Cocaine (BioDeep_00000002162)

 

Secondary id: BioDeep_00000406209

human metabolite blood metabolite Chemicals and Drugs PANOMIX_OTCML-2023 natural product


代谢物信息卡片


[1R-(exo,exo)]-3-(Benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid, methyl ester

化学式: C17H21NO4 (303.1471)
中文名称: 可卡因, 古卡因
谱图信息: 最多检出来源 Homo sapiens(blood) 29.49%

Reviewed

Last reviewed on 2024-08-21.

Cite this Page

Cocaine. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/cocaine (retrieved 2024-12-22) (BioDeep RN: BioDeep_00000002162). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CN1C2CCC1C(C(C2)OC(=O)C3=CC=CC=C3)C(=O)OC
InChI: InChI=1S/C17H21NO4/c1-18-12-8-9-13(18)15(17(20)21-2)14(10-12)22-16(19)11-6-4-3-5-7-11/h3-7,12-15H,8-10H2,1-2H3

描述信息

Cocaine, also known as coke, is an alkaloid ester obtained from the leaves of the coca plant (PMID: 20857618). It is a weakly alkaline compound and can therefore combine with acidic compounds to form white salts or powders (which is how it is typically sold and consumed). Cocaine is a strong stimulant that is most frequently used as a recreational drug. It is the second most frequently used illegal drug globally, after cannabis. The stimulant and hunger suppression properties of cocaine and coca leaf extracts have been known for thousands of years by indigenous groups in central and South America. The coca leaf was, and still is, chewed almost universally by some indigenous communities. Cocaine acts by inhibiting the reuptake of serotonin, norepinephrine, and dopamine. This inhibition leads to a number of mental and physical effects that may include loss of contact with reality, an intense feeling of happiness, periods of agitation, along with a rapid heart rate, sweating, and dialated pupils. Cocaine is highly addictive due to its effect on the reward pathway in the brain (PMID: 22856655). Cocaine addiction occurs through overexpression of the FosB protein in the nucleus accumbens of the brain, which results in altered transcriptional regulation in neurons within the nucleus accumbens. Cocaine is harmful. Its use increases the risk of stroke, myocardial infarction, lung problems (in those who smoke it), blood infections, and sudden cardiac death. Medically, cocaine is infrequently used as a local anesthetic and vasoconstrictor to cause loss of feeling or numbness before certain medical procedures (e.g., biopsy, stitches, wound cleaning) (PMID: 28956316). Topical cocaine is occasionally used as a local numbing agent to help with painful procedures in the mouth or nose. Cocaine is now predominantly used for nasal and lacrimal duct surgery. It works quickly to numb certain areas of the body (e.g., nose, ear, or throat) about 1-2 minutes after application. Cocaine functions as an anesthesia by reversibly binding to and inactivating sodium channels, thereby inhibiting excitation of nerve endings or by blocking conduction in peripheral nerves. Cocaine and its major metabolites are only found in individuals that have used or taken this drug.
D018377 - Neurotransmitter Agents > D014179 - Neurotransmitter Uptake Inhibitors > D018765 - Dopamine Uptake Inhibitors
D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D000777 - Anesthetics
R - Respiratory system > R02 - Throat preparations > R02A - Throat preparations > R02AD - Anesthetics, local
S - Sensory organs > S02 - Otologicals > S02D - Other otologicals > S02DA - Analgesics and anesthetics
N - Nervous system > N01 - Anesthetics > N01B - Anesthetics, local > N01BC - Esters of benzoic acid
S - Sensory organs > S01 - Ophthalmologicals > S01H - Local anesthetics > S01HA - Local anesthetics
D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents
D002317 - Cardiovascular Agents > D014662 - Vasoconstrictor Agents
C78272 - Agent Affecting Nervous System > C47795 - CNS Stimulant
D018377 - Neurotransmitter Agents > D015259 - Dopamine Agents
CONFIDENCE standard compound; EAWAG_UCHEM_ID 2817
EAWAG_UCHEM_ID 2817; CONFIDENCE standard compound
CONFIDENCE standard compound; INTERNAL_ID 1619
D049990 - Membrane Transport Modulators

同义名列表

33 个代谢物同义名

[1R-(exo,exo)]-3-(Benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid, methyl ester; [1R-(exo,exo)]-3-(Benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate, methyl ester; Methyl [1R-(exo,exo)]-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid; 2-Methyl-3beta-hydroxy-1alphah,5alphah-tropane-2beta-carboxylic acid benzoic acid (ester); Methyl [1R-(exo,exo)]-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate; methyl (1R,2R,3S,5S)-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate; 2-Methyl-3b-hydroxy-1alphah,5alphah-tropane-2b-carboxylic acid benzoic acid (ester); 2-Methyl-3β-hydroxy-1alphah,5alphah-tropane-2β-carboxylic acid benzoic acid (ester); 2-Methyl-3beta-hydroxy-1alphah,5alphah-tropane-2beta-carboxylate benzoate (ester); 2-Methyl-3b-hydroxy-1alphah,5alphah-tropane-2b-carboxylate benzoate (ester); 2-Methyl-3β-hydroxy-1alphah,5alphah-tropane-2β-carboxylate benzoate (ester); methyl 3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate; Hydrochloride, cocaine; Methyl benzoylecgonine; Benzoylmethylecgonine; Cocaine hydrochloride; Pseudococaine; HCL, Cocaine; (-)-Cocaine; beta-Cocain; (−)-cocaine; cocaine Hcl; Neurocaine; L-Cocaine; Β-cocain; b-Cocain; Cocainum; L-Cocain; cocaine; Cocaina; Cocain; Kokain; Cocaine



数据库引用编号

42 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(3)

BioCyc(0)

PlantCyc(0)

代谢反应

39 个相关的代谢反应过程信息。

Reactome(39)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

82 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 3 AXIN2, DBH, EGR1
Peripheral membrane protein 1 PRTN3
Endoplasmic reticulum membrane 1 SLC7A11
Nucleus 3 AXIN2, EGR1, GRM1
cytosol 4 AXIN2, COMT, LEP, PRTN3
dendrite 5 COMT, GRM1, GRM2, HTR2C, SLC18A2
centrosome 2 AXIN2, SLC18A2
nucleoplasm 1 EGR1
Cell membrane 8 COMT, GPRC5A, GRM1, GRM2, HTR2C, PRTN3, SLC1A2, SLC7A11
Cell projection, axon 1 SLC18A2
Cytoplasmic granule 1 PRTN3
Multi-pass membrane protein 8 CACNA1I, GPRC5A, GRM1, GRM2, HTR2C, SLC18A2, SLC1A2, SLC7A11
Synapse 6 COMT, CRH, DBH, GRM2, HTR2C, TAC1
cell surface 2 SLC1A2, SLC7A11
glutamatergic synapse 3 GRM1, GRM2, SLC1A2
Golgi apparatus 1 NPY
Golgi membrane 1 INS
neuronal cell body 1 TAC1
presynaptic membrane 2 GRM2, SLC1A2
synaptic vesicle 1 SLC18A2
plasma membrane 13 AXIN2, BCHE, CACNA1I, COMT, GCG, GPRC5A, GRM1, GRM2, HTR2C, PRTN3, SLC18A2, SLC1A2, SLC7A11
synaptic vesicle membrane 1 SLC18A2
terminal bouton 1 SLC18A2
Membrane 7 CACNA1I, COMT, DBH, GRM2, SLC18A2, SLC1A2, SLC7A11
axon 4 COMT, GRM2, SLC18A2, TAC1
basolateral plasma membrane 1 SLC7A11
extracellular exosome 3 COMT, GPRC5A, PRTN3
endoplasmic reticulum 1 DBH
extracellular space 9 BCHE, CRH, DBH, GCG, INS, LEP, NPY, PRTN3, TAC1
Schaffer collateral - CA1 synapse 1 GRM1
intracellular membrane-bounded organelle 5 COMT, DBH, GPRC5A, PRTN3, SLC18A2
Single-pass type I membrane protein 1 SLC7A11
Secreted 8 BCHE, CRH, DBH, GCG, INS, LEP, NPY, PRTN3
extracellular region 9 BCHE, CRH, DBH, GCG, INS, LEP, NPY, PRTN3, TAC1
Extracellular side 2 COMT, PRTN3
centriolar satellite 1 DBH
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle membrane 1 SLC18A2
varicosity 1 CRH
neuronal dense core vesicle lumen 1 CRH
perikaryon 1 CRH
beta-catenin destruction complex 1 AXIN2
nucleolus 1 GPRC5A
apical part of cell 1 SLC7A11
Single-pass type II membrane protein 2 COMT, DBH
vesicle 2 GPRC5A, SLC1A2
postsynaptic membrane 1 GRM2
Membrane raft 2 PRTN3, SLC1A2
axolemma 1 SLC1A2
GABA-ergic synapse 1 NPY
lateral plasma membrane 1 SLC7A11
Postsynaptic cell membrane 1 GRM1
receptor complex 1 GPRC5A
chromatin 1 EGR1
brush border membrane 1 SLC7A11
blood microparticle 1 BCHE
Basolateral cell membrane 1 SLC7A11
Cell projection, microvillus membrane 1 SLC7A11
microvillus membrane 1 SLC7A11
endosome lumen 1 INS
Cytoplasmic vesicle membrane 1 GPRC5A
Cell projection, dendrite 2 GRM2, SLC18A2
cell body 1 SLC1A2
plasma membrane raft 1 PRTN3
secretory granule lumen 3 DBH, GCG, INS
secretory granule membrane 2 DBH, SLC18A2
Golgi lumen 1 INS
endoplasmic reticulum lumen 3 BCHE, GCG, INS
voltage-gated calcium channel complex 1 CACNA1I
transport vesicle 1 INS
azurophil granule lumen 1 PRTN3
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
postsynaptic density membrane 1 GRM1
neuronal dense core vesicle 1 NPY
nuclear envelope lumen 1 BCHE
dopaminergic synapse 1 SLC18A2
Cytoplasmic vesicle, secretory vesicle membrane 2 DBH, SLC18A2
astrocyte projection 3 GRM2, SLC1A2, SLC7A11
Cytoplasmic vesicle, secretory vesicle, chromaffin granule lumen 1 DBH
chromaffin granule lumen 1 DBH
[Glucagon-like peptide 1]: Secreted 1 GCG
Cytoplasmic vesicle, secretory vesicle, neuronal dense core vesicle 1 NPY
transport vesicle membrane 1 DBH
neuron projection terminus 1 SLC1A2
[Soluble dopamine beta-hydroxylase]: Cytoplasmic vesicle, secretory vesicle lumen 1 DBH
Cytoplasmic vesicle, secretory vesicle, chromaffin granule membrane 1 DBH
chromaffin granule membrane 1 DBH
clathrin-sculpted monoamine transport vesicle membrane 1 SLC18A2
[Isoform Soluble]: Cytoplasm 1 COMT
[Isoform Membrane-bound]: Cell membrane 1 COMT
G protein-coupled serotonin receptor complex 1 HTR2C
membrane protein complex 1 SLC1A2
G protein-coupled receptor dimeric complex 1 GRM1
G protein-coupled receptor homodimeric complex 1 GRM1


文献列表

  • Ying Wang, Ke Li, Weijian Shen, Xingxu Huang, Lina Wu. Point-of-care testing of methamphetamine and cocaine utilizing wearable sensors. Analytical biochemistry. 2024 Aug; 691(?):115526. doi: 10.1016/j.ab.2024.115526. [PMID: 38621604]
  • Moeka Nomura, Shuheng Wen, Kana Unuma, Takeshi Funakoshi, Toshihiko Aki, Koichi Uemura. Increased fatty acid synthesis and disturbed lipid metabolism in Neuro2a cells after repeated cocaine exposure: A preliminary study. Biochemical and biophysical research communications. 2024 Feb; 695(?):149438. doi: 10.1016/j.bbrc.2023.149438. [PMID: 38160532]
  • Pamela Cabarcos-Fernández, Ivan Álvarez-Freire, Nelida Cristina Rubio, Ana Maria Bermejo-Barrera, Antonio Moreda-Piñeiro, Ines Sánchez-Sellero, Maria Jesus Tabernero-Duque. Evaluation of an Oral Fluid Collection Device and a Solid-Phase Extraction Method for the Determination of Coca Leaf Alkaloids by Gas Chromatography-Mass Spectrometry. Molecules (Basel, Switzerland). 2024 Jan; 29(3):. doi: 10.3390/molecules29030592. [PMID: 38338336]
  • Marina Bellot, Fernando Soria, Raul López-Arnau, Cristian Gómez-Canela, Carlos Barata. Daphnia magna an emerging environmental model of neuro and cardiotoxicity of illicit drugs. Environmental pollution (Barking, Essex : 1987). 2024 Jan; 344(?):123355. doi: 10.1016/j.envpol.2024.123355. [PMID: 38228265]
  • Rong Chen. Cholesterol modulation of interactions between psychostimulants and dopamine transporters. Advances in pharmacology (San Diego, Calif.). 2024; 99(?):35-59. doi: 10.1016/bs.apha.2023.09.004. [PMID: 38467486]
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  • Nikolaos Rousis, Richard Bade, Iván Romero-Sánchez, Jochen F Mueller, Nikolaos S Thomaidis, Kevin V Thomas, Emma Gracia-Lor. Festivals following the easing of COVID-19 restrictions: Prevalence of new psychoactive substances and illicit drugs. Environment international. 2023 Jun; 178(?):108075. doi: 10.1016/j.envint.2023.108075. [PMID: 37399770]
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  • Marco Carnevale Miino, Tomáš Macsek, Taťána Halešová, Tomáš Chorazy, Petr Hlavínek. Pharmaceutical and narcotics monitoring in Brno wastewater system and estimation of seasonal effect on the abuse of illicit drugs by a wastewater-based epidemiology approach. The Science of the total environment. 2023 May; ?(?):164386. doi: 10.1016/j.scitotenv.2023.164386. [PMID: 37263433]
  • Jesús Herrera-Imbroda, María Flores-López, Nerea Requena-Ocaña, Pedro Araos, Jessica Ropero, Nuria García-Marchena, Antonio Bordallo, Juan Suarez, Francisco Javier Pavón-Morón, Antonia Serrano, Fermín Mayoral, Fernando Rodríguez de Fonseca. Antipsychotic Medication Influences the Discriminative Value of Acylethanolamides as Biomarkers of Substance Use Disorder. International journal of molecular sciences. 2023 May; 24(11):. doi: 10.3390/ijms24119371. [PMID: 37298321]
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  • Taja Verovšek, Ariana Šuštarič, Maria Laimou-Geraniou, Ivona Krizman-Matasic, Helena Prosen, Tina Eleršek, Vlasta Kramarič Zidar, Vesna Mislej, Boštjan Mišmaš, Marjeta Stražar, Marjetka Levstek, Bernardka Cimrmančič, Simon Lukšič, Nataša Uranjek, Tjaša Kozlovič-Bobič, Tina Kosjek, David Kocman, David Heath, Ester Heath. Removal of residues of psychoactive substances during wastewater treatment, their occurrence in receiving river waters and environmental risk assessment. The Science of the total environment. 2023 Mar; 866(?):161257. doi: 10.1016/j.scitotenv.2022.161257. [PMID: 36608822]
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  • Andrés Angel Calderon-Garcia, Maria Perez-Fernandez, Daniel Curto-Aguilera, Ivan Rodriguez-Martin, Mercedes Sánchez-Barba, Veronica Gonzalez-Nunez. Exposure to Morphine and Cocaine Modify the Transcriptomic Landscape in Zebrafish Embryos. Neuroscience. 2022 12; 507(?):14-27. doi: 10.1016/j.neuroscience.2022.10.017. [PMID: 36404518]
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