4-Hydroxyphenylacetone

4-Hydroxyphenylacetone is the para-hydroxy 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[sources 1] 4-Hydroxyphenylacetone Phenylacetone Benzoic acid Hippuric acid Amphetamine Norephedrine 4-Hydroxyamphetamine 4-Hydroxynorephedrine Para- Hydroxylation Para- Hydroxylation Para- Hydroxylation CYP2D6 CYP2D6 unidentified Beta- Hydroxylation Beta- Hydroxylation DBH DBH [note 1] Oxidative Deamination FMO3 Oxidation unidentified Glycine Conjugation XM-ligase GLYAT In humans, 4-hydroxyphenylacetone occurs as a metabolite of amphetamine and phenylacetone.

4-Hydroxyphenylacetone

Names
Preferred IUPAC name 1-(4-Hydroxyphenyl)propan-2-one
Other names p-Hydroxyphenylacetone; para-Hydroxyphenylacetone
Identifiers
CAS Number	770-39-8 Y
3D model (JSmol)	Interactive image
ChemSpider	5382241
ECHA InfoCard	100.129.975
PubChem CID	7019274
UNII	7K79N2OO7F Y
CompTox Dashboard (EPA)	DTXSID40427095
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	150.177 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

Notes

1. 4-Hydroxyamphetamine has been shown to be metabolized into 4-hydroxynorephedrine by dopamine beta-hydroxylase (DBH) in vitro and it is presumed to be metabolized similarly in vivo.^[4][9] Evidence from studies that measured the effect of serum DBH concentrations on 4-hydroxyamphetamine metabolism in humans suggests that a different enzyme may mediate the conversion of 4-hydroxyamphetamine to 4-hydroxynorephedrine;^[9][11] however, other evidence from animal studies suggests that this reaction is catalyzed by DBH in synaptic vesicles within noradrenergic neurons in the brain.^[12][13]

Reference notes

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