m-3-g hydrate (BioDeep_00001874417)
Main id: BioDeep_00000001381
代谢物信息卡片
Morphine-3-glucuronide
化学式: C23H27NO9 (461.1686)
中文名称: 吗啡-3-Β-D-葡糖苷酸
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CN1CCC23C4C1CC5=C2C(=C(C=C5)OC6C(C(C(C(O6)C(=O)O)O)O)O)OC3C(C=C4)O
InChI: InChI=1S/C23H27NO9/c1-24-7-6-23-10-3-4-12(25)20(23)32-18-13(5-2-9(14(18)23)8-11(10)24)31-22-17(28)15(26)16(27)19(33-22)21(29)30/h2-5,10-12,15-17,19-20,22,25-28H,6-8H2,1H3,(H,29,30)/t10-,11+,12-,15-,16-,17+,19-,20-,22+,23-/m0/s1
描述信息
D002492 - Central Nervous System Depressants > D009294 - Narcotics > D053610 - Opiate Alkaloids
D002491 - Central Nervous System Agents > D000697 - Central Nervous System Stimulants
同义名列表
数据库引用编号
9 个数据库交叉引用编号
- ChEBI: CHEBI:80631
- KEGG: C16643
- PubChem: 5484731
- ChEMBL: CHEMBL1329
- CAS: 20290-09-9
- MetaboLights: MTBLC80631
- PubChem: 51090968
- NIKKAJI: J125.691B
- KNApSAcK: 80631
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
1 个相关的物种来源信息
- 3469 - Papaver somniferum: 10.1016/J.JPBA.2008.06.022
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
- Thomas Duflot, Tony Pereira, Marie-Pierre Tavolacci, Robinson Joannidès, Frédéric Aubrun, Fabien Lamoureux, Virginie Eve Lvovschi. Pharmacokinetic modeling of morphine and its glucuronides: Comparison of nebulization versus intravenous route in healthy volunteers.
CPT: pharmacometrics & systems pharmacology.
2022 01; 11(1):82-93. doi:
10.1002/psp4.12735. [PMID: 34842366] - Noora Sjöstedt, Sibylle Neuhoff, Kim L R Brouwer. Physiologically-Based Pharmacokinetic Model of Morphine and Morphine-3-Glucuronide in Nonalcoholic Steatohepatitis.
Clinical pharmacology and therapeutics.
2021 03; 109(3):676-687. doi:
10.1002/cpt.2037. [PMID: 32897538] - Kaiyuan Wang, Jian Wang, Ting Liu, Wenwen Yu, Nan Dong, Chen Zhang, Wenbin Xia, Feng Wei, Lili Yang, Xiubao Ren. Morphine-3-glucuronide upregulates PD-L1 expression via TLR4 and promotes the immune escape of non-small cell lung cancer.
Cancer biology & medicine.
2021 02; 18(1):155-171. doi:
10.20892/j.issn.2095-3941.2020.0442. [PMID: 33628591] - S R Gretler, C J Finno, P H Kass, H K Knych. Functional phenotyping of the CYP2D6 probe drug codeine in the horse.
BMC veterinary research.
2021 Feb; 17(1):77. doi:
10.1186/s12917-021-02788-y. [PMID: 33581736] - Yao-Te Yen, Yin-Jue Chang, Pin-Jung Lai, Chi-Lun Chang, Ting-Yueh Chen, San-Chong Chyueh. A Study of Opiate, Opiate Metabolites and Antihistamines in Urine after Consumption of Cold Syrups by LC-MS/MS.
Molecules (Basel, Switzerland).
2020 Feb; 25(4):. doi:
10.3390/molecules25040972. [PMID: 32098143] - Alessandro Mirra, Jasmin Birras, Sabina Diez Bernal, Claudia Spadavecchia. Morphine plasmatic concentration in a pregnant mare and its foal after long term epidural administration.
BMC veterinary research.
2020 Jan; 16(1):19. doi:
10.1186/s12917-020-2242-9. [PMID: 31959188] - Luying Wang, Chunfang Ni, Hongliang Shen, Zhenhai Sheng, Chen Liang, Rong Wang, Yurong Zhang. Comparison of the Detection Windows of Heroin Metabolites in Human Urine Using Online SPE and LC-MS/MS: Importance of Morphine-3-Glucuronide.
Journal of analytical toxicology.
2020 Jan; 44(1):22-28. doi:
10.1093/jat/bkz040. [PMID: 31095707] - S Merchaoui, A Ben Said, K Louati, A Hajri, F Safta, M Kallel. Optimization of morphine extraction method for the assay of its urinary 3-glucuronideconjuguate by gas chromatography-mass spectrometry.
Annales pharmaceutiques francaises.
2019 Nov; 77(6):468-487. doi:
10.1016/j.pharma.2019.07.004. [PMID: 31564417] - Briana D Hamamoto-Hardman, Eugene P Steffey, Daniel Weiner, Daniel S McKemie, Philip Kass, Heather K Knych. Pharmacokinetics and selected pharmacodynamics of morphine and its active metabolites in horses after intravenous administration of four doses.
Journal of veterinary pharmacology and therapeutics.
2019 Jul; 42(4):401-410. doi:
10.1111/jvp.12759. [PMID: 30919469] - Cecilie Hasselø Thaulow, Åse Marit Leere Øiestad, Sidsel Rogde, Jannike Mørch Andersen, Gudrun Høiseth, Marte Handal, Jørg Mørland, Vigdis Vindenes. Can measurements of heroin metabolites in post-mortem matrices other than peripheral blood indicate if death was rapid or delayed?.
Forensic science international.
2018 Sep; 290(?):121-128. doi:
10.1016/j.forsciint.2018.06.041. [PMID: 30015276] - H H Doyle, A Z Murphy. Sex-dependent influences of morphine and its metabolites on pain sensitivity in the rat.
Physiology & behavior.
2018 04; 187(?):32-41. doi:
10.1016/j.physbeh.2017.11.030. [PMID: 29199028] - Lorry Hachon, Rafael Reis, Laurence Labat, Christine Poitou, Aude Jacob, Xavier Declèves, Celia Lloret-Linares. Morphine and metabolites plasma levels after administration of sustained release morphine in Roux-en-Y gastric bypass subjects versus matched control subjects.
Surgery for obesity and related diseases : official journal of the American Society for Bariatric Surgery.
2017 Nov; 13(11):1869-1874. doi:
10.1016/j.soard.2017.07.030. [PMID: 28864105] - Yan Wang, Kerry B Goralski, Derek J Roberts, Kathryn Landry, Mark E Issa, Lekha Sleno, Lisa C Julien, Jeremy Wood, Richard I Hall. An observational study examining the effects of a surgically induced inflammatory response on the distribution of morphine and its metabolites into cerebrospinal fluid.
Canadian journal of anaesthesia = Journal canadien d'anesthesie.
2017 Oct; 64(10):1009-1022. doi:
10.1007/s12630-017-0933-x. [PMID: 28710563] - Astrid W Oosten, João A Abrantes, Siv Jönsson, Maja Matic, Ron H N van Schaik, Peter de Bruijn, Carin C D van der Rijt, Ron H J Mathijssen. A Prospective Population Pharmacokinetic Study on Morphine Metabolism in Cancer Patients.
Clinical pharmacokinetics.
2017 07; 56(7):733-746. doi:
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Journal of analytical toxicology.
2017 Jun; 41(5):451-454. doi:
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CPT: pharmacometrics & systems pharmacology.
2017 05; 6(5):331-339. doi:
10.1002/psp4.12185. [PMID: 28417561] - Keumhan Noh, Shu Chen, Qi J Yang, K Sandy Pang. Physiologically based pharmacokinetic modeling revealed minimal codeine intestinal metabolism in first-pass removal in rats.
Biopharmaceutics & drug disposition.
2017 Jan; 38(1):50-74. doi:
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Anesthesia and analgesia.
2016 12; 123(6):1611-1617. doi:
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Clinics (Sao Paulo, Brazil).
2016 Aug; 71(8):474-80. doi:
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Drug metabolism and disposition: the biological fate of chemicals.
2016 07; 44(7):1123-38. doi:
10.1124/dmd.116.069542. [PMID: 27098743] - Peter D Maskell, Mohammed Albeishy, Giorgia De Paoli, Nathan E Wilson, L Nitin Seetohul. Postmortem redistribution of the heroin metabolites morphine and morphine-3-glucuronide in rabbits over 24 h.
International journal of legal medicine.
2016 Mar; 130(2):519-31. doi:
10.1007/s00414-015-1185-3. [PMID: 25863436] - David Sartori, Tamorah Lewis, Autumn Breaud, William Clarke. The development of a high-performance liquid chromatography-tandem mass spectrometric method for simultaneous quantification of morphine, morphine-3-β-glucuronide, morphine-6-β-glucuronide, hydromorphone, and normorphine in serum.
Clinical biochemistry.
2015 Dec; 48(18):1283-90. doi:
10.1016/j.clinbiochem.2015.05.023. [PMID: 26118474] - Sabine J G M Ahlers, Pyry A J Välitalo, Mariska Y M Peeters, Laura van Gulik, Eric P A van Dongen, Albert Dahan, Dick Tibboel, Catherijne A J Knibbe. Morphine Glucuronidation and Elimination in Intensive Care Patients: A Comparison with Healthy Volunteers.
Anesthesia and analgesia.
2015 Nov; 121(5):1261-73. doi:
10.1213/ane.0000000000000936. [PMID: 26332855] - Yong Joo Lee, Sang-Yeon Suh, Junghan Song, Sanghee Shiny Lee, Ah-Ram Seo, Hong-Yup Ahn, Myung Ah Lee, Chul-Min Kim, Pål Klepstad. Serum and urine concentrations of morphine and morphine metabolites in patients with advanced cancer receiving continuous intravenous morphine: an observational study.
BMC palliative care.
2015 Oct; 14(?):53. doi:
10.1186/s12904-015-0052-9. [PMID: 26507979] - Nieves Velez de Mendizabal, Ricardo Jimenez-Mendez, Erin Cooke, Carolyne J Montgomery, Joy Dawes, Michael J Rieder, Katarina Aleksa, Gideon Koren, Carlos O Jacobo-Cabral, Rodrigo Gonzalez-Ramirez, Gilberto Castañeda-Hernandez, Bruce C Carleton. A Compartmental Analysis for Morphine and Its Metabolites in Young Children After a Single Oral Dose.
Clinical pharmacokinetics.
2015 Oct; 54(10):1083-90. doi:
10.1007/s40262-015-0256-4. [PMID: 25773480] - Christian Görgens, Sven Guddat, Anne-Katrin Orlovius, Gerd Sigmund, Andreas Thomas, Mario Thevis, Wilhelm Schänzer. "Dilute-and-inject" multi-target screening assay for highly polar doping agents using hydrophilic interaction liquid chromatography high resolution/high accuracy mass spectrometry for sports drug testing.
Analytical and bioanalytical chemistry.
2015 Jul; 407(18):5365-79. doi:
10.1007/s00216-015-8699-x. [PMID: 25925859] - B C Ferslew, C K Johnston, E Tsakalozou, A S Bridges, M F Paine, W Jia, P W Stewart, A S Barritt, K L R Brouwer. Altered morphine glucuronide and bile acid disposition in patients with nonalcoholic steatohepatitis.
Clinical pharmacology and therapeutics.
2015 Apr; 97(4):419-27. doi:
10.1002/cpt.66. [PMID: 25669174] - Anika L Dzierlenga, John D Clarke, Tiffanie L Hargraves, Garrett R Ainslie, Todd W Vanderah, Mary F Paine, Nathan J Cherrington. Mechanistic basis of altered morphine disposition in nonalcoholic steatohepatitis.
The Journal of pharmacology and experimental therapeutics.
2015 Mar; 352(3):462-70. doi:
10.1124/jpet.114.220764. [PMID: 25512370] - Oscar A Linares, Jeffrey Fudin, William E Schiesser, Annemarie L Daly Linares, Raymond C Boston. CYP2D6 phenotype-specific codeine population pharmacokinetics.
Journal of pain & palliative care pharmacotherapy.
2015 Mar; 29(1):4-15. doi:
10.3109/15360288.2014.997854. [PMID: 25562725] - Theresa A Isbell, Erin C Strickland, Jennifer Hitchcock, Gregory McIntire, Christa L Colyer. Capillary electrophoresis-mass spectrometry determination of morphine and its isobaric glucuronide metabolites.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2015 Feb; 980(?):65-71. doi:
10.1016/j.jchromb.2014.11.035. [PMID: 25589256] - R Klimas, G Mikus. Morphine-6-glucuronide is responsible for the analgesic effect after morphine administration: a quantitative review of morphine, morphine-6-glucuronide, and morphine-3-glucuronide.
British journal of anaesthesia.
2014 Dec; 113(6):935-44. doi:
10.1093/bja/aeu186. [PMID: 24985077] - C H Thaulow, G Høiseth, J M Andersen, M Handal, J Mørland. Pharmacokinetic interactions between ethanol and heroin: a study on post-mortem cases.
Forensic science international.
2014 Sep; 242(?):127-134. doi:
10.1016/j.forsciint.2014.06.032. [PMID: 25050840] - Ana Oliveira, Félix Carvalho, Paula Guedes Pinho, Fernando Remião, Rui Medeiros, Ricardo Jorge Dinis-Oliveira. Quantification of morphine and its major metabolites M3G and M6G in antemortem and postmortem samples.
Biomedical chromatography : BMC.
2014 Sep; 28(9):1263-70. doi:
10.1002/bmc.3158. [PMID: 25237710] - H K Knych, E P Steffey, D S McKemie. Preliminary pharmacokinetics of morphine and its major metabolites following intravenous administration of four doses to horses.
Journal of veterinary pharmacology and therapeutics.
2014 Aug; 37(4):374-81. doi:
10.1111/jvp.12098. [PMID: 24479785] - Ana Oliveira, Dora Pinho, António Albino-Teixeira, Rui Medeiros, Ricardo Jorge Dinis-Oliveira, Félix Carvalho. Morphine glucuronidation increases its analgesic effect in guinea pigs.
Life sciences.
2014 Jul; 109(2):104-10. doi:
10.1016/j.lfs.2014.06.010. [PMID: 24968302] - Simona De Gregori, Cristina E Minella, Manuela De Gregori, Carmine Tinelli, Guglielmina N Ranzani, Stefano Govoni, Massimo Allegri, Mario Regazzi. Clinical pharmacokinetics of morphine and its metabolites during morphine dose titration for chronic cancer pain.
Therapeutic drug monitoring.
2014 Jun; 36(3):335-44. doi:
10.1097/ftd.0000000000000009. [PMID: 24595069] - Nuy Chau, David J Elliot, Benjamin C Lewis, Kushari Burns, Martin R Johnston, Peter I Mackenzie, John O Miners. Morphine glucuronidation and glucosidation represent complementary metabolic pathways that are both catalyzed by UDP-glucuronosyltransferase 2B7: kinetic, inhibition, and molecular modeling studies.
The Journal of pharmacology and experimental therapeutics.
2014 Apr; 349(1):126-37. doi:
10.1124/jpet.113.212258. [PMID: 24459244] - Brittany Malik-Wolf, Shawn Vorce, Justin Holler, Thomas Bosy. Evaluation of abalone β-glucuronidase substitution in current urine hydrolysis procedures.
Journal of analytical toxicology.
2014 Apr; 38(3):171-6. doi:
10.1093/jat/bku003. [PMID: 24488113] - Xiujun Wu, Li Yuan, Jinliang Zuo, Jing Lv, Tao Guo. The impact of CYP2D6 polymorphisms on the pharmacokinetics of codeine and its metabolites in Mongolian Chinese subjects.
European journal of clinical pharmacology.
2014 Jan; 70(1):57-63. doi:
10.1007/s00228-013-1573-x. [PMID: 24077935] - Maja Matic, Elisabeth Norman, Anders Rane, Olof Beck, Maria Andersson, Laure Elens, Dick Tibboel, Vineta Fellman, Ron H N van Schaik. Effect of UGT2B7 -900G>A (-842G>A; rs7438135) on morphine glucuronidation in preterm newborns: results from a pilot cohort.
Pharmacogenomics.
2014; 15(12):1589-97. doi:
10.2217/pgs.14.115. [PMID: 25340733] - Nuggehally R Srinivas. Do we have clarity on the therapeutic levels of morphine and its metabolites: seeking answers for the dilemma?.
Journal of pain & palliative care pharmacotherapy.
2013 Jun; 27(2):163-6. doi:
10.3109/15360288.2013.788597. [PMID: 23789848] - N Dubols, C Hallet, D Luppens, M Ansseau, C Charlier. [Rapid opiate detoxification under anesthesia (RODA)].
Revue medicale de Liege.
2013 May; 68(5-6):298-302. doi:
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Molecular medicine (Cambridge, Mass.).
2012 Dec; 18(?):1320-6. doi:
10.2119/molmed.2012.00244. [PMID: 23001479] - Jane A Dickerson, Thomas J Laha, Monica B Pagano, Brendan R O'Donnell, Andrew N Hoofnagle. Improved detection of opioid use in chronic pain patients through monitoring of opioid glucuronides in urine.
Journal of analytical toxicology.
2012 Oct; 36(8):541-7. doi:
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Journal of pain and symptom management.
2012 Oct; 44(4):479-85. doi:
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Forensic science international.
2012 Jul; 220(1-3):97-102. doi:
10.1016/j.forsciint.2012.02.004. [PMID: 22410425] - Nathalia Jimenez, Gail D Anderson, Danny D Shen, Susan S Nielsen, Federico M Farin, Kristy Seidel, Anne M Lynn. Is ethnicity associated with morphine's side effects in children? Morphine pharmacokinetics, analgesic response, and side effects in children having tonsillectomy.
Paediatric anaesthesia.
2012 Jul; 22(7):669-75. doi:
10.1111/j.1460-9592.2012.03844.x. [PMID: 22486937] - Juliana P Figueiredo, William W Muir, Richard Sams. Cardiorespiratory, gastrointestinal, and analgesic effects of morphine sulfate in conscious healthy horses.
American journal of veterinary research.
2012 Jun; 73(6):799-808. doi:
10.2460/ajvr.73.6.799. [PMID: 22620693] - Maria Meringolo, Valentina Brusadin, Maria T De Luca, Christian Montanari, Christian L Montanari, Letizia Antonilli, Paolo Nencini, Aldo Badiani. Induction of morphine-6-glucuronide synthesis by heroin self-administration in the rat.
Psychopharmacology.
2012 May; 221(2):195-203. doi:
10.1007/s00213-011-2534-7. [PMID: 22016196] - Qingshan Wang, Hui Zhou, Huiming Gao, Shih-Heng Chen, Chun-Hsien Chu, Belinda Wilson, Jau-Shyong Hong. Naloxone inhibits immune cell function by suppressing superoxide production through a direct interaction with gp91phox subunit of NADPH oxidase.
Journal of neuroinflammation.
2012 Feb; 9(?):32. doi:
10.1186/1742-2094-9-32. [PMID: 22340895] - Hahck Soo Park, Jong Hak Kim, Yi Jeong Kim, Dong Yeon Kim. Plasma Concentrations of Morphine during Postoperative Pain Control.
The Korean journal of pain.
2011 Sep; 24(3):146-53. doi:
10.3344/kjp.2011.24.3.146. [PMID: 21935493] - Hala Abou Hammoud, Guy Aymard, Philippe Lechat, Nicolas Boccheciampe, Bruno Riou, Frédéric Aubrun. Relationships between plasma concentrations of morphine, morphine-3-glucuronide, morphine-6-glucuronide, and intravenous morphine titration outcomes in the postoperative period.
Fundamental & clinical pharmacology.
2011 Aug; 25(4):518-27. doi:
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Journal of clinical anesthesia.
2011 Mar; 23(2):102-6. doi:
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Pharmacy world & science : PWS.
2010 Dec; 32(6):737-43. doi:
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Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2010 Nov; 878(29):2959-66. doi:
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Journal of chromatography. A.
2010 Oct; 1217(44):6857-66. doi:
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Biomedical chromatography : BMC.
2010 Sep; 24(9):969-76. doi:
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Basic & clinical pharmacology & toxicology.
2010 Aug; 107(2):680-4. doi:
10.1111/j.1742-7843.2010.00559.x. [PMID: 20346057] - Chang-Shu Zhan, Bao-Hua Shen, Xian-Yi Zhuo. [Simultaneous determination of opioid compounds in human urine by UPLC-MS/MS].
Fa yi xue za zhi.
2010 Jun; 26(3):188-91. doi:
NULL. [PMID: 20707277] - Kirsten Abildskov, Piper Weldy, Marianne Garland. Molecular cloning of the baboon UDP-glucuronosyltransferase 2B gene family and their activity in conjugating morphine.
Drug metabolism and disposition: the biological fate of chemicals.
2010 Apr; 38(4):545-53. doi:
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European journal of clinical pharmacology.
2010 Mar; 66(3):269-73. doi:
10.1007/s00228-009-0759-8. [PMID: 19940985] - Shawn McCann, Tony L Yaksh, Charles F von Gunten. Correlation between myoclonus and the 3-glucuronide metabolites in patients treated with morphine or hydromorphone: a pilot study.
Journal of opioid management.
2010 Mar; 6(2):87-94. doi:
10.5055/jom.2010.0008. [PMID: 20481173] - Yoshitaka Hasegawa, Shuichi Kishimoto, Naoki Shibatani, Hiromichi Nomura, Yuko Ishii, Mika Onishi, Nobuo Inotsume, Yoshikazu Takeuchi, Shoji Fukushima. The pharmacokinetics of morphine and its glucuronide conjugate in a rat model of streptozotocin-induced diabetes and the expression of MRP2, MRP3 and UGT2B1 in the liver.
The Journal of pharmacy and pharmacology.
2010 Mar; 62(3):310-4. doi:
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Veterinary anaesthesia and analgesia.
2010 Mar; 37(2):186-95. doi:
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The pharmacogenomics journal.
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Analytical and bioanalytical chemistry.
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