p-Hydroxynorephedrine

p-Hydroxynorephedrine

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

See also

• Amphetamine
• Norephedrine

References

1. "p-Hydroxynorephedrine". NCBI. PubChem Compound. Retrieved 25 October 2013.
2. "Adderall XR Prescribing Information" (PDF). Medication Guide. United States Food and Drug Administration. Retrieved 7 October 2013.
3. "Amphetamine: Biomedical Effects and Toxicity". NCBI. Pubchem Compound. Retrieved 12 October 2013.
4. 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.

External links

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