Bufotenin (BioDeep_00000001441)

 

Secondary id: BioDeep_00001868113

human metabolite Endogenous


代谢物信息卡片


3-(2-(Dimethylamino)ethyl)-1H-indol-5-ol (acd/name 4.0)

化学式: C12H16N2O (204.1263)
中文名称: N,N-二甲腦激胺
谱图信息: 最多检出来源 Homo sapiens(feces) 36.91%

分子结构信息

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

描述信息

A hallucinogenic serotonin analog found in frog or toad skins, mushrooms, higher plants, and mammals, especially in the brains, plasma, and urine of schizophrenics. Bufotenin has been used as a tool in CNS studies and misused as a psychedelic. Bufotenin (5-OH-DMT), is a tryptamine related to the neurotransmitter serotonin. It is an alkaloid found in the skin of some species of toads; in mushrooms, higher plants, and mammals. Bufotenin is a chemical constituent in the venom and eggs of several species of toads belonging to the Bufo genus, but most notably in the Colorado River toad (Bufo alvarius) as it is the only toad species in which bufotenin is present in large enough quantities for a psychoactive effect. Extracts of toad venom, containing bufotenin and other bioactive compounds, have been used in some traditional medicines (probably derived from Bufo gargarizans), which has been used medicinally for centuries in China. Bufotenin is a constituent of the seeds of Anadenanthera colubrina and Anadenanthera peregrina trees. Anadenanthera seeds have been used as an ingredient in psychedelic snuff preparations by indigenous cultures of the Caribbean, Central and South America.
D018377 - Neurotransmitter Agents > D018490 - Serotonin Agents > D012702 - Serotonin Antagonists
D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D006213 - Hallucinogens
D009676 - Noxae > D011042 - Poisons > D014688 - Venoms

同义名列表

33 个代谢物同义名

3-(2-(Dimethylamino)ethyl)-1H-indol-5-ol (acd/name 4.0); {3-[(beta-dimethylamino)ethyl]-5-hydroxyindole}; 3-[beta-(Dimethylamino)ethyl]-5-hydroxyindole; 1H-indol-5-Ol, {3-[2-(dimethylamino)ethyl]-}; 3-(beta-Dimethylaminoethyl)-5-hydroxyindole; 3-[Β-(dimethylamino)ethyl]-5-hydroxyindole; 3-[b-(Dimethylamino)ethyl]-5-hydroxyindole; indol-5-Ol, {3-[2-(dimethylamino)ethyl]-}; 3-[2-(Dimethylamino)ethyl]-1H-indol-5-ol; {3-[(2-dimethylamino)ethyl]-5-indolol}; 3-[2-(Dimethylamino)ethyl]-indol-5-ol; 3-[2-(Dimethylamino)ethyl]-5-indolol; 3-[2-(Dimethylamino)ethyl]indol-5-ol; 3-(2-Dimethylaminoethyl)indol-5-ol; 3-(2-Dimethylaminoethyl)-5-indolol; 5-Hydroxy-N, N-dimethyltryptamine; N,N Dimethyl 5 hydroxytryptamine; 5-Hydroxy-N,N-dimethyltryptamine; 5 Hydroxy N,N dimethyltryptamine; N,N-Dimethyl-5-hydroxytryptamine; N, N-Dimethylserotonin; N,N-Dimethylserotonin; Dimethylserotonin; Cinobufotenine; Bufotenine; bufotenin; Mappine; Mapine; Cohoba; DM5-HT; Mappin; Bufotenine; Bufotenine



数据库引用编号

18 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

8 个相关的代谢反应过程信息。

Reactome(8)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

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 9 ANXA5, AOC3, BCL2, CASP3, CYP2D6, HTR4, INMT, MYD88, TLR4
Peripheral membrane protein 1 ANXA5
Endosome membrane 3 HTR4, MYD88, TLR4
Endoplasmic reticulum membrane 3 BCL2, CYP2D6, PLN
Mitochondrion membrane 2 MAOA, PLN
Nucleus 3 BCL2, CASP3, MYD88
cytosol 6 ANXA5, BCL2, CASP3, INMT, MAOA, MYD88
dendrite 5 HTR1B, HTR1D, HTR2A, HTR2C, HTR4
mitochondrial membrane 1 PLN
nucleoplasm 1 CASP3
Cell membrane 9 AOC3, HTR1B, HTR1D, HTR2A, HTR2C, HTR3A, HTR4, TLR4, TNF
Cytoplasmic side 1 MAOA
Cleavage furrow 1 HTR3A
Cell projection, axon 1 HTR2A
Multi-pass membrane protein 6 HTR1B, HTR1D, HTR2A, HTR2C, HTR3A, HTR4
Synapse 4 HTR1D, HTR2C, HTR3A, HTR4
cell surface 4 AOC3, MYD88, TLR4, TNF
dendritic shaft 1 HTR2A
glutamatergic synapse 3 CASP3, HTR2A, HTR4
Golgi apparatus 1 AOC3
lysosomal membrane 1 CP
mitochondrial inner membrane 1 BCS1L
neuronal cell body 3 CASP3, HTR2A, TNF
postsynapse 2 HTR3A, HTR4
presynaptic membrane 2 HTR1B, HTR2A
sarcolemma 1 ANXA5
Presynapse 1 HTR2A
endosome 1 HTR4
plasma membrane 12 AOC3, CP, HTR1B, HTR1D, HTR2A, HTR2C, HTR3A, HTR4, MYD88, TLR4, TNF, TPSG1
Membrane 11 ANXA5, AOC3, BCL2, BCS1L, CYP2D6, HTR3A, HTR4, MAOA, PLN, TLR4, TPSG1
axon 1 HTR2A
caveola 1 HTR2A
extracellular exosome 2 ANXA5, CP
endoplasmic reticulum 5 AOC3, BCL2, CYP2D6, HTR1B, PLN
extracellular space 3 CP, TNF, TPSG1
perinuclear region of cytoplasm 2 PLN, TLR4
mitochondrion 5 BCL2, BCS1L, CYP2D6, MAOA, PLN
protein-containing complex 2 BCL2, MYD88
intracellular membrane-bounded organelle 1 CYP2D6
Microsome membrane 1 CYP2D6
postsynaptic density 1 CASP3
Single-pass type I membrane protein 1 TLR4
Secreted 1 CP
extracellular region 3 ANXA5, CP, TNF
Mitochondrion outer membrane 2 BCL2, MAOA
Single-pass membrane protein 6 BCL2, BCS1L, CYP2D6, MAOA, PLN, TPSG1
mitochondrial outer membrane 2 BCL2, MAOA
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
external side of plasma membrane 3 ANXA5, TLR4, TNF
cytoplasmic vesicle 1 HTR2A
Early endosome 2 AOC3, TLR4
recycling endosome 1 TNF
Single-pass type II membrane protein 2 AOC3, TNF
postsynaptic membrane 2 HTR2A, HTR3A
Mitochondrion inner membrane 1 BCS1L
Membrane raft 1 TNF
pore complex 1 BCL2
focal adhesion 1 ANXA5
sarcoplasmic reticulum 1 PLN
collagen-containing extracellular matrix 1 ANXA5
Postsynaptic cell membrane 1 HTR3A
Cell projection, ruffle 1 TLR4
ruffle 1 TLR4
receptor complex 1 TLR4
Zymogen granule membrane 1 ANXA5
neuron projection 1 HTR3A
phagocytic cup 2 TLR4, TNF
blood microparticle 1 CP
serotonin-activated cation-selective channel complex 1 HTR3A
transmembrane transporter complex 1 HTR3A
microvillus 1 AOC3
Membrane, caveola 1 HTR2A
cell body fiber 1 HTR2A
Cell projection, dendrite 1 HTR2A
myelin sheath 1 BCL2
lipopolysaccharide receptor complex 1 TLR4
endoplasmic reticulum lumen 1 CP
Sarcoplasmic reticulum membrane 1 PLN
Single-pass type IV membrane protein 1 MAOA
neurofilament 1 HTR2A
calyx of Held 1 HTR1B
vesicle membrane 1 ANXA5
respiratory chain complex III 1 BCS1L
extrinsic component of cytoplasmic side of plasma membrane 1 MYD88
death-inducing signaling complex 1 CASP3
extrinsic component of plasma membrane 1 MYD88
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
endothelial microparticle 1 ANXA5
BAD-BCL-2 complex 1 BCL2
calcium ion-transporting ATPase complex 1 PLN
G protein-coupled serotonin receptor complex 3 HTR1B, HTR2A, HTR2C
serotonergic synapse 1 HTR1B
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Gustavo Almeida E Silva, Vinícius Galvão Wakui, Lucília Kato, Cássia A Marquezin. Spectroscopic behavior of bufotenine and bufotenine N-oxide: Solvent and pH effects and interaction with biomembrane models. Biochimica et biophysica acta. Biomembranes. 2024 Apr; 1866(4):184304. doi: 10.1016/j.bbamem.2024.184304. [PMID: 38408695]
  • Lei-Qi Liu, Jing-Ze Chen, Wu-Sheng Fu, Cui-Ying Tang. [Determination of amanita peptide and tryptamine toxins in wild mushrooms by high performance liquid chromatography-tandem mass spectrometry]. Se pu = Chinese journal of chromatography. 2023 Nov; 41(11):976-985. doi: 10.3724/sp.j.1123.2023.07013. [PMID: 37968816]
  • 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]
  • Merline Delices, Jessica de Araujo Isaias Muller, Karuppusamy Arunachalam, Domingos Tabajara de Oliveira Martins. Anadenanthera colubrina (Vell) Brenan: Ethnobotanical, phytochemical, pharmacological and toxicological aspects. Journal of ethnopharmacology. 2023 Jan; 300(?):115745. doi: 10.1016/j.jep.2022.115745. [PMID: 36162548]
  • Lili Shen, Xiang Lv, Xin Yang, Shuangbing Deng, Lina Liu, Jing Zhou, Yuyu Zhu, Hongyue Ma. Bufotenines-loaded liposome exerts anti-inflammatory, analgesic effects and reduce gastrointestinal toxicity through altering lipid and bufotenines metabolism. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2022 Sep; 153(?):113492. doi: 10.1016/j.biopha.2022.113492. [PMID: 36076586]
  • Camila Mosca Barboza, Daniel Carvalho Pimenta, Hugo Vigerelli, Andréa de Cássia Rodrigues da Silva, Jaíne Gonçalves Garcia, Raphaela Mello Zamudio, Juliana Galera Castilho, Jarbas Alves Montanha, Paulo Michel Roehe, Helena Beatriz de Carvalho Ruthner Batista. In vitro effects of bufotenine against RNA and DNA viruses. Brazilian journal of microbiology : [publication of the Brazilian Society for Microbiology]. 2021 Dec; 52(4):2475-2482. doi: 10.1007/s42770-021-00612-1. [PMID: 34562234]
  • Jiaojiao Wang, Dihui Xu, Lili Shen, Jing Zhou, Xiang Lv, Hongyue Ma, Nianguang Li, Qinan Wu, Jinao Duan. Anti-inflammatory and analgesic actions of bufotenine through inhibiting lipid metabolism pathway. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2021 Aug; 140(?):111749. doi: 10.1016/j.biopha.2021.111749. [PMID: 34058437]
  • 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]
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  • 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]
  • Hugo Vigerelli, Juliana Mozer Sciani, Maria Andrea Camarano Eula, Luciana Almeida Sato, Marta M Antoniazzi, Carlos Jared, Daniel C Pimenta. Biological Effects and Biodistribution of Bufotenine on Mice. BioMed research international. 2018; 2018(?):1032638. doi: 10.1155/2018/1032638. [PMID: 29955598]
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