Dimethyltryptamine (BioDeep_00000002081)

 

Secondary id: BioDeep_00001867768

human metabolite Endogenous blood metabolite Chemicals and Drugs


代谢物信息卡片


N-(2-(1H-indol-3-yl)Ethyl)-N,N-dimethylamine (acd/name 4.0)

化学式: C12H16N2 (188.13134159999998)
中文名称: N,N-二甲基色胺
谱图信息: 最多检出来源 Homo sapiens(urine) 33.33%

分子结构信息

SMILES: c1ccc2c(c1)c(c[nH]2)CCN(C)C
InChI: InChI=1S/C12H16N2/c1-14(2)8-7-10-9-13-12-6-4-3-5-11(10)12/h3-6,9,13H,7-8H2,1-2H3

描述信息

An N-methylated indoleamine derivative, a serotonergic hallucinogen found in several plants, especially Prestonia amazonica (Apocynaceae) and in mammalian brain, blood, and urine. It apparently acts as an agonist at some types of serotonin receptors and an antagonist at others.; DMT is a derivative of tryptamine with two additional methyl groups at the amine nitrogen atom. DMT is often synthesized by the Speeter-Anthony synthesis from indole using oxalyl chloride, dimethylamine, and lithium aluminium hydride as reagents. DMT is usually used in its base form, but it is more stable as a salt, e.g. as a fumarate. In contrast to DMTs base, its salts are water-soluble. DMT in solution degrades relatively fast and should be stored protected from air and light in a freezer. Highly pure DMT crystals, when evaporated out of a solvent and depositing upon glass, often produce small but highly defined white crystalline needles which when viewed under intense light will sparkle, and appear colorless under high magnification. In labs, it has been known to be explosive under a certain degree of heat.; DMT is a powerful psychoactive substance. If DMT is smoked, injected, or orally ingested with an MAOI, it can produce powerful entheogenic experiences including intense visual hallucinations, euphoria, even true hallucinations (perceived extensions of reality). A trip sitter is recommended to assist the drug user in staying physically and mentally healthy, and, in the case of smoked DMT, to catch the pipe if the user loses awareness of it.; DMT is classified in the United States as a Schedule I drug. In December of 2004, the Supreme Court lifted a stay thereby allowing the Brazil-based Uniaeo do Vegetal (UDV) church to use a decoction containing DMT in their Christmas services that year. This decoction is a tea made from boiled leaves and vines, known as hoasca within the UDV, and ayahuasca in different cultures. In Gonzales v. O Centro EspArita Beneficente Uniaeo do Vegetal, the Supreme Court heard arguments on November 1, 2005 and unanimously ruled in February 2006 that the U.S. federal government must allow the UDV to import and consume the tea for religious ceremonies under the 1993 Religious Freedom Restoration Act. There are no drug tests that would show DMT usage. None of the basic NIDA 5 drug tests or any extended drug test will show a result for DMT.; Dimethyltryptamine (DMT), also known as N,N-dimethyltryptamine, is a psychedelic tryptamine. It is not to be confused with 5-MeO-DMT and is similar in chemical structure to the neurotransmitter serotonin. DMT is created in small amounts by the human body during normal metabolism by the enzyme tryptamine-N-methyltransferase. Pure DMT at room temperature is a clear or white crystalline solid. DMT was first chemically synthesized in 1931. It also occurs naturally in many species of plants. DMT-containing plants are used in several South American shamanic practices. It is one of the main active constituents of snuffs like yopo and of the drink ayahuasca.; Oral ingestion: DMT, which is broken down by the digestive enzyme monoamine oxidase, is practically inactive if taken orally, unless combined with a monoamine oxidase inhibitor (MAOI). The traditional South American ayahuasca, or yage, is a tea mixture containing DMT and a MAOI. There are a number of admixtures to this brew, but most commonly it is simply the leaves of Psychotria viridis (containing DMT), and the vine Banisteriopsis caapi (the source of MAOI). Other DMT containing plants, including Diplopterys cabrerana, are sometimes used in ayahuasca in different areas of South America. Two common sources in the western US are Reed canary grass (Phalaris arundinacea) and Harding grass (Phalaris aquatica). These invasive grasses contain low levels of DMT and other alkaloids. Taken orally with an appropriate MAOI, DMT produces a long lasting (over 3 hour), slow, but deep spiritual experience. MAOIs should be used with extreme caution as they...
Dimethyltryptamine is an N-methylated indoleamine derivative, a serotonergic hallucinogen found in several plants, especially Prestonia amazonica (Apocynaceae) and in mammalian brain, blood, and urine. It apparently acts as an agonist at some types of serotonin receptors and an antagonist at others. DMT is a derivative of tryptamine with two additional methyl groups at the amine nitrogen atom. DMT is often synthesized by the Speeter-Anthony synthesis from indole using oxalyl chloride, dimethylamine, and lithium aluminium hydride as reagents. DMT is usually used in its base form, but it is more stable as a salt, e.g. as a fumarate. In contrast to DMTs base, its salts are water-soluble. DMT in solution degrades relatively fast and should be stored protected from air and light in a freezer. Highly pure DMT crystals, when evaporated out of a solvent and depositing upon glass, often produce small but highly defined white crystalline needles which when viewed under intense light will sparkle, and appear colorless under high magnification. In labs, it has been known to be explosive under a certain degree of heat. DMT is a powerful psychoactive substance. If DMT is smoked, injected, or orally ingested with an MAOI, it can produce powerful entheogenic experiences including intense visual hallucinations, euphoria, even true hallucinations (perceived extensions of reality). A trip sitter is recommended to assist the drug user in staying physically and mentally healthy, and, in the case of smoked DMT, to catch the pipe if the user loses awareness of it. DMT is classified in the United States as a Schedule I drug. There are no drug tests that would show DMT usage. None of the basic NIDA 5 drug tests or any extended drug test will show a result for DMT. Dimethyltryptamine (DMT), also known as N,N-dimethyltryptamine, is a psychedelic tryptamine. It is not to be confused with 5-MeO-DMT and is similar in chemical structure to the neurotransmitter serotonin. DMT is created in small amounts by the human body during normal metabolism by the enzyme tryptamine-N-methyltransferase. Pure DMT at room temperature is a clear or white crystalline solid. DMT was first chemically synthesized in 1931. It also occurs naturally in many species of plants. DMT-containing plants are used in several South American shamanic practices. It is one of the main active constituents of snuffs like yopo and of the drink ayahuasca. Oral ingestion: DMT, which is broken down by the digestive enzyme monoamine oxidase, is practically inactive if taken orally, unless combined with a monoamine oxidase inhibitor (MAOI). The traditional South American ayahuasca, or yage, is a tea mixture containing DMT and a MAOI. There are a number of admixtures to this brew, but most commonly it is simply the leaves of Psychotria viridis (containing DMT), and the vine Banisteriopsis caapi (the source of MAOI). Other DMT containing plants, including Diplopterys cabrerana, are sometimes used in ayahuasca in different areas of South America. Two common sources in the western US are Reed canary grass (Phalaris arundinacea) and Harding grass (Phalaris aquatica). These invasive grasses contain low levels of DMT and other alkaloids. Taken orally with an appropriate MAOI, DMT produces a long lasting (over 3 hour), slow, but deep spiritual experience. MAOIs should be used with extreme caution as they can have lethal complications with some prescription drugs, such as SSRI antidepressants, and some over-the-counter drugs. Smoked: If DMT is smoked, the maximal effects last for a short period of time (5-30 minutes dose dependent). The onset after inhalation is very fast (less than 45 seconds) and maximal effects are reached within about a minute. The Business Mans lunch trip is a common name due to the relatively short duration of vaporized, insufflated, or injected DMT.
D018377 - Neurotransmitter Agents > D018490 - Serotonin Agents > D017366 - Serotonin Receptor Agonists
D018377 - Neurotransmitter Agents > D018490 - Serotonin Agents > D012702 - Serotonin Antagonists
D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D006213 - Hallucinogens

同义名列表

21 个代谢物同义名

N-(2-(1H-indol-3-yl)Ethyl)-N,N-dimethylamine (acd/name 4.0); 2-(1H-indol-3-yl)-N,N-Dimethylethanamine (acd/name 4.0); N,N-Dimethyl-1H-indole-3-ethanamine (9ci); 2-(1H-indol-3-yl)-N,N-Dimethylethanamine; [2-(1H-indol-3-yl)ethyl]dimethylamine; N,N-Dimethyl-1H-indole-3-ethanamine; N,N-Dimethyl-1H-indole-3-ethylamine; 3-[2- (dimethylamino)Ethyl]-indole; 3-(2-(dimethylamino)Ethyl)-indole; (2-indol-3-Ylethyl)dimethylamine; 3-[2-(Dimethylamino)ethyl]indole; 2-(3-Indolyl)ethyldimethylamine; 3-(2-Dimethylaminoethyl)indole; N,N-Dimethyltryptamine (DMT); Dimethyltryptamine(DMT); N,N-DIMETHYLTRYPTAMINE; N,N Dimethyltryptamine; Indolalkylamine der; Dimethyltryptamine; (Psychogenic); DMT



数据库引用编号

17 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)

51 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

  • Eleanor White, Tom Kennedy, Simon Ruffell, Daniel Perkins, Jerome Sarris. Ayahuasca and Dimethyltryptamine Adverse Events and Toxicity Analysis: A Systematic Thematic Review. International journal of toxicology. 2024 May; 43(3):327-339. doi: 10.1177/10915818241230916. [PMID: 38363085]
  • Kenneth Shinozuka, Burton J Tabaac, Alejandro Arenas, Bryce D Beutler, Kirsten Cherian, Viviana D Evans, Chelsey Fasano, Owen S Muir. Psychedelic Therapy: A Primer for Primary Care Clinicians-N,N-Dimethyltryptamine and Ayahuasca. American journal of therapeutics. 2024 Mar; 31(2):e112-e120. doi: 10.1097/mjt.0000000000001725. [PMID: 38518268]
  • Rubi Barman, Pranjit Kumar Bora, Jadumoni Saikia, Parthapratim Konwar, Aditya Sarkar, Phirose Kemprai, Siddhartha Proteem Saikia, Saikat Haldar, Adrian Slater, Dipanwita Banik. Hypothetical biosynthetic pathways of pharmaceutically potential hallucinogenic metabolites in Myristicaceae, mechanistic convergence and co-evolutionary trends in plants and humans. Phytochemistry. 2024 Feb; 218(?):113928. doi: 10.1016/j.phytochem.2023.113928. [PMID: 38035973]
  • Fateme Zohairi, Himanshu Khandelia, Ali Asghar Hakami Zanjani. Interaction of psychedelic tryptamine derivatives with a lipid bilayer. Chemistry and physics of lipids. 2023 Mar; 251(?):105279. doi: 10.1016/j.chemphyslip.2023.105279. [PMID: 36627076]
  • Giordano Novak Rossi, Lorena T L Guerra, Glen B Baker, Serdar M Dursun, José Carlos Bouso Saiz, Jaime E C Hallak, Rafael G Dos Santos. Molecular Pathways of the Therapeutic Effects of Ayahuasca, a Botanical Psychedelic and Potential Rapid-Acting Antidepressant. Biomolecules. 2022 11; 12(11):. doi: 10.3390/biom12111618. [PMID: 36358968]
  • Albert Katchborian-Neto, Mário Ferreira Conceição Santos, Diego Fernandes Vilas-Boas, Elda Gonçalves Dos Santos, Márcia Paranho Veloso, Paula Carolina Pires Bueno, Ivo Santana Caldas, Marisi Gomes Soares, Danielle Ferreira Dias, Daniela Aparecida Chagas-Paula. Immunological Modulation and Control of Parasitaemia by Ayahuasca Compounds: Therapeutic Potential for Chagas's Disease. Chemistry & biodiversity. 2022 Oct; 19(10):e202200409. doi: 10.1002/cbdv.202200409. [PMID: 36163588]
  • Joana Gonçalves, Ângelo Luís, Eugenia Gallardo, Ana Paula Duarte. Evaluation of the In Vitro Wound-Healing Potential of Ayahuasca. Molecules (Basel, Switzerland). 2022 Sep; 27(18):. doi: 10.3390/molecules27185760. [PMID: 36144509]
  • Rafael G Dos Santos, Juliana Mendes Rocha, Giordano Novak Rossi, Flávia L Osório, Genís Ona, José Carlos Bouso, Gabriela de Oliveira Silveira, Mauricio Yonamine, Camila Marchioni, Eduardo José Crevelin, Maria Eugênia Queiroz, José Alexandre Crippa, Jaime E C Hallak. Effects of ayahuasca on the endocannabinoid system of healthy volunteers and in volunteers with social anxiety disorder: Results from two pilot, proof-of-concept, randomized, placebo-controlled trials. Human psychopharmacology. 2022 07; 37(4):e2834. doi: 10.1002/hup.2834. [PMID: 35107855]
  • Edward James, Joachim Keppler, Thomas L Robertshaw, Ben Sessa. N,N-dimethyltryptamine and Amazonian ayahuasca plant medicine. Human psychopharmacology. 2022 05; 37(3):e2835. doi: 10.1002/hup.2835. [PMID: 35175662]
  • Emma Eckernäs, Adam Bendrioua, Chiara Cancellerini, Christopher Timmermann, Robin Carhart-Harris, Kurt-Jürgen Hoffmann, Michael Ashton. Development and application of a highly sensitive LC-MS/MS method for simultaneous quantification of N,N-dimethyltryptamine and two of its metabolites in human plasma. Journal of pharmaceutical and biomedical analysis. 2022 Apr; 212(?):114642. doi: 10.1016/j.jpba.2022.114642. [PMID: 35149418]
  • Thaís F S Moraes, Ariane C Ferraz, Waleska S da Cruz Nizer, Antônio H Tótola, Débora B S Soares, Lucienir P Duarte, Sidney A Vieira-Filho, Cintia L B Magalhães, José C de Magalhães. A methanol extract and N,N-dimethyltryptamine from Psychotria viridis Ruiz & Pav. inhibit Zika virus infection in vitro. Archives of virology. 2021 Dec; 166(12):3275-3287. doi: 10.1007/s00705-021-05230-8. [PMID: 34536126]
  • Sherilyn K D Houle, Derek Evans, Caitlin A Carter, Patricia Schlagenhauf. Ayahuasca and the traveller: A scoping review of risks and possible benefits. Travel medicine and infectious disease. 2021 Nov; 44(?):102206. doi: 10.1016/j.tmaid.2021.102206. [PMID: 34785376]
  • Írisz Szabó, Viktória É Varga, Szabolcs Dvorácskó, Attila E Farkas, Tímea Körmöczi, Róbert Berkecz, Szilvia Kecskés, Ákos Menyhárt, Rita Frank, Dóra Hantosi, Nicholas V Cozzi, Ede Frecska, Csaba Tömböly, István A Krizbai, Ferenc Bari, Eszter Farkas. N,N-Dimethyltryptamine attenuates spreading depolarization and restrains neurodegeneration by sigma-1 receptor activation in the ischemic rat brain. Neuropharmacology. 2021 07; 192(?):108612. doi: 10.1016/j.neuropharm.2021.108612. [PMID: 34023338]
  • Deana Goldin, Deborah Salani. Ayahuasca: What Healthcare Providers Need to Know. Journal of addictions nursing. 2021 Apr; 32(2):167-173. doi: 10.1097/jan.0000000000000405. [PMID: 34060770]
  • Gabriela de Oliveira Silveira, Felipe Rebello Lourenço, Ana Miguel Fonseca Pego, Rafael Guimarães Dos Santos, Giordano Novak Rossi, Jaime E C Hallak, Mauricio Yonamine. Essential oil-based dispersive liquid-liquid microextraction for the determination of N,N-dimethyltryptamine and β-carbolines in human plasma: A novel solvent-free alternative. Talanta. 2021 Apr; 225(?):121976. doi: 10.1016/j.talanta.2020.121976. [PMID: 33592724]
  • Brandon Weiss, Joshua D Miller, Nathan T Carter, W Keith Campbell. Examining changes in personality following shamanic ceremonial use of ayahuasca. Scientific reports. 2021 03; 11(1):6653. doi: 10.1038/s41598-021-84746-0. [PMID: 33758236]
  • Rafael Lanaro, Sueli Moreira Mello, Kelly Francisco da Cunha, Gabriela Silveira, Nelson Francisco Corrêa-Neto, Stephen Hyslop, Oscar G Cabrices, Jose Luiz Costa, Alessandra Linardi. Kinetic profile of N,N-dimethyltryptamine and β-carbolines in saliva and serum after oral administration of ayahuasca in a religious context. Drug testing and analysis. 2021 Mar; 13(3):664-678. doi: 10.1002/dta.2955. [PMID: 33119972]
  • Helle Kaasik, Rita C Z Souza, Flávia S Zandonadi, Luís Fernando Tófoli, Alessandra Sussulini. Chemical Composition of Traditional and Analog Ayahuasca. Journal of psychoactive drugs. 2021 Jan; 53(1):65-75. doi: 10.1080/02791072.2020.1815911. [PMID: 32896230]
  • Tímea Körmöczi, Írisz Szabó, Eszter Farkas, Botond Penke, Tamás Janáky, István Ilisz, Róbert Berkecz. Heart-cutting two-dimensional liquid chromatography coupled to quadrupole-orbitrap high resolution mass spectrometry for determination of N,N-dimethyltryptamine in rat plasma and brain; Method development and application. Journal of pharmaceutical and biomedical analysis. 2020 Nov; 191(?):113615. doi: 10.1016/j.jpba.2020.113615. [PMID: 32942106]
  • Simon Ruffell, Nige Netzband, Catherine Bird, Allan H Young, Mario F Juruena. The pharmacological interaction of compounds in ayahuasca: a systematic review. Revista brasileira de psiquiatria (Sao Paulo, Brazil : 1999). 2020 Nov; 42(6):646-656. doi: 10.1590/1516-4446-2020-0884. [PMID: 32638916]
  • Nicholas V Cozzi, Paul F Daley. Synthesis and characterization of high-purity N,N-dimethyltryptamine hemifumarate for human clinical trials. Drug testing and analysis. 2020 Oct; 12(10):1483-1493. doi: 10.1002/dta.2889. [PMID: 32608093]
  • Nige Netzband, Simon Ruffell, S Linton, W F Tsang, T Wolff. Modulatory effects of ayahuasca on personality structure in a traditional framework. Psychopharmacology. 2020 Oct; 237(10):3161-3171. doi: 10.1007/s00213-020-05601-0. [PMID: 32700023]
  • Gabriela de Oliveira Silveira, Rafael Guimarães Dos Santos, Felipe Rebello Lourenço, Giordano Novak Rossi, Jaime E C Hallak, Mauricio Yonamine. Stability Evaluation of DMT and Harmala Alkaloids in Ayahuasca Tea Samples. Molecules (Basel, Switzerland). 2020 Apr; 25(9):. doi: 10.3390/molecules25092072. [PMID: 32365548]
  • Malin V Uthaug, Rafael Lancelotta, Attila Szabo, Alan K Davis, Jordi Riba, Johannes G Ramaekers. Prospective examination of synthetic 5-methoxy-N,N-dimethyltryptamine inhalation: effects on salivary IL-6, cortisol levels, affect, and non-judgment. Psychopharmacology. 2020 Mar; 237(3):773-785. doi: 10.1007/s00213-019-05414-w. [PMID: 31822925]
  • Christopher Timmermann, Leor Roseman, Michael Schartner, Raphael Milliere, Luke T J Williams, David Erritzoe, Suresh Muthukumaraswamy, Michael Ashton, Adam Bendrioua, Okdeep Kaur, Samuel Turton, Matthew M Nour, Camilla M Day, Robert Leech, David J Nutt, Robin L Carhart-Harris. Neural correlates of the DMT experience assessed with multivariate EEG. Scientific reports. 2019 11; 9(1):16324. doi: 10.1038/s41598-019-51974-4. [PMID: 31745107]
  • Chuan-Huai Liu, Wei-Lan Chu, Shu-Chen Liao, Chen-Chang Yang, Chih-Chuan Lin. Syrian rue seeds interacted with acacia tree bark in an herbal stew resulted in N,N-dimethyltryptamine poisoning. Clinical toxicology (Philadelphia, Pa.). 2019 Oct; 57(10):867-869. doi: 10.1080/15563650.2019.1576877. [PMID: 30831037]
  • Alexandra Vsl Rodrigues, Francisco Jcg Almeida, Maria A Vieira-Coelho. Dimethyltryptamine: Endogenous Role and Therapeutic Potential. Journal of psychoactive drugs. 2019 Sep; 51(4):299-310. doi: 10.1080/02791072.2019.1602291. [PMID: 31018803]
  • Rita C Z Souza, Flávia S Zandonadi, Donizete P Freitas, Luís F F Tófoli, Alessandra Sussulini. Validation of an analytical method for the determination of the main ayahuasca active compounds and application to real ayahuasca samples from Brazil. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2019 Aug; 1124(?):197-203. doi: 10.1016/j.jchromb.2019.06.014. [PMID: 31220748]
  • Balázs Nemes, Katalin Pető, Norbert Németh, Anita Mester, Zsuzsanna Magyar, Souleiman Ghanem, Viktória Sógor, Bence Tánczos, Ádám Deák, Márk Kállay, László Bidiga, Ede Frecska. N,N-dimethyltryptamine Prevents Renal Ischemia-Reperfusion Injury in a Rat Model. Transplantation proceedings. 2019 May; 51(4):1268-1275. doi: 10.1016/j.transproceed.2019.04.005. [PMID: 31101212]
  • Jeffrey D Pope, Kay Weng Choy, Olaf H Drummer, Hans G Schneider. Harmala Alkaloids Identify Ayahausca Intoxication in a Urine Drug Screen. Journal of analytical toxicology. 2019 May; 43(4):e23-e27. doi: 10.1093/jat/bky105. [PMID: 30566569]
  • Fábio Kummrow, Bianca S Maselli, Rafael Lanaro, José Luis Costa, Gisela A Umbuzeiro, Alessandra Linardi. Mutagenicity of Ayahuasca and Their Constituents to the Salmonella/Microsome Assay. Environmental and molecular mutagenesis. 2019 04; 60(3):269-276. doi: 10.1002/em.22263. [PMID: 30488498]
  • Sueli Moreira Mello, Paula Christiane Soubhia, Gabriela Silveira, Nelson Francisco Corrêa-Neto, Rafael Lanaro, José Luiz Costa, Alessandra Linardi. Effect of Ritualistic Consumption of Ayahuasca on Hepatic Function in Chronic Users. Journal of psychoactive drugs. 2019 Jan; 51(1):3-11. doi: 10.1080/02791072.2018.1557355. [PMID: 30582439]
  • Jonathan Hamill, Jaime Hallak, Serdar M Dursun, Glen Baker. Ayahuasca: Psychological and Physiologic Effects, Pharmacology and Potential Uses in Addiction and Mental Illness. Current neuropharmacology. 2019; 17(2):108-128. doi: 10.2174/1570159x16666180125095902. [PMID: 29366418]
  • Marco Aurélio Vinhosa Bastos, Paulo Roberto Haidamus de Oliveira Bastos, Maria Lucília Dos Santos, Décio Iandoli, Renata Boschi Portella, Giancarlo Lucchetti. Comparing the Detection of Endogenous Psychedelics in Individuals With and Without Alleged Mediumistic Experiences. Explore (New York, N.Y.). 2018 11; 14(6):448-452. doi: 10.1016/j.explore.2018.04.013. [PMID: 30241696]
  • Lindsay P Cameron, David E Olson. Dark Classics in Chemical Neuroscience: N, N-Dimethyltryptamine (DMT). ACS chemical neuroscience. 2018 10; 9(10):2344-2357. doi: 10.1021/acschemneuro.8b00101. [PMID: 30036036]
  • Marc Aixalà, Rafael G Dos Santos, Jaime E C Hallak, José Carlos Bouso. Psychedelics and Personality. ACS chemical neuroscience. 2018 10; 9(10):2304-2306. doi: 10.1021/acschemneuro.8b00237. [PMID: 29863323]
  • Katalin Peto, Norbert Nemeth, Anita Mester, Zsuzsanna Magyar, Souleiman Ghanem, Viktoria Somogyi, Bence Tanczos, Adam Deak, Laszlo Bidiga, Ede Frecska, Balazs Nemes. Hemorheological and metabolic consequences of renal ischemia-reperfusion and their modulation by N,N-dimethyl-tryptamine on a rat model. Clinical hemorheology and microcirculation. 2018; 70(1):107-117. doi: 10.3233/ch-170361. [PMID: 29660915]
  • Débora B S Soares, Lucienir P Duarte, André D Cavalcanti, Fernando C Silva, Ariadne D Braga, Miriam T P Lopes, Jacqueline A Takahashi, Sidney A Vieira-Filho. Psychotria viridis: Chemical constituents from leaves and biological properties. Anais da Academia Brasileira de Ciencias. 2017 Apr; 89(2):927-938. doi: 10.1590/0001-3765201720160411. [PMID: 28640347]
  • Frecska Ede, Kovács Attila, Szabó Attila, Ferencz Csaba, Móré Csaba. Basics of the medical use of ayahuasca: physiology of dimethyltryptamine. Lege artis medicinae : uj magyar orvosi hirmondo. 2016 Sep; 26(9-10):413. doi: . [PMID: 29537778]
  • K P C Kuypers, J Riba, M de la Fuente Revenga, S Barker, E L Theunissen, J G Ramaekers. Ayahuasca enhances creative divergent thinking while decreasing conventional convergent thinking. Psychopharmacology. 2016 Sep; 233(18):3395-403. doi: 10.1007/s00213-016-4377-8. [PMID: 27435062]
  • Ashton D Lesiak, Rabi A Musah. Application of ambient ionization high resolution mass spectrometry to determination of the botanical provenance of the constituents of psychoactive drug mixtures. Forensic science international. 2016 09; 266(?):271-280. doi: 10.1016/j.forsciint.2016.06.009. [PMID: 27348465]
  • José Carlos Bouso, Eduardo José Pedrero-Pérez, Sam Gandy, Miguel Ángel Alcázar-Córcoles. Measuring the subjective: revisiting the psychometric properties of three rating scales that assess the acute effects of hallucinogens. Human psychopharmacology. 2016 09; 31(5):356-72. doi: 10.1002/hup.2545. [PMID: 27470427]
  • Ede Frecska, Petra Bokor, Gabor Andrassy, Attila Kovacs. [The potential use of ayahuasca in psychiatry]. Neuropsychopharmacologia Hungarica : a Magyar Pszichofarmakologiai Egyesulet lapja = official journal of the Hungarian Association of Psychopharmacology. 2016 06; 18(2):79-86. doi: ". [PMID: 27390204]
  • Patricia E J Wiltshire, David L Hawksworth, Kevin J Edwards. Light microscopy can reveal the consumption of a mixture of psychotropic plant and fungal material in suspicious death. Journal of forensic and legal medicine. 2015 Aug; 34(?):73-80. doi: 10.1016/j.jflm.2015.05.010. [PMID: 26165663]
  • Jordi Riba, Ethan H McIlhenny, José Carlos Bouso, Steven A Barker. Metabolism and urinary disposition of N,N-dimethyltryptamine after oral and smoked administration: a comparative study. Drug testing and analysis. 2015 May; 7(5):401-6. doi: 10.1002/dta.1685. [PMID: 25069786]
  • Rafael Lanaro, Débora Bressanim de Aquino Calemi, Loraine Rezende Togni, José Luiz Costa, Maurício Yonamine, Silvia de Oliveira Santos Cazenave, Alessandra Linardi. Ritualistic Use of Ayahuasca versus Street Use of Similar Substances Seized by the Police: A Key Factor Involved in the Potential for Intoxications and Overdose?. Journal of psychoactive drugs. 2015 Apr; 47(2):132-9. doi: 10.1080/02791072.2015.1013202. [PMID: 25950593]
  • Dale Gardner, Franklin Riet-Correa, Danilo Lemos, Kevin Welch, James Pfister, Kip Panter. Teratogenic effects of Mimosa tenuiflora in a rat model and possible role of N-methyl- and N,N-dimethyltryptamine. Journal of agricultural and food chemistry. 2014 Jul; 62(30):7398-401. doi: 10.1021/jf5005176. [PMID: 24689494]
  • Ede Frecska, Attila Szabo, Michael J Winkelman, Luis E Luna, Dennis J McKenna. A possibly sigma-1 receptor mediated role of dimethyltryptamine in tissue protection, regeneration, and immunity. Journal of neural transmission (Vienna, Austria : 1996). 2013 Sep; 120(9):1295-303. doi: 10.1007/s00702-013-1024-y. [PMID: 23619992]
  • Alain Gaujac, Nicola Dempster, Sandro Navickiene, Simon D Brandt, Jailson Bittencourt de Andrade. Determination of N,N-dimethyltryptamine in beverages consumed in religious practices by headspace solid-phase microextraction followed by gas chromatography ion trap mass spectrometry. Talanta. 2013 Mar; 106(?):394-8. doi: 10.1016/j.talanta.2013.01.017. [PMID: 23598143]
  • Luigi Servillo, Alfonso Giovane, Maria Luisa Balestrieri, Domenico Cautela, Domenico Castaldo. N-methylated tryptamine derivatives in citrus genus plants: identification of N,N,N-trimethyltryptamine in bergamot. Journal of agricultural and food chemistry. 2012 Sep; 60(37):9512-8. doi: 10.1021/jf302767e. [PMID: 22957740]
  • Steven A Barker, Ethan H McIlhenny, Rick Strassman. A critical review of reports of endogenous psychedelic N, N-dimethyltryptamines in humans: 1955-2010. Drug testing and analysis. 2012 Jul; 4(7-8):617-35. doi: 10.1002/dta.422. [PMID: 22371425]
  • Jordi Riba, Ethan H McIlhenny, Marta Valle, José Carlos Bouso, Steven A Barker. Metabolism and disposition of N,N-dimethyltryptamine and harmala alkaloids after oral administration of ayahuasca. Drug testing and analysis. 2012 Jul; 4(7-8):610-6. doi: 10.1002/dta.1344. [PMID: 22514127]
  • Carolina Dizioli Rodrigues Oliveira, Guilherme Gonçalves Okai, José Luiz da Costa, Rafael Menck de Almeida, Diogo Oliveira-Silva, Mauricio Yonamine. Determination of dimethyltryptamine and β-carbolines (ayahuasca alkaloids) in plasma samples by LC-MS/MS. Bioanalysis. 2012 Jul; 4(14):1731-8. doi: 10.4155/bio.12.124. [PMID: 22877219]
  • Alain Gaujac, Sandro Navickiene, Mark I Collins, Simon D Brandt, Jailson Bittencourt de Andrade. Analytical techniques for the determination of tryptamines and β-carbolines in plant matrices and in psychoactive beverages consumed during religious ceremonies and neo-shamanic urban practices. Drug testing and analysis. 2012 Jul; 4(7-8):636-48. doi: 10.1002/dta.1343. [PMID: 22577086]
  • Mitchell B Liester, James I Prickett. Hypotheses regarding the mechanisms of ayahuasca in the treatment of addictions. Journal of psychoactive drugs. 2012 Jul; 44(3):200-8. doi: 10.1080/02791072.2012.704590. [PMID: 23061319]
  • Paulo Cesar Ribeiro Barbosa, Suely Mizumoto, Michael P Bogenschutz, Rick J Strassman. Health status of ayahuasca users. Drug testing and analysis. 2012 Jul; 4(7-8):601-9. doi: 10.1002/dta.1383. [PMID: 22761152]
  • Ethan H McIlhenny, Jordi Riba, Manel J Barbanoj, Rick Strassman, Steven A Barker. Methodology for determining major constituents of ayahuasca and their metabolites in blood. Biomedical chromatography : BMC. 2012 Mar; 26(3):301-13. doi: 10.1002/bmc.1657. [PMID: 21710581]
  • Rafael G Dos Santos, Eva Grasa, Marta Valle, Maria Rosa Ballester, José Carlos Bouso, Josep F Nomdedéu, Rosa Homs, Manel J Barbanoj, Jordi Riba. Pharmacology of ayahuasca administered in two repeated doses. Psychopharmacology. 2012 Feb; 219(4):1039-53. doi: 10.1007/s00213-011-2434-x. [PMID: 21842159]
  • Alain Gaujac, Adriano Aquino, Sandro Navickiene, Jailson Bittencourt de Andrade. Determination of N,N-dimethyltryptamine in Mimosa tenuiflora inner barks by matrix solid-phase dispersion procedure and GC-MS. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2012 Jan; 881-882(?):107-10. doi: 10.1016/j.jchromb.2011.11.014. [PMID: 22209595]
  • José Carlos Bouso, Débora González, Sabela Fondevila, Marta Cutchet, Xavier Fernández, Paulo César Ribeiro Barbosa, Miguel Ángel Alcázar-Córcoles, Wladimyr Sena Araújo, Manel J Barbanoj, Josep Maria Fábregas, Jordi Riba. Personality, psychopathology, life attitudes and neuropsychological performance among ritual users of Ayahuasca: a longitudinal study. PloS one. 2012; 7(8):e42421. doi: 10.1371/journal.pone.0042421. [PMID: 22905130]
  • Steven Maranz. An alternative paradigm for the role of antimalarial plants in Africa. TheScientificWorldJournal. 2012; 2012(?):978913. doi: 10.1100/2012/978913. [PMID: 22593717]
  • Rafael G Dos Santos, Marta Valle, José Carlos Bouso, Josep F Nomdedéu, José Rodríguez-Espinosa, Ethan H McIlhenny, Steven A Barker, Manel J Barbanoj, Jordi Riba. Autonomic, neuroendocrine, and immunological effects of ayahuasca: a comparative study with d-amphetamine. Journal of clinical psychopharmacology. 2011 Dec; 31(6):717-26. doi: 10.1097/jcp.0b013e31823607f6. [PMID: 22005052]
  • Ethan H McIlhenny, Jordi Riba, Manel J Barbanoj, Rick Strassman, Steven A Barker. Methodology for and the determination of the major constituents and metabolites of the Amazonian botanical medicine ayahuasca in human urine. Biomedical chromatography : BMC. 2011 Sep; 25(9):970-84. doi: 10.1002/bmc.1551. [PMID: 21058415]
  • Arturo A Vitale, Alicia B Pomilio, Carlos O Cañellas, Martín G Vitale, Eva Maria Putz, Jorge Ciprian-Ollivier. In vivo long-term kinetics of radiolabeled n,n-dimethyltryptamine and tryptamine. Journal of nuclear medicine : official publication, Society of Nuclear Medicine. 2011 Jun; 52(6):970-7. doi: 10.2967/jnumed.110.083246. [PMID: 21622895]
  • Molly Johannessen, Dominique Fontanilla, Timur Mavlyutov, Arnold E Ruoho, Meyer B Jackson. Antagonist action of progesterone at σ-receptors in the modulation of voltage-gated sodium channels. American journal of physiology. Cell physiology. 2011 Feb; 300(2):C328-37. doi: 10.1152/ajpcell.00383.2010. [PMID: 21084640]
  • Brian C Kelly. Legally tripping: a qualitative profile of Salvia divinorum use among young adults. Journal of psychoactive drugs. 2011 Jan; 43(1):46-54. doi: 10.1080/02791072.2011.566500. [PMID: 21615007]
  • Asmah Alias, Hazrina Hazni, Faridahanim Mohd Jaafar, Khalijah Awang, Nor Hadiani Ismail. Alkaloids from Fissistigma latifolium (Dunal) Merr. Molecules (Basel, Switzerland). 2010 Jun; 15(7):4583-8. doi: 10.3390/molecules15074583. [PMID: 20657378]
  • Gino A Kurian, Srilalitha Suryanarayanan, Archana Raman, Jose Padikkala. Antioxidant effects of ethyl acetate extract of Desmodium gangeticum root on myocardial ischemia reperfusion injury in rat hearts. Chinese medicine. 2010 Jan; 5(?):3. doi: 10.1186/1749-8546-5-3. [PMID: 20180993]
  • Nicholas V Cozzi, Anupama Gopalakrishnan, Lyndsey L Anderson, Joel T Feih, Alexander T Shulgin, Paul F Daley, Arnold E Ruoho. Dimethyltryptamine and other hallucinogenic tryptamines exhibit substrate behavior at the serotonin uptake transporter and the vesicle monoamine transporter. Journal of neural transmission (Vienna, Austria : 1996). 2009 Dec; 116(12):1591-9. doi: 10.1007/s00702-009-0308-8. [PMID: 19756361]
  • Kristian Björnstad, Peter Hultén, Olof Beck, Anders Helander. Bioanalytical and clinical evaluation of 103 suspected cases of intoxications with psychoactive plant materials. Clinical toxicology (Philadelphia, Pa.). 2009 Jul; 47(6):566-72. doi: 10.1080/15563650903037181. [PMID: 19586355]
  • Maiko Kawamura, Ruri Kikura-Hanajiri, Yukihiro Goda. [Simple and rapid screening for psychotropic natural products using Direct Analysis in Real Time (DART)-TOFMS]. Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan. 2009 Jun; 129(6):719-25. doi: 10.1248/yakushi.129.719. [PMID: 19483414]
  • Kristian Björnstad, Olof Beck, Anders Helander. A multi-component LC-MS/MS method for detection of ten plant-derived psychoactive substances in urine. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2009 Apr; 877(11-12):1162-8. doi: 10.1016/j.jchromb.2009.03.004. [PMID: 19332394]
  • Jochen Beyer, Olaf H Drummer, Hans H Maurer. Analysis of toxic alkaloids in body samples. Forensic science international. 2009 Mar; 185(1-3):1-9. doi: 10.1016/j.forsciint.2008.12.006. [PMID: 19147309]
  • Ana Paula Salum Pires, Carolina Dizioli Rodrigues De Oliveira, Sidnei Moura, Felipe Augusto Dörr, Wagner Abreu E Silva, Mauricio Yonamine. Gas chromatographic analysis of dimethyltryptamine and beta-carboline alkaloids in ayahuasca, an Amazonian psychoactive plant beverage. Phytochemical analysis : PCA. 2009 Mar; 20(2):149-53. doi: 10.1002/pca.1110. [PMID: 19140116]
  • Man-Juing Wang, Chih-Hsin Tsai, Wei-Ya Hsu, Ju-Tsung Liu, Cheng-Huang Lin. Optimization of separation and online sample concentration of N,N-dimethyltryptamine and related compounds using MEKC. Journal of separation science. 2009 Feb; 32(3):441-5. doi: 10.1002/jssc.200800492. [PMID: 19137528]
  • Cristiana Gambelunghe, Kyriaki Aroni, Riccardo Rossi, Luca Moretti, Mauro Bacci. Identification of N,N-dimethyltryptamine and beta-carbolines in psychotropic ayahuasca beverage. Biomedical chromatography : BMC. 2008 Oct; 22(10):1056-9. doi: 10.1002/bmc.1023. [PMID: 18506697]
  • Robin Rodd. Reassessing the cultural and psychopharmacological significance of Banisteriopsis caapi: preparation, classification and use among the Piaroa of Southern Venezuela. Journal of psychoactive drugs. 2008 Sep; 40(3):301-7. doi: 10.1080/02791072.2008.10400645. [PMID: 19004422]
  • Ning Gan, Xin Yang, Tian-Hua Li, Ping He. [Studies on constituents of rootsanel leaves from Desmodium blandum and their cytotoxic activity against growth of several tumor cells]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2008 Sep; 33(18):2077-80. doi: ". [PMID: 19160788]
  • Kenneth W Tupper. The globalization of ayahuasca: harm reduction or benefit maximization?. The International journal on drug policy. 2008 Aug; 19(4):297-303. doi: 10.1016/j.drugpo.2006.11.001. [PMID: 18638702]
  • Ede Frecska. Ayahuasca versus violence--a case report. Neuropsychopharmacologia Hungarica : a Magyar Pszichofarmakologiai Egyesulet lapja = official journal of the Hungarian Association of Psychopharmacology. 2008 May; 10(2):103-6. doi: ". [PMID: 18959142]
  • Manel J Barbanoj, Jordi Riba, S Clos, S Giménez, E Grasa, S Romero. Daytime Ayahuasca administration modulates REM and slow-wave sleep in healthy volunteers. Psychopharmacology. 2008 Feb; 196(2):315-26. doi: 10.1007/s00213-007-0963-0. [PMID: 18030450]
  • Nathaniel Bletter. A quantitative synthesis of the medicinal ethnobotany of the Malinké of Mali and the Asháninka of Peru, with a new theoretical framework. Journal of ethnobiology and ethnomedicine. 2007 Dec; 3(?):36. doi: 10.1186/1746-4269-3-36. [PMID: 18053260]
  • R G Santos, J Landeira-Fernandez, R J Strassman, V Motta, A P M Cruz. Effects of ayahuasca on psychometric measures of anxiety, panic-like and hopelessness in Santo Daime members. Journal of ethnopharmacology. 2007 Jul; 112(3):507-13. doi: 10.1016/j.jep.2007.04.012. [PMID: 17532158]
  • Peter Ondra, Katerina Zedníková, Ivo Válka. Detection and determination of abused hallucinogens in biological material. Neuro endocrinology letters. 2006 Dec; 27 Suppl 2(?):125-9. doi: NULL. [PMID: 17159796]
  • F Respondek, A Lallemand, V Julliand, Y Bonnaire. Urinary excretion of dietary contaminants in horses. Equine veterinary journal. Supplement. 2006 Aug; ?(36):664-7. doi: 10.1111/j.2042-3306.2006.tb05623.x. [PMID: 17402502]
  • Jordi Riba, Sergio Romero, Eva Grasa, Esther Mena, Ignasi Carrió, Manel J Barbanoj. Increased frontal and paralimbic activation following ayahuasca, the pan-Amazonian inebriant. Psychopharmacology. 2006 May; 186(1):93-8. doi: 10.1007/s00213-006-0358-7. [PMID: 16575552]
  • J C Callaway. Fast and slow metabolizers of Hoasca. Journal of psychoactive drugs. 2005 Jun; 37(2):157-61. doi: 10.1080/02791072.2005.10399797. [PMID: 16149329]
  • J C Callaway, Glacus S Brito, Edison S Neves. Phytochemical analyses of Banisteriopsis caapi and Psychotria viridis. Journal of psychoactive drugs. 2005 Jun; 37(2):145-50. doi: 10.1080/02791072.2005.10399795. [PMID: 16149327]
  • J C Callaway. Various alkaloid profiles in decoctions of Banisteriopsis caapi. Journal of psychoactive drugs. 2005 Jun; 37(2):151-5. doi: 10.1080/02791072.2005.10399796. [PMID: 16149328]
  • J Kärkkäinen, T Forsström, J Tornaeus, K Wähälä, P Kiuru, A Honkanen, U H Stenman, U Turpeinen, A Hesso. Potentially hallucinogenic 5-hydroxytryptamine receptor ligands bufotenine and dimethyltryptamine in blood and tissues. Scandinavian journal of clinical and laboratory investigation. 2005; 65(3):189-99. doi: 10.1080/00365510510013604. [PMID: 16095048]
  • Michael S Jacob, David E Presti. Endogenous psychoactive tryptamines reconsidered: an anxiolytic role for dimethyltryptamine. Medical hypotheses. 2005; 64(5):930-7. doi: 10.1016/j.mehy.2004.11.005. [PMID: 15780487]
  • María Del Pilar Nicasio, María Luisa Villarreal, Françoise Gillet, Lamine Bensaddek, Marc-André Fliniaux. Variation in the accumulation levels of N,N-dimethyltryptamine in micropropagated trees and in in vitro cultures of Mimosa tenuiflora. Natural product research. 2005 Jan; 19(1):61-7. doi: 10.1080/14786410410001658860. [PMID: 15700647]
  • 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]
  • Dennis J McKenna. Clinical investigations of the therapeutic potential of ayahuasca: rationale and regulatory challenges. Pharmacology & therapeutics. 2004 May; 102(2):111-29. doi: 10.1016/j.pharmthera.2004.03.002. [PMID: 15163593]
  • John H Halpern. Hallucinogens and dissociative agents naturally growing in the United States. Pharmacology & therapeutics. 2004 May; 102(2):131-8. doi: 10.1016/j.pharmthera.2004.03.003. [PMID: 15163594]
  • Jordi Riba, Peter Anderer, Francesc Jané, Bernd Saletu, Manel J Barbanoj. Effects of the South American psychoactive beverage ayahuasca on regional brain electrical activity in humans: a functional neuroimaging study using low-resolution electromagnetic tomography. Neuropsychobiology. 2004; 50(1):89-101. doi: 10.1159/000077946. [PMID: 15179026]
  • Jordi Riba, Marta Valle, Gloria Urbano, Mercedes Yritia, Adelaida Morte, Manel J Barbanoj. Human pharmacology of ayahuasca: subjective and cardiovascular effects, monoamine metabolite excretion, and pharmacokinetics. The Journal of pharmacology and experimental therapeutics. 2003 Jul; 306(1):73-83. doi: 10.1124/jpet.103.049882. [PMID: 12660312]
  • Mercedes Yritia, Jordi Riba, Jordi Ortuño, Ariel Ramirez, Araceli Castillo, Yolanda Alfaro, Rafael de la Torre, Manel J Barbanoj. Determination of N,N-dimethyltryptamine and beta-carboline alkaloids in human plasma following oral administration of Ayahuasca. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2002 Nov; 779(2):271-81. doi: 10.1016/s1570-0232(02)00397-5. [PMID: 12361741]
  • J Riba, A Rodríguez-Fornells, G Urbano, A Morte, R Antonijoan, M Montero, J C Callaway, M J Barbanoj. Subjective effects and tolerability of the South American psychoactive beverage Ayahuasca in healthy volunteers. Psychopharmacology. 2001 Feb; 154(1):85-95. doi: 10.1007/s002130000606. [PMID: 11292011]