4-Hydroxyamphetamine (BioDeep_00000018204)
human metabolite Endogenous blood metabolite Volatile Flavor Compounds
代谢物信息卡片
Hydrobromide, hydroxyamphetamine
化学式: C9H13NO (151.0997088)
中文名称: 4-(2-氨基丙基)苯酚, 4-（2-氨基丙基）苯酚
谱图信息:
最多检出来源 Homo sapiens(blood) 3.13%
分子结构信息
SMILES: c1c(ccc(c1)C[C@H](C)N)O
InChI: InChI=1S/C9H13NO/c1-7(10)6-8-2-4-9(11)5-3-8/h2-5,7,11H,6,10H2,1H3
描述信息
4-Hydroxyamphetamine is a metabolite of methamphetamine. Methamphetamine, also known as methamfetamine, meth, N-methylamphetamine, methylamphetamine, and desoxyephedrine, is a psychostimulant of the phenethylamine and amphetamine class of psychoactive drugs. Methamphetamine increases alertness, concentration, energy, and in high doses, can induce euphoria, enhance self-esteem and increase libido. (Wikipedia)
D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D013566 - Sympathomimetics
D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D009184 - Mydriatics
C78272 - Agent Affecting Nervous System > C29747 - Adrenergic Agent
同义名列表
17 个代谢物同义名
Hydrobromide, hydroxyamphetamine; hydroxyamphetamine hydrobromide; Hydroxyphenylisopropylamine; Para hydroxyamphetamine; Para-hydroxyamphetamine; 4-(2-aminopropyl)phenol; 4-Hydroxyamphetamine; p-Hydroxyamphetamine; p Hydroxyamphetamine; hydroxyamphetamine; HYDROXYAMFETAMINE; Hydroxyamphetamin; Oxyamphetamine; Methyltyramine; Norpholedrin; Paredrine; 4-(2-Aminopropyl)phenol
数据库引用编号
14 个数据库交叉引用编号
- ChEBI: CHEBI:103855
- PubChem: 3651
- HMDB: HMDB0060765
- DrugBank: DB09352
- ChEMBL: CHEMBL1546
- Wikipedia: 4-Hydroxyamphetamine
- MeSH: p-Hydroxyamphetamine
- KNApSAcK: C00042852
- chemspider: 3525
- CAS: 1518-86-1
- CAS: 103-86-6
- PMhub: MS000004239
- LOTUS: LTS0120328
- wikidata: Q5955531
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
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)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
2 个相关的物种来源信息
- 9606 - Homo sapiens: -
- 138013 - Senegalia berlandieri: 10.1016/S0031-9422(97)00240-9
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
- Christian Carpéné, Pénélope Viana, Jessica Fontaine, Henrik Laurell, Jean-Louis Grolleau. Multiple Direct Effects of the Dietary Protoalkaloid N-Methyltyramine in Human Adipocytes.
Nutrients.
2022 Jul; 14(15):. doi:
10.3390/nu14153118. [PMID: 35956295] - Yoshikazu Abe, Yuki Nakano, Toru Kanazawa, Takao Furihata, Takuro Endo, Mamoru Kobayashi. Investigation of Drug-Drug Interactions Between Ritobegron, a Selective β3 -Adrenoceptor Agonist, With Probenecid in Healthy Men.
Clinical pharmacology in drug development.
2016 May; 5(3):201-7. doi:
10.1002/cpdd.212. [PMID: 27163499] - Y Abe, E Ota, H Harada, H Kanbe, Y Kojima, T Kanazawa, T Endo, M Murakami, M Kobayashi. Species differences in the metabolism of ritobegron in vitro and assessment of potential interactions with transporters and cytochrome P450 enzymes.
Die Pharmazie.
2015 Jan; 70(1):38-46. doi:
NULL. [PMID: 25975097] - Y Abe, E Ota, T Endo, M Murakami, M Kobayashi. Absorption, disposition, metabolism, and excretion of ritobegron (KUC-7483), a novel selective β3-adrenoceptor agonist, in rats.
Die Pharmazie.
2014 Dec; 69(12):881-8. doi:
NULL. [PMID: 25951660] - I Davagnanam, C L Fraser, K Miszkiel, C S Daniel, G T Plant. Adult Horner's syndrome: a combined clinical, pharmacological, and imaging algorithm.
Eye (London, England).
2013 Mar; 27(3):291-8. doi:
10.1038/eye.2012.281. [PMID: 23370415] - Itaru Maruyama, Saori Yonekubo, Satoshi Tatemichi, Kazuyasu Maruyama, Yuji Hoyano, Yoshinobu Yamazaki, Hiroshi Kusama. Effects of ritobegron (KUC-7483), a novel β3-adrenoceptor agonist, on both rat bladder function following partial bladder outlet obstruction and on rat salivary secretion: a comparison with the effects of tolterodine.
Journal of smooth muscle research = Nihon Heikatsukin Gakkai kikanshi.
2012; 48(5-6):115-24. doi:
10.1540/jsmr.48.115. [PMID: 23538508] - Hiroshi Onogi, Osamu Nakagawasai, Atsushi Sato, Satoru Mitazaki, Kota Nakaya, Kenya Watanabe, Fukie Niijima-Yaoita, Koichi Tan-No, Yuichiro Arai, Tsuneaki Kikuchi, Takeshi Tadano. p-Hydroxyamphetamine causes prepulse inhibition disruption in mice: contribution of serotonin neurotransmission.
Behavioural brain research.
2011 Oct; 224(1):159-65. doi:
10.1016/j.bbr.2011.06.002. [PMID: 21689684] - E A Reese, J R Bunzow, S Arttamangkul, M S Sonders, D K Grandy. Trace amine-associated receptor 1 displays species-dependent stereoselectivity for isomers of methamphetamine, amphetamine, and para-hydroxyamphetamine.
The Journal of pharmacology and experimental therapeutics.
2007 Apr; 321(1):178-86. doi:
10.1124/jpet.106.115402. [PMID: 17218486] - Elias Miranda-G, Monserrat Sordo, Ana M Salazar, Claudia Contreras, Leoncio Bautista, Aurora E Rojas García, Patricia Ostrosky-Wegman. Determination of amphetamine, methamphetamine, and hydroxyamphetamine derivatives in urine by gas chromatography-mass spectrometry and its relation to CYP2D6 phenotype of drug users.
Journal of analytical toxicology.
2007 Jan; 31(1):31-6. doi:
10.1093/jat/31.1.31. [PMID: 17389081] - Hui-Ling Cheng, Yuh-Jyh Jong, Jih-Heng Li, Wei-Kung Ko, Shou-Mei Wu. Cation-selective exhaustive injection and sweeping MEKC for direct analysis of methamphetamine and its metabolites in urine.
Electrophoresis.
2006 Dec; 27(23):4711-6. doi:
10.1002/elps.200600174. [PMID: 17080473] - M E Soares, M Carvalho, H Carmo, F Remião, F Carvalho, M L Bastos. Simultaneous determination of amphetamine derivatives in human urine after SPE extraction and HPLC-UV analysis.
Biomedical chromatography : BMC.
2004 Mar; 18(2):125-31. doi:
10.1002/bmc.315. [PMID: 15039965] - Frank T Peters, Simone Schaefer, Roland F Staack, Thomas Kraemer, Hans H Maurer. Screening for and validated quantification of amphetamines and of amphetamine- and piperazine-derived designer drugs in human blood plasma by gas chromatography/mass spectrometry.
Journal of mass spectrometry : JMS.
2003 Jun; 38(6):659-76. doi:
10.1002/jms.483. [PMID: 12827635] - M E Soares, F Carvalho, M L Bastos. Determination of amphetamine and its metabolite p-hydroxyamphetamine in rat urine by reversed-phase high-performance liquid chromatography after dabsyl derivatization.
Biomedical chromatography : BMC.
2001 Nov; 15(7):452-6. doi:
10.1002/bmc.93. [PMID: 11746241] - M Y Law, D E Moody. Urinary excretion of 4-hydroxyamphetamine and amphetamine in male and female Sprague-Dawley and Dark Agouti rats following multiple doses of amphetamine.
Toxicology letters.
2000 Nov; 117(3):139-44. doi:
10.1016/s0378-4274(00)00256-3. [PMID: 11087979] - M Y Law, M H Slawson, D E Moody. Selective involvement of cytochrome P450 2D subfamily in in vivo 4-hydroxylation of amphetamine in rat.
Drug metabolism and disposition: the biological fate of chemicals.
2000 Mar; 28(3):348-53. doi:
NULL. [PMID: 10681381] - O Al-Dirbashi, J Qvarnstrom, K Irgum, K Nakashima. Simple and sensitive high-performance liquid chromatographic determination of methamphetamines in human urine as derivatives of 4-(4,5-diphenyl-1H-imidazol-2-yl) benzoyl chloride, a new fluorescence derivatization reagent.
Journal of chromatography. B, Biomedical sciences and applications.
1998 Aug; 712(1-2):105-12. doi:
10.1016/s0378-4347(98)00128-5. [PMID: 9698233] - N Kuroda, R Nomura, O al-Dirbashi, S Akiyama, K Nakashima. Determination of methamphetamine and related compounds by capillary electrophoresis with UV and laser-induced fluorescence detection.
Journal of chromatography. A.
1998 Mar; 798(1-2):325-34. doi:
10.1016/s0021-9673(97)00950-3. [PMID: 9542143] - K Matsushima, T Nagai, H Kanaya, Y Kato, M Takahashi, S Kamiyama. Urinary output changes in racemic ethylamphetamine and optical activity discrimination in rat urine by HPLC analysis.
Nihon hoigaku zasshi = The Japanese journal of legal medicine.
1998 Feb; 52(1):19-26. doi:
NULL. [PMID: 9591399] - H S Shin, B B Park, S N Choi, J J Oh, C P Hong, H Ryu. Identification of new urinary metabolites of famprofazone in humans.
Journal of analytical toxicology.
1998 Jan; 22(1):55-60. doi:
10.1093/jat/22.1.55. [PMID: 9491970] - D M Tomkins, S V Otton, N Joharchi, T Berns, D Wu, W A Corrigall, E M Sellers. Effect of CYP2D1 inhibition on the behavioural effects of d-amphetamine.
Behavioural pharmacology.
1997 Jun; 8(2-3):223-35. doi:
NULL. [PMID: 9833017] - K Hara, S Kashimura, Y Hieda, M Kageura. Simple extractive derivatization of methamphetamine and its metabolites in biological materials with Extrelut columns for their GC-MS determination.
Journal of analytical toxicology.
1997 Jan; 21(1):54-8. doi:
10.1093/jat/21.1.54. [PMID: 9013294] - F Carvalho, F Remião, F Amado, P Domingues, A J Correia, M L Bastos. d-Amphetamine interaction with glutathione in freshly isolated rat hepatocytes.
Chemical research in toxicology.
1996 Sep; 9(6):1031-6. doi:
10.1021/tx9501750. [PMID: 8870992] - M Y Law, D E Moody. Urinary excretion of amphetamine and 4'-hydroxyamphetamine by Sprague Dawley and dark Agouti rats.
Life sciences.
1994; 54(15):1073-9. doi:
10.1016/0024-3205(94)00417-x. [PMID: 8152328] - T Nagai, S Kamiyama. Simultaneous HPLC analysis of optical isomers of methamphetamine and its metabolites, and stereoselective metabolism of racemic methamphetamine in rat urine.
Journal of analytical toxicology.
1991 Nov; 15(6):299-304. doi:
10.1093/jat/15.6.299. [PMID: 1685757] - D E Moody, W Ruangyuttikarn, M Y Law. Quinidine inhibits in vivo metabolism of amphetamine in rats: impact upon correlation between GC/MS and immunoassay findings in rat urine.
Journal of analytical toxicology.
1990 Sep; 14(5):311-7. doi:
10.1093/jat/14.5.311. [PMID: 2263067] - T Yamamoto, R Takano, T Egashira, Y Yamanaka, M Terada. Simultaneous determination of methamphetamine and its metabolites in monkey urine by gas chromatography/mass spectrometry with selected ion monitoring.
Journal of analytical toxicology.
1989 Mar; 13(2):117-9. doi:
10.1093/jat/13.2.117. [PMID: 2733390] - K Shimosato. Urinary excretion of p-hydroxylated methamphetamine metabolites in man. II. Effect of alcohol intake on methamphetamine metabolism.
Pharmacology, biochemistry, and behavior.
1988 Apr; 29(4):733-40. doi:
10.1016/0091-3057(88)90195-5. [PMID: 3413199] - K Shimosato, H Oda, M Ohmae, M Tomita, Y Doi. Biphasic effects of alcohol drinking on methamphetamine metabolism in man.
Alcohol and alcoholism (Oxford, Oxfordshire).
1988; 23(5):351-7. doi:
10.1093/oxfordjournals.alcalc.a044828. [PMID: 3228456] - K Shimosato, M Tomita, I Ijiri. Urinary excretion of p-hydroxylated methamphetamine metabolites in man. I. A method for determination by high-performance liquid chromatography-electrochemistry.
Archives of toxicology.
1986 Oct; 59(3):135-40. doi:
10.1007/bf00316321. [PMID: 3813878] - K Shimosato, M Tomita, I Ijiri. Rapid determination of p-hydroxylated methamphetamine metabolites by column liquid chromatography-electrochemistry.
Journal of chromatography.
1986 Apr; 377(?):279-86. doi:
10.1016/s0378-4347(00)80783-5. [PMID: 3711218] - M Terada. Determination of methamphetamine and its metabolites in rat tissues by gas chromatography with a nitrogen-phosphorus detector.
Journal of chromatography.
1985 Jan; 318(2):307-18. doi:
10.1016/s0021-9673(01)90691-0. [PMID: 3980624] - P J Wellman, P A Watkins-Freeman. Effects of 4-hydroxyamphetamine on in vivo brown adipose tissue thermogenesis and feeding behavior in the rat.
Behavioral neuroscience.
1984 Dec; 98(6):1060-4. doi:
10.1037//0735-7044.98.6.1060. [PMID: 6508910] - S R Philips. Amphetamine, p-hydroxyamphetamine and beta-phenethylamine in mouse brain and urine after (-)- and (+)-deprenyl administration.
The Journal of pharmacy and pharmacology.
1981 Nov; 33(11):739-41. doi:
10.1111/j.2042-7158.1981.tb13920.x. [PMID: 6118419] - X Chen, L Y Liu, H W Deng, Y X Fang, Y W Ye. [The effects of Citrus aurantium and its active ingredient N-methyltyramine on the cardiovascular receptors (author's transl)].
Yao xue xue bao = Acta pharmaceutica Sinica.
1981 Apr; 16(4):253-9. doi:
". [PMID: 7257808] - L L Simpson. Blood pressure and heart rate response evoked by p-hydroxyamphetamine and by p-hydroxynorephedrine II. A quantitative assessment of the role of amphetamine metabolites in acute responses evoked by d-amphetamine.
The Journal of pharmacology and experimental therapeutics.
1980 Jun; 213(3):504-8. doi:
NULL. [PMID: 7205614] - L L Simpson. Blood pressure and heart rate responses evoked by p-hydroxyamphetamine and by p-hydroxynorephedrine. I. The relationship between evoked responses and plasma levels of drug.
The Journal of pharmacology and experimental therapeutics.
1979 Oct; 211(1):225-30. doi:
NULL. [PMID: 40013] - I Kitchen, J Tremblay, J André, L G Dring, J R Idle, R L Smith, R T Williams. Interindividual and interspecies variation in the metabolism of the hallucinogen 4-methoxyamphetamine.
Xenobiotica; the fate of foreign compounds in biological systems.
1979 Jul; 9(7):397-404. doi:
10.3109/00498257909038744. [PMID: 582863] - S R Bareggi, R Gomeni, R E Becker. Stereotyped behavior and hyperthermia in dogs: correlation with the levels of amphetamine and p-hydroxyamphetamine in plasma and CSF.
Psychopharmacology.
1978 Jun; 58(1):89-94. doi:
10.1007/bf00426795. [PMID: 97724] - T J Danielson, B A Davis, A A Boulton. Species variation with respect to the metabolism and excretion of d-amphetamine and d,l-N-hydroxyamphetamine succinate.
Canadian journal of physiology and pharmacology.
1977 Jun; 55(3):439-43. doi:
10.1139/y77-062. [PMID: 884602] - G J Digregorio, E K Kniaz. Radioimmunoassay of amphetamines in rat parotid saliva.
Drug and alcohol dependence.
1976 Oct; 1(6):377-82. doi:
10.1016/0376-8716(76)90002-8. [PMID: 1017382] - P S Sever, L G Dring, R T Williams. Urinary metabolites of p-hydroxyamphetamine in man, rat and guinea-pig.
Xenobiotica; the fate of foreign compounds in biological systems.
1976 Jun; 6(6):345-53. doi:
10.3109/00498257609151646. [PMID: 969562] - A Lindenbaum, K Marcher, J Wepierre, Y Cohen. [Blood-brain barrier. II. Kinetics of distribution of 3H-parahydroxyamphetamine in brain structures after intravenous administration in the rat].
Archives internationales de pharmacodynamie et de therapie.
1975 May; 215(1):168-76. doi:
NULL. [PMID: 1164084] - H Honecker, H Coper. Kinetics and metabolism of amphetamine in the brain of rats of different ages.
Naunyn-Schmiedeberg's archives of pharmacology.
1975; 291(2):111-21. doi:
10.1007/bf00500043. [PMID: 1202363] - W VONSTUDNITZ. EFFECT OF P-HYDROXYAMPHETAMINE ON CATECHOLAMINE EXCRETION IN MAN.
Acta pharmacologica et toxicologica.
1965; 22(?):172-6. doi:
NULL. [PMID: 14284195] - A SJOERDSMA, W von STUDNITZ. Dopamine-beta-oxidase activity in man, using hydroxyamphetamine as substrate.
British journal of pharmacology and chemotherapy.
1963 Apr; 20(?):278-84. doi:
10.1111/j.1476-5381.1963.tb01467.x. [PMID: 13977820] - E A OHLER, G E WAKERLIN. Further studies on the treatment of experimental renal hypertension with paredrine hydrobromide.
Federation proceedings.
1948 Mar; 7(1 Pt):87. doi:
NULL. [PMID: 18938621] - E A OHLER, G E WAKERLIN. Treatment of experimental renal hypertension with paredrine hydrobromide.
Federation proceedings.
1947; 6(1 Pt 2):171. doi:
NULL. [PMID: 20342794]