p-Hydroxynorephedrine

p-Hydroxynorephedrine
Systematic (IUPAC) name
4-(2-amino-1-hydroxypropyl)phenol
Identifiers
CAS Number 552-85-2 YesY
PubChem CID 11099
ChemSpider 10628 YesY
Synonyms 4-Hydroxynorephedrine
para-Hydroxynorephedrine
Chemical data
Formula C9H13NO2
Molar mass 167.21 g/mol

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
Graphic of several routes of amphetamine metabolism

Para-
Hydroxylation
Para-
Hydroxylation
Para-
Hydroxylation
Beta-
Hydroxylation
Beta-
Hydroxylation
Oxidative
Deamination
Oxidation
Glycine
Conjugation

The image above contains clickable links
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

References

  1. ↑ "p-Hydroxynorephedrine". NCBI. PubChem Compound. Retrieved 25 October 2013.
  2. 1 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


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