p-Hydroxynorephedrine

p-Hydroxynorephedrine
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Systematic (IUPAC) name
	4-(2-amino-1-hydroxypropyl)phenol
Identifiers
CAS Number	552-85-2
PubChem	CID: 11099
ChemSpider	10628
Synonyms	4-Hydroxynorephedrine; para-Hydroxynorephedrine
Chemical data
Formula	C9H13NO2
Molecular mass	167.21 g/mol
	InChI InChI=1S/C9H13NO2/c1-6(10)9(12)7-2-4-8(11)5-3-7/h2-6,9,11-12H,10H2,1H3 ; Key:JAYBQRKXEFDRER-UHFFFAOYSA-N ;

p-Hydroxynorephedrine, or 4-hydroxynorephedrine, is the para-hydroxy analog of norephedrine and an active sympathomimetic metabolite of amphetamine in humans.^[1]^[2] When it occurs as a metabolite of amphetamine, it is produced from both p-hydroxyamphetamine and norephedrine.^[2]^[3]^[4]

Metabolic pathways of amphetamine in humans

4-Hydroxynorephedrine

Para-
Hydroxylation

Beta-
Hydroxylation

Oxidative
Deamination

Oxidation

Glycine
Conjugation

In humans, para-hydroxynorephedrine is a metabolite of amphetamine. The hydroxylation of the substituted amphetamines in this image is mediated by CYP2D6 and dopamine β-hydroxylase.

References

p-Hydroxynorephedrine at the US National Library of Medicine Medical Subject Headings (MeSH)

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