1-Pentyl-3-(1-naphthoyl)indole (BioDeep_00000172289)

 

Secondary id: BioDeep_00000272571, BioDeep_00000397522

human metabolite blood metabolite


代谢物信息卡片


3-(naphthalene-1-carbonyl)-1-pentyl-1H-indole

化学式: C24H23NO (341.1779548)
中文名称: 1-戊基-3-(1-萘甲酰基)吲哚
谱图信息: 最多检出来源 Homo sapiens(COVID-19)(blood) 33.33%

分子结构信息

SMILES: CCCCCN1C=C(C(=O)C2=CC=CC3=CC=CC=C23)C2=CC=CC=C12
InChI: InChI=1S/C24H23NO/c1-2-3-8-16-25-17-22(20-13-6-7-15-23(20)25)24(26)21-14-9-11-18-10-4-5-12-19(18)21/h4-7,9-15,17H,2-3,8,16H2,1H3



数据库引用编号

7 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)

1 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

  • Lawrence M Carey, Saba Ghodrati, Charles P France. Discriminative stimulus properties of Cannabis sativa terpenes in rats. Behavioural pharmacology. 2024 Jun; 35(4):161-171. doi: 10.1097/fbp.0000000000000772. [PMID: 38660819]
  • Ralph Aderorho, Shadrack Wilson Lucas, Christopher D Chouinard. Separation and Characterization of Synthetic Cannabinoid Metabolite Isomers Using SLIM High-Resolution Ion Mobility-Tandem Mass Spectrometry (HRIM-MS/MS). Journal of the American Society for Mass Spectrometry. 2024 Mar; 35(3):582-589. doi: 10.1021/jasms.3c00419. [PMID: 38361441]
  • Duygu Mutluay, Şükrü Güngör, Gözde Yücel Tenekeci, Serkan Köksoy, Cennet Sinem Çoban. Effects of synthetic (JWH-018) cannabinoids treatment on spermatogenesis and sperm function. Drug and chemical toxicology. 2022 Jan; 45(1):215-222. doi: 10.1080/01480545.2019.1680686. [PMID: 31645148]
  • Eef L Theunissen, Johannes T Reckweg, Nadia R P W Hutten, Kim P C Kuypers, Stefan W Toennes, Merja A Neukamm, Sebastian Halter, Johannes G Ramaekers. Intoxication by a synthetic cannabinoid (JWH-018) causes cognitive and psychomotor impairment in recreational cannabis users. Pharmacology, biochemistry, and behavior. 2021 03; 202(?):173118. doi: 10.1016/j.pbb.2021.173118. [PMID: 33497715]
  • Adrianna N Masterson, Sumon Hati, Greta Ren, Thakshila Liyanage, Nicholas E Manicke, John V Goodpaster, Rajesh Sardar. Enhancing Nonfouling and Sensitivity of Surface-Enhanced Raman Scattering Substrates for Potent Drug Analysis in Blood Plasma via Fabrication of a Flexible Plasmonic Patch. Analytical chemistry. 2021 02; 93(4):2578-2588. doi: 10.1021/acs.analchem.0c04643. [PMID: 33432809]
  • Shivani Sachdev, Samuel D Banister, Marina Santiago, Chris Bladen, Michael Kassiou, Mark Connor. Differential activation of G protein-mediated signaling by synthetic cannabinoid receptor agonists. Pharmacology research & perspectives. 2020 04; 8(2):e00566. doi: 10.1002/prp2.566. [PMID: 32101383]
  • Marta Almada, Patrícia Alves, Bruno M Fonseca, Félix Carvalho, Cláudio R Queirós, Helena Gaspar, Cristina Amaral, Natércia A Teixeira, Georgina Correia-da-Silva. Synthetic cannabinoids JWH-018, JWH-122, UR-144 and the phytocannabinoid THC activate apoptosis in placental cells. Toxicology letters. 2020 Feb; 319(?):129-137. doi: 10.1016/j.toxlet.2019.11.004. [PMID: 31730886]
  • David Fabregat-Safont, Marie Mardal, Carolina Noble, Annelies Cannaert, Christophe P Stove, Juan V Sancho, Kristian Linnet, Félix Hernández, María Ibáñez. Comprehensive investigation on synthetic cannabinoids: Metabolic behavior and potency testing, using 5F-APP-PICA and AMB-FUBINACA as model compounds. Drug testing and analysis. 2019 Sep; 11(9):1358-1368. doi: 10.1002/dta.2659. [PMID: 31192526]
  • Jeremy Carlier, Ariane Wohlfarth, Bonita D Salmeron, Karl B Scheidweiler, Marilyn A Huestis, Michael H Baumann. Pharmacodynamic Effects, Pharmacokinetics, and Metabolism of the Synthetic Cannabinoid AM-2201 in Male Rats. The Journal of pharmacology and experimental therapeutics. 2018 12; 367(3):543-550. doi: 10.1124/jpet.118.250530. [PMID: 30266766]
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  • Amy L Patton, Kathryn A Seely, Azure L Yarbrough, William Fantegrossi, Laura P James, Keith R McCain, Ryoichi Fujiwara, Paul L Prather, Jeffery H Moran, Anna Radominska-Pandya. Altered metabolism of synthetic cannabinoid JWH-018 by human cytochrome P450 2C9 and variants. Biochemical and biophysical research communications. 2018 04; 498(3):597-602. doi: 10.1016/j.bbrc.2018.03.028. [PMID: 29522717]
  • Stefan W Toennes, Anna Geraths, Werner Pogoda, Alexander Paulke, Cora Wunder, Eef L Theunissen, Johannes G Ramaekers. Pharmacokinetic properties of the synthetic cannabinoid JWH-018 in oral fluid after inhalation. Drug testing and analysis. 2018 Apr; 10(4):644-650. doi: 10.1002/dta.2310. [PMID: 28967189]
  • Stefan W Toennes, Anna Geraths, Werner Pogoda, Alexander Paulke, Cora Wunder, Eef L Theunissen, Johannes G Ramaekers. Excretion of metabolites of the synthetic cannabinoid JWH-018 in urine after controlled inhalation. Journal of pharmaceutical and biomedical analysis. 2018 Feb; 150(?):162-168. doi: 10.1016/j.jpba.2017.12.016. [PMID: 29245085]
  • Eef L Theunissen, Nadia R P W Hutten, Natasha L Mason, Stefan W Toennes, Kim P C Kuypers, Eliza B de Sousa Fernandes Perna, Johannes G Ramaekers. Neurocognition and subjective experience following acute doses of the synthetic cannabinoid JWH-018: a phase 1, placebo-controlled, pilot study. British journal of pharmacology. 2018 01; 175(1):18-28. doi: 10.1111/bph.14066. [PMID: 29164599]
  • Benjamin M Ford, Lirit N Franks, Sherrica Tai, William E Fantegrossi, Edward L Stahl, Michael D Berquist, Christian V Cabanlong, Catheryn D Wilson, Narsimha R Penthala, Peter A Crooks, Paul L Prather. Characterization of structurally novel G protein biased CB1 agonists: Implications for drug development. Pharmacological research. 2017 Nov; 125(Pt B):161-177. doi: 10.1016/j.phrs.2017.08.008. [PMID: 28838808]
  • Katherine N Moore, Demetra Garvin, Brian F Thomas, Megan Grabenauer. Identification of Eight Synthetic Cannabinoids, Including 5F-AKB48 in Seized Herbal Products Using DART-TOF-MS and LC-QTOF-MS as Nontargeted Screening Methods. Journal of forensic sciences. 2017 Sep; 62(5):1151-1158. doi: 10.1111/1556-4029.13367. [PMID: 28597943]
  • Stephen Raso, Suzanne Bell. Qualitative Analysis and Detection of the Pyrolytic Products of JWH-018 and 11 Additional Synthetic Cannabinoids in the Presence of Common Herbal Smoking Substrates. Journal of analytical toxicology. 2017 Jul; 41(6):551-558. doi: 10.1093/jat/bkx039. [PMID: 28637216]
  • Stefan W Toennes, Anna Geraths, Werner Pogoda, Alexander Paulke, Cora Wunder, Eef L Theunissen, Johannes G Ramaekers. Pharmacokinetic properties of the synthetic cannabinoid JWH-018 and of its metabolites in serum after inhalation. Journal of pharmaceutical and biomedical analysis. 2017 Jun; 140(?):215-222. doi: 10.1016/j.jpba.2017.03.043. [PMID: 28365515]
  • Brian F Thomas, Timothy W Lefever, Ricardo A Cortes, Megan Grabenauer, Alexander L Kovach, Anderson O Cox, Purvi R Patel, Gerald T Pollard, Julie A Marusich, Richard C Kevin, Thomas F Gamage, Jenny L Wiley. Thermolytic Degradation of Synthetic Cannabinoids: Chemical Exposures and Pharmacological Consequences. The Journal of pharmacology and experimental therapeutics. 2017 04; 361(1):162-171. doi: 10.1124/jpet.116.238717. [PMID: 28087785]
  • Bertha K Madras. The Growing Problem of New Psychoactive Substances (NPS). Current topics in behavioral neurosciences. 2017 ; 32(?):1-18. doi: 10.1007/7854_2016_34. [PMID: 27571747]
  • Annelies Cannaert, Jolien Storme, Florian Franz, Volker Auwärter, Christophe P Stove. Detection and Activity Profiling of Synthetic Cannabinoids and Their Metabolites with a Newly Developed Bioassay. Analytical chemistry. 2016 12; 88(23):11476-11485. doi: 10.1021/acs.analchem.6b02600. [PMID: 27779402]
  • Herbert H Seltzman, Craig Shiner, Erin E Hirt, Anne F Gilliam, Brian F Thomas, Rangan Maitra, Rod Snyder, Sherry L Black, Purvi R Patel, Yatendra Mulpuri, Igor Spigelman. Peripherally Selective Cannabinoid 1 Receptor (CB1R) Agonists for the Treatment of Neuropathic Pain. Journal of medicinal chemistry. 2016 08; 59(16):7525-43. doi: 10.1021/acs.jmedchem.6b00516. [PMID: 27482723]
  • Joana Couceiro, Susana Bandarra, Haider Sultan, Suzanne Bell, Susana Constantino, Alexandre Quintas. Toxicological impact of JWH-018 and its phase I metabolite N-(3-hydroxypentyl) on human cell lines. Forensic science international. 2016 07; 264(?):100-5. doi: 10.1016/j.forsciint.2016.03.024. [PMID: 27054591]
  • Jeremy Carlier, Karl B Scheidweiler, Ariane Wohlfarth, Bonita D Salmeron, Michael H Baumann, Marilyn A Huestis. Quantification of [1-(5-fluoropentyl)-1H-indol-3-yl](naphthalene-1-yl)methanone (AM-2201) and 13 metabolites in human and rat plasma by liquid chromatography-tandem mass spectrometry. Journal of chromatography. A. 2016 Jun; 1451(?):97-106. doi: 10.1016/j.chroma.2016.05.020. [PMID: 27208987]
  • Maiko Kusano, Kei Zaitsu, Mayumi Yamanaka, Kazuaki Hisatsune, Tomomi Asano, Kentaro Taki, Yumi Hayashi, Hitoshi Tsuchihashi, Akira Ishii. Development of a mass spectrometric hydroxyl-position determination method for the hydroxyindole metabolites of JWH-018 by GC-MS/MS. Journal of mass spectrometry : JMS. 2016 05; 51(5):350-7. doi: 10.1002/jms.3761. [PMID: 27194519]
  • Shimpei Watanabe, Unnikrishnan Kuzhiumparambil, Zofia Winiarski, Shanlin Fu. Biotransformation of synthetic cannabinoids JWH-018, JWH-073 and AM2201 by Cunninghamella elegans. Forensic science international. 2016 Apr; 261(?):33-42. doi: 10.1016/j.forsciint.2015.12.023. [PMID: 26907475]
  • A Vigolo, A Ossato, C Trapella, F Vincenzi, C Rimondo, C Seri, K Varani, G Serpelloni, M Marti. Novel halogenated derivates of JWH-018: Behavioral and binding studies in mice. Neuropharmacology. 2015 Aug; 95(?):68-82. doi: 10.1016/j.neuropharm.2015.02.008. [PMID: 25769232]
  • Solfrid Hegstad, Andreas A Westin, Olav Spigset. Detection Times of Carboxylic Acid Metabolites of the Synthetic Cannabinoids JWH-018 and JWH-073 in Human Urine. Journal of analytical toxicology. 2015 May; 39(4):280-6. doi: 10.1093/jat/bkv013. [PMID: 25737323]
  • Buddha D Paul, Thomas Bosy. A sensitive GC-EIMS method for simultaneous detection and quantification of JWH-018 and JWH-073 carboxylic acid and hydroxy metabolites in urine. Journal of analytical toxicology. 2015 Apr; 39(3):172-82. doi: 10.1093/jat/bku178. [PMID: 25691387]
  • Yeter Erol Öztürk, Oya Yeter, Buket Alpertunga. Validation of JWH-018 and its metabolites in blood and urine by UPLC-MS/MS: Monitoring in forensic cases. Forensic science international. 2015 Mar; 248(?):88-93. doi: 10.1016/j.forsciint.2014.12.029. [PMID: 25616218]
  • Karl B Scheidweiler, Michael J Y Jarvis, Marilyn A Huestis. Nontargeted SWATH acquisition for identifying 47 synthetic cannabinoid metabolites in human urine by liquid chromatography-high-resolution tandem mass spectrometry. Analytical and bioanalytical chemistry. 2015 Jan; 407(3):883-97. doi: 10.1007/s00216-014-8118-8. [PMID: 25224637]
  • Susana Sadler Simões, Inês Silva, Antonio Castañera Ajenjo, Mário João Dias. Validation and application of an UPLC-MS/MS method for the quantification of synthetic cannabinoids in urine samples and analysis of seized materials from the Portuguese market. Forensic science international. 2014 Oct; 243(?):117-25. doi: 10.1016/j.forsciint.2014.07.022. [PMID: 25127518]
  • Veniero Gambaro, Sebastiano Arnoldi, Stefania Bellucci, Eleonora Casagni, Lucia Dell'Acqua, Laura Fumagalli, Marco Pallavicini, Gabriella Roda, Chiara Rusconi, Ermanno Valoti. Characterization of in vitro metabolites of JWH-018, JWH-073 and their 4-methyl derivatives, markers of the abuse of these synthetic cannabinoids. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2014 Apr; 957(?):68-76. doi: 10.1016/j.jchromb.2014.03.001. [PMID: 24657413]
  • Moonhee Jang, Wonkyung Yang, Ilchung Shin, Hyeyoung Choi, Hyejin Chang, Eunmi Kim. Determination of AM-2201 metabolites in urine and comparison with JWH-018 abuse. International journal of legal medicine. 2014 Mar; 128(2):285-94. doi: 10.1007/s00414-013-0884-x. [PMID: 23884698]
  • Lisa K Brents, Paul L Prather. The K2/Spice phenomenon: emergence, identification, legislation and metabolic characterization of synthetic cannabinoids in herbal incense products. Drug metabolism reviews. 2014 Feb; 46(1):72-85. doi: 10.3109/03602532.2013.839700. [PMID: 24063277]
  • Melissa J Freeman, David Z Rose, Martin A Myers, Clifton L Gooch, Andrea C Bozeman, W Scott Burgin. Ischemic stroke after use of the synthetic marijuana 'spice'. Neurology. 2013 Dec; 81(24):2090-3. doi: 10.1212/01.wnl.0000437297.05570.a2. [PMID: 24212384]
  • Amy L Patton, Kathryn A Seely, Krishna C Chimalakonda, Johnny P Tran, Matthew Trass, Art Miranda, William E Fantegrossi, Paul D Kennedy, Paul Dobrowolski, Anna Radominska-Pandya, Keith R McCain, Laura P James, Gregory W Endres, Jeffery H Moran. Targeted metabolomic approach for assessing human synthetic cannabinoid exposure and pharmacology. Analytical chemistry. 2013 Oct; 85(19):9390-9. doi: 10.1021/ac4024704. [PMID: 23987522]
  • Moonhee Jang, Wonkyung Yang, Hyeyoung Choi, Hyejin Chang, Sooyeun Lee, Eunmi Kim, Heesun Chung. Monitoring of urinary metabolites of JWH-018 and JWH-073 in legal cases. Forensic science international. 2013 Sep; 231(1-3):13-9. doi: 10.1016/j.forsciint.2013.03.053. [PMID: 23890611]
  • Fatma Gurdal, Mahmut Asirdizer, Rezzan Gulhan Aker, Senol Korkut, Yasemin Gocer, E Esra Kucukibrahimoglu, C Haluk Ince. Review of detection frequency and type of synthetic cannabinoids in herbal compounds analyzed by Istanbul Narcotic Department of the Council of Forensic Medicine, Turkey. Journal of forensic and legal medicine. 2013 Aug; 20(6):667-72. doi: 10.1016/j.jflm.2013.03.041. [PMID: 23910858]
  • Melanie Hutter, Bjoern Moosmann, Stefan Kneisel, Volker Auwärter. Characteristics of the designer drug and synthetic cannabinoid receptor agonist AM-2201 regarding its chemistry and metabolism. Journal of mass spectrometry : JMS. 2013 Jul; 48(7):885-94. doi: 10.1002/jms.3229. [PMID: 23832945]
  • Beth Emerson, Bill Durham, Jennifer Gidden, Jackson O Lay. Gas chromatography-mass spectrometry of JWH-018 metabolites in urine samples with direct comparison to analytical standards. Forensic science international. 2013 Jun; 229(1-3):1-6. doi: 10.1016/j.forsciint.2013.03.006. [PMID: 23683902]
  • Jason M Wiebelhaus, Justin L Poklis, Alphonse Poklis, Robert E Vann, Aron H Lichtman, Laura E Wise. Inhalation exposure to smoke from synthetic 'marijuana' produces potent cannabimimetic effects in mice. Drug and alcohol dependence. 2012 Dec; 126(3):316-23. doi: 10.1016/j.drugalcdep.2012.05.034. [PMID: 22776442]
  • Enrique G Yanes, Dennis P Lovett. High-throughput bioanalytical method for analysis of synthetic cannabinoid metabolites in urine using salting-out sample preparation and LC-MS/MS. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2012 Nov; 909(?):42-50. doi: 10.1016/j.jchromb.2012.10.013. [PMID: 23153643]
  • Krishna C Chimalakonda, Kathryn A Seely, Stacie M Bratton, Lisa K Brents, Cindy L Moran, Gregory W Endres, Laura P James, Paul F Hollenberg, Paul L Prather, Anna Radominska-Pandya, Jeffery H Moran. Cytochrome P450-mediated oxidative metabolism of abused synthetic cannabinoids found in K2/Spice: identification of novel cannabinoid receptor ligands. Drug metabolism and disposition: the biological fate of chemicals. 2012 Nov; 40(11):2174-84. doi: 10.1124/dmd.112.047530. [PMID: 22904561]
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  • Justin L Poklis, Dorra Amira, Laura E Wise, Jason M Wiebelhaus, Brenda J Haggerty, Alphonse Poklis. Detection and disposition of JWH-018 and JWH-073 in mice after exposure to 'Magic Gold' smoke. Forensic science international. 2012 Jul; 220(1-3):91-6. doi: 10.1016/j.forsciint.2012.02.003. [PMID: 22405481]
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  • Cindy L Moran, Vi-Huyen Le, Krishna C Chimalakonda, Amy L Smedley, Felisia D Lackey, Suzanne N Owen, Paul D Kennedy, Gregory W Endres, Fred L Ciske, James B Kramer, Andrei M Kornilov, L D Bratton, Paul J Dobrowolski, William D Wessinger, William E Fantegrossi, Paul L Prather, Laura P James, Anna Radominska-Pandya, Jeffery H Moran. Quantitative measurement of JWH-018 and JWH-073 metabolites excreted in human urine. Analytical chemistry. 2011 Jun; 83(11):4228-36. doi: 10.1021/ac2005636. [PMID: 21506519]
  • Andrej Grigoryev, Sergey Savchuk, Aleksandra Melnik, Natal'ja Moskaleva, Jurij Dzhurko, Mihail Ershov, Aleksandr Nosyrev, Aleksandr Vedenin, Boris Izotov, Irina Zabirova, Vladimir Rozhanets. Chromatography-mass spectrometry studies on the metabolism of synthetic cannabinoids JWH-018 and JWH-073, psychoactive components of smoking mixtures. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2011 May; 879(15-16):1126-36. doi: 10.1016/j.jchromb.2011.03.034. [PMID: 21481654]
  • Jörg Teske, Jens-Peter Weller, Armin Fieguth, Thomas Rothämel, Yvonne Schulz, Hans Dieter Tröger. Sensitive and rapid quantification of the cannabinoid receptor agonist naphthalen-1-yl-(1-pentylindol-3-yl)methanone (JWH-018) in human serum by liquid chromatography-tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2010 Oct; 878(27):2659-63. doi: 10.1016/j.jchromb.2010.03.016. [PMID: 20378423]
  • Tim Sobolevsky, Ilya Prasolov, Grigory Rodchenkov. Detection of JWH-018 metabolites in smoking mixture post-administration urine. Forensic science international. 2010 Jul; 200(1-3):141-7. doi: 10.1016/j.forsciint.2010.04.003. [PMID: 20430547]
  • Brady K Atwood, John Huffman, Alex Straiker, Ken Mackie. JWH018, a common constituent of 'Spice' herbal blends, is a potent and efficacious cannabinoid CB receptor agonist. British journal of pharmacology. 2010 Jun; 160(3):585-93. doi: 10.1111/j.1476-5381.2009.00582.x. [PMID: 20100276]