods of analysis for detection of 11-nor-Δ9-tetrahydrocannabinol-9-carboxylic acid in biological matrices
Bronner, W. E., & Xu, A. S. (1992) · Journal of Chromatography B Biomedical Sciences and Applications · doi:10.1016/0378-4347(92)80528-x · Cited by 16
Optimization of the quantitative analysis of the major cannabis metabolite (11-nor-9-COOH-Δ9-tetrahydrocannabinol) in urine by gas chromatography/mass spectrometry
Congost, M. P., de la Torre, R., & Segura, J. (1988) · Journal of Mass Spectrometry · doi:10.1002/bms.1200160172 · Cited by 16
Pharmacology of Cannabis
Howlett, A. C. (1998) · Springer eBooks · doi:10.1007/978-1-4757-2913-9_8 · Cited by 16
Oxygenation mechanism in the oxidation of xenobiotic aldehyde to carboxylic acid by mouse hepatic microsomes
Yamamoto, I., Watanabe, K., Narimatsu, S., et al. (1988) · Biochemical and Biophysical Research Communications · doi:10.1016/s0006-291x(88)81163-x · Cited by 16
THC (Δ9‐Tetrahydrocannabinol) Exerts Neuroprotective Effect in Glutamate‐affected Murine Primary Mesencephalic Cultures Through Restoring Mitochondrial Membrane Potential and Anti‐apoptosis Involving CB1Receptor‐dependent Mechanism
Nguyen, C. H., Krewenka, C., Radad, K., Kranner, B., Huber, A., Duvigneau, J. C., Miller, I., & Moldzio, R. (2016) · Phytotherapy Research · doi:10.1002/ptr.5712 · Cited by 15
“Furthermore, plasma levels of THC decrease around 10% after 1–2h and complete elimination from the body after several days (Agurell et al., 1986).”
BackgroundInfluential
Self-Medication with Cannabis
Hazekamp, A., & Pappas, G. J. (2014) · Oxford University Press eBooks · doi:10.1093/acprof:oso/9780199662685.003.0017 · Cited by 15
Medical marijuana: emerging applications for the management of neurologic disorders
Carter, G. T., & Ugalde, V. (2004) · Physical Medicine and Rehabilitation Clinics of North America · doi:10.1016/j.pmr.2004.03.005 · Cited by 15
“Approximately 60 of these subtypes are chemically classified as cannabinoids [6,16].”
Background
Structure–Activity Relationships of Classical Cannabinoids
Razdan, R. K. (2008) · Humana Press eBooks · doi:10.1007/978-1-59745-503-9_1 · Cited by 14
Fragment-based drug discovery and biological evaluation of novel cannabinol-based inhibitors of oxytosis/ferroptosis for neurological disorders
Liang, Z., Candib, A., Soriano‐Castell, D., Fischer, W. H., Finley, K. D., & Maher, P. A. (2024) · Redox Biology · doi:10.1016/j.redox.2024.103138 · Cited by 14
Impact of smoking cannabidiol (CBD)-rich marijuana on driving ability
Gelmi, T. J., Weinmann, W., & Pfäffli, M. (2021) · Forensic Sciences Research · doi:10.1080/20961790.2021.1946924 · Cited by 13
“31) could be explained by inter-individual differences in puff duration, inhaled smoke volume and breath-holding after inhalation [54].”
Background
Behaviour in rats maintained by low differential reinforcement rate: Effects of Δ1-tetrahydrocannabinol, cannabinol and cannabidiol, alone and in combination
Hiltunen, A. J., Järbe, T. U. C., Kamkar, M., et al. (1989) · Neuropharmacology · doi:10.1016/0028-3908(89)90055-5 · Cited by 13
Polycaprolactone microparticles for the subcutaneous administration of cannabidiol: in vitro and in vivo release
Fraguas‐Sánchez, A. I., Hernán, D., Montejo, C., et al. (2023) · Drug Delivery and Translational Research · doi:10.1007/s13346-023-01444-2 · Cited by 12
“The rapid distribution phase corresponds to the partition of CBD to lipophilic tissues, due to its high lipid nature, like all cannabinoids [40–43].”
Cannabinoid Mixture Affects the Fate and Functions of B Cells through the Modulation of the Caspase and MAP Kinase Pathways
Lampron, M.-C., Paré, I., Al-Zharani, M. M., Semlali, A., & Loubaki, L. (2023) · Cells · doi:10.3390/cells12040588 · Cited by 12
“28 × 1014 molecules/mL [43], suggesting the rapid elimination of cannabinoids and, more importantly, a large difference between the administered dose and that measured in the blood.”
Background
Cannabis Use Disorders
Duncan, P. M. (2020) · Cambridge University Press eBooks · doi:10.1017/9781139025515.013 · Cited by 12
Mechanism of biological formation of cannabielsion from cannabidiol in the guinea-pig, mouse, rat and rabbit.
Yamamoto, I., GOHDA, H., Narimatsu, S., et al. (1989) · Journal of Pharmacobio-Dynamics · doi:10.1248/bpb1978.12.488 · Cited by 12
Cannabinoids in Models of Chronic Inflammatory Conditions
Mechoulam, R., Sumariwalla, P. F., Feldmann, M., & Gallily, R. (2005) · Phytochemistry Reviews · doi:10.1007/s11101-004-1534-1 · Cited by 11
“A major metabolic route of THC, both in the D- and the D-THC series, is oxidation at C-11, initially leading to 11-0H-THC and then to THC11-oic acid (Agurell et al., 1986; Mechoulam et al., 1973).”
Background
Enhancement of the behavioral effects of endogenous and exogenous cannabinoid agonists by phenylmethyl sulfonyl fluoride
Vann, R. E., Walentiny, D. M., Burston, J. J., Tobey, K. M., Gamage, T. F., & Wiley, J. L. (2011) · Neuropharmacology · doi:10.1016/j.neuropharm.2011.10.011 · Cited by 11
“While PMSF-induced inhibition of FAAH offers a ready explanation of its enhancement of all of the in vivo and in vitro pharmacological effects of anandamide reported here, THC and CP 55,940 are both degraded by cytochrome P450 enzymes rather than FAAH (Agurell et al., 1986).”
Increasing cannabis use and importance as an environmental contaminant mixture and associated risks to exposed biota: A review
Kennedy, E. K. C., Perono, G. A., Nemez, D. B., Holloway, A. C., Thomas, P. J., Letcher, R. J., Märvin, C. H., Stetefeld, J., Stout, J. M., Peters, O., et al. (2020) · Critical Reviews in Environmental Science and Technology · doi:10.1080/10643389.2020.1819730 · Cited by 11
“Similar to D9-THC, CBD is carboxylated, glucuronidated and excreted in urine (Agurell et al., 1986).”
Background
Cannabidiol: Science, Marketing, and Legal Perspectives
Wiley, J. L., Gourdet, C., & Thomas, B. F. (2020) · doi:10.3768/rtipress.2020.op.0065.2004 · Cited by 13
“CBD absorption into the plasma is also more efficient via smoking/vaping (estimated 31 percent bioavailability; [Agurell et al., 1986; Grotenhermen, 2003; Lucas et al., 2018; Ohlsson et al., 1986]), as this route of administration avoids exposure to gastric juices and first-pass metabolism by the…”
Background
Letters to the Editor
McBay, A. J., McGee, M., Lalonde, S., et al. (1988) · Journal of Forensic Sciences · doi:10.1520/jfs12510j · Cited by 11
The Association Between Cannabinoids and Psychosis
Tikka, S. K., & D’Souza, D. C. (2018) · Springer eBooks · doi:10.1007/978-3-319-90365-1_14 · Cited by 10
The growing dilemma of legalized cannabis and heart transplantation
Olt, C. K., Faulkenberg, K. D., & Hsich, E. (2021) · The Journal of Heart and Lung Transplantation · doi:10.1016/j.healun.2021.03.024 · Cited by 10
Docking and QSAR studies of new 1,4-dihydropyridines containing 4(5)-chloro-2-methyl-5(4)-imidazolyl substituent
Davood, A., Iman, M., Nematollahi, A., et al. (2011) · Medicinal Chemistry Research · doi:10.1007/s00044-010-9515-y · Cited by 10
Effects of Δ9-tetrahydrocannabinol in individuals with a familial vulnerability to alcoholism
Ranganathan, M., Sewell, R. A., Carbuto, M., Elander, J., Martin, A. M. S., Radhakrishnan, R., Pittman, B. P., & D’Souza, D. C. (2014) · Psychopharmacology · doi:10.1007/s00213-013-3402-4 · Cited by 10
ALSUntangled No. 16: Cannabis
The ALSUntangled Group (2012) · Amyotrophic Lateral Sclerosis · doi:10.3109/17482968.2012.687264 · Cited by 11
“Delta-9 tetrahydrocannabinol (THC) and delta-8 THC appear to produce the majority of the psychoactive effects of cannabis (18,19).”
Background
Cardiovascular Effects of Marihuana and Cannabinoids
Trouvé, R., & Nahas, G. G. (1999) · Humana Press eBooks · doi:10.1007/978-1-59259-710-9_30 · Cited by 10
Prescribing Cannabinoids for Multiple Sclerosis
Pertwee, R. G. (1999) · CNS Drugs · doi:10.2165/00023210-199911050-00001 · Cited by 10
Los productos de Cannabis sativa: situación actual y perspectivas en medicina
Carranza, R. R. (2012) · LA Referencia (Red Federada de Repositorios Institucionales de Publicaciones Científicas) · Cited by 9
11-Nor-9-carboxy-∆ 9 -tetrahydrocannabinol - a ubiquitous yet underresearched cannabinoid. A re- view of the literature
Ujváry, I., & Grotenhermen, F. (2014) · Cited by 9
Regioselective Cascade Synthesis of Chloro-Substituted 6H-Benzo[c]chromenes via Benzannulation
Muralidhar, B., & Reddy, S. R. (2017) · Bulletin of the Chemical Society of Japan · doi:10.1246/bcsj.20170261 · Cited by 9
An Unsteady Walk in the Park
Blackstone, M. M., & Callahan, J. M. (2008) · Pediatric Emergency Care · doi:10.1097/pec.0b013e31816a2874 · Cited by 9
“Although there is greater systemic absorption and a faster onset of action with inhalation, ingested forms of marijuana have a longer duration of action, lasting up to several hours.(2) Although marijuana is a commonly used drug of abuse in the adolescent population,(3) cannabis intoxication is an uncommonly observed…”
Background
The role of fluorine substitution in the structure–activity relationships (SAR) of classical cannabinoids
Crocker, P. J., Mahadevan, A., Wiley, J. L., et al. (2007) · Bioorganic & Medicinal Chemistry Letters · doi:10.1016/j.bmcl.2007.01.006 · Cited by 9
Inhibition of A23187–induced release of leukotriene B4 in mouse whole blood Ex vivo and human polymorphonuclear cells in vitro by the cannabinoid analgesic cannabidiol
Formukong, E. A., EVANS, A. T., Evans, F. J., & GARLAND, L. G. (1991) · Phytotherapy Research · doi:10.1002/ptr.2650050606 · Cited by 9
Laboratory Detection of Cannabinoids
King, D. L., Martel, P. A., & O'Donnell, C. M. (1987) · Clinics in Laboratory Medicine · doi:10.1016/s0272-2712(18)30736-4 · Cited by 9
Cannabinol (CBN) Cross-Reacts with Two Urine Immunoassays Designed to Detect Tetrahydrocannabinol (THC) Metabolite
Kroner, G., Johnson‐Davis, K. L., Doyle, K. J., et al. (2020) · The Journal of Applied Laboratory Medicine · doi:10.1093/jalm/jfaa020 · Cited by 8
Palmitic acid ester of tetrahydrocannabinol (THC) and palmitic acid diester of 11-hydroxy-THC — Unsuccessful search for additional THC metabolites in human body fluids and tissues
Krämer, M., Broecker, S., Diehl, B. W. K., Madea, B., & Heß, C. (2018) · Forensic Science International · doi:10.1016/j.forsciint.2018.11.005 · Cited by 7
Les grands traits de la pharmacocinétique du delta-9- tétrahydrocannabinol (THC) ; les nouveaux cannabinoïdes de synthèse ; le cannabis et la sécurité routière
Goullé, J., & Guerbet, M. (2014) · Bulletin de l Académie Nationale de Médecine · doi:10.1016/s0001-4079(19)31321-4 · Cited by 8
Chirality in ocular agents
Leonov, A., & Bielory, L. (2007) · Current Opinion in Allergy and Clinical Immunology · doi:10.1097/aci.0b013e3282ef705b · Cited by 8
A novel methodology for the synthesis of 1-desoxy-Δ8-tetrahydrocannabinol (THC) analogues
Sun, H., Mahadevan, A., & Razdan, R. K. (2003) · Tetrahedron Letters · doi:10.1016/j.tetlet.2003.10.176 · Cited by 8
Techniques and Technologies for The Bioanalysis of Sativex®, Metabolites and Related Compounds
Molnár, A. B., & Fu, S. (2016) · Bioanalysis · doi:10.4155/bio-2015-0021 · Cited by 7
“When CBD was smoked, bioavailability ranged from 11% to 45% with an average of 31% across five subjects [21].”
BackgroundInfluential
Oral Cannabidiol for Seborrheic Dermatitis in Patients With Parkinson Disease: Randomized Clinical Trial
Weber, I., Zagona-Prizio, C., Sivesind, T. E., Adelman, M., Szeto, M. D., Liu, Y., Sillau, S. H., Bainbridge, J., Klawitter, J., Sempio, C., et al. (2024) · JMIR Dermatology · doi:10.2196/49965 · Cited by 7
“The half-life of oral CBD and oral THC is approximately 2 days and 4 hours, respectively [16].”
Background
Evaluating the Impact of THC in Hemp Foods and Cosmetics on Human Health and Workplace Drug Tests
Grotenhermen, F., Leson, G., & Pless, P. (2003) · Journal of Industrial Hemp · doi:10.1300/j237v08n02_02 · Cited by 7
“THC is also a photo-labile and easily oxidized substance (Agurell et al., 1986; Touitou et al., 1988); thus, some degradation of the applied THC will occur immediately after application of the body care product.”
BackgroundInfluential
Decreased serum cotinine levels in smokers of both tobacco and marijuana as compared with smokers of tobacco only
Vunakis, H. V., Tashkin, D. P., Simmons, M., & Clark, V. A. (1988) · Pharmacology Biochemistry and Behavior · doi:10.1016/0091-3057(88)90116-5 · Cited by 7
Perceptual Drug Discriminative Aspects of the Endocannabinoid Signaling System in Animals And Man
Järbe, T. U. C. (2011) · Wiley eBooks · doi:10.1002/9781118023150.ch8 · Cited by 7
Quantification of ∆9-tetrahydrocannabinol, 11-OH-THC, THC-COOH, hexahydrocannabinol, and cannabidiol in human plasma and blood by liquid chromatography–tandem mass spectrometry
Pavlic, M., Innerhofer, C., & Pitterl, F. (2024) · Journal of Analytical Toxicology · doi:10.1093/jat/bkae094 · Cited by 6
Substance Use Disorders
Duncan, P. M. (2020) · Cambridge University Press eBooks · doi:10.1017/9781139025515 · Cited by 8
Major Cytochrome P450 Enzymes Responsible for Microsomal Aldehyde Oxygenation of 11-Oxo-Δ8-tetrahydrocannabinol and 9-Anthraldehyde in Human Liver
Watanabe, K., Matsunaga, T., Kimura, T., et al. (2002) · Drug Metabolism and Pharmacokinetics · doi:10.2133/dmpk.17.516 · Cited by 6
Ocular toxicology of marijuana: an update
Green, K. D., & Thomas, F. M. (1987) · Journal of Toxicology Cutaneous and Ocular Toxicology · doi:10.3109/15569528709052178 · Cited by 6

Authors: Agurell, S., Halldin, M., Lindgren, J. E., Ohlsson, A., Widman, M., Gillespie, H., & Hollister, L.
ORCID: Halldin, M
Ohlsson, A
Venue: Pharmacological Reviews
Publisher: Elsevier BV
Published: 1986-03
Volume: 38
Issue: 1
Pages: 21-43
ISSN: 0031-6997 (ISSN-L)
DOI: 10.1016/s0031-6997(25)06861-9
OpenAlex: W2107684761
Cited by: 406
References: 0
Citations by year: 2026: 4 · 2025: 6 · 2024: 10 · 2023: 7 · 2022: 5 · 2021: 8 · 2020: 45 · 2019: 17 · 2018: 12 · 2017: 11 · 2016: 21 · 2015: 14 · 2014: 14 · 2013: 8 · 2012: 10
FWCI: 7.34
Type: journal article
Language: en
Open access: closed
Licence: www.elsevier.com/tdm/userlicense/1.0/ (tdm)
www.elsevier.com/legal/tdmrep-license (tdm)
Locations: Pharmacological Reviews (publishedVersion)
PubMed (publishedVersion)
PubMed
Topics: Health Sciences › Medicine › Pharmacology (medical) › Cannabis and Cannabinoid Research
Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Toxicology › Forensic Toxicology and Drug Analysis
Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Pharmacology › Pharmacogenetics and Drug Metabolism
Keywords: delta-1-tetrahydrocannabinol, cannabinoids, pharmacokinetics, drug metabolism, human metabolism
MeSH terms: Animals, Biotransformation, Cannabidiol, Cannabinoids, Drug Tolerance, Feces, Humans, Kinetics, Dronabinol, Tissue Distribution

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Pharmacokinetics and metabolism of delta 1-tetrahydrocannabinol and other cannabinoids with emphasis on man.

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