mescaline (BioDeep_00000408275)

Main id: BioDeep_00000001490

 

natural product


代谢物信息卡片


mescaline

化学式: C11H17NO3 (211.1208372)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: COC1=CC(=CC(=C1OC)OC)CCN
InChI: InChI=1S/C11H17NO3/c1-13-9-6-8(4-5-12)7-10(14-2)11(9)15-3/h6-7H,4-5,12H2,1-3H3

描述信息

A phenethylamine alkaloid that is phenethylamine substituted at positions 3, 4 and 5 by methoxy groups.
D018377 - Neurotransmitter Agents > D018490 - Serotonin Agents > D017366 - Serotonin Receptor Agonists
D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D006213 - Hallucinogens

同义名列表

1 个代谢物同义名

mescaline



数据库引用编号

14 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)

39 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

  • Lucas Apolinário Chibli, Bruna Ribeiro de Lima, Ariadne Magalhães Carneiro, Harley Cardoso Figueiró, Serhat Sezai Cicek, Verena Spiegler, Cristiano Soleo Funari. Toward a More Sustainable Sample Preparation in Phytochemistry: Case Studies in Four Subclasses of Alkaloids. Journal of natural products. 2024 Mar; 87(3):470-479. doi: 10.1021/acs.jnatprod.3c01048. [PMID: 38381880]
  • Gwendolyn K Kirschner. Breaking bad buttons: mescaline biosynthesis in peyote. The Plant journal : for cell and molecular biology. 2023 11; 116(3):633-634. doi: 10.1111/tpj.16503. [PMID: 37861456]
  • Jacinta L Watkins, Qiushi Li, Sam Yeaman, Peter J Facchini. Elucidation of the mescaline biosynthetic pathway in peyote (Lophophora williamsii). The Plant journal : for cell and molecular biology. 2023 Sep; ?(?):. doi: 10.1111/tpj.16447. [PMID: 37675639]
  • Minji Lee, Ju Yeon Jung, Sungsoo Choi, Ilung Seol, Seohyun Moon, In Kwan Hwang. Single Nucleotide Polymorphism Assay for Genetic Identification of Lophophora williamsii. Journal of forensic sciences. 2020 Nov; 65(6):2117-2120. doi: 10.1111/1556-4029.14515. [PMID: 32725909]
  • Cameron M Longo, Rabi A Musah. An Efficient Ambient Ionization Mass Spectrometric Approach to Detection and Quantification of the Mescaline Content of Commonly Abused Cacti from the Echinopsis Genus. Journal of forensic sciences. 2020 Jan; 65(1):61-66. doi: 10.1111/1556-4029.14134. [PMID: 31310334]
  • William E Rosa, Stephanie Hope, Marianne Matzo. Palliative Nursing and Sacred Medicine: A Holistic Stance on Entheogens, Healing, and Spiritual Care. Journal of holistic nursing : official journal of the American Holistic Nurses' Association. 2019 Mar; 37(1):100-106. doi: 10.1177/0898010118770302. [PMID: 29669454]
  • Abigail Moreno-Pedraza, Ignacio Rosas-Román, Nancy Shyrley Garcia-Rojas, Héctor Guillén-Alonso, Cesaré Ovando-Vázquez, David Díaz-Ramírez, Jessica Cuevas-Contreras, Fredd Vergara, Nayelli Marsch-Martínez, Jorge Molina-Torres, Robert Winkler. Elucidating the Distribution of Plant Metabolites from Native Tissues with Laser Desorption Low-Temperature Plasma Mass Spectrometry Imaging. Analytical chemistry. 2019 02; 91(4):2734-2743. doi: 10.1021/acs.analchem.8b04406. [PMID: 30636413]
  • Bruce K Cassels, Patricio Sáez-Briones. Dark Classics in Chemical Neuroscience: Mescaline. ACS chemical neuroscience. 2018 10; 9(10):2448-2458. doi: 10.1021/acschemneuro.8b00215. [PMID: 29847089]
  • Adrienne E Ng, Ernesto Sandoval, Terence M Murphy. Identification and Individualization of Lophophora using DNA Analysis of the trnL/trnF Region and rbcL Gene. Journal of forensic sciences. 2016 Jan; 61 Suppl 1(?):S226-9. doi: 10.1111/1556-4029.12936. [PMID: 27405021]
  • Dilek Battal, Allan J Barnes, Marisol S Castaneto, Thomas M Martin, Kevin L Klette, Marilyn A Huestis. Urine Mescaline Screening With a Biochip Array Immunoassay and Quantification by Gas Chromatography-Mass Spectrometry. Therapeutic drug monitoring. 2015 Dec; 37(6):805-11. doi: 10.1097/ftd.0000000000000220. [PMID: 25992796]
  • Enrique Ibarra-Laclette, Flor Zamudio-Hernández, Claudia Anahí Pérez-Torres, Victor A Albert, Enrique Ramírez-Chávez, Jorge Molina-Torres, Araceli Fernández-Cortes, Carlos Calderón-Vázquez, José Luis Olivares-Romero, Alfredo Herrera-Estrella, Luis Herrera-Estrella. De novo sequencing and analysis of Lophophora williamsii transcriptome, and searching for putative genes involved in mescaline biosynthesis. BMC genomics. 2015 Sep; 16(?):657. doi: 10.1186/s12864-015-1821-9. [PMID: 26330142]
  • Cristiana Gambelunghe, Remo Marsili, Kyriaki Aroni, Mauro Bacci, Riccardo Rossi. GC-MS and GC-MS/MS in PCI mode determination of mescaline in peyote tea and in biological matrices. Journal of forensic sciences. 2013 Jan; 58(1):270-8. doi: 10.1111/j.1556-4029.2012.02249.x. [PMID: 22900815]
  • S Lerch, K J Shingfield, A Ferlay, A Vanhatalo, Y Chilliard. Rapeseed or linseed in grass-based diets: effects on conjugated linoleic and conjugated linolenic acid isomers in milk fat from Holstein cows over 2 consecutive lactations. Journal of dairy science. 2012 Dec; 95(12):7269-87. doi: 10.3168/jds.2012-5654. [PMID: 22999291]
  • Christine A Strick, Cheryl Li, Liam Scott, Brian Harvey, Mihály Hajós, Stefanus J Steyn, Mary A Piotrowski, Larry C James, James T Downs, Brian Rago, Stacey L Becker, Ayman El-Kattan, Youfen Xu, Alan H Ganong, F David Tingley, Andres D Ramirez, Patricia A Seymour, Victor Guanowsky, Mark J Majchrzak, Carol B Fox, Christopher J Schmidt, Allen J Duplantier. Modulation of NMDA receptor function by inhibition of D-amino acid oxidase in rodent brain. Neuropharmacology. 2011 Oct; 61(5-6):1001-15. doi: 10.1016/j.neuropharm.2011.06.029. [PMID: 21763704]
  • Masako Aragane, Yohei Sasaki, Jun'ichi Nakajima, Nobutaka Fukumori, Masao Yoshizawa, Yukiko Suzuki, Shigemi Kitagawa, Ken'ichiro Mori, Shuzo Ogino, Ichiro Yasuda, Seiji Nagumo. Peyote identification on the basis of differences in morphology, mescaline content, and trnL/trnF sequence between Lophophora williamsii and L. diffusa. Journal of natural medicines. 2011 Jan; 65(1):103-10. doi: 10.1007/s11418-010-0469-7. [PMID: 20890669]
  • Olabode Ogunbodede, Douglas McCombs, Keeper Trout, Paul Daley, Martin Terry. New mescaline concentrations from 14 taxa/cultivars of Echinopsis spp. (Cactaceae) ('San Pedro') and their relevance to shamanic practice. Journal of ethnopharmacology. 2010 Sep; 131(2):356-62. doi: 10.1016/j.jep.2010.07.021. [PMID: 20637277]
  • Kristian Björnstad, Anders Helander, Olof Beck. Development and clinical application of an LC-MS-MS method for mescaline in urine. Journal of analytical toxicology. 2008 Apr; 32(3):227-31. doi: 10.1093/jat/32.3.227. [PMID: 18397574]
  • Tomás Pálenícek, Marie Balíková, Vera Bubeníková-Valesová, Jirí Horácek. Mescaline effects on rat behavior and its time profile in serum and brain tissue after a single subcutaneous dose. Psychopharmacology. 2008 Jan; 196(1):51-62. doi: 10.1007/s00213-007-0926-5. [PMID: 17922234]
  • Hesham R El-Seedi, Peter A G M De Smet, Olof Beck, Göran Possnert, Jan G Bruhn. Prehistoric peyote use: alkaloid analysis and radiocarbon dating of archaeological specimens of Lophophora from Texas. Journal of ethnopharmacology. 2005 Oct; 101(1-3):238-42. doi: 10.1016/j.jep.2005.04.022. [PMID: 15990261]
  • Vilma Habrdova, Frank T Peters, Denis S Theobald, Hans H Maurer. Screening for and validated quantification of phenethylamine-type designer drugs and mescaline in human blood plasma by gas chromatography/mass spectrometry. Journal of mass spectrometry : JMS. 2005 Jun; 40(6):785-95. doi: 10.1002/jms.853. [PMID: 15827969]
  • M Franco-Molina, R Gomez-Flores, P Tamez-Guerra, R Tamez-Guerra, L Castillo-Leon, C Rodríguez-Padilla. In vitro immunopotentiating properties and tumour cell toxicity induced by Lophophora williamsii (peyote) cactus methanolic extract. Phytotherapy research : PTR. 2003 Nov; 17(9):1076-81. doi: 10.1002/ptr.1313. [PMID: 14595591]
  • Marlene Dobkin de Rios, Charles S Grob, John R Baker. Hallucinogens and redemption. Journal of psychoactive drugs. 2002 Jul; 34(3):239-48. doi: 10.1080/02791072.2002.10399960. [PMID: 12422934]
  • Takahiko Isobe, Ayumi Ohsaki, Kumiko Nagata. [Antibacterial constituents against Helicobacter pylori of Brazilian medicinal plant, Pariparoba]. Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan. 2002 Apr; 122(4):291-4. doi: 10.1248/yakushi.122.291. [PMID: 11968842]
  • K Watanabe, Y Kayano, T Matsunaga, I Yamamoto, H Yoshimura. 3,4,5-Trimethoxyphenylacetaldehyde, an intermediate metabolite of mescaline, is a substrate for microsomal aldehyde oxygenase in the mouse liver. Biological & pharmaceutical bulletin. 1995 May; 18(5):696-9. doi: 10.1248/bpb.18.696. [PMID: 7492985]
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  • P C Reynolds, E J Jindrich. A mescaline associated fatality. Journal of analytical toxicology. 1985 Jul; 9(4):183-4. doi: 10.1093/jat/9.4.183. [PMID: 4033076]
  • N S Shah, O D Gulati. Effect of clozapine and molindone on plasma and brain levels of mescaline in mice. European journal of drug metabolism and pharmacokinetics. 1984 Oct; 9(4):307-9. doi: 10.1007/bf03189681. [PMID: 6532803]
  • G Morgan. Hispano-Indian trade of an Indian ceremonial plant, peyote (Lophophohora williamsii), on the Mustang Plains of Texas. Journal of ethnopharmacology. 1983 Dec; 9(2-3):319-21. doi: 10.1016/0378-8741(83)90039-9. [PMID: 6677822]
  • C Van Peteghem, A Heyndrickx, W Van Zele. Pharmacokinetic parameters of mescaline in rabbits. European journal of drug metabolism and pharmacokinetics. 1982 Jan; 7(1):1-3. doi: 10.1007/bf03189535. [PMID: 7067718]
  • P Jacob, A T Shulgin. Sulfur analogues of psychotomimetic agents. Monothio analogues of mescaline and isomescaline. Journal of medicinal chemistry. 1981 Nov; 24(11):1348-53. doi: 10.1021/jm00143a017. [PMID: 7310812]
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  • C Van Peteghem, A Heyndrickx, W Van Zele. GLC-mass spectral determination of mescaline in plasma of rabbits after intravenous injection. Journal of pharmaceutical sciences. 1980 Jan; 69(1):118-20. doi: 10.1002/jps.2600690139. [PMID: 7354425]
  • L Demisch, M Neubauer. Stimulation of human prolactin secretion by mescaline. Psychopharmacology. 1979 Sep; 64(3):361-3. doi: 10.1007/bf00427525. [PMID: 116281]
  • N S Shah, S D Hudnall, D May, D Eargle, J Yates. Neurolepticlike actions of l-methadone: effect on mescaline-induced altered behavior and on tissue levels of mescaline in mice. Biological psychiatry. 1979 Aug; 14(4):587-94. doi: . [PMID: 486615]
  • H Y Meltzer, R G Fessler, M Simonovic, V S Fang. The effect of mescaline, 3, 4-dimethoxyphenethylamine and 2, 5-dimethoxy-4-methylamphetamine on rat plasma prolactin: evidence for serotonergic mediation. Life sciences. 1978 Sep; 23(11):1185-92. doi: 10.1016/0024-3205(78)90353-3. [PMID: 152377]
  • L Demisch, P Kaczmarczyk, N Seiler. 3,4,5-Trimethoxybenzoic acid, a new mescaline metabolite in humans. Drug metabolism and disposition: the biological fate of chemicals. 1978 Sep; 6(5):507-9. doi: NULL. [PMID: 30599]
  • H Bekemeier, A J Giessler, E Vogel. Influence of MAO-inhibitors, neuroleptics, morphine, mescaline, divascan, aconitine, and pyrogenes on prostaglandin-biosynthesis. Pharmacological research communications. 1977 Jun; 9(6):587-98. doi: 10.1016/s0031-6989(77)80087-8. [PMID: 19774]
  • R A Roth, J A Roth, C N Gillis. Disposition of 14C-mescaline by rabbit lung. The Journal of pharmacology and experimental therapeutics. 1977 Feb; 200(2):394-401. doi: NULL. [PMID: 839444]
  • H Korr, N Seiler. Autoradiographic studies on the distribution of 3H-2,3,4-trimethoxy-beta-phenylethylamine in the mouse. Psychopharmacologia. 1976; 46(1):53-8. doi: 10.1007/bf00421549. [PMID: 1257367]
  • W F Geber, S S Lefkowitz, C Y Hung. Effect of morphine, hydromorphone, methadone, mescaline, trypan blue, vitamin A, sodium salicylate, and caffeine on the serum interferon level in response to viral infection. Archives internationales de pharmacodynamie et de therapie. 1975 Apr; 214(2):322-7. doi: . [PMID: 50766]
  • N S Shah, K R Shah, R S Lawrence, A E Neely. The uptake and distribution of 14-C-mescaline in different organs of developing rat. Drug metabolism and disposition: the biological fate of chemicals. 1975 Mar; 3(2):74-9. doi: NULL. [PMID: 236161]
  • L Demisch, N Seiler. Oxidative metabolism of mescaline in the central nervous system--V. In vitro deamination of mescaline to 3,4,5-trimethoxy-benzoic acid. Biochemical pharmacology. 1975 Mar; 24(5):575-80. doi: 10.1016/0006-2952(75)90176-8. [PMID: 1125061]
  • L J Riceberg, M Simon, H Van Vunakis, R H Abeles. Effects of aminoacetonitrile, an amine oxidase inhibitor, on mescaline metabolism in the rabbit. Biochemical pharmacology. 1975 Jan; 24(1):119-25. doi: 10.1016/0006-2952(75)90323-8. [PMID: 1168468]
  • R Utzinger. Hapten-immunological studies on mescaline. Psychopharmacologia. 1975; 41(3):301-4. doi: 10.1007/bf00428941. [PMID: 807928]
  • L J Riceberg, H Van Vunakis, L Levine. Radioimmunoassays of 3,4,5-trimethoxyphenethylamine (mescaline) and 2,5-dimethoxy-4-methylphenyl-isopropylamine(DOM). Analytical biochemistry. 1974 Aug; 60(2):551-9. doi: 10.1016/0003-2697(74)90266-8. [PMID: 4210779]
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  • N S Shah, C Green. Tissue levels of mescaline in mice: influence of chlorpromazine on repeated administration of mescaline. European journal of pharmacology. 1973 Dec; 24(3):334-40. doi: 10.1016/0014-2999(73)90159-3. [PMID: 4766694]
  • N S Shah, K R Shah, R S Lawrence, A E Neely. Effects of chlorpromazine and haloperidol on the disposition of mescaline-14C in mice. The Journal of pharmacology and experimental therapeutics. 1973 Aug; 186(2):297-304. doi: . [PMID: 4719782]
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