4-羟基苯基丙酮

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。

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]

苯丙胺的代谢途径^{[sources 1]}

4-Hydroxyamphetamine（英语：4-Hydroxyamphetamine）

4-Hydroxynorephedrine（英语：p-Hydroxynorephedrine）

Para-
Hydroxylation

Beta-
Hydroxylation

Oxidative
Deamination

Oxidation

Glycine
Conjugation

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

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

参考资料

^ ^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.
^ 4-Hydroxyphenylacetone. NCBI. PubChem Compound. [2013-10-25]. （原始内容存档于2014-01-08）.
^ ^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）.
^ 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）.
^ 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）.
^ 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）
^ 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.
^ 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.
^ 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.
^ 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

医学主题词表（MeSH）：4-hydroxyphenylacetone

[amphetamine_metabolism-11] [3]^[4]^[5]^[6]^[7]^[8]^[9]^[10]

[pmid12191709-1] 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）.

[FDA_Pharmacokinetics-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）.

[Substituted_amphetamines,_FMO,_and_DBH-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）.

[DBH_amph_primary-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）.

[FMO-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）

[FMO3-Primary-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.

[Metabolites-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.

[pmid13977820-9] 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.

[Glycine_conjugation_review-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.

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