维基百科

4-羟基苯基丙酮

苯基丙酮的羟基类似物

4-羟基苯基丙酮（4-Hydroxyphenylacetone）是苯基丙酮（苯丙胺在人体中的不活泼代谢产物）的羟基类似物。[1][2]当它作为苯丙胺的代谢产物出现时，它通常是由不活泼的代谢物苯基丙酮中直接产生。[1][3]

4-羟基苯基丙酮
IUPAC名
1-(4-Hydroxyphenyl)propan-2-one
别名 p-Hydroxyphenylacetone; para-Hydroxyphenylacetone
识别
CAS号 770-39-8
PubChem 7019274
ChemSpider 5382241
SMILES
 
  • CC(=O)CC1=CC=C(C=C1)O
InChI
 
  • 1S/C9H10O2/c1-7(10)6-8-2-4-9(11)5-3-8/h2-5,11H,6H2,1H3
InChIKey VWMVAQHMFFZQGD-UHFFFAOYSA-N
性质
化学式 C9H10O2
摩尔质量 150.17 g·mol−1
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。
苯丙胺的代謝途徑[sources 1]
Graphic of several routes of amphetamine metabolism
Para-
Hydroxylation
Para-
Hydroxylation
Para-
Hydroxylation
Beta-
Hydroxylation
Beta-
Hydroxylation
Oxidative
Deamination
Oxidation
Glycine
Conjugation
图像顶端包含可点击的链接
人体中，4-羟基苯基丙酮是苯丙胺和苯基丙酮的代谢产物。

参注

  1. ^ [3][4][5][6][7][8][9][10]

参考资料

  1. ^ 1.0 1.1 Santagati NA, Ferrara G, Marrazzo A, Ronsisvalle G. Simultaneous determination of amphetamine and one of its metabolites by HPLC with electrochemical detection. J. Pharm. Biomed. Anal. September 2002, 30 (2): 247–55. PMID 12191709. doi:10.1016/S0731-7085(02)00330-8. 
  2. ^ 4-Hydroxyphenylacetone. NCBI. PubChem Compound. [2013-10-25]. （原始内容存档于2014-01-08）. 
  3. ^ 3.0 3.1 Adderall XR Prescribing Information (PDF). United States Food and Drug Administration. Shire US Inc: 12–13. December 2013 [30 December 2013]. （原始内容存档 (PDF)于2018-07-18）. 
  4. ^ Glennon RA. Phenylisopropylamine stimulants: amphetamine-related agents. Lemke TL, Williams DA, Roche VF, Zito W (编). Foye's principles of medicinal chemistry 7th. Philadelphia, USA: Wolters Kluwer Health/Lippincott Williams & Wilkins. 2013: 646–648 [2018-06-20]. ISBN 9781609133450. （原始内容存档于2020-07-26）. 
  5. ^ Taylor KB. Dopamine-beta-hydroxylase. Stereochemical course of the reaction (PDF). J. Biol. Chem. January 1974, 249 (2): 454–458 [6 November 2014]. PMID 4809526. （原始内容存档 (PDF)于2019-04-04）. 
  6. ^ Krueger SK, Williams DE. Mammalian flavin-containing monooxygenases: structure/function, genetic polymorphisms and role in drug metabolism. Pharmacol. Ther. June 2005, 106 (3): 357–387. PMC 1828602  . PMID 15922018. doi:10.1016/j.pharmthera.2005.01.001. 
    Table 5: N-containing drugs and xenobiotics oxygenated by FMO （页面存档备份，存于互联网档案馆）
  7. ^ Cashman JR, Xiong YN, Xu L, Janowsky A. N-oxygenation of amphetamine and methamphetamine by the human flavin-containing monooxygenase (form 3): role in bioactivation and detoxication. J. Pharmacol. Exp. Ther. March 1999, 288 (3): 1251–1260. PMID 10027866. 
  8. ^ Santagati NA, Ferrara G, Marrazzo A, Ronsisvalle G. Simultaneous determination of amphetamine and one of its metabolites by HPLC with electrochemical detection. J. Pharm. Biomed. Anal. September 2002, 30 (2): 247–255. PMID 12191709. doi:10.1016/S0731-7085(02)00330-8. 
  9. ^ Sjoerdsma A, von Studnitz W. Dopamine-beta-oxidase activity in man, using hydroxyamphetamine as substrate. Br. J. Pharmacol. Chemother. April 1963, 20: 278–284. PMC 1703637  . PMID 13977820. doi:10.1111/j.1476-5381.1963.tb01467.x. 
  10. ^ Badenhorst CP, van der Sluis R, Erasmus E, van Dijk AA. Glycine conjugation: importance in metabolism, the role of glycine N-acyltransferase, and factors that influence interindividual variation. Expert Opin. Drug Metab. Toxicol. September 2013, 9 (9): 1139–1153. PMID 23650932. doi:10.1517/17425255.2013.796929. 

外部链接

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