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Phenylacetone

Synopsis, Chemistry

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Also known as: 1-phenylpropan-2-one, 103-79-7, 1-phenyl-2-propanone, Benzyl methyl ketone, Methyl benzyl ketone, Phenyl-2-propanone

Molecular Formula

C₉H₁₀O

Molecular Weight

134.17 g/mol

InChI Key

QCCDLTOVEPVEJK-UHFFFAOYSA-N

FDA UNII

O7IZH10V9Y

phenylacetone is a natural product found in Streptomyces and Gossypium hirsutum with data available.

1 2D Structure

Phenylacetone

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-phenylpropan-2-one

2.1.2 InChI

InChI=1S/C9H10O/c1-8(10)7-9-5-3-2-4-6-9/h2-6H,7H2,1H3

2.1.3 InChI Key

QCCDLTOVEPVEJK-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC(=O)CC1=CC=CC=C1

2.2 Other Identifiers

2.2.1 UNII

O7IZH10V9Y

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 1-phenyl-2-propanone

2. Benzyl Methyl Ketone

2.3.2 Depositor-Supplied Synonyms

1. 1-phenylpropan-2-one

2. 103-79-7

3. 1-phenyl-2-propanone

4. Benzyl Methyl Ketone

5. Methyl Benzyl Ketone

6. Phenyl-2-propanone

7. 1-phenylacetone

8. 2-propanone, 1-phenyl-

9. 3-phenyl-2-propanone

10. Phenylmethyl Methyl Ketone

11. Phenyl Acetone

12. 1-phenyl-propan-2-one

13. 136675-26-8

14. O7izh10v9y

15. Chembl3800510

16. Nsc-9827

17. Nsc 9827

18. Phenylacetone, 99%

19. Einecs 203-144-4

20. Unii-o7izh10v9y

21. (phenyl)acetone

22. Ai3-02938

23. Dea No. 8501

24. Methylbenzyl Ketone

25. Phenyl 2-propanone

26. 1-phenylpropane-2-one

27. Phenylacetone [mi]

28. Schembl43943

29. Ghl.pd_mitscher_leg0.660

30. Dtxsid1059280

31. Schembl13341529

32. Chebi:52052

33. Hsdb 8385

34. Nsc9827

35. Phenylacetone, Analytical Standard

36. Bcp22277

37. Zinc1700205

38. Bdbm50167968

39. Stl373560

40. Akos004905656

41. Dextroamphetamine Related Compound B

42. Ft-0673719

43. Dextroamphetamine Related Compound B Cii

44. A800807

45. Q418831

46. Amfetamine Sulfate Impurity B [ep Impurity]

47. Dextroamphetamine Related Compound B [usp-rs]

48. Dextroamphetamine Related Compound B [usp Impurity]

49. Dextroamphetamine Related Compound B, United States Pharmacopeia (usp) Reference Standard

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₉H₁₀O
Molecular Weight	134.17 g/mol
XLogP3	1.4
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	2
Exact Mass	134.073164938 g/mol
Monoisotopic Mass	134.073164938 g/mol
Topological Polar Surface Area	17.1 Å²
Heavy Atom Count	10
Formal Charge	0
Complexity	112
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 Metabolism/Metabolites

Marked differences were observed, in the ability of fortified 9000 g liver homogenate supernatants from three species to reduce 1-phenyl-2-propanone to the corresponding alcohol. This metabolic keto-reduction was negligible in homogenates from the rat and extensive in the rabbit; guinea-pig liver homogenates had intermediate ability. Metabolic oxidation of 1-phenyl-2-propanol was negligible in all three species. The amount of deamination of amphetamine and of N-n-propylamphetamine was approximately equal, in vitro, in rats and guinea-pigs but two to three times greater in liver homogenates from rabbits. Approximately three times more deaminated products were formed from the in vitro metabolism of N-n-propylamphetamine than from amphetamine metabolism by all three species.

PMID:27606 Coutts RT et al; J Pharm Pharmacol 30 (7): 415-8 (1978)

Phenylacetone was found to be the major metabolite formed when 2-nitro-1-phenylpropane was incubated with rabbit liver microsomes. The enzymatic character of the reaction was demonstrated by the increase of product with microsomal protein and dependency on NADPH and oxygen. Furthermore, phenobarbital induction markedly increased the formation of phenylacetone. Carbon monoxide decreased the reaction indicating the involvement of a metalloenzyme. Experiments with H2(18)O indicated that the carbonyl oxygen originated from water. It is suggested that the microsomal metabolism of 2-nitro-1-phenylpropane involves an enzymatic step followed by chemical hydrolysis of an intermediate, possibly a secondary nitronic acid.

PMID:905635 Jonsson J et al; Res Commun Chem Pathol Pharmacol 18 (1): 75-82 (1977)

Amphetamine is deaminated oxidatively by highly purified rat liver mitochondria. This monoamineoxidase (MAO) is an enzyme of the mitochondrial outer membrane and its activity is about two times higher than that of the microsomal MAO. Anaerobic incubations with mitochondria reduce phenylacetone, an important metabolite of amphetamine, to phenylisopropanol. The ketoreductase is localized in the mitochondrial inner membrane or its matrix.

PMID:7196246 Blume H; Arzneimittelforschung 31 (6): 994-7 (1981)

Fenetylline is metabolized in humans on two pathways. In addition to previously described degradation to amphetamine and 7-oxyethyltheophylline fenetylline undergoes moreover oxydative N-dealkylation to yield 7-aminoethyltheophylline and phenylacetone.

PMID:6742951 Goenechea S, Brzezinka H; Arch Kriminol 173 (3-4): 7-102 (1984)