11-nor-9-carboxy-Delta(9)-tetrahydrocannabinol (BioDeep_00000020908)

   

human metabolite


代谢物信息卡片


1-hydroxy-6,6-dimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromene-9-carboxylic acid

化学式: C21H28O4 (344.1987)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CCCCCC1=CC(=C2C3C=C(CCC3C(OC2=C1)(C)C)C(=O)O)O
InChI: InChI=1S/C21H28O4/c1-4-5-6-7-13-10-17(22)19-15-12-14(20(23)24)8-9-16(15)21(2,3)25-18(19)11-13/h10-12,15-16,22H,4-9H2,1-3H3,(H,23,24)

描述信息

11-nor-9-carboxy-Delta(9)-tetrahydrocannabinol, also known as delta(1)-Tetrahydrocannabinol-7-Oic acid or delta-9-11-Carboxytetrahydrocannabinol, is classified as a member of the 2,2-dimethyl-1-benzopyrans. 2,2-dimethyl-1-benzopyrans are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. 11-nor-9-carboxy-Delta(9)-tetrahydrocannabinol is considered to be practically insoluble (in water) and acidic

同义名列表

15 个代谢物同义名

1-hydroxy-6,6-dimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromene-9-carboxylic acid; 1-Hydroxy-6,6-dimethyl-3-pentyl-6H,6ah,7H,8H,10ah-benzo[c]isochromene-9-carboxylate; (6AR-trans)-isomer OF 11-nor-delta(9)-tetrahydrocannabinol-9-carboxylic acid; Hexadeutero-11-nor-delta(9)-tetrahydrocannabinol-9-carboxylic acid; 11-Nor-delta(9)-tetrahydrocannabinol-9-carboxylic acid; 11-nor-9-carboxy-Delta(9)-tetrahydrocannabinol; 11-Nor-9-carboxy-delta-9-tetrahydrocannabinol; 11-Nor-9-carboxy-δ(9)-tetrahydrocannabinol; delta(9)-Tetrahydrocannabinol-11-oic-acid; delta(1)-Tetrahydrocannabinol-7-Oic acid; delta-9-11-Carboxytetrahydrocannabinol; Tetrahydrocannabinol-7-Oic acid; 11-Nor-9-carboxy-thc; THC-11-Oic acid; THC-11-Oate



数据库引用编号

7 个数据库交叉引用编号

分类词条

相关代谢途径

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代谢反应

1 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(1)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

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1 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。

亚细胞结构定位 关联基因列表


文献列表

  • Xin Chen, Jashvant D Unadkat, Qingcheng Mao. Tetrahydrocannabinol and Its Major Metabolites Are Not (or Are Poor) Substrates or Inhibitors of Human P-Glycoprotein [ATP-Binding Cassette (ABC) B1] and Breast Cancer Resistance Protein (ABCG2). Drug metabolism and disposition: the biological fate of chemicals. 2021 10; 49(10):910-918. doi: 10.1124/dmd.121.000505. [PMID: 34326138]
  • Mohamed Abou El Hassan, David Colantonio, Sergei Likhodii, Bassam A Nassar. The analytical performance of six urine drug screens on cobas 6000 and ARCHITECT i2000 compared to LC-MS/MS gold standard. Clinical biochemistry. 2021 Jul; 93(?):99-103. doi: 10.1016/j.clinbiochem.2021.04.003. [PMID: 33844982]
  • Claudia Mariottini, Ilkka Ojanperä, Pirkko Kriikku. Increase in drugs-of-abuse findings in post-mortem toxicology due to COVID-19 restrictions-First observations in Finland. Drug testing and analysis. 2021 Apr; 13(4):867-870. doi: 10.1002/dta.2982. [PMID: 33217177]
  • Melike Aydoğdu, Serap Annette Akgür. Urine drug-testing tampering approaches: Turkish probationers. Medicine, science, and the law. 2021 Jan; 61(1):6-13. doi: 10.1177/0025802420956453. [PMID: 32924786]
  • Melissa A Hoffman, Amber Trochta, Ray D Gary, Robert L Fitzgerald, Iain M McIntyre. An evaluation of postmortem concentrations of Δ9-tetrahydrocannabinol (THC) and 11-nor-9-carboxy-Δ9-tetrahydrocannabinol (THCCOOH). Forensic science international. 2020 Oct; 315(?):110414. doi: 10.1016/j.forsciint.2020.110414. [PMID: 32738674]
  • Randi Melissa Schuster, Kevin Potter, Ryan Vandrey, Maya Hareli, Jodi Gilman, David Schoenfeld, A Eden Evins. Urinary 11-nor-9-carboxy-tetrahydrocannabinol elimination in adolescent and young adult cannabis users during one month of sustained and biochemically-verified abstinence. Journal of psychopharmacology (Oxford, England). 2020 02; 34(2):197-210. doi: 10.1177/0269881119872206. [PMID: 31535597]
  • Agostina Chiavola, Maria Rosaria Boni, Camilla Di Marcantonio, Giancarlo Cecchini, Stefano Biagioli, Alessandro Frugis. A laboratory-study on the analytical determination and removal processes of THC-COOH and bezoylecgonine in the activated sludge reactor. Chemosphere. 2019 May; 222(?):83-90. doi: 10.1016/j.chemosphere.2019.01.117. [PMID: 30690404]
  • Lill Dannevig Müller, Mimi Stokke Opdal. Developing a rapid semi-automated sample preparation with alkaline hydrolysis in a 96-well plate for quantification of 11-nor-Δ9-tetrahydrocannabinol-9-carboxylic acid in urine samples by UHPLC-MS/MS. Journal of pharmaceutical and biomedical analysis. 2018 Nov; 161(?):296-304. doi: 10.1016/j.jpba.2018.08.045. [PMID: 30189411]
  • Randi Melissa Schuster, Jodi Gilman, David Schoenfeld, John Evenden, Maya Hareli, Christine Ulysse, Emily Nip, Ailish Hanly, Haiyue Zhang, A Eden Evins. One Month of Cannabis Abstinence in Adolescents and Young Adults Is Associated With Improved Memory. The Journal of clinical psychiatry. 2018 10; 79(6):. doi: 10.4088/jcp.17m11977. [PMID: 30408351]
  • Huan Huang, Avery L McIntosh, Gregory G Martin, Lawrence J Dangott, Ann B Kier, Friedhelm Schroeder. Structural and Functional Interaction of Δ9-Tetrahydrocannabinol with Liver Fatty Acid Binding Protein (FABP1). Biochemistry. 2018 10; 57(41):6027-6042. doi: 10.1021/acs.biochem.8b00744. [PMID: 30232874]
  • Ljerka Prester, Anja Mikolić, Andreja Jurič, Nino Fuchs, Marijana Neuberg, Ana Lucić Vrdoljak, Irena Brčić Karačonji. Effects of Δ9-tetrahydrocannabinol on irinotecan-induced clinical effects in rats. Chemico-biological interactions. 2018 Oct; 294(?):128-134. doi: 10.1016/j.cbi.2018.08.009. [PMID: 30130528]
  • Udo Bonnet, Ali Canbay, Michael Specka, Norbert Scherbaum. Long-Term Heavy Recreational Cannabis Use and Serum Delta-9-Tetrahydrocannabinol Levels are not Associated with an Impaired Liver Function in Cannabis Dependents. Journal of psychoactive drugs. 2018 Sep; 50(4):355-360. doi: 10.1080/02791072.2018.1482031. [PMID: 30052163]
  • Jennifer A Manuzak, Toni M Gott, Jay S Kirkwood, Ernesto Coronado, Tiffany Hensley-McBain, Charlene Miller, Ryan K Cheu, Ann C Collier, Nicholas T Funderburg, Jeffery N Martin, Michael C Wu, Nina Isoherranen, Peter W Hunt, Nichole R Klatt. Heavy Cannabis Use Associated With Reduction in Activated and Inflammatory Immune Cell Frequencies in Antiretroviral Therapy-Treated Human Immunodeficiency Virus-Infected Individuals. Clinical infectious diseases : an official publication of the Infectious Diseases Society of America. 2018 06; 66(12):1872-1882. doi: 10.1093/cid/cix1116. [PMID: 29471387]
  • Nicolas J Schlienz, Edward J Cone, Evan S Herrmann, Natalie A Lembeck, John M Mitchell, George E Bigelow, Ronald Flegel, Charles P LoDico, Eugene D Hayes, Ryan Vandrey. Pharmacokinetic Characterization of 11-nor-9-carboxy-Δ9-tetrahydrocannabinol in Urine Following Acute Oral Cannabis Ingestion in Healthy Adults. Journal of analytical toxicology. 2018 May; 42(4):232-247. doi: 10.1093/jat/bkx102. [PMID: 29300962]
  • Darryl P Arfsten, Erick Roman Perez, Neal C Goebel. Estimation of Measurement Uncertainty in Quantitation of Benzoylecgonine (BZE) and 11-nor-Δ9-THC-9-carboxylic acid (THCA). Journal of analytical toxicology. 2018 Apr; 42(3):141-148. doi: 10.1093/jat/bkx100. [PMID: 29351661]
  • Amie C Hayley, Luke A Downey, Glyn Hansen, Ashley Dowell, Dale Savins, Richard Buchta, Reinilda Catubig, Robert Houlden, Con K K Stough. Detection of delta-9-tetrahydrocannabinol (THC) in oral fluid, blood and urine following oral consumption of low-content THC hemp oil. Forensic science international. 2018 Mar; 284(?):101-106. doi: 10.1016/j.forsciint.2017.12.033. [PMID: 29408718]
  • Ângela Carvalho, Esben Halkjær Hansen, Oliver Kayser, Simon Carlsen, Felix Stehle. Designing microorganisms for heterologous biosynthesis of cannabinoids. FEMS yeast research. 2017 06; 17(4):. doi: 10.1093/femsyr/fox037. [PMID: 28582498]
  • Chih-Wei Chang, Chun-Wei Tung, Chin-Chuan Tsai, Yu-Tse Wu, Mei-Chich Hsu. Determination of cannabinoids in hemp nut products in Taiwan by HPLC-MS/MS coupled with chemometric analysis: quality evaluation and a pilot human study. Drug testing and analysis. 2017 Jun; 9(6):888-897. doi: 10.1002/dta.2062. [PMID: 27590030]
  • Rohitash Jamwal, Ariel R Topletz, Bharat Ramratnam, Fatemeh Akhlaghi. Ultra-high performance liquid chromatography tandem mass-spectrometry for simple and simultaneous quantification of cannabinoids. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2017 Mar; 1048(?):10-18. doi: 10.1016/j.jchromb.2017.02.007. [PMID: 28192758]
  • Aurélie Berthet, Mariangela De Cesare, Bernard Favrat, Frank Sporkert, Marc Augsburger, Aurélien Thomas, Christian Giroud. A systematic review of passive exposure to cannabis. Forensic science international. 2016 Dec; 269(?):97-112. doi: 10.1016/j.forsciint.2016.11.017. [PMID: 27883985]
  • Frederic Been, Christian Schneider, Frank Zobel, Olivier Delémont, Pierre Esseiva. Integrating environmental and self-report data to refine cannabis prevalence estimates in a major urban area of Switzerland. The International journal on drug policy. 2016 10; 36(?):33-42. doi: 10.1016/j.drugpo.2016.06.008. [PMID: 27455466]
  • Stephanie Hanisch, Alexander Paulke, Stefan W Toennes. Investigation of a recently detected 11-nor-9-carboxy-Δ(9)-tetrahydrocannabinol isomer: Studies on the degradation of 11-nor-9-carboxy-Δ(9)-tetrahydrocannabinol glucuronide. Journal of pharmaceutical and biomedical analysis. 2016 Sep; 129(?):294-298. doi: 10.1016/j.jpba.2016.07.019. [PMID: 27448313]
  • Erin L Karschner, Madeleine J Swortwood, Jussi Hirvonen, Robert S Goodwin, Wendy M Bosker, Johannes G Ramaekers, Marilyn A Huestis. Extended plasma cannabinoid excretion in chronic frequent cannabis smokers during sustained abstinence and correlation with psychomotor performance. Drug testing and analysis. 2016 Jul; 8(7):682-9. doi: 10.1002/dta.1825. [PMID: 26097154]
  • Kirsten Purschke, Sonja Heinl, Oliver Lerch, Freidoon Erdmann, Florian Veit. Development and validation of an automated liquid-liquid extraction GC/MS method for the determination of THC, 11-OH-THC, and free THC-carboxylic acid (THC-COOH) from blood serum. Analytical and bioanalytical chemistry. 2016 Jun; 408(16):4379-88. doi: 10.1007/s00216-016-9537-5. [PMID: 27116418]
  • Casey J Roulette, Mirdad Kazanji, Sébastien Breurec, Edward H Hagen. High prevalence of cannabis use among Aka foragers of the Congo Basin and its possible relationship to helminthiasis. American journal of human biology : the official journal of the Human Biology Council. 2016 Jan; 28(1):5-15. doi: 10.1002/ajhb.22740. [PMID: 26031406]
  • John Lewis, Anna Molnar, David Allsop, Jan Copeland, Shanlin Fu. Rapid elimination of Carboxy-THC in a cohort of chronic cannabis users. International journal of legal medicine. 2016 Jan; 130(1):147-52. doi: 10.1007/s00414-015-1241-z. [PMID: 26233612]
  • Paulien Meersseman, Simon Vanhoutte, Joris Van Damme, Lea Maes, Gilbert Lemmens, Gunter Heylens, Alain G Verstraete. A comparative study of screening instruments and biomarkers for the detection of cannabis use. Substance abuse. 2016; 37(1):176-80. doi: 10.1080/08897077.2015.1037947. [PMID: 26158599]
  • Nandkishor S Chindarkar, Hyung-Doo Park, Judith A Stone, Robert L Fitzgerald. Comparison of Different Time of Flight-Mass Spectrometry Modes for Small Molecule Quantitative Analysis. Journal of analytical toxicology. 2015 Nov; 39(9):675-85. doi: 10.1093/jat/bkv057. [PMID: 26239972]
  • Udo Bonnet, Thorsten Borda, Norbert Scherbaum, Michael Specka. Abstinence phenomena of chronic cannabis-addicts prospectively monitored during controlled inpatient detoxification (Part II): Psychiatric complaints and their relation to delta-9-tetrahydrocannabinol and its metabolites in serum. Drug and alcohol dependence. 2015 Oct; 155(?):302-6. doi: 10.1016/j.drugalcdep.2015.08.003. [PMID: 26298553]
  • Philip M Kemp, Patrick S Cardona, Arvind K Chaturvedi, John W Soper. Distribution of ∆(9)-Tetrahydrocannabinol and 11-Nor-9-Carboxy-∆(9)-Tetrahydrocannabinol Acid in Postmortem Biological Fluids and Tissues From Pilots Fatally Injured in Aviation Accidents. Journal of forensic sciences. 2015 Jul; 60(4):942-9. doi: 10.1111/1556-4029.12751. [PMID: 25800046]
  • Stefan W Toennes, Stephanie Hanisch, Werner Pogoda, Cora Wunder, Alexander Paulke. Pitfall in cannabinoid analysis--detection of a previously unrecognized interfering compound in human serum. Analytical and bioanalytical chemistry. 2015 Jan; 407(2):463-70. doi: 10.1007/s00216-014-8301-y. [PMID: 25391576]
  • Andreas Austgulen Westin, George Mjønes, Ola Burchardt, Ole Martin Fuskevåg, Lars Slørdal. Can physical exercise or food deprivation cause release of fat-stored cannabinoids?. Basic & clinical pharmacology & toxicology. 2014 Nov; 115(5):467-71. doi: 10.1111/bcpt.12235. [PMID: 24674455]
  • Kang Mi Lee, Ho Jun Kim, Junghyun Son, Ju-Hyung Park, Oh-Seung Kwon, Jaeick Lee. Simple quantitation of formoterol and 11-nor-Δ(9)-tetrahydrocannabinol-9-carboxylic acid in human urine by liquid chromatography-tandem mass spectrometry in doping control. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2014 Sep; 967(?):8-12. doi: 10.1016/j.jchromb.2014.07.009. [PMID: 25063922]
  • E Lendoiro, A de Castro, H Fernández-Vega, M C Cela-Pérez, J M López-Vilariño, M V González-Rodríguez, A Cruz, M López-Rivadulla. Molecularly imprinted polymer for selective determination of Δ9-tetrahydrocannabinol and 11-nor-Δ9-tetrahydrocannabinol carboxylic acid using LC-MS/MS in urine and oral fluid. Analytical and bioanalytical chemistry. 2014 Jun; 406(15):3589-97. doi: 10.1007/s00216-013-7599-1. [PMID: 24429976]
  • Marc J Rumpler. Quantitative analysis of 11-nor-9-carboxy-tetrahydrocannbinol (THC-COOH) in urine by LC-MS/MS following a simple filtration. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2014 Apr; 957(?):77-83. doi: 10.1016/j.jchromb.2014.02.056. [PMID: 24657414]
  • Nathalie A Desrosiers, Sarah K Himes, Karl B Scheidweiler, Marta Concheiro-Guisan, David A Gorelick, Marilyn A Huestis. Phase I and II cannabinoid disposition in blood and plasma of occasional and frequent smokers following controlled smoked cannabis. Clinical chemistry. 2014 Apr; 60(4):631-43. doi: 10.1373/clinchem.2013.216507. [PMID: 24563491]
  • Jin Young Kim, Woonyong Kwon, Hee Seung Kim, Sungill Suh, Moon Kyo In. Estimation of measurement uncertainty for the quantification of 11-nor-delta 9-tetrahydrocannabinol-9-carboxylic acid and its glucuronide in urine using liquid chromatography-tandem mass spectrometry. Journal of analytical toxicology. 2014 Apr; 38(3):164-70. doi: 10.1093/jat/bku008. [PMID: 24519562]
  • Allan J Barnes, Karl B Scheidweiler, Marilyn A Huestis. Quantification of 11-nor-9-carboxy-δ9-tetrahydrocannabinol in human oral fluid by gas chromatography-tandem mass spectrometry. Therapeutic drug monitoring. 2014 Apr; 36(2):225-33. doi: 10.1097/01.ftd.0000443071.30662.01. [PMID: 24622724]
  • Meejung Park, Jihyun Kim, Yuran Park, Sanghwan In, Eunmi Kim, Yonghoon Park. Quantitative determination of 11-nor-9-carboxy-tetrahydrocannabinol in hair by column switching LC-ESI-MS(3). Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2014 Feb; 947-948(?):179-85. doi: 10.1016/j.jchromb.2013.12.036. [PMID: 24434565]
  • Nathalie A Desrosiers, Dayong Lee, Karl B Scheidweiler, Marta Concheiro-Guisan, David A Gorelick, Marilyn A Huestis. In vitro stability of free and glucuronidated cannabinoids in urine following controlled smoked cannabis. Analytical and bioanalytical chemistry. 2014 Jan; 406(3):785-92. doi: 10.1007/s00216-013-7524-7. [PMID: 24292435]
  • Iria González-Mariño, Isaac Rodríguez, José Benito Quintana, Rafael Cela. Investigation of the transformation of 11-nor-9-carboxy-Δ(9)-tetrahydrocannabinol during water chlorination by liquid chromatography-quadrupole-time-of-flight-mass spectrometry. Journal of hazardous materials. 2013 Oct; 261(?):628-36. doi: 10.1016/j.jhazmat.2013.08.006. [PMID: 23995559]
  • Marina Nestić, Sandra Babić, Dragana Mutavdžić Pavlović, Davorka Sutlović. Molecularly imprinted solid phase extraction for simultaneous determination of Δ9-tetrahydrocannabinol and its main metabolites by gas chromatography-mass spectrometry in urine samples. Forensic science international. 2013 Sep; 231(1-3):317-24. doi: 10.1016/j.forsciint.2013.06.009. [PMID: 23890655]
  • Karl B Scheidweiler, David M Schwope, Erin L Karschner, Nathalie A Desrosiers, David A Gorelick, Marilyn A Huestis. In vitro stability of free and glucuronidated cannabinoids in blood and plasma following controlled smoked cannabis. Clinical chemistry. 2013 Jul; 59(7):1108-17. doi: 10.1373/clinchem.2012.201467. [PMID: 23519966]
  • Mateus M Bergamaschi, Erin L Karschner, Robert S Goodwin, Karl B Scheidweiler, Jussi Hirvonen, Regina H C Queiroz, Marilyn A Huestis. Impact of prolonged cannabinoid excretion in chronic daily cannabis smokers' blood on per se drugged driving laws. Clinical chemistry. 2013 Mar; 59(3):519-26. doi: 10.1373/clinchem.2012.195503. [PMID: 23449702]
  • Marie Fabritius, Christian Staub, Patrice Mangin, Christian Giroud. Distribution of free and conjugated cannabinoids in human bile samples. Forensic science international. 2012 Nov; 223(1-3):114-8. doi: 10.1016/j.forsciint.2012.08.013. [PMID: 22980143]
  • Karl B Scheidweiler, Nathalie A Desrosiers, Marilyn A Huestis. Simultaneous quantification of free and glucuronidated cannabinoids in human urine by liquid chromatography tandem mass spectrometry. Clinica chimica acta; international journal of clinical chemistry. 2012 Nov; 413(23-24):1839-47. doi: 10.1016/j.cca.2012.06.034. [PMID: 22771478]
  • Yoshiaki Iwamuro, Reiko Iio-Ishimaru, Satoshi Chinaka, Nariaki Takayama, Kazuichi Hayakawa. Analysis of 11-nor-Δ9 -tetrahydrocannabinol-9-carboxylic acid and its glucuronide in urine by capillary electrophoresis/mass spectrometry. Biomedical chromatography : BMC. 2012 Nov; 26(11):1452-6. doi: 10.1002/bmc.2719. [PMID: 22419476]
  • Erin L Karschner, David M Schwope, Eugene W Schwilke, Robert S Goodwin, Deanna L Kelly, David A Gorelick, Marilyn A Huestis. Predictive model accuracy in estimating last Δ9-tetrahydrocannabinol (THC) intake from plasma and whole blood cannabinoid concentrations in chronic, daily cannabis smokers administered subchronic oral THC. Drug and alcohol dependence. 2012 Oct; 125(3):313-9. doi: 10.1016/j.drugalcdep.2012.03.005. [PMID: 22464363]
  • Yannick Lecompte, Martine Perrin, Sophie Salle, Olivier Roussel. Impact of lowering confirmatory test cutoff value in pre-enlistment urine cannabinoids screening: about five years' experience in the French Gendarmerie. Journal of analytical toxicology. 2012 Oct; 36(8):569-74. doi: 10.1093/jat/bks067. [PMID: 22933660]
  • David M Schwope, Wendy M Bosker, Johannes G Ramaekers, David A Gorelick, Marilyn A Huestis. Psychomotor performance, subjective and physiological effects and whole blood Δ⁹-tetrahydrocannabinol concentrations in heavy, chronic cannabis smokers following acute smoked cannabis. Journal of analytical toxicology. 2012 Jul; 36(6):405-12. doi: 10.1093/jat/bks044. [PMID: 22589524]
  • Carsten Rygaard Hjorthøj, Allan Fohlmann, Anne-Mette Larsen, Mikkel Arendt, Merete Nordentoft. Correlations and agreement between delta-9-tetrahydrocannabinol (THC) in blood plasma and timeline follow-back (TLFB)-assisted self-reported use of cannabis of patients with cannabis use disorder and psychotic illness attending the CapOpus randomized clinical trial. Addiction (Abingdon, England). 2012 Jun; 107(6):1123-31. doi: 10.1111/j.1360-0443.2011.03757.x. [PMID: 22151583]
  • Markus Joerger, Justin Wilkins, Stefania Fagagnini, Reto Baldinger, Rudolf Brenneisen, Ursula Schneider, Bea Goldman, Markus Weber. Single-dose pharmacokinetics and tolerability of oral delta-9- tetrahydrocannabinol in patients with amyotrophic lateral sclerosis. Drug metabolism letters. 2012 Jun; 6(2):102-8. doi: NULL. [PMID: 22594565]
  • Vanessa de M Prata, Elissandro S Emídio, Haroldo S Dorea. New catalytic ultrasound method for derivatization of 11-nor-Δ9-tetrahydrocannabinol-9-carboxylic acid in urine, with analysis by GC-MS/MS. Analytical and bioanalytical chemistry. 2012 Apr; 403(2):625-32. doi: 10.1007/s00216-012-5827-8. [PMID: 22367244]
  • Gabriele Zanchetti, Ivan Floris, Alberto Piccinotti, Silvia Tameni, Aldo Polettini. Rapid and robust confirmation and quantification of 11-nor-Δ9-tetrahydrocannabinol-9-carboxylic acid (THC-COOH) in urine by column switching LC-MS-MS analysis. Journal of mass spectrometry : JMS. 2012 Jan; 47(1):124-30. doi: 10.1002/jms.2034. [PMID: 22282098]
  • Garry Milman, David M Schwope, Eugene W Schwilke, William D Darwin, Deanna L Kelly, Robert S Goodwin, David A Gorelick, Marilyn A Huestis. Oral fluid and plasma cannabinoid ratios after around-the-clock controlled oral Δ(9)-tetrahydrocannabinol administration. Clinical chemistry. 2011 Nov; 57(11):1597-606. doi: 10.1373/clinchem.2011.169490. [PMID: 21875944]
  • Michael G Holland, David M Schwope, Robert Stoppacher, Shane B Gillen, Marilyn A Huestis. Postmortem redistribution of Δ9-tetrahydrocannabinol (THC), 11-hydroxy-THC (11-OH-THC), and 11-nor-9-carboxy-THC (THCCOOH). Forensic science international. 2011 Oct; 212(1-3):247-51. doi: 10.1016/j.forsciint.2011.06.028. [PMID: 21764230]
  • Eunyoung Han, Hwakyung Choi, Sangki Lee, Heesun Chung, Joon Myong Song. A comparative study on the concentrations of 11-nor-Δ9-tetrahydrocannabinol-9-carboxylic acid (THCCOOH) in head and pubic hair. Forensic science international. 2011 Oct; 212(1-3):238-41. doi: 10.1016/j.forsciint.2011.06.026. [PMID: 21802874]
  • David M Schwope, Erin L Karschner, David A Gorelick, Marilyn A Huestis. Identification of recent cannabis use: whole-blood and plasma free and glucuronidated cannabinoid pharmacokinetics following controlled smoked cannabis administration. Clinical chemistry. 2011 Oct; 57(10):1406-14. doi: 10.1373/clinchem.2011.171777. [PMID: 21836075]
  • Eunyoung Han, Yonghoon Park, Eunmi Kim, Sangwhan In, Wonkyung Yang, Sooyeun Lee, Hwakyung Choi, Sangki Lee, Heesun Chung, Joon Myong Song. Simultaneous analysis of Δ(9)-tetrahydrocannabinol and 11-nor-9-carboxy-tetrahydrocannabinol in hair without different sample preparation and derivatization by gas chromatography-tandem mass spectrometry. Journal of pharmaceutical and biomedical analysis. 2011 Jul; 55(5):1096-103. doi: 10.1016/j.jpba.2011.03.020. [PMID: 21497038]
  • Eunyoung Han, Hwakyung Choi, Sangki Lee, Heesun Chung, Joon Myong Song. A study on the concentrations of 11-nor-Δ(9)-tetrahydrocannabinol-9-carboxylic acid (THCCOOH) in hair root and whole hair. Forensic science international. 2011 Jul; 210(1-3):201-5. doi: 10.1016/j.forsciint.2011.03.017. [PMID: 21497466]
  • Matteo Conti, Valeria Tazzari, Maria Bertona, Maura Brambilla, Paolo Brambilla. Surface-activated chemical ionization combined with electrospray ionization and mass spectrometry for the analysis of cannabinoids in biological samples. Part I: analysis of 11-nor-9-carboxytetrahydro-cannabinol. Rapid communications in mass spectrometry : RCM. 2011 Jun; 25(11):1552-8. doi: 10.1002/rcm.5029. [PMID: 21594929]
  • Peter Van Eenoo, Wim Van Gansbeke, Nik De Brabanter, Koen Deventer, Frans T Delbeke. A fast, comprehensive screening method for doping agents in urine by gas chromatography-triple quadrupole mass spectrometry. Journal of chromatography. A. 2011 May; 1218(21):3306-16. doi: 10.1016/j.chroma.2010.09.082. [PMID: 20970803]
  • Zoran Mihailovic, Slobodan Savic, Irina Damjanjuk, Aleksandar Stanojevic, Miroslav Milosevic. A case of a fatal Himalayan black bear attack in the zoo. Journal of forensic sciences. 2011 May; 56(3):806-9. doi: 10.1111/j.1556-4029.2011.01721.x. [PMID: 21361947]
  • Andreas Austgulen Westin. [Cannabis and urine samples]. Tidsskrift for den Norske laegeforening : tidsskrift for praktisk medicin, ny raekke. 2011 Mar; 131(6):577-80. doi: 10.4045/tidsskr.09.1111. [PMID: 21423309]
  • Eugene W Schwilke, Rod G Gullberg, William D Darwin, C Nora Chiang, Jean Lud Cadet, David A Gorelick, Harrison G Pope, Marilyn A Huestis. Differentiating new cannabis use from residual urinary cannabinoid excretion in chronic, daily cannabis users. Addiction (Abingdon, England). 2011 Mar; 106(3):499-506. doi: 10.1111/j.1360-0443.2010.03228.x. [PMID: 21134021]
  • H El Marroun, H Tiemeier, V W V Jaddoe, A Hofman, F C Verhulst, W van den Brink, A C Huizink. Agreement between maternal cannabis use during pregnancy according to self-report and urinalysis in a population-based cohort: the Generation R Study. European addiction research. 2011; 17(1):37-43. doi: 10.1159/000320550. [PMID: 20975275]
  • Erin L Karschner, W David Darwin, Robert S Goodwin, Stephen Wright, Marilyn A Huestis. Plasma cannabinoid pharmacokinetics following controlled oral delta9-tetrahydrocannabinol and oromucosal cannabis extract administration. Clinical chemistry. 2011 Jan; 57(1):66-75. doi: 10.1373/clinchem.2010.152439. [PMID: 21078841]
  • Peter R Stout, Nichole D Bynum, Cynthia M Lewallen, John M Mitchell, Michael R Baylor, Jeri D Ropero-Miller. A comparison of the validity of gas chromatography-mass spectrometry and liquid chromatography-tandem mass spectrometry analysis of urine samples II: amphetamine, methamphetamine, (±)-3,4-methylenedioxyamphetamine, (±)-3,4-methylenedioxymethamphetamine, (±)-3,4-methylenedioxyethylamphetamine, phencyclidine, and (±)-11-nor-9-carboxy-Δ⁹-tetrahydrocannabinol. Journal of analytical toxicology. 2010 Oct; 34(8):430-43. doi: 10.1093/jat/34.8.430. [PMID: 21819787]
  • Erin L Karschner, Allan J Barnes, Ross H Lowe, Karl B Scheidweiler, Marilyn A Huestis. Validation of a two-dimensional gas chromatography mass spectrometry method for the simultaneous quantification of cannabidiol, Delta(9)-tetrahydrocannabinol (THC), 11-hydroxy-THC, and 11-nor-9-carboxy-THC in plasma. Analytical and bioanalytical chemistry. 2010 May; 397(2):603-11. doi: 10.1007/s00216-010-3599-6. [PMID: 20306180]
  • J Röhrich, I Schimmel, S Zörntlein, J Becker, S Drobnik, T Kaufmann, V Kuntz, R Urban. Concentrations of delta9-tetrahydrocannabinol and 11-nor-9-carboxytetrahydrocannabinol in blood and urine after passive exposure to Cannabis smoke in a coffee shop. Journal of analytical toxicology. 2010 May; 34(4):196-203. doi: 10.1093/jat/34.4.196. [PMID: 20465865]
  • C Chebbah, O J Pozo, K Deventer, P Van Eenoo, F T Delbeke. Direct quantification of 11-nor-Delta(9)-tetrahydrocannabinol-9-carboxylic acid in urine by liquid chromatography/tandem mass spectrometry in relation to doping control analysis. Rapid communications in mass spectrometry : RCM. 2010 Apr; 24(8):1133-41. doi: 10.1002/rcm.4499. [PMID: 20301101]
  • Dennis V Canfield, Kurt M Dubowski, James E Whinnery, Russell J Lewis, Roxane M Ritter, Paul B Rogers. Increased cannabinoids concentrations found in specimens from fatal aviation accidents between 1997 and 2006. Forensic science international. 2010 Apr; 197(1-3):85-8. doi: 10.1016/j.forsciint.2009.12.060. [PMID: 20074884]
  • Thomas Nadulski, Simona Bleeck, Johannes Schräder, Wolf-Rainer Bork, Fritz Pragst. 11-nor-Delta9-tetrahydrocannabinol-9-carboxylic acid ethyl ester (THC-COOEt): unsuccessful search for a marker of combined cannabis and alcohol consumption. Forensic science international. 2010 Mar; 196(1-3):78-84. doi: 10.1016/j.forsciint.2009.12.026. [PMID: 20074877]
  • Volker Auwärter, Ariane Wohlfarth, Jessica Traber, Detlef Thieme, Wolfgang Weinmann. Hair analysis for Delta9-tetrahydrocannabinolic acid A--new insights into the mechanism of drug incorporation of cannabinoids into hair. Forensic science international. 2010 Mar; 196(1-3):10-3. doi: 10.1016/j.forsciint.2009.12.023. [PMID: 20129747]
  • Anna Minkkilä, Susanna Saario, Tapio Nevalainen. Discovery and development of endocannabinoid-hydrolyzing enzyme inhibitors. Current topics in medicinal chemistry. 2010; 10(8):828-58. doi: 10.2174/156802610791164238. [PMID: 20370710]
  • C Clinton Frazee, Michael Kiscoan, Uttam Garg. Quantitation of total 11-nor-9-carboxy-delta 9-tetrahydrocannabinol in urine and blood using gas chromatography-mass spectrometry (GC-MS). Methods in molecular biology (Clifton, N.J.). 2010; 603(?):137-44. doi: 10.1007/978-1-60761-459-3_13. [PMID: 20077066]
  • Eugene W Schwilke, David M Schwope, Erin L Karschner, Ross H Lowe, William D Darwin, Deanna L Kelly, Robert S Goodwin, David A Gorelick, Marilyn A Huestis. Delta9-tetrahydrocannabinol (THC), 11-hydroxy-THC, and 11-nor-9-carboxy-THC plasma pharmacokinetics during and after continuous high-dose oral THC. Clinical chemistry. 2009 Dec; 55(12):2180-9. doi: 10.1373/clinchem.2008.122119. [PMID: 19833841]
  • Andreas A Westin, Marilyn A Huestis, Kjell Aarstad, Olav Spigset. Short communication: Urinary excretion of 11-nor-9-carboxy-Delta(9)-tetrahydrocannabinol in a pregnant woman following heavy, chronic cannabis use. Journal of analytical toxicology. 2009 Nov; 33(9):610-4. doi: 10.1093/jat/33.9.610. [PMID: 20040136]
  • P V Robandt, K L Klette, M Sibum. Automated solid-phase extraction-liquid chromatography-tandem mass spectrometry analysis of 11-nor-Delta9-tetrahydrocannabinol-9-carboxylic acid in human urine specimens: application to a high-throughput urine analysis laboratory. Journal of analytical toxicology. 2009 Oct; 33(8):456-60. doi: 10.1093/jat/33.8.456. [PMID: 19874652]
  • Erin L Karschner, Eugene W Schwilke, Ross H Lowe, W David Darwin, Ronald I Herning, Jean Lud Cadet, Marilyn A Huestis. Implications of plasma Delta9-tetrahydrocannabinol, 11-hydroxy-THC, and 11-nor-9-carboxy-THC concentrations in chronic cannabis smokers. Journal of analytical toxicology. 2009 Oct; 33(8):469-77. doi: 10.1093/jat/33.8.469. [PMID: 19874654]
  • Elizabeth Kiely, C Jeff Lee, Laureen Marinetti. A fatality from an oral ingestion of methamphetamine. Journal of analytical toxicology. 2009 Oct; 33(8):557-60. doi: 10.1093/jat/33.8.557. [PMID: 19874669]
  • NULL. Inadvertent ingestion of marijuana - Los Angeles, California, 2009. MMWR. Morbidity and mortality weekly report. 2009 Sep; 58(34):947-50. doi: NULL. [PMID: 19730407]
  • Isvett Josefina Flores-Sanchez, Jaroslav Pec, Junni Fei, Young Hae Choi, Jaroslav Dusek, Robert Verpoorte. Elicitation studies in cell suspension cultures of Cannabis sativa L. Journal of biotechnology. 2009 Aug; 143(2):157-68. doi: 10.1016/j.jbiotec.2009.05.006. [PMID: 19500620]
  • María del Mar Ramírez Fernández, Sarah M R Wille, Nele Samyn, Michelle Wood, Manuel López-Rivadulla, Gert De Boeck. On-line solid-phase extraction combined with liquid chromatography-tandem mass spectrometry for high throughput analysis of 11-nor-Delta9-tetrahydrocannabinol-9-carboxylic acid in urine. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2009 Jul; 877(22):2153-7. doi: 10.1016/j.jchromb.2009.04.047. [PMID: 19535306]
  • Eugene W Schwilke, Erin L Karschner, Ross H Lowe, Ann M Gordon, Jean Lud Cadet, Ronald I Herning, Marilyn A Huestis. Intra- and intersubject whole blood/plasma cannabinoid ratios determined by 2-dimensional, electron impact GC-MS with cryofocusing. Clinical chemistry. 2009 Jun; 55(6):1188-95. doi: 10.1373/clinchem.2008.114405. [PMID: 19264857]
  • Michael L Smith, Allan J Barnes, Marilyn A Huestis. Identifying new cannabis use with urine creatinine-normalized THCCOOH concentrations and time intervals between specimen collections. Journal of analytical toxicology. 2009 May; 33(4):185-9. doi: 10.1093/jat/33.4.185. [PMID: 19470219]
  • M Sergi, E Bafile, D Compagnone, R Curini, G D'Ascenzo, F S Romolo. Multiclass analysis of illicit drugs in plasma and oral fluids by LC-MS/MS. Analytical and bioanalytical chemistry. 2009 Jan; 393(2):709-18. doi: 10.1007/s00216-008-2456-3. [PMID: 18982317]
  • Massimiliano Aragona, Emanuela Onesti, Valentina Tomassini, Antonella Conte, Shiva Gupta, Francesca Gilio, Patrizia Pantano, Carlo Pozzilli, Maurizio Inghilleri. Psychopathological and cognitive effects of therapeutic cannabinoids in multiple sclerosis: a double-blind, placebo controlled, crossover study. Clinical neuropharmacology. 2009 Jan; 32(1):41-7. doi: 10.1097/wnf.0b013e3181633497. [PMID: 18978501]
  • Claudine C Hunault, Tjeert T Mensinga, Irma de Vries, Hermien H Kelholt-Dijkman, Jani Hoek, Maaike Kruidenier, Marianne E C Leenders, Jan Meulenbelt. Delta-9-tetrahydrocannabinol (THC) serum concentrations and pharmacological effects in males after smoking a combination of tobacco and cannabis containing up to 69 mg THC. Psychopharmacology. 2008 Dec; 201(2):171-81. doi: 10.1007/s00213-008-1260-2. [PMID: 18695931]
  • Jennifer L Schroeder, Laureen J Marinetti, Roy K Smith, William E Brewer, Brandi L Clelland, Stephen L Morgan. The analysis of delta9-tetrahydrocannabinol and metabolite in whole blood and 11-nor-delta9-tetrahydrocannabinol-9-carboxylic acid in urine using disposable pipette extraction with confirmation and quantification by gas chromatography-mass spectrometry. Journal of analytical toxicology. 2008 Oct; 32(8):659-66. doi: 10.1093/jat/32.8.659. [PMID: 19007518]
  • Robert S Goodwin, William D Darwin, C Nora Chiang, Ming Shih, Shou-Hua Li, Marilyn A Huestis. Urinary elimination of 11-nor-9-carboxy-delta9-tetrahydrocannnabinol in cannabis users during continuously monitored abstinence. Journal of analytical toxicology. 2008 Oct; 32(8):562-9. doi: 10.1093/jat/32.8.562. [PMID: 19007504]
  • Nikolai Stephanson, Martin Josefsson, Robert Kronstrand, Olof Beck. Accurate identification and quantification of 11-nor-delta(9)-tetrahydrocannabinol-9-carboxylic acid in urine drug testing: evaluation of a direct high efficiency liquid chromatographic-mass spectrometric method. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2008 Aug; 871(1):101-8. doi: 10.1016/j.jchromb.2008.06.047. [PMID: 18620911]
  • Scott J Larson, Justin M Holler, Joseph Magluilo, Christopher S Dunkley, Aaron Jacobs. Papain adulteration in 11-nor-Delta9-tetrahydrocannabinol- 9-carboxylic acid-positive urine samples. Journal of analytical toxicology. 2008 Jul; 32(6):438-43. doi: 10.1093/jat/32.6.438. [PMID: 18652751]
  • Laura Mercolini, Alessandro Musenga, Irene Comin, Cesare Baccini, Matteo Conti, Maria Augusta Raggi. Determination of plasma and urine levels of Delta9-tetrahydrocannabinol and its main metabolite by liquid chromatography after solid-phase extraction. Journal of pharmaceutical and biomedical analysis. 2008 May; 47(1):156-63. doi: 10.1016/j.jpba.2007.12.023. [PMID: 18242913]
  • Gisela Skopp, Lucia Pötsch. Cannabinoid concentrations in spot serum samples 24-48 hours after discontinuation of cannabis smoking. Journal of analytical toxicology. 2008 Mar; 32(2):160-4. doi: 10.1093/jat/32.2.160. [PMID: 18334100]
  • M L Holland, D T T Lau, J D Allen, J C Arnold. The multidrug transporter ABCG2 (BCRP) is inhibited by plant-derived cannabinoids. British journal of pharmacology. 2007 Nov; 152(5):815-24. doi: 10.1038/sj.bjp.0707467. [PMID: 17906686]
  • Tsadik T Abraham, Ross H Lowe, Stephane O Pirnay, William D Darwin, Marilyn A Huestis. Simultaneous GC-EI-MS determination of Delta9-tetrahydrocannabinol, 11-hydroxy-Delta9-tetrahydrocannabinol, and 11-nor-9-carboxy-Delta9-tetrahydrocannabinol in human urine following tandem enzyme-alkaline hydrolysis. Journal of analytical toxicology. 2007 Oct; 31(8):477-85. doi: 10.1093/jat/31.8.477. [PMID: 17988462]
  • Ross H Lowe, Erin L Karschner, Eugene W Schwilke, Allan J Barnes, Marilyn A Huestis. Simultaneous quantification of Delta9-tetrahydrocannabinol, 11-hydroxy-Delta9-tetrahydrocannabinol, and 11-nor-Delta9-tetrahydrocannabinol-9-carboxylic acid in human plasma using two-dimensional gas chromatography, cryofocusing, and electron impact-mass spectrometry. Journal of chromatography. A. 2007 Sep; 1163(1-2):318-27. doi: 10.1016/j.chroma.2007.06.069. [PMID: 17640656]
  • A Glaz-Sandberg, L Dietz, H Nguyen, H Oberwittler, Rolf Aderjan, Gerd Mikus. Pharmacokinetics of 11-nor-9-carboxy-Delta(9)-tetrahydrocannabinol (CTHC) after intravenous administration of CTHC in healthy human subjects. Clinical pharmacology and therapeutics. 2007 Jul; 82(1):63-9. doi: 10.1038/sj.clpt.6100199. [PMID: 17410118]