Psilocin (BioDeep_00000002566)

 

Secondary id: BioDeep_00001868108

human metabolite Endogenous Chemicals and Drugs natural product Volatile Flavor Compounds


代谢物信息卡片


3-[2-(Dimethylamino)ethyl]-1H-indol-4-ol

化学式: C12H16N2O (204.12625659999998)
中文名称: 4-羟基-N,N-二甲基色胺
谱图信息: 最多检出来源 Viridiplantae(plant) 2.63%

分子结构信息

SMILES: CN(C)CCC1=CNC2=C1C(=CC=C2)O
InChI: InChI=1S/C12H16N2O/c1-14(2)7-6-9-8-13-10-4-3-5-11(15)12(9)10/h3-5,8,13,15H,6-7H2,1-2H3

描述信息

Psilocin (4-OH-DMT), an aromatic compound, sometimes also spelled psilocine, psilocyn, or psilotsin, is a psychedelic mushroom alkaloid. It is found in most psychedelic mushrooms together with its phosphorylated counterpart psilocybin. Psilocin is a Schedule I drug under the Convention on Psychotropic Substances. The mind-altering effects of psilocin are highly variable and subjective, but resemble those caused by LSD and mescaline. The effects typically last anywhere from three to eight hours depending on certain variables (such as metabolism, food interaction); however the effects can seem to last much longer due to psilocins ability to distort the perception of time. Sulfur analogs are known with a benzothienyl replacement as well as 4-SH-DMT. N1-methylpsilocin is a functionally 5-HT2C receptor preferring agonists. 4-fluoro-N,N-dimethyltryptamine is known. O-Acetylpsilocin is an acetylized analog of psilocin, also known as 4-AcO-DMT. Additionally, substitution of a methyl group at the dimethylated nitrogen with an isopropyl or ethyl group yields 4-HO-MIPT (4-Hydroxy-N-Methyl-N-Isopropyltryptamine) and 4-HO-MET (4-Hydroxy-N-Methyl-N-Ethyltryptamine), respectively.
D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D006213 - Hallucinogens

同义名列表

13 个代谢物同义名

3-[2-(Dimethylamino)ethyl]-1H-indol-4-ol; 3-[2-(Dimethylamino)ethyl]-indol-4-ol; (3-(2-Dimethylamino)ethyl)indol-4-ol; 3-(2-(Dimethylamino)ethyl)indol-4-ol; N,N-Dimethyl-4-hydroxytryptamine; 4-Hydroxy-N,N-dimethyltryptamine; Psilocin tartrate (1:1); Psilocin hydrochloride; Psilocine; Psilotsin; 4-OH-DMT; PSILOCIN; Psilocin



数据库引用编号

16 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)

100 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

  • Martin K Madsen, Dea S Stenbæk, Albin Arvidsson, Sophia Armand, Maja R Marstrand-Joergensen, Sys S Johansen, Kristian Linnet, Brice Ozenne, Gitte M Knudsen, Patrick M Fisher. Psilocybin-induced changes in brain network integrity and segregation correlate with plasma psilocin level and psychedelic experience. European neuropsychopharmacology : the journal of the European College of Neuropsychopharmacology. 2021 09; 50(?):121-132. doi: 10.1016/j.euroneuro.2021.06.001. [PMID: 34246868]
  • 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]
  • Karolina E Kolaczynska, Matthias E Liechti, Urs Duthaler. Development and validation of an LC-MS/MS method for the bioanalysis of psilocybin's main metabolites, psilocin and 4-hydroxyindole-3-acetic acid, in human plasma. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2021 Feb; 1164(?):122486. doi: 10.1016/j.jchromb.2020.122486. [PMID: 33485158]
  • Martin K Madsen, Gitte M Knudsen. Plasma psilocin critically determines behavioral and neurobiological effects of psilocybin. Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology. 2021 01; 46(1):257-258. doi: 10.1038/s41386-020-00823-4. [PMID: 32843702]
  • Júlia Nagy, Tibor Veress. Systematic Error for Extraction of Controlled Substances from Plant/Fungal Materials. Journal of chromatographic science. 2020 Oct; 58(10):985-991. doi: 10.1093/chromsci/bmaa067. [PMID: 32945334]
  • Janis Fricke, Robert Kargbo, Lars Regestein, Claudius Lenz, Gundela Peschel, Miriam A Rosenbaum, Alexander Sherwood, Dirk Hoffmeister. Scalable Hybrid Synthetic/Biocatalytic Route to Psilocybin. Chemistry (Weinheim an der Bergstrasse, Germany). 2020 Jul; 26(37):8281-8285. doi: 10.1002/chem.202000134. [PMID: 32101345]
  • Anna Poliwoda, Katarzyna Zielińska, Piotr P Wieczorek. Direct Analysis of Psilocin and Muscimol in Urine Samples Using Single Drop Microextraction Technique In-Line with Capillary Electrophoresis. Molecules (Basel, Switzerland). 2020 Mar; 25(7):. doi: 10.3390/molecules25071566. [PMID: 32235328]
  • 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]
  • Emma Honyiglo, Angélique Franchi, Nathalie Cartiser, Charline Bottinelli, Anne-Sophie Advenier, Fabien Bévalot, Laurent Fanton. Unpredictable Behavior Under the Influence of 'Magic Mushrooms': A Case Report and Review of the Literature. Journal of forensic sciences. 2019 Jul; 64(4):1266-1270. doi: 10.1111/1556-4029.13982. [PMID: 30548541]
  • Randall T Brown, Christopher R Nicholas, Nicholas V Cozzi, Michele C Gassman, Karen M Cooper, Daniel Muller, Chantelle D Thomas, Scott J Hetzel, Kelsey M Henriquez, Alexandra S Ribaudo, Paul R Hutson. Pharmacokinetics of Escalating Doses of Oral Psilocybin in Healthy Adults. Clinical pharmacokinetics. 2017 12; 56(12):1543-1554. doi: 10.1007/s40262-017-0540-6. [PMID: 28353056]
  • Rafaela Martin, Jennifer Schürenkamp, Heidi Pfeiffer, Matthias Lehr, Helga Köhler. Synthesis, hydrolysis and stability of psilocin glucuronide. Forensic science international. 2014 Apr; 237(?):1-6. doi: 10.1016/j.forsciint.2014.01.006. [PMID: 24513688]
  • Anders Helander, Olof Beck, Robert Hägerkvist, Peter Hultén. Identification of novel psychoactive drug use in Sweden based on laboratory analysis--initial experiences from the STRIDA project. Scandinavian journal of clinical and laboratory investigation. 2013 Aug; 73(5):400-6. doi: 10.3109/00365513.2013.793817. [PMID: 23692208]
  • Rafaela Martin, Jennifer Schürenkamp, Angela Gasse, Heidi Pfeiffer, Helga Köhler. Determination of psilocin, bufotenine, LSD and its metabolites in serum, plasma and urine by SPE-LC-MS/MS. International journal of legal medicine. 2013 May; 127(3):593-601. doi: 10.1007/s00414-012-0796-1. [PMID: 23183899]
  • Rafaela Martin, Jennifer Schürenkamp, Heidi Pfeiffer, Helga Köhler. A validated method for quantitation of psilocin in plasma by LC-MS/MS and study of stability. International journal of legal medicine. 2012 Nov; 126(6):845-9. doi: 10.1007/s00414-011-0652-8. [PMID: 22138681]
  • Takuji Shoda, Kiyoshi Fukuhara, Yukihiro Goda, Haruhiro Okuda. Enzyme-assisted synthesis of the glucuronide conjugate of psilocin, an hallucinogenic component of magic mushrooms. Drug testing and analysis. 2011 Sep; 3(9):594-6. doi: 10.1002/dta.244. [PMID: 21960543]
  • Jianbo Chen, Meijia Li, Xitao Yan, Enqi Wu, Hongmei Zhu, Kwan Jun Lee, Van Men Chu, Lifeng Zhan, Wonjae Lee, Jong Seong Kang. Determining the pharmacokinetics of psilocin in rat plasma using ultra-performance liquid chromatography coupled with a photodiode array detector after orally administering an extract of Gymnopilus spectabilis. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2011 Sep; 879(25):2669-72. doi: 10.1016/j.jchromb.2011.07.003. [PMID: 21820980]
  • Tim Laussmann, Sigrid Meier-Giebing. Forensic analysis of hallucinogenic mushrooms and khat (Catha edulis Forsk) using cation-exchange liquid chromatography. Forensic science international. 2010 Feb; 195(1-3):160-4. doi: 10.1016/j.forsciint.2009.12.013. [PMID: 20047807]
  • Sławomir Majdanik, Krzysztof Borowiak, Maria Brzezńska, Anna Machoy-Mokrzyńska. [Concentration of selected microelements in blood serum of rats exposed to the action of psilocin and phenylethylamine]. Annales Academiae Medicae Stetinensis. 2007; 53 Suppl 2(?):153-8. doi: . [PMID: 20143700]
  • Nicholas B Tiscione, Mattheu I Miller. Psilocin identified in a DUID investigation. Journal of analytical toxicology. 2006 Jun; 30(5):342-5. doi: 10.1093/jat/30.5.342. [PMID: 16839473]
  • C Albers, H Köhler, M Lehr, B Brinkmann, J Beike. Development of a psilocin immunoassay for serum and blood samples. International journal of legal medicine. 2004 Dec; 118(6):326-31. doi: 10.1007/s00414-004-0469-9. [PMID: 15526212]
  • Kenji Tsujikawa, Tatsuyuki Kanamori, Yuko Iwata, Yoshihito Ohmae, Ritsuko Sugita, Hiroyuki Inoue, Tohru Kishi. Morphological and chemical analysis of magic mushrooms in Japan. Forensic science international. 2003 Dec; 138(1-3):85-90. doi: 10.1016/j.forsciint.2003.08.009. [PMID: 14642723]
  • Tooru Kamata, Mayumi Nishikawa, Munehiro Katagi, Hitoshi Tsuchihashi. Optimized glucuronide hydrolysis for the detection of psilocin in human urine samples. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2003 Nov; 796(2):421-7. doi: 10.1016/j.jchromb.2003.08.030. [PMID: 14581081]
  • K Huikko, P Ostman, K Grigoras, S Tuomikoski, V-M Tiainen, A Soininen, K Puolanne, A Manz, S Franssila, R Kostiainen, T Kotiaho. Poly(dimethylsiloxane) electrospray devices fabricated with diamond-like carbon-poly(dimethylsiloxane) coated SU-8 masters. Lab on a chip. 2003 May; 3(2):67-72. doi: 10.1039/b300345k. [PMID: 15100784]
  • Felix Hasler, Daniel Bourquin, Rudolf Brenneisen, Franz X Vollenweider. Renal excretion profiles of psilocin following oral administration of psilocybin: a controlled study in man. Journal of pharmaceutical and biomedical analysis. 2002 Sep; 30(2):331-9. doi: 10.1016/s0731-7085(02)00278-9. [PMID: 12191719]
  • Christian Albers, Matthias Lehr, Justus Beike, Helga Köhler, Bernd Brinkmann. Synthesis of a psilocin hapten and a protein-hapten conjugate. The Journal of pharmacy and pharmacology. 2002 Sep; 54(9):1265-70. doi: 10.1211/002235702320402116. [PMID: 12356281]
  • A F Grieshaber, K A Moore, B Levine. The detection of psilocin in human urine. Journal of forensic sciences. 2001 May; 46(3):627-30. doi: . [PMID: 11373000]
  • G Sticht, H Käferstein. Detection of psilocin in body fluids. Forensic science international. 2000 Sep; 113(1-3):403-7. doi: 10.1016/s0379-0738(00)00213-9. [PMID: 10978655]
  • H Lindenblatt, E Krämer, P Holzmann-Erens, E Gouzoulis-Mayfrank, K A Kovar. Quantitation of psilocin in human plasma by high-performance liquid chromatography and electrochemical detection: comparison of liquid-liquid extraction with automated on-line solid-phase extraction. Journal of chromatography. B, Biomedical sciences and applications. 1998 May; 709(2):255-63. doi: 10.1016/s0378-4347(98)00067-x. [PMID: 9657222]
  • F Hasler, D Bourquin, R Brenneisen, T Bär, F X Vollenweider. Determination of psilocin and 4-hydroxyindole-3-acetic acid in plasma by HPLC-ECD and pharmacokinetic profiles of oral and intravenous psilocybin in man. Pharmaceutica acta Helvetiae. 1997 Jun; 72(3):175-84. doi: 10.1016/s0031-6865(97)00014-9. [PMID: 9204776]
  • R Kysilka. Determination of psilocin in rat urine by high-performance liquid chromatography with electrochemical detection. Journal of chromatography. 1990 Dec; 534(?):287-90. doi: 10.1016/s0378-4347(00)82176-3. [PMID: 2094720]
  • B M Thomson. Analysis of psilocybin and psilocin in mushroom extracts by reversed-phase high performance liquid chromatography. Journal of forensic sciences. 1980 Oct; 25(4):779-85. doi: ". [PMID: 7191888]