Heroin (BioDeep_00000001475)
Chemicals and Drugs
代谢物信息卡片
Diacetylmorphine (Heroin)
化学式: C21H23NO5 (369.15761480000003)
中文名称: 海洛因
谱图信息:
最多检出来源 Viridiplantae(plant) 87.5%
分子结构信息
SMILES: CC(=O)OC1C=CC2C3CC4=C5C2(C1OC5=C(C=C4)OC(=O)C)CCN3C
InChI: InChI=1S/C21H23NO5/c1-11(23)25-16-6-4-13-10-15-14-5-7-17(26-12(2)24)20-21(14,8-9-22(15)3)18(13)19(16)27-20/h4-7,14-15,17,20H,8-10H2,1-3H3/t14-,15+,17-,20-,21-/m0/s1
描述信息
A morphinane alkaloid that is morphine bearing two acetyl substituents on the O-3 and O-6 positions. As with other opioids, heroin is used as both an analgesic and a recreational drug. Frequent and regular administration is associated with tolerance and physical dependence, which may develop into addiction. Its use includes treatment for acute pain, such as in severe physical trauma, myocardial infarction, post-surgical pain, and chronic pain, including end-stage cancer and other terminal illnesses.
N - Nervous system > N07 - Other nervous system drugs > N07B - Drugs used in addictive disorders > N07BC - Drugs used in opioid dependence
D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D009294 - Narcotics
D002492 - Central Nervous System Depressants > D009294 - Narcotics > D053610 - Opiate Alkaloids
C78272 - Agent Affecting Nervous System > C67413 - Opioid Receptor Agonist > C1657 - Opiate
D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents
D002491 - Central Nervous System Agents > D000700 - Analgesics
CONFIDENCE standard compound; INTERNAL_ID 1533
同义名列表
4 个代谢物同义名
Heroin; Diacetylmorphine (Heroin); Diamorphine (heroin); Acetomorphin
数据库引用编号
20 个数据库交叉引用编号
- ChEBI: CHEBI:27808
- KEGG: C06534
- KEGGdrug: D07286
- PubChem: 5462328
- PubChem: 3592
- Metlin: METLIN1987
- DrugBank: DB01452
- ChEMBL: CHEMBL459324
- MeSH: Heroin
- CAS: 561-27-3
- MoNA: AU153305
- MoNA: AU153304
- MoNA: AU153303
- MoNA: AU153302
- MoNA: AU153301
- PMhub: MS000000595
- MetaboLights: MTBLC27808
- PubChem: 8764
- 3DMET: B02057
- NIKKAJI: J6.494G
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
2 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PharmGKB(0)
0 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
- 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.
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The Science of the total environment.
2023 May; ?(?):164386. doi:
10.1016/j.scitotenv.2023.164386. [PMID: 37263433] - Fataneh Hashem-Dabaghian, Saeed Kianbakht. A randomized controlled trial on the seeds of Sophora alopecuroides var. alopecuroides for the treatment of acute heroin withdrawal syndrome.
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2023 Feb; 51(?):101740. doi:
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Toxicology.
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Journal of analytical toxicology.
2019 Jul; 43(6):444-451. doi:
10.1093/jat/bkz032. [PMID: 31062851] - Rong-Jun Zhang, Xiao-Rong Hou, Xing-Hui Cai, Xiao-Ge Song, Sheng-Bing Wu, Meng-Jie Zhao. [Influence of acupuncture plus moxibustion on changes of synaptic structure and expression of synaptic skeleton related genes and proteins in prefrontal cortex of heroin re-addicted rats].
Zhen ci yan jiu = Acupuncture research.
2019 May; 44(5):323-8. doi:
10.13702/j.1000-0607.180437. [PMID: 31155863] - 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] - Satnam Singh. Dynamics of heroin molecule inside the lipid membrane: a molecular dynamics study.
Journal of molecular modeling.
2019 Apr; 25(5):121. doi:
10.1007/s00894-019-4002-y. [PMID: 31020452] - Brantley P Jarvis, August F Holtyn, Anthony DeFulio, Mikhail N Koffarnus, Jeannie-Marie S Leoutsakos, Annie Umbricht, Michael Fingerhood, George E Bigelow, Kenneth Silverman. The effects of extended-release injectable naltrexone and incentives for opiate abstinence in heroin-dependent adults in a model therapeutic workplace: A randomized trial.
Drug and alcohol dependence.
2019 04; 197(?):220-227. doi:
10.1016/j.drugalcdep.2018.12.026. [PMID: 30852374] - Trajche Ivanovski, Ana María Espino Ibañez, Bernardino Barcelo Martin, Isabel Gomila Muñiz. Acute extensive myelopathy after single heroin and cocaine exposure in a patient with toxicological evidence of long-term drug abstinence.
BMJ case reports.
2019 Mar; 12(3):. doi:
10.1136/bcr-2018-228335. [PMID: 30936344] - Sharon L Smith, Reginald L Dean, Mark S Todtenkopf, David J Heal. Investigation of the reinforcing potential of samidorphan and naltrexone by fixed and progressive ratio intravenous self-administration testing in heroin-maintained rats.
Journal of psychopharmacology (Oxford, England).
2019 03; 33(3):383-391. doi:
10.1177/0269881118822111. [PMID: 30676189] - 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] - Mei-Yun Cheng, Shy-Chyi Chin, Yen-Chung Chang, Tony Wu, Siew-Na Lim, Hsiang-Yao Hsieh, Jung-Lung Hsu, Chun-Wei Chang, Wei-En Johnny Tseng, Han-Tao Li, Hsing-I Chiang, Bao-Luen Chang, Meng-Han Tsai, Long-Sun Ro. Different routes of heroin intake cause various heroin-induced leukoencephalopathies.
Journal of neurology.
2019 Feb; 266(2):316-329. doi:
10.1007/s00415-018-9131-1. [PMID: 30478618] - Monica J Barratt, Julie Latimer, Marianne Jauncey, Emma Tay, Suzanne Nielsen. Urine drug screening for early detection of unwitting use of fentanyl and its analogues among people who inject heroin in Sydney, Australia.
Drug and alcohol review.
2018 11; 37(7):847-850. doi:
10.1111/dar.12864. [PMID: 30289187] - Maxwell S Krieger, William C Goedel, Jane A Buxton, Mark Lysyshyn, Edward Bernstein, Susan G Sherman, Josiah D Rich, Scott E Hadland, Traci C Green, Brandon D L Marshall. Use of rapid fentanyl test strips among young adults who use drugs.
The International journal on drug policy.
2018 11; 61(?):52-58. doi:
10.1016/j.drugpo.2018.09.009. [PMID: 30344005] - Rebecca T DeRienz, Daniel D Baker, Nancy E Kelly, Amber M Mullins, Rachel Y Barnett, Jennifer M Hobbs, John A Daniels, Kent E Harshbarger, Anahi M Ortiz. Child Fatalities Due to Heroin/Fentanyl Exposure: What the Case History Missed.
Journal of analytical toxicology.
2018 Oct; 42(8):581-585. doi:
10.1093/jat/bky052. [PMID: 30371840] - Kai Yue, Theresa A Kopajtic, Jonathan L Katz. Abuse liability of mitragynine assessed with a self-administration procedure in rats.
Psychopharmacology.
2018 Oct; 235(10):2823-2829. doi:
10.1007/s00213-018-4974-9. [PMID: 30039246] - 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] - Mohammad Karamouzian, Carolyn Dohoo, Sara Forsting, Ryan McNeil, Thomas Kerr, Mark Lysyshyn. Evaluation of a fentanyl drug checking service for clients of a supervised injection facility, Vancouver, Canada.
Harm reduction journal.
2018 09; 15(1):46. doi:
10.1186/s12954-018-0252-8. [PMID: 30200991] - Cecilie Hasselø Thaulow, Åse Marit Leere Øiestad, Sidsel Rogde, Jannike Mørch Andersen, Gudrun Høiseth, Marte Handal, Jørg Mørland, Vigdis Vindenes. Can measurements of heroin metabolites in post-mortem matrices other than peripheral blood indicate if death was rapid or delayed?.
Forensic science international.
2018 Sep; 290(?):121-128. doi:
10.1016/j.forsciint.2018.06.041. [PMID: 30015276] - Sanjeev Sethi. The Changing Spectrum of Heroin-Associated Kidney Disease.
Clinical journal of the American Society of Nephrology : CJASN.
2018 07; 13(7):975-976. doi:
10.2215/cjn.06080518. [PMID: 29907616] - Oscar B Torres, Alexander J Duval, Agnieszka Sulima, Joshua F G Antoline, Arthur E Jacobson, Kenner C Rice, Carl R Alving, Gary R Matyas. A rapid solution-based method for determining the affinity of heroin hapten-induced antibodies to heroin, its metabolites, and other opioids.
Analytical and bioanalytical chemistry.
2018 Jun; 410(16):3885-3903. doi:
10.1007/s00216-018-1060-4. [PMID: 29675707] - 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] - M Soichot, S Julliand, J Filatriau, A Hurbain, E Bourgogne, A Mihoubi, H Gourlain, B Delhotal-Landes. Diagnosis of Heroin Overdose in an 8-Year-Old Boy: Reliable Contribution of Toxicological Investigations.
Journal of analytical toxicology.
2018 May; 42(4):255-264. doi:
10.1093/jat/bkx111. [PMID: 29301012] - Thai Hoang, Hong Nguyen, Ray W Shiraishi, Mai Nguyen, Trista Bingham, Diep Nguyen, Tam Nguyen, Hao Duong, Sheryl Lyss, Hien Tran. Factors associated with concurrent heroin use among patients on methadone maintenance treatment in Vietnam: A 24-month retrospective analysis of a nationally representative sample.
The International journal on drug policy.
2018 05; 55(?):113-120. doi:
10.1016/j.drugpo.2018.02.020. [PMID: 29550740] - Michael D Raleigh, Megan Laudenbach, Federico Baruffaldi, Samantha J Peterson, Michaela J Roslawski, Angela K Birnbaum, F Ivy Carroll, Scott P Runyon, Scott Winston, Paul R Pentel, Marco Pravetoni. Opioid Dose- and Route-Dependent Efficacy of Oxycodone and Heroin Vaccines in Rats.
The Journal of pharmacology and experimental therapeutics.
2018 05; 365(2):346-353. doi:
10.1124/jpet.117.247049. [PMID: 29535156] - Tingting Ning, Changlong Leng, Lin Chen, Baomiao Ma, Xiaokang Gong. Metabolomics analysis of serum in a rat heroin self-administration model undergoing reinforcement based on 1H-nuclear magnetic resonance spectra.
BMC neuroscience.
2018 03; 19(1):4. doi:
10.1186/s12868-018-0404-5. [PMID: 29502536] - Mohammad-Javad Morabbi, Emran Razaghi, Ehsan Moazen-Zadeh, Hamideh Safi-Aghdam, Mohamad R Zarrindast, Nasim Vousoghi, Shahin Akhondzadeh. Pexacerfont as a CRF1 antagonist for the treatment of withdrawal symptoms in men with heroin/methamphetamine dependence: a randomized, double-blind, placebo-controlled clinical trial.
International clinical psychopharmacology.
2018 03; 33(2):111-119. doi:
10.1097/yic.0000000000000200. [PMID: 29064909] - Michael A Marciano, Sini X Panicker, Garrett D Liddil, Danielle Lindgren, Kevin S Sweder. Development of a Method to Extract Opium Poppy (Papaver somniferum L.) DNA from Heroin.
Scientific reports.
2018 02; 8(1):2590. doi:
10.1038/s41598-018-20996-9. [PMID: 29416103] - Brantley P Jarvis, August F Holtyn, Meredith S Berry, Shrinidhi Subramaniam, Annie Umbricht, Michael Fingerhood, George E Bigelow, Kenneth Silverman. Predictors of induction onto extended-release naltrexone among unemployed heroin-dependent adults.
Journal of substance abuse treatment.
2018 02; 85(?):38-44. doi:
10.1016/j.jsat.2017.04.012. [PMID: 28449955] - Agnieszka Sulima, Rashmi Jalah, Joshua F G Antoline, Oscar B Torres, Gregory H Imler, Jeffrey R Deschamps, Zoltan Beck, Carl R Alving, Arthur E Jacobson, Kenner C Rice, Gary R Matyas. A Stable Heroin Analogue That Can Serve as a Vaccine Hapten to Induce Antibodies That Block the Effects of Heroin and Its Metabolites in Rodents and That Cross-React Immunologically with Related Drugs of Abuse.
Journal of medicinal chemistry.
2018 01; 61(1):329-343. doi:
10.1021/acs.jmedchem.7b01427. [PMID: 29236495] - Matthew K Griswold, Peter R Chai, Alex J Krotulski, Melissa Friscia, Brittany Chapman, Edward W Boyer, Barry K Logan, Kavita M Babu. Self-identification of nonpharmaceutical fentanyl exposure following heroin overdose.
Clinical toxicology (Philadelphia, Pa.).
2018 Jan; 56(1):37-42. doi:
10.1080/15563650.2017.1339889. [PMID: 28681615] - Ling Shen, Sawitri Assanangkornchai, Wei Liu, Le Cai, Fei Li, Songyuan Tang, Jiucheng Shen, Edward B McNeil, Virasakdi Chongsuvivatwong. Influence of social network on drug use among clients of methadone maintenance treatment centers in Kunming, China.
PloS one.
2018; 13(7):e0200105. doi:
10.1371/journal.pone.0200105. [PMID: 29969481] - Ernesto de Bernardis. Comment on 'Methadone Dose Adjustments, Plasma R-Methadone Levels and Therapeutic Outcome of Heroin Users: A Randomized Clinical Trial'.
European addiction research.
2018; 24(2):88. doi:
10.1159/000488719. [PMID: 29902789] - Elena G Shcherbakova, Ben Zhang, Samer Gozem, Tsuyoshi Minami, Peter Y Zavalij, Mariia Pushina, Lyle D Isaacs, Pavel Anzenbacher. Supramolecular Sensors for Opiates and Their Metabolites.
Journal of the American Chemical Society.
2017 10; 139(42):14954-14960. doi:
10.1021/jacs.7b06371. [PMID: 28820934] - 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] - Olafur Sveinsson, Lars Herrman, Max Albert Hietala. Heroin-induced acute myelopathy with extreme high levels of CSF glial fibrillar acidic protein indicating a toxic effect on astrocytes.
BMJ case reports.
2017 Jun; 2017(?):. doi:
10.1136/bcr-2017-219903. [PMID: 28659367] - Yixin Li, Baijuan Xia, Rongrong Li, Dan Yin, Wenmei Liang. Changes in Expression of Dopamine, Its Receptor, and Transporter in Nucleus Accumbens of Heroin-Addicted Rats with Brain-Derived Neurotrophic Factor (BDNF) Overexpression.
Medical science monitor : international medical journal of experimental and clinical research.
2017 Jun; 23(?):2805-2815. doi:
10.12659/msm.904670. [PMID: 28598964] - 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] - Heather Palis, Kirsten Marchand, Daphne Guh, Suzanne Brissette, Kurt Lock, Scott MacDonald, Scott Harrison, Aslam H Anis, Michael Krausz, David C Marsh, Martin T Schechter, Eugenia Oviedo-Joekes. Men's and women's response to treatment and perceptions of outcomes in a randomized controlled trial of injectable opioid assisted treatment for severe opioid use disorder.
Substance abuse treatment, prevention, and policy.
2017 05; 12(1):25. doi:
10.1186/s13011-017-0110-9. [PMID: 28526048] - Lee W Hutson, Christina L Lebonville, Meghan E Jones, Rita A Fuchs, Donald T Lysle. Interleukin-1 signaling in the basolateral amygdala is necessary for heroin-conditioned immunosuppression.
Brain, behavior, and immunity.
2017 May; 62(?):171-179. doi:
10.1016/j.bbi.2017.01.017. [PMID: 28131792] - Luke N Rodda, Jennifer L Pilgrim, Matthew Di Rago, Kerryn Crump, Dimitri Gerostamoulos, Olaf H Drummer. A Cluster of Fentanyl-Laced Heroin Deaths in 2015 in Melbourne, Australia.
Journal of analytical toxicology.
2017 May; 41(4):318-324. doi:
10.1093/jat/bkx013. [PMID: 28158759] - Jia-Wu Zhu, Feng-Liang Liu, Dan Mu, De-Yao Deng, Yong-Tang Zheng. Heroin use is associated with lower levels of restriction factors and type I interferon expression and facilitates HIV-1 replication.
Microbes and infection.
2017 Apr; 19(4-5):288-294. doi:
10.1016/j.micinf.2017.01.002. [PMID: 28104465] - Alexandra Maas, Michael Krämer, Konrad Sydow, Pai-Shan Chen, Torsten Dame, Frank Musshoff, Bernd W K Diehl, Burkhard Madea, Cornelius Hess. Urinary excretion study following consumption of various poppy seed products and investigation of the new potential street heroin marker ATM4G.
Drug testing and analysis.
2017 Mar; 9(3):470-478. doi:
10.1002/dta.2058. [PMID: 27565444] - Arani Nanavati, Leal C Herlitz. Tubulointerstitial Injury and Drugs of Abuse.
Advances in chronic kidney disease.
2017 03; 24(2):80-85. doi:
10.1053/j.ackd.2016.09.008. [PMID: 28284383] - Rilana Schuster, Alexandra Kleimann, Marie-Kathrin Rehme, Leonie Taschner, Alexander Glahn, Adrian Groh, Helge Frieling, Ralf Lichtinghagen, Thomas Hillemacher, Stefan Bleich, Annemarie Heberlein. Elevated methylation and decreased serum concentrations of BDNF in patients in levomethadone compared to diamorphine maintenance treatment.
European archives of psychiatry and clinical neuroscience.
2017 Feb; 267(1):33-40. doi:
10.1007/s00406-016-0668-7. [PMID: 26801497]