5-Methoxytryptamine (BioDeep_00000269409)

Main id: BioDeep_00000001334

 

natural product Volatile Flavor Compounds


代谢物信息卡片


5-Methoxy-3-indoleaceate

化学式: C11H14N2O (190.1106074)
中文名称: 5-甲氧基色胺
谱图信息: 最多检出来源 Homo sapiens(urine) 0.2%

分子结构信息

SMILES: c12c(cc(cc1)OC)c(c[nH]2)CCN
InChI: InChI=1S/C11H14N2O/c1-14-9-2-3-11-10(6-9)8(4-5-12)7-13-11/h2-3,6-7,13H,4-5,12H2,1H3

描述信息

A member of the class of tryptamines that is the methyl ether derivative of serotonin.

同义名列表

3 个代谢物同义名

5-Methoxy-3-indoleaceate; 5-Methoxytryptamine; 5-Methoxytryptamine



数据库引用编号

34 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(3)

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)

2 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

  • Muhammad Aamir Manzoor, Yan Xu, Zhengxin Lv, Jieming Xu, Yuxuan Wang, Wanxia Sun, Xunju Liu, Li Wang, Muhammad Abdullah, Ruie Liu, Songtao Jiu, Caixi Zhang. Comparative genomics of N-acetyl-5-methoxytryptamine members in four Prunus species with insights into bud dormancy and abiotic stress responses in Prunus avium. Plant cell reports. 2024 Mar; 43(4):89. doi: 10.1007/s00299-024-03184-0. [PMID: 38462577]
  • Sen Zhao, Jinyuan Chen, Chenhao Zhong, Liang Meng, Yanjiao Wang. Nontargeted metabolomic insights into the behavioral effects of 5-MeO-MiPT in zebrafish (Danio rerio). Ecotoxicology and environmental safety. 2024 Mar; 272(?):116044. doi: 10.1016/j.ecoenv.2024.116044. [PMID: 38295732]
  • Kaixin Wang, Qufan Xing, Golam Jalal Ahammed, Jie Zhou. Functions and prospects of melatonin in plant growth, yield, and quality. Journal of experimental botany. 2022 09; 73(17):5928-5946. doi: 10.1093/jxb/erac233. [PMID: 35640564]
  • Lijing Liao, Yuanze Zhou, Youdong Xu, Yuhao Zhang, Xikai Liu, Biao Liu, Xinxin Chen, Yan Guo, Zhixiong Zeng, Yucheng Zhao. Structural and Molecular Dynamics Analysis of Plant Serotonin N-Acetyltransferase Reveal an Acid/Base-Assisted Catalysis in Melatonin Biosynthesis. Angewandte Chemie (International ed. in English). 2021 05; 60(21):12020-12026. doi: 10.1002/anie.202100992. [PMID: 33682300]
  • 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]
  • Yoko Hagino, Frank Scott Hall, George R Uhl, Ichiro Sora, Kazutaka Ikeda. Dual actions of 5-MeO-DIPT at the serotonin transporter and serotonin 5-HT1A receptor in the mouse striatum and prefrontal cortex. Neuropsychopharmacology reports. 2021 03; 41(1):91-101. doi: 10.1002/npr2.12161. [PMID: 33547882]
  • Xiuying Yan, Shuai Yuan, Zhiguo Yu, Yunli Zhao, Sujing Zhang, Hejian Wu, Hui Yan, Ping Xiang. Development of an LC-MS/MS method for determining 5-MeO-DIPT in dried urine spots and application to forensic cases. Journal of forensic and legal medicine. 2020 May; 72(?):101963. doi: 10.1016/j.jflm.2020.101963. [PMID: 32452453]
  • Xiuying Yan, Ping Xiang, Yunli Zhao, Zhiguo Yu, Hui Yan. Determination of 5-MeO-DIPT in Human Urine Using Gas Chromatography Coupled with High-Resolution Orbitrap Mass Spectrometry. Journal of analytical toxicology. 2020 Apr; 44(5):461-469. doi: 10.1093/jat/bkaa005. [PMID: 32020169]
  • Tiantian Ye, Xiaoming Yin, Lei Yu, Shu-Jian Zheng, Wen-Jing Cai, Yan Wu, Yu-Qi Feng. Metabolic analysis of the melatonin biosynthesis pathway using chemical labeling coupled with liquid chromatography-mass spectrometry. Journal of pineal research. 2019 Jan; 66(1):e12531. doi: 10.1111/jpi.12531. [PMID: 30299556]
  • Dorottya Nagy-Szakal, Dinesh K Barupal, Bohyun Lee, Xiaoyu Che, Brent L Williams, Ellie J R Kahn, Joy E Ukaigwe, Lucinda Bateman, Nancy G Klimas, Anthony L Komaroff, Susan Levine, Jose G Montoya, Daniel L Peterson, Bruce Levin, Mady Hornig, Oliver Fiehn, W Ian Lipkin. Insights into myalgic encephalomyelitis/chronic fatigue syndrome phenotypes through comprehensive metabolomics. Scientific reports. 2018 07; 8(1):10056. doi: 10.1038/s41598-018-28477-9. [PMID: 29968805]
  • Achim T Caspar, Jonas B Gaab, Julian A Michely, Simon D Brandt, Markus R Meyer, Hans H Maurer. Metabolism of the tryptamine-derived new psychoactive substances 5-MeO-2-Me-DALT, 5-MeO-2-Me-ALCHT, and 5-MeO-2-Me-DIPT and their detectability in urine studied by GC-MS, LC-MSn , and LC-HR-MS/MS. Drug testing and analysis. 2018 Jan; 10(1):184-195. doi: 10.1002/dta.2197. [PMID: 28342193]
  • D Fabregat-Safont, M Barneo-Muñoz, F Martinez-Garcia, J V Sancho, F Hernández, M Ibáñez. Proposal of 5-methoxy-N-methyl-N-isopropyltryptamine consumption biomarkers through identification of in vivo metabolites from mice. Journal of chromatography. A. 2017 Jul; 1508(?):95-105. doi: 10.1016/j.chroma.2017.06.010. [PMID: 28602505]
  • Katherine C Faulkner, Katherine A Hurley, Douglas B Weibel. 5-Alkyloxytryptamines are membrane-targeting, broad-spectrum antibiotics. Bioorganic & medicinal chemistry letters. 2016 11; 26(22):5539-5544. doi: 10.1016/j.bmcl.2016.10.004. [PMID: 27765507]
  • John M Corkery, Emma Durkin, Simon Elliott, Fabrizio Schifano, A Hamid Ghodse. The recreational tryptamine 5-MeO-DALT (N,N-diallyl-5-methoxytryptamine): a brief review. Progress in neuro-psychopharmacology & biological psychiatry. 2012 Dec; 39(2):259-62. doi: 10.1016/j.pnpbp.2012.05.022. [PMID: 22683457]
  • Tadashi Hayama, Yohei Sakaguchi, Hideyuki Yoshida, Miki Itoyama, Kenichiro Todoroki, Masatoshi Yamaguchi, Hitoshi Nohta. Binary fluorous alkylation of biogenic primary amines with perfluorinated aldehyde followed by fluorous liquid chromatography-tandem mass spectrometry analysis. Analytical chemistry. 2012 Oct; 84(19):8407-14. doi: 10.1021/ac3020092. [PMID: 22950579]
  • Natalia Fagali, Angel Catalá. The antioxidant behaviour of melatonin and structural analogues during lipid peroxidation depends not only on their functional groups but also on the assay system. Biochemical and biophysical research communications. 2012 Jul; 423(4):873-7. doi: 10.1016/j.bbrc.2012.06.060. [PMID: 22713457]
  • Jeff Dyche, A Michael Anch, Kethera A J Fogler, David W Barnett, Cecil Thomas. Effects of power frequency electromagnetic fields on melatonin and sleep in the rat. Emerging health threats journal. 2012; 5(?):. doi: 10.3402/ehtj.v5i0.10904. [PMID: 22529876]
  • Ming J Jin, Changbae Jin, Jin Y Kim, Moon K In, Oh S Kwon, Hye H Yoo. A quantitative method for simultaneous determination of 5-methoxy-N,N-diisopropyltryptamine and its metabolites in urine using liquid chromatography-electrospray ionization-tandem mass spectrometry. Journal of forensic sciences. 2011 Jul; 56(4):1044-8. doi: 10.1111/j.1556-4029.2011.01753.x. [PMID: 21418218]
  • Eduardo Alves de Almeida, Paolo Di Mascio, Tatsuo Harumi, D Warren Spence, Adam Moscovitch, Rüdiger Hardeland, Daniel P Cardinali, Gregory M Brown, S R Pandi-Perumal. Measurement of melatonin in body fluids: standards, protocols and procedures. Child's nervous system : ChNS : official journal of the International Society for Pediatric Neurosurgery. 2011 Jun; 27(6):879-91. doi: 10.1007/s00381-010-1278-8. [PMID: 21104186]
  • Kine Gregersen, Jørgen Valeur, Kristine Lillestøl, Livar Frøyland, Pedro Araujo, Gülen Arslan Lied, Arnold Berstad. Subjective food hypersensitivity: assessment of enterochromaffin cell markers in blood and gut lavage fluid. International journal of general medicine. 2011; 4(?):555-60. doi: 10.2147/ijgm.s18349. [PMID: 21887108]
  • André Welp, Bernhard Manz, Elmar Peschke. Development and validation of a high throughput direct radioimmunoassay for the quantitative determination of serum and plasma melatonin (N-acetyl-5-methoxytryptamine) in mice. Journal of immunological methods. 2010 Jun; 358(1-2):1-8. doi: 10.1016/j.jim.2010.03.018. [PMID: 20363223]
  • Liaoyuan A Hu, Tian Zhou, Jinwoo Ahn, Shuli Wang, Julia Zhou, Yi Hu, Qingyun Liu. Human and mouse trace amine-associated receptor 1 have distinct pharmacology towards endogenous monoamines and imidazoline receptor ligands. The Biochemical journal. 2009 Oct; 424(1):39-45. doi: 10.1042/bj20090998. [PMID: 19725810]
  • Takayuki Nakagawa, Shuji Kaneko. Neuropsychotoxicity of abused drugs: molecular and neural mechanisms of neuropsychotoxicity induced by methamphetamine, 3,4-methylenedioxymethamphetamine (ecstasy), and 5-methoxy-N,N-diisopropyltryptamine (foxy). Journal of pharmacological sciences. 2008 Jan; 106(1):2-8. doi: 10.1254/jphs.fm0070141. [PMID: 18198474]
  • Natalia Fagali, Angel Catalá. The effect of melatonin and structural analogues on the lipid peroxidation of triglycerides enriched in omega-3 polyunsaturated fatty acids. Life sciences. 2007 Jul; 81(4):299-305. doi: 10.1016/j.lfs.2007.05.013. [PMID: 17603083]
  • Michael T Williams, Nicole R Herring, Tori L Schaefer, Matthew R Skelton, Nicholas G Campbell, Jack W Lipton, Anne E McCrea, Charles V Vorhees. Alterations in body temperature, corticosterone, and behavior following the administration of 5-methoxy-diisopropyltryptamine ('foxy') to adult rats: a new drug of abuse. Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology. 2007 Jun; 32(6):1404-20. doi: 10.1038/sj.npp.1301232. [PMID: 17047665]
  • C Sogawa, N Sogawa, J Tagawa, A Fujino, K Ohyama, M Asanuma, M Funada, S Kitayama. 5-Methoxy-N,N-diisopropyltryptamine (Foxy), a selective and high affinity inhibitor of serotonin transporter. Toxicology letters. 2007 Apr; 170(1):75-82. doi: 10.1016/j.toxlet.2007.02.007. [PMID: 17382495]
  • Masanari Itokawa, Ken Iwata, Misako Takahashi, Gen-Ichi Sugihara, Takeshi Sasaki, Yu-Ichiro Abe, Minari Uno, Mizue Hobo, Daisuke Jitoku, Kikue Inoue, Makoto Arai, Ichiro Yasuda, Masahiro Shintani. Acute confusional state after designer tryptamine abuse. Psychiatry and clinical neurosciences. 2007 Apr; 61(2):196-9. doi: 10.1111/j.1440-1819.2007.01638.x. [PMID: 17362440]
  • Benita Sjögren, Mark W Hamblin, Per Svenningsson. Cholesterol depletion reduces serotonin binding and signaling via human 5-HT(7(a)) receptors. European journal of pharmacology. 2006 Dec; 552(1-3):1-10. doi: 10.1016/j.ejphar.2006.08.069. [PMID: 17064686]
  • Einosuke Tanaka, Tooru Kamata, Munehiro Katagi, Hitoshi Tsuchihashi, Katsuya Honda. A fatal poisoning with 5-methoxy-N,N-diisopropyltryptamine, Foxy. Forensic science international. 2006 Nov; 163(1-2):152-4. doi: 10.1016/j.forsciint.2005.11.026. [PMID: 16406422]
  • Tangbin Yang, Jianhe Wang, Lina Qu, Ping Zhong, Yanhong Yuan. Preparation and identification of anti-melatonin monoclonal antibodies. Journal of pineal research. 2006 May; 40(4):350-4. doi: 10.1111/j.1600-079x.2006.00314.x. [PMID: 16635023]
  • Tooru Kamata, Munehiro Katagi, Hiroe T Kamata, Akihiro Miki, Noriaki Shima, Kei Zaitsu, Mayumi Nishikawa, Einosuke Tanaka, Katsuya Honda, Hitoshi Tsuchihashi. Metabolism of the psychotomimetic tryptamine derivative 5-methoxy-N,N-diisopropyltryptamine in humans: identification and quantification of its urinary metabolites. Drug metabolism and disposition: the biological fate of chemicals. 2006 Feb; 34(2):281-7. doi: 10.1124/dmd.105.005835. [PMID: 16280455]
  • Ewa Pobozy, Aleksander Michalski, Joanna Sotowska-Brochocka, Marek Trojanowicz. Determination of melatonin and its precursors and metabolites using capillary electrophoresis with UV and fluorometric detection. Journal of separation science. 2005 Nov; 28(16):2165-72. doi: 10.1002/jssc.200500095. [PMID: 16318213]
  • Rüdiger Hardeland, S R Pandi-Perumal. Melatonin, a potent agent in antioxidative defense: actions as a natural food constituent, gastrointestinal factor, drug and prodrug. Nutrition & metabolism. 2005 Sep; 2(?):22. doi: 10.1186/1743-7075-2-22. [PMID: 16153306]
  • Tomomi Ishida, Keiko Kudo, Akiko Kiyoshima, Hiromasa Inoue, Akiko Tsuji, Noriaki Ikeda. Sensitive determination of alpha-methyltryptamine (AMT) and 5-methoxy-N,N-diisopropyltryptamine (5MeO-DIPT) in whole blood and urine using gas chromatography-mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2005 Aug; 823(1):47-52. doi: 10.1016/j.jchromb.2004.10.067. [PMID: 16055053]
  • John M Wilson, Frank McGeorge, Susan Smolinske, Robert Meatherall. A foxy intoxication. Forensic science international. 2005 Feb; 148(1):31-6. doi: 10.1016/j.forsciint.2004.04.017. [PMID: 15607587]
  • Yasir El-Sherif, Paula Witt-Enderby, Pui-Kai Li, Jene Tesoriero, Michael V Hogan, Andrzej Wieraszko. The actions of a charged melatonin receptor ligand, TMEPI, and an irreversible MT2 receptor agonist, BMNEP, on mouse hippocampal evoked potentials in vitro. Life sciences. 2004 Nov; 75(26):3147-56. doi: 10.1016/j.lfs.2004.06.009. [PMID: 15488894]
  • Shawn P Vorce, Jason H Sklerov. A general screening and confirmation approach to the analysis of designer tryptamines and phenethylamines in blood and urine using GC-EI-MS and HPLC-electrospray-MS. Journal of analytical toxicology. 2004 Sep; 28(6):407-10. doi: 10.1093/jat/28.6.407. [PMID: 15516287]
  • Do Yu Soung, Hye Rhi Choi, Ji Young Kim, Jae Kyung No, Jee Hyun Lee, Min Sun Kim, Sook Hee Rhee, Jin Seng Park, Myung Jung Kim, Ryung Yang, Hae Young Chung. Peroxynitrite scavenging activity of indole derivatives: interaction of indoles with peroxynitrite. Journal of medicinal food. 2004; 7(1):84-9. doi: 10.1089/109662004322984752. [PMID: 15117558]
  • Eduardo A Almeida, Clécio F Klitzke, Glaucia R Martinez, Marisa H G Medeiros, Paolo Di Mascio. Synthesis of internal labeled standards of melatonin and its metabolite N1-acetyl-N2-formyl-5-methoxykynuramine for their quantification using an on-line liquid chromatography-electrospray tandem mass spectrometry system. Journal of pineal research. 2004 Jan; 36(1):64-71. doi: 10.1046/j.1600-079x.2003.00098.x. [PMID: 14675132]
  • Rüdiger Hardeland, Ana Coto-Montes, Burkhard Poeggeler. Circadian rhythms, oxidative stress, and antioxidative defense mechanisms. Chronobiology international. 2003 Nov; 20(6):921-62. doi: 10.1081/cbi-120025245. [PMID: 14680136]
  • Julie Y Crider, Gary W Williams, Colene D Drace, Parvaneh Katoli, Michelle Senchyna, Najam A Sharif. Pharmacological characterization of a serotonin receptor (5-HT7) stimulating cAMP production in human corneal epithelial cells. Investigative ophthalmology & visual science. 2003 Nov; 44(11):4837-44. doi: 10.1167/iovs.02-1292. [PMID: 14578406]
  • Jean Y Zhang, Stanley Nawoschik, Dianne Kowal, Deborah Smith, Taylor Spangler, Rafal Ochalski, Lee Schechter, John Dunlop. Characterization of the 5-HT6 receptor coupled to Ca2+ signaling using an enabling chimeric G-protein. European journal of pharmacology. 2003 Jul; 472(1-2):33-8. doi: 10.1016/s0014-2999(03)01855-7. [PMID: 12860470]
  • Robert Meatherall, Pankaj Sharma. Foxy, a designer tryptamine hallucinogen. Journal of analytical toxicology. 2003 Jul; 27(5):313-7. doi: 10.1093/jat/27.5.313. [PMID: 12908946]
  • Andrzej Slominski, Alexander Pisarchik, Blazej Zbytek, Desmond J Tobin, Söbia Kauser, Jacobo Wortsman. Functional activity of serotoninergic and melatoninergic systems expressed in the skin. Journal of cellular physiology. 2003 Jul; 196(1):144-53. doi: 10.1002/jcp.10287. [PMID: 12767050]
  • Ai-Ming Yu, Jeffrey R Idle, Linda G Byrd, Kristopher W Krausz, Adrian Küpfer, Frank J Gonzalez. Regeneration of serotonin from 5-methoxytryptamine by polymorphic human CYP2D6. Pharmacogenetics. 2003 Mar; 13(3):173-81. doi: 10.1097/01.fpc.0000054066.98065.7b. [PMID: 12618595]
  • Mariana Gavazza, Angel Catalá. Melatonin preserves arachidonic and docosapentaenoic acids during ascorbate-Fe2+ peroxidation of rat testis microsomes and mitochondria. The international journal of biochemistry & cell biology. 2003 Mar; 35(3):359-66. doi: 10.1016/s1357-2725(02)00256-x. [PMID: 12531249]
  • N V Kondakova, V V Sakharova, N V Ripa, L B Rebrov, A A Mandrugin, V M Fedoseev. [Study of the antiradical and radioprotective properties of S-containing compounds using the complex of in vitro test-systems]. Radiatsionnaia biologiia, radioecologiia. 2002 Sep; 42(5):503-10. doi: ". [PMID: 12449817]
  • Armelle Pindon, Geert van Hecke, Paul van Gompel, Anne S Lesage, Josée E Leysen, Mirek Jurzak. Differences in signal transduction of two 5-HT4 receptor splice variants: compound specificity and dual coupling with Galphas- and Galphai/o-proteins. Molecular pharmacology. 2002 Jan; 61(1):85-96. doi: 10.1124/mol.61.1.85. [PMID: 11752209]
  • H X Wang, F Liu, T B Ng. Examination of pineal indoles and 6-methoxy-2-benzoxazolinone for antioxidant and antimicrobial effects. Comparative biochemistry and physiology. Toxicology & pharmacology : CBP. 2001 Nov; 130(3):379-88. doi: 10.1016/s1532-0456(01)00264-2. [PMID: 11701394]
  • Y Oner-Iyidoğan, F Gürdöl, P Oner. The effects of acute melatonin and ethanol treatment on antioxidant enzyme activities in rat testes. Pharmacological research. 2001 Aug; 44(2):89-93. doi: 10.1006/phrs.2001.0828. [PMID: 11516256]
  • D L Van Tassel, S D O'Neill. Putative regulatory molecules in plants: evaluating melatonin. Journal of pineal research. 2001 Aug; 31(1):1-7. doi: 10.1034/j.1600-079x.2001.310101.x. [PMID: 11484999]
  • F Liu, T B Ng. Effect of pineal indoles on activities of the antioxidant defense enzymes superoxide dismutase, catalase, and glutathione reductase, and levels of reduced and oxidized glutathione in rat tissues. Biochemistry and cell biology = Biochimie et biologie cellulaire. 2000; 78(4):447-53. doi: 10.1139/o00-018. [PMID: 11012083]
  • R Hardeland. Melatonin and 5-methoxytryptamine in non-metazoans. Reproduction, nutrition, development. 1999 May; 39(3):399-408. doi: 10.1051/rnd:19990311. [PMID: 10420441]
  • Y Teramoto, T Urano, N Nagai, Y Takada, K Ikeda, A Takada. Plasma levels of 5-HT and 5-HIAA increased after intestinal ischemia/reperfusion in rats. The Japanese journal of physiology. 1998 Oct; 48(5):333-9. doi: 10.2170/jjphysiol.48.333. [PMID: 9852341]
  • P Li, S F Pang, C L Chan, C W Tsang. Identification and diurnal studies of pineal and serum 5-methoxytryptamine in the rat and quail. Neuroscience letters. 1997 May; 228(1):63-5. doi: 10.1016/s0304-3940(97)00361-3. [PMID: 9197288]
  • J Yamada, Y Sugimoto, T Yoshikawa, K Horisaka. Hyperglycemia induced by the 5-HT receptor agonist, 5-methoxytryptamine, in rats: involvement of the peripheral 5-HT2A receptor. European journal of pharmacology. 1997 Apr; 323(2-3):235-40. doi: 10.1016/s0014-2999(97)00029-0. [PMID: 9128844]
  • M Hara, M Iigo, R Ohtani-Kaneko, N Nakamura, T Suzuki, R J Reiter, K Hirata. Administration of melatonin and related indoles prevents exercise-induced cellular oxidative changes in rats. Biological signals. 1997 Mar; 6(2):90-100. doi: 10.1159/000109113. [PMID: 9266096]
  • J E Leysen, W Gommeren, L Heylen, W H Luyten, I Van de Weyer, P Vanhoenacker, G Haegeman, A Schotte, P Van Gompel, R Wouters, A S Lesage. Alniditan, a new 5-hydroxytryptamine1D agonist and migraine-abortive agent: ligand-binding properties of human 5-hydroxytryptamine1D alpha, human 5-hydroxytryptamine1D beta, and calf 5-hydroxytryptamine1D receptors investigated with [3H]5-hydroxytryptamine and [3H]alniditan. Molecular pharmacology. 1996 Dec; 50(6):1567-80. doi: . [PMID: 8967979]
  • C Haldar. Harderian gland function of Indian tropical palm squirrel, Funambulus pennanti. Microscopy research and technique. 1996 May; 34(1):39-47. doi: 10.1002/(sici)1097-0029(19960501)34:1<39::aid-jemt6>3.0.co;2-r. [PMID: 9156608]
  • S Oaknin-Bendahan, Y Anis, I Nir, N Zisapel. Effects of long-term administration of melatonin and a putative antagonist on the ageing rat. Neuroreport. 1995 Mar; 6(5):785-8. doi: 10.1097/00001756-199503270-00020. [PMID: 7605949]
  • W Y Chan, T B Ng. Effects of pineal indoles on ovarian response to gonadotropin-induced ovulation in mice. Journal of neural transmission. General section. 1995; 100(3):239-46. doi: 10.1007/bf01276461. [PMID: 8748669]
  • D Müller-Wieland, B Behnke, K Koopmann, W Krone. Melatonin inhibits LDL receptor activity and cholesterol synthesis in freshly isolated human mononuclear leukocytes. Biochemical and biophysical research communications. 1994 Aug; 203(1):416-21. doi: 10.1006/bbrc.1994.2198. [PMID: 8074686]
  • Y Shen, F J Monsma, M A Metcalf, P A Jose, M W Hamblin, D R Sibley. Molecular cloning and expression of a 5-hydroxytryptamine7 serotonin receptor subtype. The Journal of biological chemistry. 1993 Aug; 268(24):18200-4. doi: . [PMID: 8394362]
  • N Adham, H T Kao, L E Schecter, J Bard, M Olsen, D Urquhart, M Durkin, P R Hartig, R L Weinshank, T A Branchek. Cloning of another human serotonin receptor (5-HT1F): a fifth 5-HT1 receptor subtype coupled to the inhibition of adenylate cyclase. Proceedings of the National Academy of Sciences of the United States of America. 1993 Jan; 90(2):408-12. doi: 10.1073/pnas.90.2.408. [PMID: 8380639]
  • R D Platonova, O S Medvedev. [Systemic and regional hemodynamic in rats after use of 5-methoxytryptamine: mechanisms of 'pharmacological adaptation' to hypoxia]. Voprosy meditsinskoi khimii. 1992 Mar; 38(2):53-5. doi: NULL. [PMID: 1413634]
  • F Raynaud, P Pévet. Determination of 5-methoxyindoles in pineal gland and plasma samples by high-performance liquid chromatography with electrochemical detection. Journal of chromatography. 1991 Mar; 564(1):103-13. doi: 10.1016/0378-4347(91)80073-l. [PMID: 1713596]
  • F Raynaud, P Pévet. 5-Methoxytryptamine is metabolized by monoamine oxidase A in the pineal gland and plasma of golden hamsters. Neuroscience letters. 1991 Feb; 123(2):172-4. doi: 10.1016/0304-3940(91)90923-h. [PMID: 2027530]
  • F Raynaud, B Vivien-Roels, M Masson-Pévet, P Pévet. Plasma concentrations of 5-methoxytryptamine, 5-methoxytryptophol and melatonin after 5-methoxytryptamine administration of golden hamsters: physiological implications. Journal of neural transmission. General section. 1991; 84(1-2):33-43. doi: 10.1007/bf01249107. [PMID: 2054148]
  • B Manz, A Seidel, H Alexander, L Vollrath, B Wagner, G Zimmermann, K Wiedemann, K Pollow. Development and validation of a radioimmunoassay for serum melatonin. Journal of clinical chemistry and clinical biochemistry. Zeitschrift fur klinische Chemie und klinische Biochemie. 1989 Oct; 27(10):797-802. doi: 10.1515/cclm.1989.27.10.797. [PMID: 2600552]
  • M Nordio, M K Vaughan, N Zisapel, S Migliaccio, A van Jaarsveld, R J Reiter. A novel melatonin antagonist, N-(2,4-dinitrophenyl)-5-methoxytryptamine neutralizes some effects of melatonin in the female Syrian hamster. Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine (New York, N.Y.). 1989 Sep; 191(4):321-5. doi: 10.3181/00379727-191-42926. [PMID: 2505262]
  • G A Lincoln, R W Kelly. Test of ML23 as an antagonist to the effects of melatonin in the ram. Journal of reproduction and fertility. 1989 Jul; 86(2):737-43. doi: 10.1530/jrf.0.0860737. [PMID: 2503613]
  • F Raynaud, J L Miguel, B Vivien-Roels, M Masson-Pévet, P Pévet. The effect of 5-methoxytryptamine on golden hamster gonads is not a consequence of its acetylation into melatonin. The Journal of endocrinology. 1989 Jun; 121(3):507-12. doi: 10.1677/joe.0.1210507. [PMID: 2754374]
  • D J Morton. Effect of methoxyindole administration on plasma cation levels in the rat. Journal of pineal research. 1989; 6(2):141-7. doi: 10.1111/j.1600-079x.1989.tb00411.x. [PMID: 2464684]
  • V S Shcherbakova, E S Rom-Buguslavskaia. [Epiphysis cerebri-thyroid interrelations. Distorting effect of partial thyroidectomy on the antithyroid action of epiphyseal methoxyindoles in animal experiments]. Biulleten' eksperimental'noi biologii i meditsiny. 1988 May; 105(5):542-5. doi: NULL. [PMID: 3164221]
  • M Laudon, Z Yaron, N Zisapel. N-(2,4-dinitrophenyl)-5-methoxytryptamine, a novel melatonin antagonist: effects on sexual maturation of the male and female rat and on oestrous cycles of the female rat [corrected]. The Journal of endocrinology. 1988 Jan; 116(1):43-53. doi: 10.1677/joe.0.1160043. [PMID: 2828507]
  • D E Blask, S M Hill. Effects of melatonin on cancer: studies on MCF-7 human breast cancer cells in culture. Journal of neural transmission. Supplementum. 1986; 21(?):433-49. doi: . [PMID: 3462341]
  • J van Benthem, J de Koning, I Ebels, M G Balemans. The effect of different photoperiods on the methylating capacity of the pineal gland of adult, male golden hamsters, with special reference to 5-methoxyindoles. Journal of neural transmission. 1986; 67(1-2):147-62. doi: 10.1007/bf01243367. [PMID: 3097253]
  • U Lang, M L Aubert, R W Rivest, J C Vinas-Bradtke, P C Sizonenko. Inhibitory action of exogenous melatonin, 5-methoxytryptamine, and 6-hydroxymelatonin on sexual maturation of male rats: activity of 5-methoxytryptamine might be due to its conversion to melatonin. Biology of reproduction. 1985 Oct; 33(3):618-28. doi: 10.1095/biolreprod33.3.618. [PMID: 3931709]
  • M Geffard, J Dulluc, A M Rock. Antisera against the indolealkylamines: tryptophan, 5-hydroxytryptophan, 5-hydroxytryptamine, 5-methoxytryptophan, and 5-methoxytryptamine tested by an enzyme-linked immunosorbent assay method. Journal of neurochemistry. 1985 Apr; 44(4):1221-8. doi: 10.1111/j.1471-4159.1985.tb08747.x. [PMID: 3919158]
  • R M Leone, R E Silman. An investigation of demethylation in the metabolism of methoxytryptamine and methoxytryptophol. Journal of pineal research. 1985; 2(1):87-94. doi: 10.1111/j.1600-079x.1985.tb00630.x. [PMID: 2420959]
  • M K Vaughan, B A Richardson, L J Petterborg, A P Holtorf, G M Vaughan, T H Champney, R J Reiter. Effects of injections and/or chronic implants of melatonin and 5-methoxytryptamine on plasma thyroid hormones in male and female Syrian hamsters. Neuroendocrinology. 1984 Oct; 39(4):361-6. doi: 10.1159/000124005. [PMID: 6593601]
  • F Chimenti, M C Casanova, V Zagarese, P Turin, S Sabatini. [Substances inhibiting monoamine oxidase. II. Inhibition of bovine plasma amine oxidase by N-cyclopropyltryptamines]. Il Farmaco; edizione scientifica. 1983 Jun; 38(6):425-8. doi: NULL. [PMID: 6575920]
  • J Benesová-Půlpánová, M Ledvina. [The efect of ionizing radiation and fasting on the excretion of o-iodobenzoic acid 125I and its conjugates in the urine of rats protected by radioprotective agents]. Sbornik vedeckych praci Lekarske fakulty Karlovy univerzity v Hradci Kralove. Supplementum. 1983; 26(3):201-15. doi: NULL. [PMID: 6335783]
  • J Půlpánová, H Kovárová, M Ledvina. [Concentration of reduced glutathione and glutathione reductase activity in various rat tissues following the administration of radioprotective substances]. Radiobiologia, radiotherapia. 1982 Jan; 23(1):42-9. doi: NULL. [PMID: 6953526]
  • F Chimenti, M C Casanova, P Turini, S Sabatini. [Monoamine oxidase inhibitors. I. Synthesis of N-cyclopropyltryptamines]. Il Farmaco; edizione scientifica. 1980 Sep; 35(9):785-90. doi: NULL. [PMID: 6935082]
  • J Krízala, P Kuna, A Stoklasová, M Ledvina, M Dostál. Influence of radioprotective agents on the activities of isoenzymes of blood serum alkaline phosphatase in irradiated dogs. Strahlentherapie. 1980 May; 156(5):365-7. doi: . [PMID: 6930747]
  • J R Yandrasitz, R M Cohn, B Masley, D DelRowe. Evaluation of the binding of serotonin by isolated CNS acidic lipids. Neurochemical research. 1980 May; 5(5):465-77. doi: 10.1007/bf00964984. [PMID: 6930543]
  • P Klír, J Pospísil, E Skala, Z Dienstbier, O Tachecí. [Effect of radioprotective substances on the antiheparin activity of platelet-free plasma of rats subjected to whole-body irradiation]. Sbornik lekarsky. 1980; 82(4):124-8. doi: NULL. [PMID: 6930098]
  • J Krízala, P Kuna, M Bĕlská, V Stuchlíková, M Ledvina, M Dostál. [The effect of radioprotective agents on the activity of alkaline phosphatase isoenzymes in the blood serum of irradiated large laboratory animals]. Sbornik vedeckych praci Lekarske fakulty Karlovy univerzity v Hradci Kralove. Supplementum. 1980; 23(3):297-309. doi: NULL. [PMID: 6969435]
  • B W Wilson, W Snedden. Capillary column GCMS detection of 5-methoxytryptamine in human plasma using selected ion monitoring. Journal of neurochemistry. 1979 Oct; 33(4):939-41. doi: 10.1111/j.1471-4159.1979.tb09924.x. [PMID: 290766]
  • M K Samson, R L Stephens, S Rivkin, M Opipari, T Maloney, C W Groppe, R Fisher. Vinblastine, bleomycin, and cis-dichlorodiammineplatinum(II) in disseminated testicular cancer: preliminary report of a Southwest Oncology Group Study. Cancer treatment reports. 1979 Sep; 63(9-10):1663-7. doi: . [PMID: 91435]
  • C A Laud, I Smith. The binding of methoxyindoles to human plasma proteins. Progress in brain research. 1979; 52(?):513-5. doi: 10.1016/s0079-6123(08)62958-1. [PMID: 297247]
  • L Peyrin, J M Cottet-Emard, F Javoy, Y Agid, A Herbet, J Glowinski. Long-term effects of unilateral 6-hydroxydopamine destruction of the dopaminergic nigrostriatal pathway on the urinary excretion of catecholamines (dopamine, norepinephrine, epinephrine) and their metabolites in the rat. Brain research. 1978 Mar; 143(3):567-72. doi: 10.1016/0006-8993(78)90369-4. [PMID: 274167]
  • J A Hoskins, R J Pollitt. The determination of 5-methoxyindole-3-acetic acid in human urine by mass fragmentography. Journal of chromatography. 1978 Mar; 145(2):285-9. doi: 10.1016/s0378-4347(00)81349-3. [PMID: 274448]
  • L Huszka, D H Zabek, J W Doust. Urinary excretion of n,n-dimethylated tryptamines in chronic schizophrenia. A review of the present status of the hypothesis. Canadian Psychiatric Association journal. 1976 Dec; 21(8):541-6. doi: 10.1177/070674377602100808. [PMID: 1071579]
  • L Levine, L J Riceberg. Radioimmunoassay for melatonin. Research communications in chemical pathology and pharmacology. 1975 Apr; 10(4):693-702. doi: . [PMID: 1057224]
  • P Kuna. Acute cardiovascular responses to radioprotective mixture of cystamine and 5-methoxytryptamine in rats. Acta biologica et medica Germanica. 1975; 34(11-12):1843-9. doi: . [PMID: 1067710]
  • G A Smythe, J F Brandstater, L Lazarus. Serotoninergic control of rat growth hormone secretion. Neuroendocrinology. 1975; 17(3):245-57. doi: 10.1159/000122360. [PMID: 1056508]
  • L M Pavlova, A G Sverdlov, S A Grachev, G A Bagiian. [Determination of H3-mexamine in the mouse body and liver cells]. Radiobiologiia. 1975 MAR; 15(2):306-8. doi: NULL. [PMID: 1057217]