PSILOCIN (BioDeep_00001868108)

Main id: BioDeep_00000002566

 

natural product


代谢物信息卡片


PSILOCIN

化学式: C12H16N2O (204.1263)
中文名称: 4-羟基-N,N-二甲基色胺
谱图信息: 最多检出来源 () 0%

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

A tryptamine alkaloid that is N,N-dimethyltryptamine carrying an additional hydroxy substituent at position 4. A hallucinogenic alkaloid isolated in trace amounts from Psilocybe mushrooms (also known as Teonanacatl or "magic mushrooms").
D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D006213 - Hallucinogens

同义名列表

2 个代谢物同义名

PSILOCIN; Psilocin



数据库引用编号

12 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)

99 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。

亚细胞结构定位 关联基因列表
Cytoplasm 6 ALB, AOC3, BDNF, EP300, GGPS1, NTRK2
Peripheral membrane protein 1 OSBP2
Endosome membrane 2 NTRK2, SLC6A4
Endoplasmic reticulum membrane 3 UGT1A10, UGT1A6, UGT1A9
Nucleus 3 ALB, EP300, FOS
cytosol 6 ALB, EP300, FOS, GGPS1, NTRK2, OSBP2
dendrite 4 BDNF, HTR2A, HTR2C, NTRK2
centrosome 1 ALB
nucleoplasm 3 EP300, FOS, GGPS1
RNA polymerase II transcription regulator complex 1 FOS
Cell membrane 7 AOC3, HTR2A, HTR2C, KCNH2, NTRK2, SLC6A2, SLC6A4
Cell projection, axon 2 HTR2A, NTRK2
Early endosome membrane 1 NTRK2
Multi-pass membrane protein 6 HTR2A, HTR2C, KCNA3, KCNH2, SLC6A2, SLC6A4
Synapse 2 HTR2C, SLC6A4
cell surface 3 AOC3, KCNH2, SLC6A2
dendritic shaft 1 HTR2A
glutamatergic synapse 2 HTR2A, KCNA3
Golgi apparatus 2 ALB, AOC3
lysosomal membrane 1 CP
neuronal cell body 1 HTR2A
presynaptic membrane 4 HTR2A, KCNA3, SLC6A2, SLC6A4
synaptic vesicle 1 BDNF
Presynapse 2 HTR2A, SLC6A4
acrosomal vesicle 1 OSBP2
plasma membrane 10 AOC3, CP, HTR2A, HTR2C, KCNA3, KCNH2, NTRK2, OSBP2, SLC6A2, SLC6A4
synaptic vesicle membrane 1 SLC6A2
terminal bouton 1 NTRK2
Membrane 11 AOC3, BDNF, KCNA3, KCNH2, NTRK2, OSBP2, SLC6A2, SLC6A4, UGT1A10, UGT1A6, UGT1A9
axon 5 BDNF, HTR2A, KCNA3, NTRK2, SLC6A2
caveola 1 HTR2A
extracellular exosome 2 ALB, CP
endoplasmic reticulum 6 ALB, AOC3, FOS, UGT1A10, UGT1A6, UGT1A9
extracellular space 4 ALB, BDNF, CP, IL6
perinuclear region of cytoplasm 5 BDNF, GGPS1, KCNA3, KCNH2, NTRK2
mitochondrion 1 SARS2
protein-containing complex 1 ALB
intracellular membrane-bounded organelle 1 UGT1A6
postsynaptic density 1 NTRK2
Single-pass type I membrane protein 1 NTRK2
Secreted 4 ALB, BDNF, CP, IL6
extracellular region 4 ALB, BDNF, CP, IL6
Single-pass membrane protein 3 UGT1A10, UGT1A6, UGT1A9
neuronal cell body membrane 1 SLC6A2
Mitochondrion matrix 1 SARS2
mitochondrial matrix 1 SARS2
anchoring junction 1 ALB
transcription regulator complex 1 EP300
dendritic spine 1 NTRK2
Z disc 1 GGPS1
cytoplasmic vesicle 1 HTR2A
Early endosome 2 AOC3, NTRK2
Single-pass type II membrane protein 1 AOC3
postsynaptic membrane 3 HTR2A, KCNA3, SLC6A4
Cytoplasm, perinuclear region 2 GGPS1, NTRK2
Membrane raft 2 KCNA3, SLC6A4
Cell junction, focal adhesion 1 SLC6A4
focal adhesion 1 SLC6A4
receptor complex 1 NTRK2
Cell projection, neuron projection 1 SLC6A4
neuron projection 1 SLC6A4
ciliary basal body 1 ALB
chromatin 2 EP300, FOS
Chromosome 1 EP300
centriole 1 ALB
Cytoplasmic vesicle, secretory vesicle, acrosome 1 OSBP2
spindle pole 1 ALB
blood microparticle 2 ALB, CP
[Isoform 2]: Cell membrane 1 KCNA3
Endomembrane system 1 SLC6A4
microvillus 1 AOC3
Membrane, caveola 1 HTR2A
monoatomic ion channel complex 1 KCNH2
cell body fiber 1 HTR2A
Cell projection, dendrite 2 HTR2A, NTRK2
Cytoplasm, myofibril, sarcomere, Z line 1 GGPS1
inward rectifier potassium channel complex 1 KCNH2
voltage-gated potassium channel complex 2 KCNA3, KCNH2
endoplasmic reticulum lumen 4 ALB, BDNF, CP, IL6
nuclear matrix 1 FOS
platelet alpha granule lumen 1 ALB
axon terminus 1 NTRK2
perinuclear endoplasmic reticulum 1 OSBP2
neurofilament 1 HTR2A
calyx of Held 1 KCNA3
histone acetyltransferase complex 1 EP300
protein-DNA complex 2 EP300, FOS
apical dendrite 1 OSBP2
[Isoform 1]: Cell membrane 1 KCNA3
transcription factor AP-1 complex 1 FOS
interleukin-6 receptor complex 1 IL6
[Isoform 3]: Cytoplasm, perinuclear region 1 KCNA3
[Neurotrophic factor BDNF precursor form]: Secreted 1 BDNF
G protein-coupled serotonin receptor complex 2 HTR2A, HTR2C
serotonergic synapse 1 SLC6A4
ciliary transition fiber 1 ALB


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]