(-)-11-nor-9-carboxy-delta9-thc (BioDeep_00000625035)
代谢物信息卡片
11-Nor-delta(9)-tetrahydrocannabinol-9-carboxylic acid
化学式: C21H28O4 (344.19874880000003)
中文名称: DEA限制
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)/t15-,16-/m0/s1
数据库引用编号
10 个数据库交叉引用编号
- ChEBI: CHEBI:183960
- ChEBI: CHEBI:77273
- PubChem: 44814488
- PubChem: 108207
- Metlin: METLIN96631
- ChEMBL: CHEMBL3263381
- CAS: 114028-39-6
- CAS: 104874-50-2
- CAS: 56354-06-4
- CAS: 64280-14-4
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
1 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
0 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
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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] - 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] - 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] - 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] - 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] - 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] - 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] - 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] - Lisa Dietz, Anna Glaz-Sandberg, Hang Nguyen, Gisela Skopp, Gerd Mikus, Rolf Aderjan. The urinary disposition of intravenously administered 11-nor-9-carboxy-delta-9-tetrahydrocannabinol in humans.
Therapeutic drug monitoring.
2007 Jun; 29(3):368-72. doi:
10.1097/ftd.0b013e31805ba6fd. [PMID: 17529896] - Grant D Beardsley, J Mark Christensen. Elimination of 11-nor-9-carboxy-delta-9-tetrahydrocannabinol when normalized to urinary creatinine.
Research communications in molecular pathology and pharmacology.
2007 200; 120-121(1-6):67-78. doi:
NULL. [PMID: 21469505] - Christine Moore, Wayne Ross, Cynthia Coulter, Laura Adams, Sumandeep Rana, Michael Vincent, James Soares. Detection of the marijuana metabolite 11-nor-Delta9-tetrahydrocannabinol-9-carboxylic acid in oral fluid specimens and its contribution to positive results in screening assays.
Journal of analytical toxicology.
2006 Sep; 30(7):413-8. doi:
10.1093/jat/30.7.413. [PMID: 16959132] - 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] - Marilyn A Huestis, Mahmoud Elsohly, Wesenyalsh Nebro, Allan Barnes, Richard A Gustafson, Michael L Smith. Estimating time of last oral ingestion of cannabis from plasma THC and THCCOOH concentrations.
Therapeutic drug monitoring.
2006 Aug; 28(4):540-4. doi:
10.1097/00007691-200608000-00009. [PMID: 16885722]