Harman (BioDeep_00000000032)

 

Secondary id: BioDeep_00000397976, BioDeep_00000865256

human metabolite PANOMIX_OTCML-2023


代谢物信息卡片


1-methyl-9H-pyrido[3,4-b]indole

化学式: C12H10N2 (182.084394)
中文名称: 哈尔满碱
谱图信息: 最多检出来源 Viridiplantae(plant) 0.09%

Reviewed

Last reviewed on 2024-06-29.

Cite this Page

Harman. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/harman (retrieved 2024-11-10) (BioDeep RN: BioDeep_00000000032). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CC1=C2NC3=CC=CC=C3C2=CC=N1
InChI: InChI=1S/C12H10N2/c1-8-12-10(6-7-13-8)9-4-2-3-5-11(9)14-12/h2-7,14H,1H3

描述信息

Harman is an indole alkaloid fundamental parent with a structure of 9H-beta-carboline carrying a methyl substituent at C-1. It has been isolated from the bark of Sickingia rubra, Symplocus racemosa, Passiflora incarnata, Peganum harmala, Banisteriopsis caapi and Tribulus terrestris, as well as from tobacco smoke. It is a specific, reversible inhibitor of monoamine oxidase A. It has a role as an anti-HIV agent, a plant metabolite and an EC 1.4.3.4 (monoamine oxidase) inhibitor. It is an indole alkaloid, an indole alkaloid fundamental parent and a harmala alkaloid.
Harman is a natural product found in Ophiopogon, Strychnos johnsonii, and other organisms with data available.
An indole alkaloid fundamental parent with a structure of 9H-beta-carboline carrying a methyl substituent at C-1. It has been isolated from the bark of Sickingia rubra, Symplocus racemosa, Passiflora incarnata, Peganum harmala, Banisteriopsis caapi and Tribulus terrestris, as well as from tobacco smoke. It is a specific, reversible inhibitor of monoamine oxidase A.
Isolated from roots of Panax ginseng and Codonopsis lanceolata (todok). Struct. has now been shown to be identical with 1-Acetyl-b-carboline CHK59-M
Harman is found in chicory. Harman is an alkaloid from the may pop (Passiflora incarnata, Passifloraceae) and many other Passiflora sp

[Raw Data] CB042_Harman_pos_30eV_CB000019.txt
[Raw Data] CB042_Harman_pos_20eV_CB000019.txt
[Raw Data] CB042_Harman_pos_40eV_CB000019.txt
[Raw Data] CB042_Harman_pos_10eV_CB000019.txt
[Raw Data] CB042_Harman_pos_50eV_CB000019.txt
[Raw Data] CB042_Harman_neg_50eV_000012.txt
[Raw Data] CB042_Harman_neg_30eV_000012.txt
[Raw Data] CB042_Harman_neg_40eV_000012.txt
[Raw Data] CB042_Harman_neg_20eV_000012.txt
[Raw Data] CB042_Harman_neg_10eV_000012.txt

Harman. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=486-84-0 (retrieved 2024-06-29) (CAS RN: 486-84-0). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Harmane, a β-Carboline alkaloid (BCA), is a potent neurotoxin that causes severe action tremors and psychiatric manifestations. Harmane shows 1000-fold selectivity for I1-Imidazoline receptor (IC50=30 nM) over α2-adrenoceptor (IC50=18 μM). Harmane is also a potent and selective inhibitor of monoamine oxidase (MAO) (IC50s=0.5 and 5 μM for human MAO A/B, respectively). Harmane exhibits comutagenic effect[1][2][3][4].
Harmane, a β-Carboline alkaloid (BCA), is a potent neurotoxin that causes severe action tremors and psychiatric manifestations. Harmane shows 1000-fold selectivity for I1-Imidazoline receptor (IC50=30 nM) over α2-adrenoceptor (IC50=18 μM). Harmane is also a potent and selective inhibitor of monoamine oxidase (MAO) (IC50s=0.5 and 5 μM for human MAO A/B, respectively). Harmane exhibits comutagenic effect[1][2][3][4].
Harmane, a β-Carboline alkaloid (BCA), is a potent neurotoxin that causes severe action tremors and psychiatric manifestations. Harmane shows 1000-fold selectivity for I1-Imidazoline receptor (IC50=30 nM) over α2-adrenoceptor (IC50=18 μM). Harmane is also a potent and selective inhibitor of monoamine oxidase (MAO) (IC50s=0.5 and 5 μM for human MAO A/B, respectively). Harmane exhibits comutagenic effect[1][2][3][4].

同义名列表

68 个代谢物同义名

InChI=1/C12H10N2/c1-8-12-10(6-7-13-8)9-4-2-3-5-11(9)14-12/h2-7,14H,1H; 5-23-08-00261 (Beilstein Handbook Reference); Harmane ( 1-Methyl-9H-pyrido[3,4-b]indole); 1-Methyl-9H-pyrido[3,4-b]indole, 9CI; 1-Methyl-9H-beta-carboline (Harman); 9H-Pyrido(3,4-b)indole, 1-methyl-; 9H-Pyrido[3,4-b]indole, 1-methyl-; 1-Methyl-9H-pyrido(3,4-b)indole; 1-Methyl-9H-Pyrido[3,4-6]indole; 1-Methyl-9H-pyrido[3,4-b]indole; Na-Formyl-1-methyl-b-carboline; 1-Methyl-9H-pyrid(3,4-b)indole; 1-Methyl-9H-pyrid[3,4-b]indole; 1-Methyl-9H-beta-carboline #; 1-Methyl-9H-beta-carboline; 1-Methyl-9H-I(2)-carboline; 1-Methyl-.beta.-carboline; PYRIDOBINDOLE, L-METHYL-; 2-Methyl-beta-carboline; 1-methyl-beta-carboline; 1-Methyl-9H-β-carboline; 1-Methyl-9H-b-carboline; L-Methyl-Pyridobindole; L-methylpyridobindole; 1-Methyl-b-carboline; Passiflorin-13C2,15N; 1-Methyl-β-carboline; harman hydrochloride; methylbeta-carboline; 3-Methyl-4-carboline; 1-methyl-2-carboline; Cyanoaceticacid-Osu; Harmane, free base; Prestwick3_000620; 1-Methylnorharman; Harman-d3 (Major); Prestwick2_000620; Prestwick1_000620; Prestwick0_000620; Spectrum3_000905; Spectrum4_001003; UNII-82D6J0535P; Harman-13C2,15N; Harmane, 98\\%; Lopac0_000605; DivK1c_006705; BPBio1_000616; Oprea1_152883; Tox21_500605; KBio3_001850; KBio2_001606; Passiflorine; Zygofabagine; KBio1_001649; KBio2_004174; KBio2_006742; HARMAN [MI]; Passiflorin; 82D6J0535P; Locuturine; Harman-d3; Locuturin; Loturine; Aribine; Harmane; Aribin; Harman; CN9



数据库引用编号

49 个数据库交叉引用编号

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)

77 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

  • Bao Tan Nguyen, Nguyen Thi Hai Yen, Ninh Khac Thanh Tung, Gil-Saeng Jeong, Jong Seong Kang, Nguyen Phuoc Long, Hyung Min Kim. Lipid class-dependent alterations of Caenorhabditis elegans under harmane exposure. Journal of pharmaceutical and biomedical analysis. 2023 Jul; 231(?):115401. doi: 10.1016/j.jpba.2023.115401. [PMID: 37105045]
  • Soching Luikham, Mavani A, Jhimli Bhattacharyya. Deciphering binding affinity, energetics, and base specificity of plant alkaloid Harmane with AT and GC hairpin duplex DNA. Luminescence : the journal of biological and chemical luminescence. 2022 May; 37(5):691-701. doi: 10.1002/bio.4210. [PMID: 35156295]
  • Wei Liu, Zhaoyu Yang, Lili Shi, Ziyu Cui, Yun Li. Degradation of β-Carbolines Harman and Norharman in Edible Oils during Heating. Molecules (Basel, Switzerland). 2021 Nov; 26(22):. doi: 10.3390/molecules26227018. [PMID: 34834111]
  • Andrew B Hawkey, Julia Hoeng, Manuel C Peitsch, Edward D Levin, Kyoko Koshibu. Subchronic effects of plant alkaloids on anxiety-like behavior in zebrafish. Pharmacology, biochemistry, and behavior. 2021 08; 207(?):173223. doi: 10.1016/j.pbb.2021.173223. [PMID: 34197843]
  • Vivek Lawana, Se Young Um, Rachel M Foguth, Jason R Cannon. Neuromelanin formation exacerbates HAA-induced mitochondrial toxicity and mitophagy impairments. Neurotoxicology. 2020 12; 81(?):147-160. doi: 10.1016/j.neuro.2020.10.005. [PMID: 33058929]
  • Chen-Xia Zhang, Jun Xi, Tian-Pei Zhao, Yu-Xiang Ma, Xue-De Wang. β-carbolines norharman and harman in vegetable oils in China. Food additives & contaminants. Part B, Surveillance. 2020 Sep; 13(3):193-199. doi: 10.1080/19393210.2020.1759701. [PMID: 32364007]
  • Renata Zawirska-Wojtasiak, Agnieszka Fedoruk-Wyszomirska, Paulina Piechowska, Sylwia Mildner-Szkudlarz, Joanna Bajerska, Elżbieta Wojtowicz, Krzysztof Przygoński, Dorota Gurda, Wiktoria Kubicka, Eliza Wyszko. β-Carbolines in Experiments on Laboratory Animals. International journal of molecular sciences. 2020 Jul; 21(15):. doi: 10.3390/ijms21155245. [PMID: 32722000]
  • Falco Beer, Felix Urbat, Charles M A P Franz, Melanie Huch, Sabine E Kulling, Mirko Bunzel, Diana Bunzel. The Human Fecal Microbiota Metabolizes Foodborne Heterocyclic Aromatic Amines by Reuterin Conjugation and Further Transformations. Molecular nutrition & food research. 2019 05; 63(10):e1801177. doi: 10.1002/mnfr.201801177. [PMID: 30815965]
  • Paulina Piechowska, Renata Zawirska-Wojtasiak, Sylwia Mildner-Szkudlarz. Bioactive β-Carbolines in Food: A Review. Nutrients. 2019 Apr; 11(4):. doi: 10.3390/nu11040814. [PMID: 30978920]
  • Ram B Jain. Concentrations of selected heterocyclic aromatic amines among US population aged ≥ 6 years: data from NHANES 2013-2014. Environmental science and pollution research international. 2018 Jul; 25(20):19859-19874. doi: 10.1007/s11356-018-2210-0. [PMID: 29737487]
  • Haroon Khan, Seema Patel, Mohammad A Kamal. Pharmacological and Toxicological Profile of Harmane-β-Carboline Alkaloid: Friend or Foe. Current drug metabolism. 2017; 18(9):853-857. doi: 10.2174/1389200218666170607100947. [PMID: 28595532]
  • Shuping Li, Liang Teng, Wei Liu, Xuemei Cheng, Bo Jiang, Zhengtao Wang, Chang-Hong Wang. Pharmacokinetic study of harmane and its 10 metabolites in rat after intravenous and oral administration by UPLC-ESI-MS/MS. Pharmaceutical biology. 2016 Sep; 54(9):1768-81. doi: 10.3109/13880209.2015.1127978. [PMID: 26730489]
  • Tomás Herraiz, Juan Galisteo. Naturally-occurring tetrahydro-β-carboline alkaloids derived from tryptophan are oxidized to bioactive β-carboline alkaloids by heme peroxidases. Biochemical and biophysical research communications. 2014 Aug; 451(1):42-7. doi: 10.1016/j.bbrc.2014.07.047. [PMID: 25035927]
  • Sudhakar Manda, Shabana I Khan, Surendra K Jain, Shabber Mohammed, Babu L Tekwani, Ikhlas A Khan, Ram A Vishwakarma, Sandip B Bharate. Synthesis, antileishmanial and antitrypanosomal activities of N-substituted tetrahydro-β-carbolines. Bioorganic & medicinal chemistry letters. 2014 Aug; 24(15):3247-50. doi: 10.1016/j.bmcl.2014.06.030. [PMID: 24980054]
  • Shuping Li, Wei Liu, Liang Teng, Xuemei Cheng, Zhengtao Wang, Changhong Wang. Metabolites identification of harmane in vitro/in vivo in rats by ultra-performance liquid chromatography combined with electrospray ionization quadrupole time-of-flight tandem mass spectrometry. Journal of pharmaceutical and biomedical analysis. 2014 Apr; 92(?):53-62. doi: 10.1016/j.jpba.2014.01.003. [PMID: 24486683]
  • Celesztina Domonkos, Ilona Fitos, Júlia Visy, Ferenc Zsila. Fatty acid modulated human serum albumin binding of the β-carboline alkaloids norharmane and harmane. Molecular pharmaceutics. 2013 Dec; 10(12):4706-16. doi: 10.1021/mp400531n. [PMID: 24171410]
  • Karen L Smith, Gemma K Ford, David S Jessop, David P Finn. Behavioural, neurochemical and neuroendocrine effects of the endogenous β-carboline harmane in fear-conditioned rats. Journal of psychopharmacology (Oxford, England). 2013 Feb; 27(2):162-70. doi: 10.1177/0269881112460108. [PMID: 23015542]
  • Mohammad Nasehi, Morteza Piri, Mojgan Abdollahian, Mohammad Reza Zarrindast. Involvement of nitrergic system of CA1in harmane induced learning and memory deficits. Physiology & behavior. 2013 Jan; 109(?):23-32. doi: 10.1016/j.physbeh.2012.10.006. [PMID: 23103833]
  • G- B Zhang, B Zhang, X- X Zhang, F- H Bing. Homonojirimycin, an alkaloid from dayflower inhibits the growth of influenza A virus in vitro. Acta virologica. 2013; 57(1):85-6. doi: 10.4149/av_2013_01_85. [PMID: 23530829]
  • Arkadiusz Szterk, Marek Roszko, Krystian Małek, Marcin Kurek, Monika Zbieć, Bożena Waszkiewicz-Robak. Profiles and concentrations of heterocyclic aromatic amines formed in beef during various heat treatments depend on the time of ripening and muscle type. Meat science. 2012 Dec; 92(4):587-95. doi: 10.1016/j.meatsci.2012.06.004. [PMID: 22762996]
  • Monika Gibis, Jochen Weiss. Antioxidant capacity and inhibitory effect of grape seed and rosemary extract in marinades on the formation of heterocyclic amines in fried beef patties. Food chemistry. 2012 Sep; 134(2):766-74. doi: 10.1016/j.foodchem.2012.02.179. [PMID: 23107689]
  • Bharathi Avula, Yan-Hong Wang, Chidananda Swamy Rumalla, Troy J Smillie, Ikhlas A Khan. Simultaneous determination of alkaloids and flavonoids from aerial parts of Passiflora species and dietary supplements using UPLC-UV-MS and HPTLC. Natural product communications. 2012 Sep; 7(9):1177-80. doi: . [PMID: 23074901]
  • Mohammad Nasehi, Shahrbano Sharifi, Mohammad Reza Zarrindast. Involvement of the cholinergic system of CA1 on harmane-induced amnesia in the step-down passive avoidance test. Journal of psychopharmacology (Oxford, England). 2012 Aug; 26(8):1151-61. doi: 10.1177/0269881111421972. [PMID: 21965190]
  • Bijan Kumar Paul, Nikhil Guchhait. Differential interactions of a biological photosensitizer with liposome membranes having varying surface charges. Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology. 2012 Apr; 11(4):661-73. doi: 10.1039/c2pp05346b. [PMID: 22266915]
  • Eric G Mworia, Takashi Yoshikawa, Nadiah Salikon, Chisato Oda, William O Asiche, Naoki Yokotani, Daigo Abe, Koichiro Ushijima, Ryohei Nakano, Yasutaka Kubo. Low-temperature-modulated fruit ripening is independent of ethylene in 'Sanuki Gold' kiwifruit. Journal of experimental botany. 2012 Jan; 63(2):963-71. doi: 10.1093/jxb/err324. [PMID: 22058408]
  • Jian-Hui Xiao, Dai-Min Xiao, Dai-Xiong Chen, Yu Xiao, Zong-Qi Liang, Jian-Jiang Zhong. Polysaccharides from the Medicinal Mushroom Cordyceps taii Show Antioxidant and Immunoenhancing Activities in a D-Galactose-Induced Aging Mouse Model. Evidence-based complementary and alternative medicine : eCAM. 2012; 2012(?):273435. doi: 10.1155/2012/273435. [PMID: 22536281]
  • Xing-Tai Li, Ya-Kui Zhang, Hai-Xue Kuang, Feng-Xin Jin, De-Wen Liu, Ming-Bo Gao, Ze Liu, Xiao-Juan Xin. Mitochondrial protection and anti-aging activity of Astragalus polysaccharides and their potential mechanism. International journal of molecular sciences. 2012; 13(2):1747-1761. doi: 10.3390/ijms13021747. [PMID: 22408421]
  • Nicole Shangming Hou, Stefan Taubert. Function and Regulation of Lipid Biology in Caenorhabditis elegans Aging. Frontiers in physiology. 2012; 3(?):143. doi: 10.3389/fphys.2012.00143. [PMID: 22629250]
  • Janick Mathys, Kaat De Cremer, Pieter Timmermans, Stefan Van Kerckhove, Bart Lievens, Mieke Vanhaecke, Bruno P A Cammue, Barbara De Coninck. Genome-Wide Characterization of ISR Induced in Arabidopsis thaliana by Trichoderma hamatum T382 Against Botrytis cinerea Infection. Frontiers in plant science. 2012; 3(?):108. doi: 10.3389/fpls.2012.00108. [PMID: 22661981]
  • Steven Maranz. An alternative paradigm for the role of antimalarial plants in Africa. TheScientificWorldJournal. 2012; 2012(?):978913. doi: 10.1100/2012/978913. [PMID: 22593717]
  • Mat Ropi Muktar, Norfaizah Osman, Khalijah Awang, Hazrina Hazni, Ahmad Kaleem Qureshi, A Hamid A Hadi, Kazuma Zaima, Hiroshi Morita, Marc Litaudon. Neonaucline, a new indole alkaloid from the leaves of Ochreinauclea maingayii (Hook. f.) Ridsd. (Rubiaceae). Molecules (Basel, Switzerland). 2011 Dec; 17(1):267-74. doi: 10.3390/molecules17010267. [PMID: 22205092]
  • Ting Zhao, Yu-qi He, Jun Wang, Ke-min Ding, Chang-hong Wang, Zheng-tao Wang. Inhibition of human cytochrome P450 enzymes 3A4 and 2D6 by β-carboline alkaloids, harmine derivatives. Phytotherapy research : PTR. 2011 Nov; 25(11):1671-7. doi: 10.1002/ptr.3458. [PMID: 21433154]
  • Emily B Merewitz, Thomas Gianfagna, Bingru Huang. Protein accumulation in leaves and roots associated with improved drought tolerance in creeping bentgrass expressing an ipt gene for cytokinin synthesis. Journal of experimental botany. 2011 Nov; 62(15):5311-33. doi: 10.1093/jxb/err166. [PMID: 21831843]
  • Marcelo F de Araújo, Ivo J Curcino Vieira, Raimundo Braz-Filho, Mário G de Carvalho. Simiranes A and B: erythroxylanes diterpenes and other compounds from Simira eliezeriana (Rubiaceae). Natural product research. 2011 Oct; 25(18):1713-9. doi: 10.1080/14786419.2011.560575. [PMID: 21936665]
  • Bijan Kumar Paul, Nikhil Guchhait. Modulation of prototropic activity and rotational relaxation dynamics of a cationic biological photosensitizer within the motionally constrained bio-environment of a protein. The journal of physical chemistry. B. 2011 Sep; 115(34):10322-34. doi: 10.1021/jp2015275. [PMID: 21790166]
  • Hedi Ben Mansour, Sonia Yatouji, Sihem Mbarek, Ikram Houas, Afef Delai, Dorra Dridi. Correlation between antibutyrylcholinesterasic and antioxidant activities of three aqueous extracts from Tunisian Rhus pentaphyllum. Annals of clinical microbiology and antimicrobials. 2011 Aug; 10(?):32. doi: 10.1186/1476-0711-10-32. [PMID: 21880140]
  • David P Dixon, Jonathan D Sellars, Robert Edwards. The Arabidopsis phi class glutathione transferase AtGSTF2: binding and regulation by biologically active heterocyclic ligands. The Biochemical journal. 2011 Aug; 438(1):63-70. doi: 10.1042/bj20101884. [PMID: 21631432]
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  • Lidia Błaszczyk, Delfina Popiel, Jerzy Chełkowski, Grzegorz Koczyk, Gary J Samuels, Krzysztof Sobieralski, Marek Siwulski. Species diversity of Trichoderma in Poland. Journal of applied genetics. 2011 May; 52(2):233-43. doi: 10.1007/s13353-011-0039-z. [PMID: 21465156]
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  • Fernando De Andrés, Mohammed Zougagh, Gregorio Castañeda, José Luis Sánchez-Rojas, Angel Ríos. Screening of non-polar heterocyclic amines in urine by microextraction in packed sorbent-fluorimetric detection and confirmation by capillary liquid chromatography. Talanta. 2011 Feb; 83(5):1562-7. doi: 10.1016/j.talanta.2010.11.060. [PMID: 21238752]
  • Hironori Tsuchiya. Comparative Effects of α-, β-, and γ-Carbolines on Platelet Aggregation and Lipid Membranes. Journal of toxicology. 2011; 2011(?):151596. doi: 10.1155/2011/151596. [PMID: 21876689]
  • A Daniel Martin, Barbara K Smith, Paul D Davenport, Eloise Harman, Ricardo J Gonzalez-Rothi, Maher Baz, A Joseph Layon, Michael J Banner, Lawrence J Caruso, Harsha Deoghare, Tseng-Tien Huang, Andrea Gabrielli. Inspiratory muscle strength training improves weaning outcome in failure to wean patients: a randomized trial. Critical care (London, England). 2011; 15(2):R84. doi: 10.1186/cc10081. [PMID: 21385346]
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  • Monika Gibis, Jochen Weiss. Inhibitory effect of marinades with hibiscus extract on formation of heterocyclic aromatic amines and sensory quality of fried beef patties. Meat science. 2010 Aug; 85(4):735-42. doi: 10.1016/j.meatsci.2010.03.034. [PMID: 20418021]
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  • Michal Shoresh, Gary E Harman. Differential expression of maize chitinases in the presence or absence of Trichoderma harzianum strain T22 and indications of a novel exo- endo-heterodimeric chitinase activity. BMC plant biology. 2010 Jul; 10(?):136. doi: 10.1186/1471-2229-10-136. [PMID: 20594307]
  • Mohammad Nasehi, Morteza Piri, Maryam Nouri, Davood Farzin, Touraj Nayer-Nouri, Mohammad Reza Zarrindast. Involvement of dopamine D1/D2 receptors on harmane-induced amnesia in the step-down passive avoidance test. European journal of pharmacology. 2010 May; 634(1-3):77-83. doi: 10.1016/j.ejphar.2010.02.027. [PMID: 20188725]
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