11-hydroxy-Delta(9)-tetrahydrocannabinol (BioDeep_00000055157)

 

Secondary id: BioDeep_00000017948, BioDeep_00001874469

human metabolite


代谢物信息卡片


(6AR,10ar)-6a,7,8,10a-tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl-6H-dibenzo[b,D]pyran-9-methanol

化学式: C21H30O3 (330.21948299999997)
中文名称: 11-羟基-Δ9-四氢大麻酚
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)CO)O
InChI: InChI=1S/C21H30O3/c1-4-5-6-7-14-11-18(23)20-16-10-15(13-22)8-9-17(16)21(2,3)24-19(20)12-14/h10-12,16-17,22-23H,4-9,13H2,1-3H3/t16-,17-/m1/s1

描述信息

11-hydroxy-Delta(9)-tetrahydrocannabinol, also known as (-)-11-Hydroxy-Delta(9)-THC or 11-OH-THC, 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-hydroxy-Delta(9)-tetrahydrocannabinol is considered to be practically insoluble (in water) and acidic

同义名列表

16 个代谢物同义名

(6AR,10ar)-6a,7,8,10a-tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl-6H-dibenzo[b,D]pyran-9-methanol; (6aR,10aR)-9-(hydroxymethyl)-6,6-dimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromen-1-ol; (6aR,10aR)-9-(hydroxymethyl)-6,6-dimethyl-3-pentyl-6aH,7H,8H,10aH-benzo[c]isochromen-1-ol; 11-Hydroxy-delta(9)-tetrahydrocannabinol, (6ar-trans)-isomer; 11-Hydroxy-delta(9)-tetrahydrocannabinol, (trans)-isomer; (-)-11-Hydroxy-Delta(9)-tetrahydrocannabinol; (-)-11-Hydroxy-δ(9)-tetrahydrocannabinol; 11-Hydroxy-delta(9)-tetrahydrocannabinol; 7-Hydroxy-delta(1)-tetrahydrocannabinol; 11-Hydroxy-δ(9)-tetrahydrocannabinol; 11-Hydroxytetrahydrocannabinol; (-)-11-Hydroxy-Delta(9)-THC; (+/-)-11-HYDROXY-DELTA9-THC; 11-Hydroxy-delta(9)-THC; (-)-11-Hydroxy-δ(9)-THC; 11-OH-THC



数据库引用编号

8 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

0 个相关的代谢反应过程信息。

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WikiPathways(0)

Plant Reactome(0)

INOH(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。



文献列表

  • Gabriela I Patilea-Vrana, Jashvant D Unadkat. Development and Verification of a Linked Δ 9-THC/11-OH-THC Physiologically Based Pharmacokinetic Model in Healthy, Nonpregnant Population and Extrapolation to Pregnant Women. Drug metabolism and disposition: the biological fate of chemicals. 2021 07; 49(7):509-520. doi: 10.1124/dmd.120.000322. [PMID: 33952608]
  • Angela Gasse, Marielle Vennemann, Helga Köhler, Jennifer Schürenkamp. Toxicogenetic analysis of Δ9-THC-metabolizing enzymes. International journal of legal medicine. 2020 Nov; 134(6):2095-2103. doi: 10.1007/s00414-020-02380-3. [PMID: 32712703]
  • Christoph Hassenberg, Florian Clausen, Grete Hoffmann, Armido Studer, 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. 2020 Nov; 134(6):2105-2119. doi: 10.1007/s00414-020-02387-w. [PMID: 32808050]
  • Charles Guidet, Matthieu Gregoire, Alexiane Le Dreau, Benedicte Vrignaud, Guillaume Deslandes, Catherine Monteil-Ganière. Cannabis intoxication after accidental ingestion in infants: urine and plasma concentrations of Δ-9-tetrahydrocannabinol (THC), THC-COOH and 11-OH-THC in 10 patients. Clinical toxicology (Philadelphia, Pa.). 2020 05; 58(5):421-423. doi: 10.1080/15563650.2019.1655569. [PMID: 31441354]
  • William R Wolowich, Robert Greif, Maren Kleine-Brueggeney, Werner Bernhard, Lorenz Theiler. Minimal Physiologically Based Pharmacokinetic Model of Intravenously and Orally Administered Delta-9-Tetrahydrocannabinol in Healthy Volunteers. European journal of drug metabolism and pharmacokinetics. 2019 Oct; 44(5):691-711. doi: 10.1007/s13318-019-00559-7. [PMID: 31114948]
  • Gabriela I Patilea-Vrana, Olena Anoshchenko, Jashvant D Unadkat. Hepatic Enzymes Relevant to the Disposition of (-)-∆9-Tetrahydrocannabinol (THC) and Its Psychoactive Metabolite, 11-OH-THC. Drug metabolism and disposition: the biological fate of chemicals. 2019 03; 47(3):249-256. doi: 10.1124/dmd.118.085548. [PMID: 30567877]
  • Julia Sophie Schneider, Angela Gasse, Marianne Schürenkamp, Ursula Sibbing, Sabrina Banken, Heidi Pfeiffer, Jennifer Schürenkamp, Marielle Vennemann. Multiplex analysis of genetic polymorphisms within UGT1A9, a gene involved in phase II of Δ9-THC metabolism. International journal of legal medicine. 2019 Mar; 133(2):365-372. doi: 10.1007/s00414-018-1919-0. [PMID: 30191314]
  • Michael Kraemer, Sebastian Broecker, Bernd W K Diehl, Burkhard Madea, Cornelius Hess. 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. Forensic science international. 2019 Jan; 294(?):86-95. doi: 10.1016/j.forsciint.2018.11.005. [PMID: 30481665]
  • 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]
  • 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]
  • 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]
  • 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]
  • 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]
  • Rebecca L Hartman, Timothy L Brown, Gary Milavetz, Andrew Spurgin, David A Gorelick, Gary Gaffney, Marilyn A Huestis. Controlled Cannabis Vaporizer Administration: Blood and Plasma Cannabinoids with and without Alcohol. Clinical chemistry. 2015 Jun; 61(6):850-69. doi: 10.1373/clinchem.2015.238287. [PMID: 26019183]
  • 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]
  • U Bonnet, M Specka, U Stratmann, R Ochwadt, N Scherbaum. Abstinence phenomena of chronic cannabis-addicts prospectively monitored during controlled inpatient detoxification: cannabis withdrawal syndrome and its correlation with delta-9-tetrahydrocannabinol and -metabolites in serum. Drug and alcohol dependence. 2014 Oct; 143(?):189-97. doi: 10.1016/j.drugalcdep.2014.07.027. [PMID: 25127704]
  • 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]
  • 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]
  • 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]
  • 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]
  • Gisela Skopp, Georg Schmitt. [Does a positive finding of tetrahydrocannabinol in the blood result from ingestion of Indian frankincense (Boswellia serrata)?]. Archiv fur Kriminologie. 2012 May; 229(5-6):154-62. doi: ". [PMID: 22834359]
  • 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]
  • 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]
  • David A Gorelick, Robert S Goodwin, Eugene Schwilke, David M Schwope, William D Darwin, Deanna L Kelly, Robert P McMahon, Fang Liu, Catherine Ortemann-Renon, Denis Bonnet, Marilyn A Huestis. Antagonist-elicited cannabis withdrawal in humans. Journal of clinical psychopharmacology. 2011 Oct; 31(5):603-12. doi: 10.1097/jcp.0b013e31822befc1. [PMID: 21869692]
  • 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]
  • 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]
  • Stefan W Toennes, Jörg Röhrich, Cora Wunder. [Interpretation of blood analysis data found after passive exposure to cannabis]. Archiv fur Kriminologie. 2010 Mar; 225(3-4):90-8. doi: NULL. [PMID: 20506708]
  • 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]
  • Ross H Lowe, Tsadik T Abraham, William D Darwin, Ronald Herning, Jean Lud Cadet, Marilyn A Huestis. Extended urinary Delta9-tetrahydrocannabinol excretion in chronic cannabis users precludes use as a biomarker of new drug exposure. Drug and alcohol dependence. 2009 Nov; 105(1-2):24-32. doi: 10.1016/j.drugalcdep.2009.05.027. [PMID: 19631478]
  • 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]
  • 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]
  • 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]
  • 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]
  • Robert S Goodwin, Richard A Gustafson, Allan Barnes, Wesenyalsh Nebro, Eric T Moolchan, Marilyn A Huestis. Delta(9)-tetrahydrocannabinol, 11-hydroxy-delta(9)-tetrahydrocannabinol and 11-nor-9-carboxy-delta(9)-tetrahydrocannabinol in human plasma after controlled oral administration of cannabinoids. Therapeutic drug monitoring. 2006 Aug; 28(4):545-51. doi: 10.1097/00007691-200608000-00010. [PMID: 16885723]
  • Thomas Nadulski, Frank Sporkert, Martin Schnelle, Andreas M Stadelmann, Patrik Roser, Tom Schefter, Fritz Pragst. Simultaneous and sensitive analysis of THC, 11-OH-THC, THC-COOH, CBD, and CBN by GC-MS in plasma after oral application of small doses of THC and cannabis extract. Journal of analytical toxicology. 2005 Nov; 29(8):782-9. doi: 10.1093/jat/29.8.782. [PMID: 16356335]
  • Rebecka Coles, Thomas T Clements, Gordon J Nelson, Gwendolyn A McMillin, Francis M Urry. Simultaneous analysis of the Delta9-THC metabolites 11-nor-9-carboxy-Delta9-THC and 11-hydroxy-Delta9-THC in meconium by GC-MS. Journal of analytical toxicology. 2005 Sep; 29(6):522-7. doi: 10.1093/jat/29.6.522. [PMID: 16168173]
  • David L Burrows, Andrea Nicolaides, Peter J Rice, Michelle Dufforc, David A Johnson, Kenneth E Ferslew. Papain: a novel urine adulterant. Journal of analytical toxicology. 2005 Jul; 29(5):275-95. doi: 10.1093/jat/29.5.275. [PMID: 16105251]
  • Maciej Kochanowski, Maria Kała. Tetrahydrocannabinols in clinical and forensic toxicology. Przeglad lekarski. 2005; 62(6):576-80. doi: NULL. [PMID: 16225128]
  • Dong-Liang Lin, Reng-Lang Lin. Distribution of 11-nor-9-carboxy-Delta9-tetrahydrocannabinol in traffic fatality cases. Journal of analytical toxicology. 2005 Jan; 29(1):58-61. doi: 10.1093/jat/29.1.58. [PMID: 15808015]
  • Albert D Fraser, David Worth. Urinary excretion profiles of 11-nor-9-carboxy-delta9-tetrahydrocannabinol and 11-hydroxy-delta9-THC: cannabinoid metabolites to creatinine ratio study IV. Forensic science international. 2004 Jul; 143(2-3):147-52. doi: 10.1016/j.forsciint.2004.02.034. [PMID: 15240035]
  • Barbora Maralikova, Wolfgang Weinmann. Simultaneous determination of Delta9-tetrahydrocannabinol, 11-hydroxy-Delta9-tetrahydrocannabinol and 11-nor-9-carboxy- Delta9-tetrahydrocannabinol in human plasma by high-performance liquid chromatography/tandem mass spectrometry. Journal of mass spectrometry : JMS. 2004 May; 39(5):526-31. doi: 10.1002/jms.616. [PMID: 15170748]
  • Richard A Gustafson, Eric T Moolchan, Allan Barnes, Barry Levine, Marilyn A Huestis. Validated method for the simultaneous determination of Delta 9-tetrahydrocannabinol (THC), 11-hydroxy-THC and 11-nor-9-carboxy-THC in human plasma using solid phase extraction and gas chromatography-mass spectrometry with positive chemical ionization. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2003 Dec; 798(1):145-54. doi: 10.1016/j.jchromb.2003.09.022. [PMID: 14630369]
  • Gisela Skopp, Barbara Richter, Lucia Pötsch. [Serum cannabinoid levels 24 to 48 hours after cannabis smoking]. Archiv fur Kriminologie. 2003 Sep; 212(3-4):83-95. doi: NULL. [PMID: 14639811]
  • C Giroud, A Ménétrey, M Augsburger, T Buclin, P Sanchez-Mazas, P Mangin. Delta(9)-THC, 11-OH-Delta(9)-THC and Delta(9)-THCCOOH plasma or serum to whole blood concentrations distribution ratios in blood samples taken from living and dead people. Forensic science international. 2001 Dec; 123(2-3):159-64. doi: 10.1016/s0379-0738(01)00538-2. [PMID: 11728742]
  • J E Manno, B R Manno, P M Kemp, D D Alford, I K Abukhalaf, M E McWilliams, F N Hagaman, M J Fitzgerald. Temporal indication of marijuana use can be estimated from plasma and urine concentrations of delta9-tetrahydrocannabinol, 11-hydroxy-delta9-tetrahydrocannabinol, and 11-nor-delta9-tetrahydrocannabinol-9-carboxylic acid. Journal of analytical toxicology. 2001 Oct; 25(7):538-49. doi: 10.1093/jat/25.7.538. [PMID: 11599597]
  • D Wilkins, H Haughey, E Cone, M Huestis, R Foltz, D Rollins. Quantitative analysis of THC, 11-OH-THC, and THCCOOH in human hair by negative ion chemical ionization mass spectrometry. Journal of analytical toxicology. 1995 Oct; 19(6):483-91. doi: 10.1093/jat/19.6.483. [PMID: 8926743]
  • C C Nelson, M D Fraser, J K Wilfahrt, R L Foltz. Gas chromatography/tandem mass spectrometry measurement of delta 9-tetrahydrocannabinol, naltrexone, and their active metabolites in plasma. Therapeutic drug monitoring. 1993 Dec; 15(6):557-62. doi: 10.1097/00007691-199312000-00019. [PMID: 8122294]
  • J Gerostamoulos, O H Drummer. Incidence of psychoactive cannabinoids in drivers killed in motor vehicle accidents. Journal of forensic sciences. 1993 May; 38(3):649-56. doi: NULL. [PMID: 8390554]
  • Y Nakahara, H Sekine, C E Cook. Confirmation of cannabis use. II. Determination of tetrahydrocannabinol metabolites in urine and plasma by HPLC with ECD. Journal of analytical toxicology. 1989 Jan; 13(1):22-4. doi: 10.1093/jat/13.1.22. [PMID: 2540383]
  • C J Hillard, R A Harris, A S Bloom. Effects of the cannabinoids on physical properties of brain membranes and phospholipid vesicles: fluorescence studies. The Journal of pharmacology and experimental therapeutics. 1985 Mar; 232(3):579-88. doi: NULL. [PMID: 2983062]
  • T W Klein, C A Newton, R Widen, H Friedman. The effect of delta-9-tetrahydrocannabinol and 11-hydroxy-delta-9-tetrahydrocannabinol on T-lymphocyte and B-lymphocyte mitogen responses. Journal of immunopharmacology. 1985; 7(4):451-66. doi: 10.3109/08923978509026487. [PMID: 3003204]
  • J R Johnson, T A Jennison, M A Peat, R L Foltz. Stability of delta 9-tetrahydrocannabinol (THC), 11-hydroxy-THC, and 11-nor-9-carboxy-THC in blood and plasma. Journal of analytical toxicology. 1984 Sep; 8(5):202-4. doi: 10.1093/jat/8.5.202. [PMID: 6094914]
  • R L Foltz, B J Hidy. Quantitative analysis for delta 9-THC, 11-hydroxy-delta 9-THC, and 9-carboxy-delta 9-THC in plasma using GC/CI-MS. NIDA research monograph. 1982; 42(?):99-118. doi: NULL. [PMID: 6294528]
  • J M Scherrmann, H Hoellinger, Nguyen-Hoang-Nam, L Boudet, J Pichon, Do-Cao-Thang. Detection and quantitation of cannabinoids in biological fluids: specificity and kinetics after smoking. Clinical toxicology. 1981 May; 18(5):565-71. doi: 10.3109/15563658108990283. [PMID: 6268351]
  • J H Greenberg, A Mellors, J C McGowan. Molar volume relationships and the specific inhibition of a synaptosomal enzyme by psychoactive cannabinoids. Journal of medicinal chemistry. 1978 Dec; 21(12):1208-12. doi: 10.1021/jm00210a007. [PMID: 722729]