Lysergide (BioDeep_00000002970)
代谢物信息卡片
(6aR,9R)-N,N-diethyl-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
化学式: C20H25N3O (323.1998)
中文名称: 麦角乙二胺, 麦角酸二乙基酰胺
谱图信息:
最多检出来源 Homo sapiens(not specific) 28%
分子结构信息
SMILES: CCN(CC)C(=O)C1C=C2c3cccc4[nH]cc(c34)CC2N(C)C1
InChI: InChI=1S/C20H25N3O/c1-4-23(5-2)20(24)14-9-16-15-7-6-8-17-19(15)13(11-21-17)10-18(16)22(3)12-14/h6-9,11,14,18,21H,4-5,10,12H2,1-3H3
描述信息
Lysergic acid diethylamide is an ergoline alkaloid arising from formal condensation of lysergic acid with diethylamine. It has a role as a hallucinogen, a serotonergic agonist and a dopamine agonist. It is an ergoline alkaloid, an organic heterotetracyclic compound and a monocarboxylic acid amide. It is functionally related to a lysergamide.
D018377 - Neurotransmitter Agents > D018490 - Serotonin Agents > D017366 - Serotonin Receptor Agonists
D018377 - Neurotransmitter Agents > D018490 - Serotonin Agents > D012702 - Serotonin Antagonists
D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D006213 - Hallucinogens
C78272 - Agent Affecting Nervous System > C66885 - Serotonin Antagonist
C78272 - Agent Affecting Nervous System > C47794 - Serotonin Agonist
同义名列表
数据库引用编号
22 个数据库交叉引用编号
- ChEBI: CHEBI:6605
- ChEBI: CHEBI:182684
- KEGG: C07542
- PubChem: 5761
- PubChem: 3981
- Metlin: METLIN66677
- DrugBank: DB04829
- ChEMBL: CHEMBL263881
- ChEMBL: CHEMBL463207
- ChEMBL: CHEMBL4764888
- MeSH: Lysergic Acid Diethylamide
- CAS: 50-37-3
- MoNA: WA001257
- MoNA: WA001256
- MoNA: WA001255
- MoNA: WA001254
- MoNA: WA001253
- PMhub: MS000007555
- PubChem: 9745
- PDB-CCD: 7LD
- NIKKAJI: J9.239H
- KNApSAcK: 182684
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
- 3039 - Euglena gracilis: 10.3389/FBIOE.2021.662655
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
- Himanshu Sekhar Swain, Basanta Kumar Das, Aurobinda Upadhyay, Mitesh Hiradas Ramteke, Vikas Kumar, Dharmendra Kumar Meena, Uttam Kumar Sarkar, Narinder Kumar Chadha, Kiran Dube Rawat. Stocking density mediated stress modulates growth attributes in cage reared Labeo rohita (Hamilton) using multifarious biomarker approach.
Scientific reports.
2022 06; 12(1):9869. doi:
10.1038/s41598-022-13570-x. [PMID: 35701448] - Hongyu Lu, Chengxun Deng, Zhimin Yu, Dianya Zhang, Weiping Li, Jun Huang, Teng Bao, Xiaowei Liu. Synergistic degradation of fluorene in soil by dielectric barrier discharge plasma combined with P25/NH2-MIL-125(Ti).
Chemosphere.
2022 Jun; 296(?):133950. doi:
10.1016/j.chemosphere.2022.133950. [PMID: 35176305] - Friederike Holze, Toya V Caluori, Patrick Vizeli, Matthias E Liechti. Safety pharmacology of acute LSD administration in healthy subjects.
Psychopharmacology.
2022 Jun; 239(6):1893-1905. doi:
10.1007/s00213-021-05978-6. [PMID: 34515824] - Ahmed Al-Imam, Marek A Motyka, Zuzanna Witulska, Manal Younus, Michał Michalak. Spatiotemporal Mapping of Online Interest in Cannabis and Popular Psychedelics before and during the COVID-19 Pandemic in Poland.
International journal of environmental research and public health.
2022 05; 19(11):. doi:
10.3390/ijerph19116619. [PMID: 35682204] - Kelcie N Britton, Chey R Steen, Kyle A Davis, Jessi K Sampson, Daniel G Panaccione. Contribution of a novel gene to lysergic acid amide synthesis in Metarhizium brunneum.
BMC research notes.
2022 May; 15(1):183. doi:
10.1186/s13104-022-06068-2. [PMID: 35585609] - Friederike Holze, Laura Ley, Felix Müller, Anna M Becker, Isabelle Straumann, Patrick Vizeli, Sebastian Silva Kuehne, Marc A Roder, Urs Duthaler, Karolina E Kolaczynska, Nimmy Varghese, Anne Eckert, Matthias E Liechti. Direct comparison of the acute effects of lysergic acid diethylamide and psilocybin in a double-blind placebo-controlled study in healthy subjects.
Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology.
2022 05; 47(6):1180-1187. doi:
10.1038/s41386-022-01297-2. [PMID: 35217796] - Manlu Wang, Juan He, Jin Luo, Jing Hu, Xiandeng Hou. Ultrasensitive determination and non-chromatographic speciation of inorganic arsenic in foods and water by photochemical vapor generation-ICPMS using CdS/MIL-100(Fe) as adsorbent and photocatalyst.
Food chemistry.
2022 May; 375(?):131841. doi:
10.1016/j.foodchem.2021.131841. [PMID: 34923400] - Dan-Li Jiang, Xiao-Li Zhou, Yang-Long Xu, Sui Liufu, Xin-Liang Fu, Dan-Ning Xu, Yun-Bo Tian, Xu Shen, Yun-Mao Huang. Effects of stocking density on ovarian development and maturation during the rearing period in Shan-ma ducks.
Poultry science.
2022 May; 101(5):101809. doi:
10.1016/j.psj.2022.101809. [PMID: 35358924] - Erin T Strovel, Kristina Cusmano-Ozog, Tim Wood, Chunli Yu. Measurement of lysosomal enzyme activities: A technical standard of the American College of Medical Genetics and Genomics (ACMG).
Genetics in medicine : official journal of the American College of Medical Genetics.
2022 04; 24(4):769-783. doi:
10.1016/j.gim.2021.12.013. [PMID: 35394426] - Neiloufar Family, Peter S Hendricks, Luke Tj Williams, David Luke, Erwin Krediet, Emeline L Maillet, Shlomi Raz. Safety, tolerability, pharmacokinetics, and subjective effects of 50, 75, and 100 µg LSD in healthy participants within a novel intervention paradigm: A proof-of-concept study.
Journal of psychopharmacology (Oxford, England).
2022 Mar; 36(3):321-336. doi:
10.1177/02698811211069103. [PMID: 35253516] - Abigail M Jones, Chey R Steen, Daniel G Panaccione. Independent Evolution of a Lysergic Acid Amide in Aspergillus Species.
Applied and environmental microbiology.
2021 11; 87(24):e0180121. doi:
10.1128/aem.01801-21. [PMID: 34586904] - Shouliang Qi, Caiwen Xu, Chen Li, Bin Tian, Shuyue Xia, Jigang Ren, Liming Yang, Hanlin Wang, Hui Yu. DR-MIL: deep represented multiple instance learning distinguishes COVID-19 from community-acquired pneumonia in CT images.
Computer methods and programs in biomedicine.
2021 Nov; 211(?):106406. doi:
10.1016/j.cmpb.2021.106406. [PMID: 34536634] - Rachel Aakerøy, Wenche Rødseth Brede, Stian Bergseng Stølen, Hege-Merete Krabseth, Lisbeth Solem Michelsen, Trine Naalsund Andreassen, Tiina Ader, Joachim Frost, Grete Slettom, Ole Martin Steihaug, Lars Slørdal. Severe Neurological Sequelae after a Recreational Dose of LSD.
Journal of analytical toxicology.
2021 Aug; 45(7):e1-e3. doi:
10.1093/jat/bkaa145. [PMID: 33031536] - Yuting Wang, Liyan He, Guoyan Dang, Hui Li, Xiaoli Li. Preparation of Fe-MIL(100)-encapsulated magnetic g-C3N4 for adsorption of PPCPs from aqueous solution.
Environmental science and pollution research international.
2021 Aug; 28(29):39769-39786. doi:
10.1007/s11356-021-13550-0. [PMID: 33761079] - Patrick Vizeli, Isabelle Straumann, Friederike Holze, Yasmin Schmid, Patrick C Dolder, Matthias E Liechti. Genetic influence of CYP2D6 on pharmacokinetics and acute subjective effects of LSD in a pooled analysis.
Scientific reports.
2021 05; 11(1):10851. doi:
10.1038/s41598-021-90343-y. [PMID: 34035391] - Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
Cell reports.
2021 04; 35(4):109040. doi:
10.1016/j.celrep.2021.109040. [PMID: 33910017] - Yameng Zhao, Lingyi Zhang, Licheng Cao, Lei Zhang, Weibing Zhang. A metal oxide affinity probe derived from MIL-125 for selective enrichment of endogenous phosphopeptides.
The Analyst.
2021 Apr; 146(7):2255-2263. doi:
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Clinical pharmacology and therapeutics.
2021 03; 109(3):658-666. doi:
10.1002/cpt.2057. [PMID: 32975835] - Ingrid Anna Teigen, Jon Andsnes Berg, Kristoffer Brodwall. An apathetic child with hallucinations.
Tidsskrift for den Norske laegeforening : tidsskrift for praktisk medicin, ny raekke.
2021 02; 141(3):. doi:
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Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology.
2021 02; 46(3):537-544. doi:
10.1038/s41386-020-00883-6. [PMID: 33059356] - Christina Grumann, Kerstin Henkel, Simon D Brandt, Alexander Stratford, Torsten Passie, Volker Auwärter. Pharmacokinetics and subjective effects of 1P-LSD in humans after oral and intravenous administration.
Drug testing and analysis.
2020 Aug; 12(8):1144-1153. doi:
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Neuropharmacology.
2020 08; 172(?):107856. doi:
10.1016/j.neuropharm.2019.107856. [PMID: 31756337] - Brendan Le Daré, Thomas Gicquel, Alain Baert, Isabelle Morel, Renaud Bouvet. Self-inflicted neck wounds under influence of lysergic acid diethylamide: A case report and literature review.
Medicine.
2020 Jul; 99(27):e20868. doi:
10.1097/md.0000000000020868. [PMID: 32629675] - Elias Lützen, Michael Holtkamp, Imke Stamme, Robin Schmid, Michael Sperling, Michael Pütz, Uwe Karst. Multimodal imaging of hallucinogens 25C- and 25I-NBOMe on blotter papers.
Drug testing and analysis.
2020 Apr; 12(4):465-471. doi:
10.1002/dta.2751. [PMID: 31846172] - Neiloufar Family, Emeline L Maillet, Luke T J Williams, Erwin Krediet, Robin L Carhart-Harris, Tim M Williams, Charles D Nichols, Daniel J Goble, Shlomi Raz. Safety, tolerability, pharmacokinetics, and pharmacodynamics of low dose lysergic acid diethylamide (LSD) in healthy older volunteers.
Psychopharmacology.
2020 Mar; 237(3):841-853. doi:
10.1007/s00213-019-05417-7. [PMID: 31853557] - Friederike Holze, Patrick Vizeli, Felix Müller, Laura Ley, Raoul Duerig, Nimmy Varghese, Anne Eckert, Stefan Borgwardt, Matthias E Liechti. Distinct acute effects of LSD, MDMA, and D-amphetamine in healthy subjects.
Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology.
2020 02; 45(3):462-471. doi:
10.1038/s41386-019-0569-3. [PMID: 31733631] - Adam Blumenberg, Robert G Hendrickson. A letter reporting a case of fatal ventricular dysrhythmia associated with the LSD analog AL-LAD.
Clinical toxicology (Philadelphia, Pa.).
2020 02; 58(2):143-145. doi:
10.1080/15563650.2019.1609685. [PMID: 31050301] - Tao Yan, Tingting Wu, Shiyuan Wei, Haoqi Wang, Meng Sun, Liangguo Yan, Qin Wei, Huangxian Ju. Photoelectrochemical competitive immunosensor for 17β-estradiol detection based on ZnIn2S4@NH2-MIL-125(Ti) amplified by PDA NS/Mn:ZnCdS.
Biosensors & bioelectronics.
2020 Jan; 148(?):111739. doi:
10.1016/j.bios.2019.111739. [PMID: 31731075] - Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Molecular pharmacology.
2019 11; 96(5):629-640. doi:
10.1124/mol.119.115964. [PMID: 31515284] - Ricardo Alves Bernardo, Lidya Cardozo da Silva, Maria Eugênia C Queiroz, Boniek Gontijo Vaz, Andréa Rodrigues Chaves. Lab-made solid phase microextraction phases for off line extraction and direct mass spectrometry analysis: Evaluating the extraction parameters.
Journal of chromatography. A.
2019 Oct; 1603(?):23-32. doi:
10.1016/j.chroma.2019.06.038. [PMID: 31230878] - Christina Grumann, Kerstin Henkel, Alexander Stratford, Maren Hermanns-Clausen, Torsten Passie, Simon D Brandt, Volker Auwärter. Validation of an LC-MS/MS method for the quantitative analysis of 1P-LSD and its tentative metabolite LSD in fortified urine and serum samples including stability tests for 1P-LSD under different storage conditions.
Journal of pharmaceutical and biomedical analysis.
2019 Sep; 174(?):270-276. doi:
10.1016/j.jpba.2019.05.062. [PMID: 31181490] - Friederike Holze, Urs Duthaler, Patrick Vizeli, Felix Müller, Stefan Borgwardt, Matthias E Liechti. Pharmacokinetics and subjective effects of a novel oral LSD formulation in healthy subjects.
British journal of clinical pharmacology.
2019 07; 85(7):1474-1483. doi:
10.1111/bcp.13918. [PMID: 30883864] - Lea Wagmann, Lilian H J Richter, Tobias Kehl, Franziska Wack, Madeleine Pettersson Bergstrand, Simon D Brandt, Alexander Stratford, Hans H Maurer, Markus R Meyer. In vitro metabolic fate of nine LSD-based new psychoactive substances and their analytical detectability in different urinary screening procedures.
Analytical and bioanalytical chemistry.
2019 Jul; 411(19):4751-4763. doi:
10.1007/s00216-018-1558-9. [PMID: 30617391] - Marc Aixalà, Rafael G Dos Santos, Jaime E C Hallak, José Carlos Bouso. Psychedelics and Personality.
ACS chemical neuroscience.
2018 10; 9(10):2304-2306. doi:
10.1021/acschemneuro.8b00237. [PMID: 29863323] - Laura Sánchez-Marín, David Ladrón de Guevara-Miranda, M Carmen Mañas-Padilla, Francisco Alén, Román D Moreno-Fernández, Caridad Díaz-Navarro, José Pérez-Del Palacio, María García-Fernández, Carmen Pedraza, Francisco J Pavón, Fernando Rodríguez de Fonseca, Luis J Santín, Antonia Serrano, Estela Castilla-Ortega. Systemic blockade of LPA1/3 lysophosphatidic acid receptors by ki16425 modulates the effects of ethanol on the brain and behavior.
Neuropharmacology.
2018 05; 133(?):189-201. doi:
10.1016/j.neuropharm.2018.01.033. [PMID: 29378212] - Jakob A Shimshoni, Eyal Sobol, Ezekiel Golan, Yulius Ben Ari, Orit Gal. Pharmacokinetic and pharmacodynamic evaluation of 5-methoxy-2-aminoindane (MEAI): A new binge-mitigating agent.
Toxicology and applied pharmacology.
2018 03; 343(?):29-39. doi:
10.1016/j.taap.2018.02.009. [PMID: 29458138] - Patrick C Dolder, Matthias E Liechti, Katharina M Rentsch. Development and validation of an LC-MS/MS method to quantify lysergic acid diethylamide (LSD), iso-LSD, 2-oxo-3-hydroxy-LSD, and nor-LSD and identify novel metabolites in plasma samples in a controlled clinical trial.
Journal of clinical laboratory analysis.
2018 Feb; 32(2):. doi:
10.1002/jcla.22265. [PMID: 28548305] - Achim T Caspar, Andreas B Kollas, Hans H Maurer, Markus R Meyer. Development of a quantitative approach in blood plasma for low-dosed hallucinogens and opioids using LC-high resolution mass spectrometry.
Talanta.
2018 Jan; 176(?):635-645. doi:
10.1016/j.talanta.2017.08.063. [PMID: 28917801] - Matthias E Liechti. Modern Clinical Research on LSD.
Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology.
2017 Oct; 42(11):2114-2127. doi:
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Drug testing and analysis.
2017 Oct; 9(10):1641-1649. doi:
10.1002/dta.2196. [PMID: 28342178] - Camille Ponté, Maryse Lapeyre-Mestre. [Psychoactive effects of 'legal high': About lysergic acid amide (LSA)].
Therapie.
2017 Oct; 72(5):605-608. doi:
10.1016/j.therap.2017.01.012. [PMID: 28457570] - Patrick C Dolder, Yasmin Schmid, Andrea E Steuer, Thomas Kraemer, Katharina M Rentsch, Felix Hammann, Matthias E Liechti. Pharmacokinetics and Pharmacodynamics of Lysergic Acid Diethylamide in Healthy Subjects.
Clinical pharmacokinetics.
2017 Oct; 56(10):1219-1230. doi:
10.1007/s40262-017-0513-9. [PMID: 28197931] - Marie Mardal, Sys Stybe Johansen, Ragnar Thomsen, Kristian Linnet. Advantages of analyzing postmortem brain samples in routine forensic drug screening-Case series of three non-natural deaths tested positive for lysergic acid diethylamide (LSD).
Forensic science international.
2017 Sep; 278(?):e14-e18. doi:
10.1016/j.forsciint.2017.07.025. [PMID: 28803722] - Claudia Oellig. Lysergic acid amide as chemical marker for the total ergot alkaloids in rye flour - Determination by high-performance thin-layer chromatography-fluorescence detection.
Journal of chromatography. A.
2017 Jul; 1507(?):124-131. doi:
10.1016/j.chroma.2017.05.043. [PMID: 28554863] - Andrea E Steuer, Michael Poetzsch, Lorena Stock, Lisa Eisenbeiss, Yasmin Schmid, Matthias E Liechti, Thomas Kraemer. Development and validation of an ultra-fast and sensitive microflow liquid chromatography-tandem mass spectrometry (MFLC-MS/MS) method for quantification of LSD and its metabolites in plasma and application to a controlled LSD administration study in humans.
Drug testing and analysis.
2017 May; 9(5):788-797. doi:
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Psychopharmacology.
2017 05; 234(9-10):1499-1510. doi:
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Translational psychiatry.
2017 04; 7(4):e1084. doi:
10.1038/tp.2017.54. [PMID: 28375205] - Xialin Luo, Gongke Li, Yufei Hu. In-tube solid-phase microextraction based on NH2-MIL-53(Al)-polymer monolithic column for online coupling with high-performance liquid chromatography for directly sensitive analysis of estrogens in human urine.
Talanta.
2017 Apr; 165(?):377-383. doi:
10.1016/j.talanta.2016.12.050. [PMID: 28153270] - Camille Richeval, Delphine Allorge, Xavier Vanhoye, Jean-Michel Gaulier. LSD Detection and Interpretation in Hair.
Current pharmaceutical design.
2017; 23(36):5496-5501. doi:
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Clinical chemistry and laboratory medicine.
2017 Jan; 55(1):e10-e12. doi:
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Journal of medical toxicology : official journal of the American College of Medical Toxicology.
2016 12; 12(4):396-401. doi:
10.1007/s13181-016-0571-7. [PMID: 27456262] - P Strajhar, Y Schmid, E Liakoni, P C Dolder, K M Rentsch, D V Kratschmar, A Odermatt, M E Liechti. Acute Effects of Lysergic Acid Diethylamide on Circulating Steroid Levels in Healthy Subjects.
Journal of neuroendocrinology.
2016 Mar; 28(3):12374. doi:
10.1111/jne.12374. [PMID: 26849997] - Evan J Kyzar, Adam Michael Stewart, Allan V Kalueff. Effects of LSD on grooming behavior in serotonin transporter heterozygous (Sert⁺/⁻) mice.
Behavioural brain research.
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Journal of pharmaceutical and biomedical analysis.
2015 Nov; 115(?):138-43. doi:
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Biological psychiatry.
2015 Oct; 78(8):544-53. doi:
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The international journal of neuropsychopharmacology.
2015 Jun; 19(1):. doi:
10.1093/ijnp/pyv072. [PMID: 26108222] - Patrick C Dolder, Matthias E Liechti, Katharina M Rentsch. Development and validation of a rapid turboflow LC-MS/MS method for the quantification of LSD and 2-oxo-3-hydroxy LSD in serum and urine samples of emergency toxicological cases.
Analytical and bioanalytical chemistry.
2015 Feb; 407(6):1577-84. doi:
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Talanta.
2014 Dec; 130(?):456-61. doi:
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2014 Nov; 81(4):403-9. doi:
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