Phenylacetone

Phenylacetone
Names
IUPAC name
1-Phenylpropan-2-one
Other names
Benzyl methyl ketone; Methyl benzyl ketone; Phenyl-2-propanone
Identifiers
103-79-7 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:52052 YesY
ChemSpider 21106366 YesY
ECHA InfoCard 100.002.859
KEGG C15512 YesY
PubChem 7678
UNII O7IZH10V9Y YesY
Properties
C9H10O
Molar mass 134.18 g·mol−1
Appearance Colorless, pleasant odor
Density 1.006 g/mL
Melting point −15 °C (5 °F; 258 K)
Boiling point 214 to 216 °C (417 to 421 °F; 487 to 489 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Phenylacetone is an organic compound with the chemical formula C6H5CH2C(O)CH3. It is a colorless oil that is soluble in organic solvents. This substance is used in the manufacture of methamphetamine and amphetamine, where it is commonly known as P2P. Due to the illicit uses in clandestine chemistry, it was declared a schedule II controlled substance in the United States in 1980.[1] In humans, phenylacetone occurs as a metabolite of amphetamine and methamphetamine via FMO3-mediated oxidative deamination.[2][3]

Applications

Phenylacetone is used as an intermediate in the production of pesticides and anticoagulants.

Amphetamine metabolism

Metabolic pathways of amphetamine in humans[sources 1]
Graphic of several routes of amphetamine metabolism

Para-
Hydroxylation
Para-
Hydroxylation
Para-
Hydroxylation
unidentified
Beta-
Hydroxylation
Beta-
Hydroxylation
Oxidative
Deamination
Oxidation
unidentified
Glycine
Conjugation

See also

Reference notes

  1. ↑ [2][3][4][5][6][7][8][9][10]

References

  1. ↑ "Lists of: Scheduling Actions, Controlled Substances, Regulated Chemicals" (PDF). U.S. Department of Justice, Drug Enforcement Administration.
  2. 1 2 Krueger SK, Williams DE (June 2005). "Mammalian flavin-containing monooxygenases: structure/function, genetic polymorphisms and role in drug metabolism". Pharmacol. Ther. 106 (3): 357–387. doi:10.1016/j.pharmthera.2005.01.001. PMC 1828602Freely accessible. PMID 15922018.
    "Table 5: N-containing drugs and xenobiotics oxygenated by FMO"
  3. 1 2 Cashman JR, Xiong YN, Xu L, Janowsky A (March 1999). "N-oxygenation of amphetamine and methamphetamine by the human flavin-containing monooxygenase (form 3): role in bioactivation and detoxication". J. Pharmacol. Exp. Ther. 288 (3): 1251–1260. PMID 10027866.
  4. ↑ "Adderall XR Prescribing Information" (PDF). United States Food and Drug Administration. Shire US Inc. December 2013. pp. 12–13. Retrieved 30 December 2013.
  5. ↑ Glennon RA (2013). "Phenylisopropylamine stimulants: amphetamine-related agents". In Lemke TL, Williams DA, Roche VF, Zito W. Foye's principles of medicinal chemistry (7th ed.). Philadelphia, USA: Wolters Kluwer Health/Lippincott Williams & Wilkins. pp. 646–648. ISBN 9781609133450. Retrieved 11 September 2015. The simplest unsubstituted phenylisopropylamine, 1-phenyl-2-aminopropane, or amphetamine, serves as a common structural template for hallucinogens and psychostimulants. Amphetamine produces central stimulant, anorectic, and sympathomimetic actions, and it is the prototype member of this class (39). ... The phase 1 metabolism of amphetamine analogs is catalyzed by two systems: cytochrome P450 and flavin monooxygenase. ... Amphetamine can also undergo aromatic hydroxylation to p-hydroxyamphetamine. ... Subsequent oxidation at the benzylic position by DA β-hydroxylase affords p-hydroxynorephedrine. Alternatively, direct oxidation of amphetamine by DA β-hydroxylase can afford norephedrine.
  6. ↑ Taylor KB (January 1974). "Dopamine-beta-hydroxylase. Stereochemical course of the reaction" (PDF). J. Biol. Chem. 249 (2): 454–458. PMID 4809526. Retrieved 6 November 2014. Dopamine-β-hydroxylase catalyzed the removal of the pro-R hydrogen atom and the production of 1-norephedrine, (2S,1R)-2-amino-1-hydroxyl-1-phenylpropane, from d-amphetamine.
  7. ↑ Horwitz D, Alexander RW, Lovenberg W, Keiser HR (May 1973). "Human serum dopamine-β-hydroxylase. Relationship to hypertension and sympathetic activity". Circ. Res. 32 (5): 594–599. doi:10.1161/01.RES.32.5.594. PMID 4713201. Subjects with exceptionally low levels of serum dopamine-β-hydroxylase activity showed normal cardiovascular function and normal β-hydroxylation of an administered synthetic substrate, hydroxyamphetamine.
  8. ↑ Santagati NA, Ferrara G, Marrazzo A, Ronsisvalle G (September 2002). "Simultaneous determination of amphetamine and one of its metabolites by HPLC with electrochemical detection". J. Pharm. Biomed. Anal. 30 (2): 247–255. doi:10.1016/S0731-7085(02)00330-8. PMID 12191709.
  9. ↑ "Substrate/Product". butyrate-CoA ligase. BRENDA. Technische Universität Braunschweig. Retrieved 7 May 2014.
  10. ↑ "Substrate/Product". glycine N-acyltransferase. BRENDA. Technische Universität Braunschweig. Retrieved 7 May 2014.
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