P-Hydroxynorephedrine

p-Hydroxynorephedrine (PHN 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]

p-Hydroxynorephedrine

Clinical data
Other names	4-Hydroxynorephedrine para-Hydroxynorephedrine
Identifiers
IUPAC name 4-(2-amino-1-hydroxypropyl)phenol
CAS Number	771-91-5 Y
PubChem CID	6931143
ChemSpider	5305318 Y
UNII	O6914L7189
Chemical and physical data
Formula	C9H13NO2
Molar mass	167.208 g·mol−1
3D model (JSmol)	Interactive image
SMILES [C@@H]([C@H](C)N)(O)C1=CC=C(O)C=C1
InChI InChI=1S/C9H13NO2/c1-6(10)9(12)7-2-4-8(11)5-3-7/h2-6,9,11-12H,10H2,1H3/t6-,9-/m0/s1 Key:JAYBQRKXEFDRER-RCOVLWMOSA-N

Amphetamine metabolism

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

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.^[6][11] 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;^[11][13] however, other evidence from animal studies suggests that this reaction is catalyzed by DBH in synaptic vesicles within noradrenergic neurons in the brain.^[14][15]

See also

• Hydroxynorephedrine

References

1. ^{[5][6][7][8][9][10][11][12]}