6-Acetylmorphine (BioDeep_00000001413)

 

Secondary id: BioDeep_00000397507

human metabolite Endogenous


代谢物信息卡片


10-hydroxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10,15-tetraen-14-yl acetate

化学式: C19H21NO4 (327.14705060000006)
中文名称: 甲醇(6 -乙酰吗啡)
谱图信息: 最多检出来源 Escherichia coli(natural_products) 75%

分子结构信息

SMILES: CC(=O)OC1C=CC2C3CC4=C5C2(C1OC5=C(C=C4)O)CCN3C
InChI: InChI=1S/C19H21NO4/c1-10(21)23-15-6-4-12-13-9-11-3-5-14(22)17-16(11)19(12,18(15)24-17)7-8-20(13)2/h3-6,12-13,15,18,22H,7-9H2,1-2H3

描述信息

6-acetylmorphine belongs to the family of Morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic.
D002492 - Central Nervous System Depressants > D009294 - Narcotics > D053610 - Opiate Alkaloids

同义名列表

14 个代谢物同义名

10-hydroxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10,15-tetraen-14-yl acetate; 6-O-Monoacetylmorphine hydrochloride, (5alpha,6alpha)-isomer; 6-O-Monoacetylmorphine; O6 Monoacetylmorphine; a-Monoacetyl-morphine; 6-Monoacetylmorphine; 6-(0-Acetyl)morphine; Morphine 6-acetate; Morphine-6-acetate; 6-O-Acetylmorphine; Monoacetylmorphine; 6-acetylmorphine; 6-MAM CPD; 6-MAM



数据库引用编号

11 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

1 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(1)

PharmGKB(0)

1 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

  • Wei-Ru Chen, Po-Hsin Kong, Christoph Sauer, Huei-Wen Chen, Hsiang-Yu Chan, Da-Peng Yang, Yung-Cheng Jair, Hsin-Tung Liu, Tsang-Yaw Lin, Muh-Yong Yen, Yung-Feng Yen, Sheng-Huang Chang, Lan-Hui Li, Claire George, Ya-Chi Chang, Yi-Hsin Wu, Hsiao-Lin Hwa, Chia-Yang Chen, Jung-Hsuan Chen, Andrew T Kicman, Hans H Maurer, Pai-Shan Chen. A proposed approach to confirm heroin administration - Regional differences in heroin purity is a major factor. Regulatory toxicology and pharmacology : RTP. 2022 Feb; 128(?):105097. doi: 10.1016/j.yrtph.2021.105097. [PMID: 34902532]
  • Shanti Nassibou, Camille Richeval, Jean-François Wiart, Florian Hakim, Delphine Allorge, Jean-Michel Gaulier. In Heroin-Related Fatalities, Testing for 6-Acetylmorphine in Vitreous Humor Seems to Be of Higher Sensitivity than in Blood or Urine. Journal of analytical toxicology. 2021 Jan; 44(9):e9-e10. doi: 10.1093/jat/bkaa116. [PMID: 32860697]
  • Ahmed I Al-Asmari. Postmortem Liver and Kidney Tissue Concentrations of Heroin Biomarkers and Their Metabolites in Heroin-Related Fatalities*†. Journal of forensic sciences. 2020 Nov; 65(6):2087-2093. doi: 10.1111/1556-4029.14537. [PMID: 33460103]
  • Shi Qiao, Haishan Xu, Wenfang Zhang, Wei Yang, Danming Guo, Wei Wang, Weizhe Xu, Yongsuo Liu, Guoru Liu, Yujing Cui, Hongyan Yu, Qingyan Li. Identification of characteristic heroin metabolites in urine based on data-mining technology and multivariate statistics analysis combined with a targeted verification approach for distinguishing heroin abusers. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2020 Sep; 1152(?):122251. doi: 10.1016/j.jchromb.2020.122251. [PMID: 32673834]
  • Bernardino González-de-la-Presa, Rosa Fernández-Bonifacio, Esther Fernández-Galán, Lourdes Mares, Rebeca Muñoz, Marina Parra-Robert, Jordi To-Figueras. Evaluation of an immunoassay procedure to measure 6-monoacetylmorphine. Toxicology mechanisms and methods. 2020 Jul; 30(6):450-453. doi: 10.1080/15376516.2020.1760985. [PMID: 32375552]
  • Ahmed I Al-Asmari. Postmortem Fluid Concentrations of Heroin Biomarkers and Their Metabolites. Journal of forensic sciences. 2020 Mar; 65(2):570-579. doi: 10.1111/1556-4029.14200. [PMID: 31566759]
  • Yao-Te Yen, Yin-Jue Chang, Pin-Jung Lai, Chi-Lun Chang, Ting-Yueh Chen, San-Chong Chyueh. A Study of Opiate, Opiate Metabolites and Antihistamines in Urine after Consumption of Cold Syrups by LC-MS/MS. Molecules (Basel, Switzerland). 2020 Feb; 25(4):. doi: 10.3390/molecules25040972. [PMID: 32098143]
  • Luying Wang, Chunfang Ni, Hongliang Shen, Zhenhai Sheng, Chen Liang, Rong Wang, Yurong Zhang. Comparison of the Detection Windows of Heroin Metabolites in Human Urine Using Online SPE and LC-MS/MS: Importance of Morphine-3-Glucuronide. Journal of analytical toxicology. 2020 Jan; 44(1):22-28. doi: 10.1093/jat/bkz040. [PMID: 31095707]
  • Amy J Reisinger, Autumn C Miller, Lacey A Shaw, Jana L Champion, Marc A Neiswonger. Oral Cavity Fluid as an Investigative Approach for Qualitative and Quantitative Evaluations of Drugs in Postmortem Subjects. Journal of analytical toxicology. 2019 Jul; 43(6):444-451. doi: 10.1093/jat/bkz032. [PMID: 31062851]
  • Michael Böttcher, Stefan Lierheimer, Andreas Peschel, Olof Beck. Detection of heroin intake in patients in substitution treatment using oral fluid as specimen for drug testing. Drug and alcohol dependence. 2019 05; 198(?):136-139. doi: 10.1016/j.drugalcdep.2019.02.011. [PMID: 30927716]
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  • Fabian Picht, Olof Beck, Michael Böttcher. Evaluation of an on-site test device for the heroin metabolite 6-acetylmorphine in urine. Drug testing and analysis. 2019 Mar; 11(3):536-540. doi: 10.1002/dta.2559. [PMID: 30569568]
  • Kyungbo Kim, Jianzhuang Yao, Zhenyu Jin, Fang Zheng, Chang-Guo Zhan. Kinetic characterization of cholinesterases and a therapeutically valuable cocaine hydrolase for their catalytic activities against heroin and its metabolite 6-monoacetylmorphine. Chemico-biological interactions. 2018 Sep; 293(?):107-114. doi: 10.1016/j.cbi.2018.08.002. [PMID: 30080993]
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  • Cecilie Hasselø Thaulow, Åse Marit Leere Øiestad, Sidsel Rogde, Ritva Karinen, Gerd Wenche Brochmann, Jannike Mørch Andersen, Gudrun Høiseth, Marte Handal, Jørg Mørland, Marianne Arnestad, Elisabeth Leere Øiestad, Dag Helge Strand, Vigdis Vindenes. Metabolites of Heroin in Several Different Post-mortem Matrices. Journal of analytical toxicology. 2018 Jun; 42(5):311-320. doi: 10.1093/jat/bky002. [PMID: 29409037]
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  • Belin G Teklezgi, Annapurna Pamreddy, Sooraj Baijnath, Nirmala D Gopal, Tricia Naicker, Hendrik G Kruger, Thavendran Govender. Post heroin dose tissue distribution of 6-monoacetylmorphine (6-MAM) with MALDI imaging. Journal of molecular histology. 2017 Aug; 48(4):285-292. doi: 10.1007/s10735-017-9726-3. [PMID: 28550642]
  • Gudrun Høiseth, André Gottås, Thomas Berg, Marianne Arnestad, Per Steinar Halvorsen, Liliana C Bachs. Urinary Kinetics of Heroin Metabolites in Pigs Shortly After Intake. Journal of analytical toxicology. 2017 Jun; 41(5):451-454. doi: 10.1093/jat/bkx017. [PMID: 28335030]
  • Ashley D Ellis, Gerald McGwin, Gregory G Davis, Daniel W Dye. Identifying cases of heroin toxicity where 6-acetylmorphine (6-AM) is not detected by toxicological analyses. Forensic science, medicine, and pathology. 2016 Sep; 12(3):243-7. doi: 10.1007/s12024-016-9780-2. [PMID: 27114260]
  • Guohong Wang, Kim Huynh, Rekha Barhate, Jialin Liu, Phillip Tam, Warren Rodrigues, Cynthia Coulter, Christine Moore, James Soares. Validation of a New Recombinant Antibody Fragment (rFab)-Based Homogeneous Enzyme Immunoassay for the Highly Specific Detection of 6-Acetylmorphine in Urine. Journal of analytical toxicology. 2015 Nov; 39(9):726-33. doi: 10.1093/jat/bkv090. [PMID: 26311850]
  • Maria Andersson, Linda Björkhem-Bergman, Olof Beck. Possible mechanism for inhibition of morphine formation from 6-acetylmorphine after intake of street heroin. Forensic science international. 2015 Jul; 252(?):150-6. doi: 10.1016/j.forsciint.2015.05.002. [PMID: 26002801]
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  • Sten Carlsson, Robert Olsson, Irene Lindkvist, Olof Beck. Application of drug testing using exhaled breath for compliance monitoring of drug addicts in treatment. Scandinavian journal of clinical and laboratory investigation. 2015 Apr; 75(2):156-61. doi: 10.3109/00365513.2014.993336. [PMID: 25562730]
  • Renata Borriello, Anna Carfora, Paola Cassandro, Raffaella Petrella. Clinical and Forensic Diagnosis of Very Recent Heroin Intake by 6-acetylmorphine Immunoassay Test and LC-MS/MS Analysis in Urine and Blood. Annals of clinical and laboratory science. 2015; 45(4):414-8. doi: NULL. [PMID: 26275692]
  • Julie A Warren, Gerald Siefring, Nihmat Morjana. Development of application protocols of the Emit® II Plus 6-Acetylmorphine Assay on the ADVIA® 1800 and 2400 Chemistry Systems. Forensic science international. 2014 Nov; 244(?):122-7. doi: 10.1016/j.forsciint.2014.08.014. [PMID: 25233020]
  • Kristen J Mertz, Jennifer K Janssen, Karl E Williams. Underrepresentation of heroin involvement in unintentional drug overdose deaths in Allegheny County, PA. Journal of forensic sciences. 2014 Nov; 59(6):1583-5. doi: 10.1111/1556-4029.12541. [PMID: 25041514]
  • Julie Knight, Brandi L Puet, Anne DePriest, Rebecca Heltsley, Cheryl Hild, David L Black, Timothy Robert, Yale H Caplan, Edward J Cone. Prevalence of heroin markers in urine for pain management patients. Forensic science international. 2014 Oct; 243(?):79-83. doi: 10.1016/j.forsciint.2014.04.037. [PMID: 24858136]
  • Gregory Sarris, Damon Borg, Stephanie Liao, Richard Stripp. Validation of an EMIT® screening method to detect 6-acetylmorphine in oral fluid. Journal of analytical toxicology. 2014 Oct; 38(8):605-9. doi: 10.1093/jat/bku072. [PMID: 25217554]
  • Min Shen, Hang Chen, Ping Xiang. Determination of opiates in human fingernail--comparison to hair. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2014 Sep; 967(?):84-9. doi: 10.1016/j.jchromb.2014.07.014. [PMID: 25086417]
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  • Courtney Heideloff, Jessica Gabler, Chao Yuan, Lin Zhang, Sihe Wang. In vitro conversion of morphine to 6-acetylmorphine in urine samples during enzymatic hydrolysis. Clinical chemistry. 2014 Sep; 60(9):1234-5. doi: 10.1373/clinchem.2014.226720. [PMID: 25024270]
  • Oliver Lerch, Oliver Temme, Thomas Daldrup. Comprehensive automation of the solid phase extraction gas chromatographic mass spectrometric analysis (SPE-GC/MS) of opioids, cocaine, and metabolites from serum and other matrices. Analytical and bioanalytical chemistry. 2014 Jul; 406(18):4443-51. doi: 10.1007/s00216-014-7815-7. [PMID: 24788888]
  • Gudrun Høiseth, Bente Fjeld, Margrete Larsen Burns, Dag Helge Strand, Vigdis Vindenes. Long-term stability of morphine, codeine, and 6-acetylmorphine in real-life whole blood samples, stored at -20°C. Forensic science international. 2014 Jun; 239(?):6-10. doi: 10.1016/j.forsciint.2014.03.008. [PMID: 24709028]
  • Fabien Bévalot, Charline Bottinelli, Nathalie Cartiser, Laurent Fanton, Jérôme Guitton. Quantification of five compounds with heterogeneous physicochemical properties (morphine, 6-monoacetylmorphine, cyamemazine, meprobamate and caffeine) in 11 fluids and tissues, using automated solid-phase extraction and gas chromatography-tandem mass spectrometry. Journal of analytical toxicology. 2014 Jun; 38(5):256-64. doi: 10.1093/jat/bku029. [PMID: 24790060]
  • Thilo Beck, Christian Haasen, Uwe Verthein, Stephan Walcher, Christoph Schuler, Markus Backmund, Christian Ruckes, Jens Reimer. Maintenance treatment for opioid dependence with slow-release oral morphine: a randomized cross-over, non-inferiority study versus methadone. Addiction (Abingdon, England). 2014 Apr; 109(4):617-26. doi: 10.1111/add.12440. [PMID: 24304412]
  • Maria Andersson, Nikolai Stephanson, Inger Ohman, Tommy Terzuoli, Jonatan D Lindh, Olof Beck. Direct and efficient liquid chromatographic-tandem mass spectrometric method for opiates in urine drug testing - importance of 6-acetylmorphine and reduction of analytes. Drug testing and analysis. 2014 Apr; 6(4):317-24. doi: 10.1002/dta.1486. [PMID: 23720205]
  • Gary R Matyas, Kenner C Rice, Kejun Cheng, Fuying Li, Joshua F G Antoline, Malliga R Iyer, Arthur E Jacobson, Alexander V Mayorov, Zoltan Beck, Oscar B Torres, Carl R Alving. Facial recognition of heroin vaccine opiates: type 1 cross-reactivities of antibodies induced by hydrolytically stable haptenic surrogates of heroin, 6-acetylmorphine, and morphine. Vaccine. 2014 Mar; 32(13):1473-9. doi: 10.1016/j.vaccine.2014.01.028. [PMID: 24486371]
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