Dimethyltryptamine (BioDeep_00000002081)

 

Secondary id: BioDeep_00001867768

human metabolite Endogenous blood metabolite Chemicals and Drugs natural product


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 (188.1313)
中文名称: N,N-二甲基色胺
谱图信息: 最多检出来源 Homo sapiens(plant) 14.71%

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

23 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; N,N-Dimethyltryptamine; N,N-Dimethyltryptamine



数据库引用编号

19 个数据库交叉引用编号

分类词条

相关代谢途径

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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)

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PharmGKB(0)

108 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 7 APAF1, BDNF, CYP2C19, CYP2D6, INMT, MTOR, POMC
Peripheral membrane protein 1 MTOR
Endosome membrane 1 SLC6A4
Endoplasmic reticulum membrane 5 CYP2C19, CYP2D6, MTOR, PNMT, SIGMAR1
Mitochondrion membrane 2 MAOA, PNMT
Nucleus 2 APAF1, MTOR
cytosol 8 APAF1, INMT, MAOA, MTOR, NNMT, PNMT, SIGMAR1, TCHH
dendrite 5 BDNF, HTR1A, HTR2A, HTR2C, MTOR
mitochondrial membrane 1 PNMT
phagocytic vesicle 1 MTOR
nucleoplasm 1 MTOR
Cell membrane 7 HTR1A, HTR2A, HTR2C, OPRD1, SIGMAR1, SLC38A5, SLC6A4
Cytoplasmic side 2 MAOA, MTOR
Cell projection, axon 1 HTR2A
Multi-pass membrane protein 8 HTR1A, HTR2A, HTR2C, OPRD1, PNMT, SLC38A5, SLC6A4, TMBIM4
Golgi apparatus membrane 2 MTOR, TMBIM4
Synapse 3 HTR1A, HTR2C, SLC6A4
dendritic shaft 1 HTR2A
glutamatergic synapse 2 HTR2A, SIGMAR1
Golgi apparatus 1 TMBIM4
Golgi membrane 2 MTOR, TMBIM4
growth cone 1 SIGMAR1
lysosomal membrane 1 MTOR
neuronal cell body 1 HTR2A
presynaptic membrane 3 HTR2A, OPRD1, SLC6A4
synaptic vesicle 1 BDNF
Lysosome 1 MTOR
Presynapse 2 HTR2A, SLC6A4
plasma membrane 7 CYP2C19, HTR1A, HTR2A, HTR2C, OPRD1, SLC38A5, SLC6A4
synaptic vesicle membrane 1 OPRD1
Membrane 10 APAF1, BDNF, CYP2D6, MAOA, MTOR, OPRD1, SIGMAR1, SLC38A5, SLC6A4, TMBIM4
axon 2 BDNF, HTR2A
caveola 1 HTR2A
extracellular exosome 1 APAF1
Lysosome membrane 1 MTOR
endoplasmic reticulum 3 CYP2D6, PNMT, SIGMAR1
extracellular space 3 BDNF, IL10, POMC
perinuclear region of cytoplasm 1 BDNF
mitochondrion 3 CYP2D6, MAOA, PNMT
protein-containing complex 1 APAF1
intracellular membrane-bounded organelle 3 CYP2C19, CYP2D6, PNMT
Microsome membrane 2 CYP2D6, MTOR
postsynaptic density 1 SIGMAR1
TORC1 complex 1 MTOR
TORC2 complex 1 MTOR
Secreted 3 BDNF, IL10, POMC
extracellular region 4 APAF1, BDNF, IL10, POMC
Mitochondrion outer membrane 2 MAOA, MTOR
Single-pass membrane protein 3 CYP2D6, MAOA, SIGMAR1
mitochondrial outer membrane 2 MAOA, MTOR
anchoring junction 1 SIGMAR1
cytoplasmic vesicle 2 HTR2A, SIGMAR1
postsynaptic membrane 2 HTR2A, SLC6A4
Membrane raft 1 SLC6A4
Cell junction, focal adhesion 1 SLC6A4
focal adhesion 1 SLC6A4
Nucleus, PML body 1 MTOR
PML body 1 MTOR
secretory granule 1 POMC
Nucleus inner membrane 1 SIGMAR1
Nucleus outer membrane 1 SIGMAR1
nuclear inner membrane 1 SIGMAR1
nuclear outer membrane 1 SIGMAR1
Cell projection, neuron projection 1 SLC6A4
neuron projection 2 OPRD1, SLC6A4
cytoskeleton 1 TCHH
nuclear envelope 2 MTOR, SIGMAR1
Nucleus envelope 1 SIGMAR1
Endomembrane system 2 MTOR, SLC6A4
Lipid droplet 1 SIGMAR1
Membrane, caveola 1 HTR2A
Cornified envelope 1 TCHH
[Isoform 1]: Endoplasmic reticulum membrane 1 PNMT
cell body fiber 1 HTR2A
Cell projection, dendrite 2 HTR1A, HTR2A
Golgi stack 1 TMBIM4
ficolin-1-rich granule lumen 1 APAF1
secretory granule lumen 2 APAF1, POMC
endoplasmic reticulum lumen 1 BDNF
axon terminus 1 OPRD1
postsynaptic density membrane 2 OPRD1, SIGMAR1
neuronal dense core vesicle 1 OPRD1
Single-pass type IV membrane protein 1 MAOA
apoptosome 1 APAF1
neurofilament 1 HTR2A
dendrite membrane 1 OPRD1
[Isoform 2]: Endoplasmic reticulum membrane 1 PNMT
Cytoplasmic vesicle, phagosome 1 MTOR
[Neurotrophic factor BDNF precursor form]: Secreted 1 BDNF
G protein-coupled serotonin receptor complex 2 HTR2A, HTR2C
serotonergic synapse 1 SLC6A4
spine apparatus 1 OPRD1


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]
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  • 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]
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  • 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]
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