o-Cresol (BioDeep_00000004708)
Secondary id: BioDeep_00000405504, BioDeep_00000863200
human metabolite blood metabolite natural product
代谢物信息卡片
化学式: C7H8O (108.0575)
中文名称: 邻甲酚
谱图信息:
最多检出来源 Homo sapiens(blood) 16.36%
分子结构信息
SMILES: CC1=CC=CC=C1O
InChI: InChI=1S/C7H8O/c1-6-4-2-3-5-7(6)8/h2-5,8H,1H3
描述信息
o-Cresol is a minor urinary metabolite of toluene, O-cresol is a cresol that is phenol substituted by a methyl group at position 2. It is a minor urinary metabolite of toluene. It has a role as a human xenobiotic metabolite. It is widely used chemical with neurotoxicological properties (PMID:15687000). o-Cresol is used commercially as a disinfectant. Exposure may occur by inhalation, by cutaneous adsorption or by oral ingestion. o-Cresol denature and precipitate cellular proteins and thus may rapidly cause poisoning. o-Cresol is metabolized by conjugation and oxidation. Ingestion of o-Cresol cause intense burning of mouth and throat, followed by marked abdominal pain and distress. The minimum lethal dose of cresol by mouth is about 2 g (PMID 15040915). o-Cresol is a microbial metabolite that can be found in Pseudomonas. Besides, o-Cresol is one of the chemical compounds found in castoreum. This compound is gathered from the beavers castor glands and found in the white cedar consumed by the beavers. Together with many other compounds, o-cresol is traditionally extracted from coal tar, the volatile materials obtained in the production of coke from coal. A similar source material is petroleum residues. These residue contains a few percent by weight of phenol and isomeric cresols. In addition to the materials derived from these natural sources, about two thirds of the Western worlds supply is produced by methylation of phenol using methanol.
Flavouring ingredient. 2-Methylphenol is found in many foods, some of which are yellow bell pepper, pepper (c. annuum), arabica coffee, and asparagus.
同义名列表
22 个代谢物同义名
2-Hydroxy-1-methylbenzene; 1-Methyl-2-hydroxybenzene; 1-Hydroxy-2-methylbenzene; 2-Cresol, potassium salt; 2-Cresol, ammonium salt; 2-Cresol, sodium salt; 2-Hydroxytoluene; O-Hydroxytoluene; O-Methylphenylol; O-Cresylic acid; 2-Methylphenol; O-Methylphenol; Ortho-cresol; O-Oxytoluene; O-Cresylate; Orthocresol; O-Toluol; O-Kresol; o-cresol; 2-Cresol; o-Cresol; o-Cresol
数据库引用编号
21 个数据库交叉引用编号
- ChEBI: CHEBI:28054
- KEGG: C01542
- PubChem: 335
- HMDB: HMDB0002055
- Metlin: METLIN58085
- ChEMBL: CHEMBL46931
- Wikipedia: O-Cresol
- MetaCyc: CPD-109
- KNApSAcK: C00030878
- foodb: FDB008785
- chemspider: 13835772
- CAS: 70837-27-3
- CAS: 95-48-7
- PMhub: MS000017271
- PubChem: 4703
- PDB-CCD: JZ0
- 3DMET: B00313
- NIKKAJI: J1.176B
- RefMet: o-Cresol
- KNApSAcK: 28054
- LOTUS: LTS0108586
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
3 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(3)
- toluene degradation I (aerobic) (via o-cresol):
NAD+ + acetaldehyde + coenzyme A ⟶ H+ + NADH + acetyl-CoA
- toluene degradation to 2-hydroxypentadienoate I (via o-cresol):
H+ + NADH + O2 + toluene ⟶ 2-methylphenol + H2O + NAD+
- superpathway of aerobic toluene degradation:
4-methylphenol + H2O + an oxidized azurin ⟶ 4-hydroxybenzyl alcohol + H+ + a reduced azurin
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
90 个相关的物种来源信息
- 4037 - Apiaceae: LTS0108586
- 4219 - Artemisia: LTS0108586
- 265783 - Artemisia capillaris:
- 265783 - Artemisia capillaris: 10.1002/(SICI)1521-4168(19990401)22:4<222::AID-JHRC222>3.0.CO;2-6
- 265783 - Artemisia capillaris: 10.1016/S0021-9673(01)00513-1
- 265783 - Artemisia capillaris: LTS0108586
- 401888 - Artemisia compacta: 10.1007/BF00568255
- 401888 - Artemisia compacta: LTS0108586
- 1227631 - Artemisia macrocephala: 10.1007/BF00568255
- 1227631 - Artemisia macrocephala: LTS0108586
- 401922 - Artemisia obtusiloba: 10.1007/BF00568255
- 401922 - Artemisia obtusiloba: LTS0108586
- 4890 - Ascomycota: LTS0108586
- 1131492 - Aspergillaceae: LTS0108586
- 5052 - Aspergillus: LTS0108586
- 41067 - Aspergillus candidus: 10.1016/S0045-6535(99)00015-6
- 41067 - Aspergillus candidus: LTS0108586
- 4210 - Asteraceae: LTS0108586
- 124942 - Azadirachta: LTS0108586
- 124943 - Azadirachta indica: 10.1246/CL.1979.1137
- 124943 - Azadirachta indica: LTS0108586
- 260123 - Blepharocalyx: LTS0108586
- 375214 - Blepharocalyx salicifolius: 10.1021/NP50035A036
- 375214 - Blepharocalyx salicifolius: LTS0108586
- 260124 - Blepharocalyx tweediei: 10.1021/NP50035A036
- 260124 - Blepharocalyx tweediei: LTS0108586
- 4071 - Capsicum: LTS0108586
- 4072 - Capsicum annuum: 10.1006/JFCA.1997.0535
- 4072 - Capsicum annuum: LTS0108586
- 260594 - Cedronella: LTS0108586
- 260595 - Cedronella canariensis: 10.1016/0031-9422(95)00241-X
- 260595 - Cedronella canariensis: LTS0108586
- 13442 - Coffea: LTS0108586
- 13443 - Coffea arabica: 10.1021/JF60160A010
- 13443 - Coffea arabica: LTS0108586
- 406287 - Curio: LTS0108586
- 189231 - Curio articulatus: 10.1016/S0031-9422(97)00141-6
- 66679 - Daphne: LTS0108586
- 329675 - Daphne odora: 10.1271/BBB1961.47.483
- 329675 - Daphne odora: LTS0108586
- 2715869 - Daphne papyracea: 10.1271/BBB1961.47.483
- 2715869 - Daphne papyracea: LTS0108586
- 41574 - Erigeron: LTS0108586
- 72930 - Erigeron philadelphicus: 10.1271/BBB1961.45.507
- 72930 - Erigeron philadelphicus: LTS0108586
- 2759 - Eukaryota: LTS0108586
- 147545 - Eurotiomycetes: LTS0108586
- 3803 - Fabaceae: LTS0108586
- 4751 - Fungi: LTS0108586
- 46347 - Glycyrrhiza: LTS0108586
- 49827 - Glycyrrhiza glabra:
- 49827 - Glycyrrhiza glabra: 10.1021/JF60214A042
- 49827 - Glycyrrhiza glabra: 10.1271/NOGEIKAGAKU1924.61.1119
- 49827 - Glycyrrhiza glabra: LTS0108586
- 9606 - Homo sapiens: -
- 4136 - Lamiaceae: LTS0108586
- 3398 - Magnoliopsida: LTS0108586
- 43707 - Meliaceae: LTS0108586
- 3931 - Myrtaceae: LTS0108586
- 49557 - Osmorhiza: LTS0108586
- 49558 - Osmorhiza aristata: 10.1248/YAKUSHI1947.99.11_1116
- 49558 - Osmorhiza aristata: LTS0108586
- 13625 - Paeonia: LTS0108586
- 35924 - Paeonia lactiflora: 10.1271/BBB1961.48.2847
- 35924 - Paeonia lactiflora: LTS0108586
- 45171 - Paeonia suffruticosa: 10.1080/00021369.1983.10866058
- 45171 - Paeonia suffruticosa: LTS0108586
- 24943 - Paeoniaceae: LTS0108586
- 4275 - Polygala: LTS0108586
- 174549 - Polygala senega: 10.1002/FFJ.2730100408
- 174549 - Polygala senega: LTS0108586
- 4274 - Polygalaceae: LTS0108586
- 24966 - Rubiaceae: LTS0108586
- 21880 - Salvia: LTS0108586
- 342065 - Salvia trijuga: 10.1076/PHBI.41.5.375.15938
- 342065 - Salvia trijuga: LTS0108586
- 4139 - Scutellaria: LTS0108586
- 65409 - Scutellaria baicalensis: 10.1271/BBB1961.51.1449
- 65409 - Scutellaria baicalensis: LTS0108586
- 99101 - Seriphidium: LTS0108586
- 4070 - Solanaceae: LTS0108586
- 35493 - Streptophyta: LTS0108586
- 39987 - Thymelaeaceae: LTS0108586
- 58023 - Tracheophyta: LTS0108586
- 28568 - Trichocomaceae: LTS0108586
- 33090 - Viridiplantae: LTS0108586
- 3602 - Vitaceae: LTS0108586
- 3603 - Vitis: LTS0108586
- 29760 - Vitis vinifera: 10.3389/FMICB.2017.00457
- 29760 - Vitis vinifera: LTS0108586
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
- Pengfei Feng, Yunshuang Li, Kangshuai Li, Weiyan Duan, Ran Guo. Effects of o-cresol on the growth and biochemical compositions in marine microalgae.
Marine environmental research.
2023 Sep; 191(?):106164. doi:
10.1016/j.marenvres.2023.106164
. [PMID: 37713779] - Falko Frenzel, Thorsten Buhrke, Irina Wenzel, Jennifer Andrack, Jan Hielscher, Alfonso Lampen. Use of in silico models for prioritization of heat-induced food contaminants in mutagenicity and carcinogenicity testing.
Archives of toxicology.
2017 Sep; 91(9):3157-3174. doi:
10.1007/s00204-016-1924-3
. [PMID: 28091709] - Muhammad Imran, Hafiz Faisal Usman, Humera Shafi, Muhammad Sarwar, Muhammad Ashraf Tahir. Development of Rapid and Economical Colorimetric Screening Method for p-Phenylenediamine in Variety of Biological Matrices and its Application to Eleven Fatal Cases of p-Phenylenediamine Poisoning.
Journal of forensic sciences.
2017 Mar; 62(2):483-487. doi:
10.1111/1556-4029.13297
. [PMID: 27957731] - Alberto Thalison Silveira, Ana Carolina Campos Albuquerque, José Salvador Lepera, Isarita Martins. Diazepam influences urinary bioindicator of occupational toluene exposure.
Environmental toxicology and pharmacology.
2016 Dec; 48(?):191-196. doi:
10.1016/j.etap.2016.10.012
. [PMID: 27816004] - Axelle Marchand, Rocio Aranda-Rodriguez, Robert Tardif, Andy Nong, Sami Haddad. Evaluation and modeling of the impact of coexposures to VOC mixtures on urinary biomarkers.
Inhalation toxicology.
2016; 28(6):260-73. doi:
10.3109/08958378.2016.1162232
. [PMID: 27053005] - M N Gallucci, M E Carezzano, M M Oliva, M S Demo, R P Pizzolitto, M P Zunino, J A Zygadlo, J S Dambolena. In vitro activity of natural phenolic compounds against fluconazole-resistant Candida species: a quantitative structure-activity relationship analysis.
Journal of applied microbiology.
2014 Apr; 116(4):795-804. doi:
10.1111/jam.12432
. [PMID: 24387763] - Frédéric Cosnier, Benoît Cossec, Manuella Burgart, Hervé Nunge, Céline Brochard, Marie-Josèphe Décret, Aurélie Rémy. Biomarkers of toluene exposure in rats: mercapturic acids versus traditional indicators (urinary hippuric acid and o-cresol and blood toluene).
Xenobiotica; the fate of foreign compounds in biological systems.
2013 Aug; 43(8):651-60. doi:
10.3109/00498254.2012.754114
. [PMID: 23278281] - Mariya S Liyasova, Lawrence M Schopfer, Oksana Lockridge. Cresyl saligenin phosphate makes multiple adducts on free histidine, but does not form an adduct on histidine 438 of human butyrylcholinesterase.
Chemico-biological interactions.
2013 Mar; 203(1):103-7. doi:
10.1016/j.cbi.2012.07.006
. [PMID: 22898212] - Mariya S Liyasova, Lawrence M Schopfer, Oksana Lockridge. Cresyl saligenin phosphate, an organophosphorus toxicant, makes covalent adducts with histidine, lysine, and tyrosine residues of human serum albumin.
Chemical research in toxicology.
2012 Aug; 25(8):1752-61. doi:
10.1021/tx300215g
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Molecules (Basel, Switzerland).
2012 Mar; 17(3):3181-201. doi:
10.3390/molecules17033181
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Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica.
2012 Mar; 37(5):658-62. doi:
NULL
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Environmental technology.
2012 Jan; 33(1-3):329-39. doi:
10.1080/09593330.2011.572923
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Biotechnology for biofuels.
2011 Oct; 4(?):43. doi:
10.1186/1754-6834-4-43
. [PMID: 22018114] - Juanjuan Feng, Min Sun, Lili Xu, Jubai Li, Xia Liu, Shengxiang Jiang. Preparation of metal wire supported solid-phase microextraction fiber coated with multi-walled carbon nanotubes.
Journal of separation science.
2011 Sep; 34(18):2482-8. doi:
10.1002/jssc.201100375
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Environmental health perspectives.
2011 Sep; 119(9):1218-26. doi:
10.1289/ehp.1103500
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Legal medicine (Tokyo, Japan).
2011 Jul; 13(4):180-5. doi:
10.1016/j.legalmed.2011.04.001
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PloS one.
2010 Aug; 5(8):e12138. doi:
10.1371/journal.pone.0012138
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Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
2010 Jul; 48(7):1796-800. doi:
10.1016/j.fct.2010.04.003
. [PMID: 20385193] - Sohel Dalal, Munishwar Nath Gupta. Purification and characterization of a peroxidase isozyme from Indian turnip roots.
Journal of agricultural and food chemistry.
2010 May; 58(9):5545-52. doi:
10.1021/jf904431t
. [PMID: 20405843] - Tamer Essam, Magdy Aly Amin, Ossama El Tayeb, Bo Mattiasson, Benoit Guieysse. Kinetics and metabolic versatility of highly tolerant phenol degrading Alcaligenes strain TW1.
Journal of hazardous materials.
2010 Jan; 173(1-3):783-8. doi:
10.1016/j.jhazmat.2009.09.006
. [PMID: 19783362] - Beata Janasik, Marek Jakubowski, Wiktor Wesołowski, Małgorzata Kucharska. Unmetabolized VOCs in urine as biomarkers of low level occupational exposure.
International journal of occupational medicine and environmental health.
2010; 23(1):21-6. doi:
10.2478/v10001-010-0003-x
. [PMID: 20442059] - Irène Sari-Minodier, Ginette Truchon, Ginette Charest-Tardif, Anick Bérubé, Robert Tardif. The effect of workload on biological monitoring of occupational exposure to toluene and n-Hexane: contribution of physiologically based toxicokinetic modeling.
Journal of occupational and environmental hygiene.
2009 Jul; 6(7):415-32. doi:
10.1080/15459620902928141
. [PMID: 19384711] - Silvia Fustinoni, Rosa Mercadante, Laura Campo. Self-collected urine sampling to study the kinetics of urinary toluene (and o-cresol) and define the best sampling time for biomonitoring.
International archives of occupational and environmental health.
2009 May; 82(6):703-13. doi:
10.1007/s00420-008-0393-2
. [PMID: 19125274] - Osamu Inoue, Toshio Kawai, Hirohiko Ukai, Yuki Maejima, Yoshinari Fukui, Fumiko Ohashi, Satoru Okamoto, Shiro Takada, Haruhiko Sakurai, Masayuki Ikeda. Limited validity of o-cresol and benzylmercapturic acid in urine as biomarkers of occupational exposure to toluene at low levels.
Industrial health.
2008 Aug; 46(4):318-25. doi:
10.2486/indhealth.46.318
. [PMID: 18716379] - M Ferrari, S Negri, P Zadra, S Ghittori, M Imbriani. Saliva as an analytical tool to measure occupational exposure to toluene.
International archives of occupational and environmental health.
2008 Aug; 81(8):1021-8. doi:
10.1007/s00420-007-0295-8
. [PMID: 18172667] - Masayuki Ikeda, Hirohiko Ukai, Toshio Kawai, Osamu Inoue, Yuki Maejima, Yoshinari Fukui, Fumiko Ohashi, Satoru Okamoto, Shiro Takada, Haruhiko Sakurai. Changes in correlation coefficients of exposure markers as a function of intensity of occupational exposure to toluene.
Toxicology letters.
2008 Jul; 179(3):148-54. doi:
10.1016/j.toxlet.2008.05.003
. [PMID: 18583070] - Radhouane Chakroun, Fayçal Faidi, Abderrazek Hedhili, Kaouther Charbaji, Habib Nouaigui, Mohamed Ben Laiba. Inhalant abuse detection and evaluation in young Tunisians.
Journal of forensic sciences.
2008 Jan; 53(1):232-7. doi:
10.1111/j.1556-4029.2007.00623.x
. [PMID: 18279264] - P Ducos, M Berode, J M Francin, C Arnoux, C Lefèvre. Biological monitoring of exposure to solvents using the chemical itself in urine: application to toluene.
International archives of occupational and environmental health.
2008 Jan; 81(3):273-84. doi:
10.1007/s00420-007-0210-3
. [PMID: 17605034] - Hirohiko Ukai, Toshio Kawai, Osamu Inoue, Yuki Maejima, Yoshinari Fukui, Fumiko Ohashi, Satoru Okamoto, Shiro Takada, Haruhiko Sakurai, Masayuki Ikeda. Comparative evaluation of biomarkers of occupational exposure to toluene.
International archives of occupational and environmental health.
2007 Oct; 81(1):81-93. doi:
10.1007/s00420-007-0193-0
. [PMID: 17653568] - G Koppen, G Verheyen, A Maes, U Van Gorp, G Schoeters, E Den Hond, J Staessen, T Nawrot, H A Roels, R Vlietinck, L Verschaeve. A battery of DNA effect biomarkers to evaluate environmental exposure of Flemish adolescents.
Journal of applied toxicology : JAT.
2007 May; 27(3):238-46. doi:
10.1002/jat.1174
. [PMID: 17226746] - I Sperlingová, L Dabrowská, V Stránský, J Kucera, M Tichý. Human urine certified reference material CZ 6010: creatinine and toluene metabolites (hippuric acid and o-cresol) and a benzene metabolite (phenol).
Analytical and bioanalytical chemistry.
2007 Apr; 387(7):2419-24. doi:
10.1007/s00216-006-0708-7
. [PMID: 16953321] - Joe MacDaniel, Vikhyat S Bebarta, Harvey A Schwertner, James F Martin. Comparison of urine and serum testing for early detection of acetaminophen ingestion.
Military medicine.
2007 Apr; 172(4):399-401. doi:
10.7205/milmed.172.4.399
. [PMID: 17484311] - María Eugenia Suarez-Ojeda, Albert Guisasola, Juan A Baeza, Azael Fabregat, Frank Stüber, Agustí Fortuny, Josep Font, Julián Carrera. Integrated catalytic wet air oxidation and aerobic biological treatment in a municipal WWTP of a high-strength o-cresol wastewater.
Chemosphere.
2007 Feb; 66(11):2096-105. doi:
10.1016/j.chemosphere.2006.09.035
. [PMID: 17095041] - Silvia Fustinoni, Rosa Mercadante, Laura Campo, Licia Scibetta, Carla Valla, Dario Consonni, Vito Foà. Comparison between urinary o-cresol and toluene as biomarkers of toluene exposure.
Journal of occupational and environmental hygiene.
2007 Jan; 4(1):1-9. doi:
10.1080/15459620601044844
. [PMID: 17162475] - Taozhi Zhang, Xinmiao Chen, Pei Liang, Cuixia Liu. Determination of phenolic compounds in wastewater by liquid-phase microextraction coupled with gas chromatography.
Journal of chromatographic science.
2006 Nov; 44(10):619-24. doi:
10.1093/chromsci/44.10.619
. [PMID: 17254372] - Véronique Nadeau, Ginette Truchon, Martin Brochu, Robert Tardif. Effect of physical exertion on the biological monitoring of exposure of various solvents following exposure by inhalation in human volunteers: I. Toluene.
Journal of occupational and environmental hygiene.
2006 Sep; 3(9):481-9. doi:
10.1080/15459620600862782
. [PMID: 16857647] - Jaya Dasgupta, Sita Subbaram, Kip M Connor, Ana M Rodriguez, Oren Tirosh, Joseph S Beckman, David Jourd'Heuil, J Andrés Melendez. Manganese superoxide dismutase protects from TNF-alpha-induced apoptosis by increasing the steady-state production of H2O2.
Antioxidants & redox signaling.
2006 Jul; 8(7-8):1295-305. doi:
10.1089/ars.2006.8.1295
. [PMID: 16910777] - Ana-Lilia González-Yebra, Carlos Kornhauser, Kazimierz Wrobel, Elva-Leticia Pérez-Luque, Katarzina Wrobel, Gloria Barbosa. Occupational exposure to toluene and its possible causative role in renal damage development in shoe workers.
International archives of occupational and environmental health.
2006 Mar; 79(3):259-64. doi:
10.1007/s00420-005-0001-7
. [PMID: 16001213] - Alan Andersen. Final report on the safety assessment of sodium p-chloro-m-cresol, p-chloro-m-cresol, chlorothymol, mixed cresols, m-cresol, o-cresol, p-cresol, isopropyl cresols, thymol, o-cymen-5-ol, and carvacrol.
International journal of toxicology.
2006; 25 Suppl 1(?):29-127. doi:
10.1080/10915810600716653
. [PMID: 16835130] - Agata Pietrzycka, Marek Stepniewski, Anna M Waszkielewicz, Henryk Marona. Preliminary evaluation of antioxidant activity of some 1-(phenoxyethyl)-piperazine derivatives.
Acta poloniae pharmaceutica.
2006 Jan; 63(1):19-24. doi:
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. [PMID: 17515325] - Gertrud Haeseler, Jörg Ahrens, Klaus Krampfl, Johannes Bufler, Reinhard Dengler, Hartmut Hecker, Jeffrey K Aronson, Martin Leuwer. Structural features of phenol derivatives determining potency for activation of chloride currents via alpha(1) homomeric and alpha(1)beta heteromeric glycine receptors.
British journal of pharmacology.
2005 Aug; 145(7):916-25. doi:
10.1038/sj.bjp.0706254
. [PMID: 15912136] - Jeong-Hee Kim, Ja-Kyoung Kim, Byong-Kwan Son, Ji-Eun Oh, Dae-Hyun Lim, Kwan-Hee Lee, Youn-Chol Hong, Sung-Il Cho. Effects of air pollutants on childhood asthma.
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