4-Hydroxyphenylacetone

4-Hydroxyphenylacetone

Names
IUPAC name 1-(4-Hydroxyphenyl)propan-2-one
Other names p-Hydroxyphenylacetone; para-Hydroxyphenylacetone
Identifiers
CAS Number	770-39-8
ChemSpider	5382241
Jmol 3D model	Interactive image
PubChem	7019274
InChI InChI=1S/C9H10O2/c1-7(10)6-8-2-4-9(11)5-3-8/h2-5,11H,6H2,1H3 Key: VWMVAQHMFFZQGD-UHFFFAOYSA-N
SMILES CC(=O)CC1=CC=C(C=C1)O
Properties
Chemical formula	C9H10O2
Molar mass	150.18 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

4-Hydroxyphenylacetone is the parahydroxy analog of phenylacetone, an inactive metabolite of amphetamine in humans.^[1][2] When it occurs as a metabolite of amphetamine, it is produced directly from the inactive metabolite phenylacetone.^[1][3]

Metabolic pathways of amphetamine in humans

4-Hydroxyphenylacetone

Phenylacetone

Benzoic acid

Hippuric acid

Amphetamine

Norephedrine

4-Hydroxyamphetamine

4-Hydroxynorephedrine

Para-
Hydroxylation

Para-
Hydroxylation

Para-
Hydroxylation

Beta-
Hydroxylation

Beta-
Hydroxylation

Oxidative
Deamination

Oxidation

Glycine
Conjugation

In humans, 4-hydroxyphenylacetone occurs as a metabolite of amphetamine.

References

1. 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): 247–55. doi:10.1016/S0731-7085(02)00330-8. PMID 12191709.
2. "4-Hydroxyphenylacetone". NCBI. PubChem Compound. Retrieved 25 October 2013.
3. "Adderall XR Prescribing Information" (PDF). Medication Guide. United States Food and Drug Administration. pp. 12–13. Retrieved 7 October 2013.

External links

• 4-hydroxyphenylacetone at the US National Library of Medicine Medical Subject Headings (MeSH)