View source for P-Hydroxynorephedrine

{{Short description|Chemical compound}}
{{Use dmy dates|date=April 2014}}
{{DISPLAYTITLE:''p''-Hydroxynorephedrine}}
{{Drugbox
| Verifiedfields = 
| Watchedfields = 
| verifiedrevid =
| IUPAC_name = 4-(2-amino-1-hydroxypropyl)phenol
| image = P-HO-Norephedrine Structure.svg
| width = 200
| drug_name = ''p''-Hydroxynorephedrine
<!--Clinical data-->
| tradename =  
| legal_status = 
| routes_of_administration =
<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 771-91-5
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = O6914L7189
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ATC_prefix = 
| ATC_suffix = 
| PubChem = 6931143
| ChemSpiderID = 5305318
| ChEMBL = 
| NIAID_ChemDB = 
| smiles = [C@@H]([C@H](C)N)(O)C1=CC=C(O)C=C1
| StdInChI = 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
| StdInChIKey = JAYBQRKXEFDRER-RCOVLWMOSA-N
<!--Chemical data-->
| C=9 | H=13 | N=1 | O=2
| synonyms = 4-Hydroxynorephedrine<br/>''para''-Hydroxynorephedrine
}}

'''''p''-Hydroxynorephedrine''' ('''PHN''' or '''4-hydroxynorephedrine''') is the ''para''-hydroxy [[structural analog|analog]] of [[phenylpropanolamine|norephedrine]] and an active [[sympathomimetic]] metabolite of [[amphetamine]] in humans.<ref>{{cite web|title=p-Hydroxynorephedrine|url=https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=11099|work=NCBI|publisher=PubChem Compound|accessdate=25 October 2013}}</ref><ref name="FDA side effects">{{cite web | title = Adderall XR Prescribing Information | url = http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021303s024lbl.pdf | work = Medication Guide | publisher = United States Food and Drug Administration | accessdate = 7 October 2013}}</ref>  When it occurs as a metabolite of amphetamine, it is produced from both [[P-Hydroxyamfetamine|''p''-hydroxyamphetamine]] and norephedrine.<ref name="FDA side effects" /><ref name="Pubchem Kinetics">{{cite web|title=Amphetamine: Biomedical Effects and Toxicity|url=https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=3007#x332|work=NCBI|publisher=Pubchem Compound|accessdate=12 October 2013}}</ref><ref name="pmid12191709">{{cite journal |vauthors=Santagati NA, Ferrara G, Marrazzo A, Ronsisvalle G | title = Simultaneous determination of amphetamine and one of its metabolites by HPLC with electrochemical detection | journal = J. Pharm. Biomed. Anal. | volume = 30 | issue = 2 | pages = 247–55 |date=September 2002 | pmid = 12191709 | doi =10.1016/S0731-7085(02)00330-8 }}</ref>

==Amphetamine metabolism==
{{Amphetamine pharmacokinetics|align=left|caption=In humans, para-hydroxynorephedrine is a metabolite of amphetamine.  The [[Simple aromatic ring|aromatic ring]] hydroxylation of the [[substituted amphetamines]] in this image is mediated by [[CYP2D6]] and [[dopamine β-hydroxylase]].}}{{clear}}

==Notes==
{{reflist|group=note}}

==See also==
*[[Hydroxynorephedrine]]

==References==
{{reflist|group=sources}}

== References ==
{{Reflist}}

== External links ==
* {{MeshName|p-Hydroxynorephedrine}}

{{Amphetamine}}
{{Phenethylamines}}

{{DEFAULTSORT:Hydroxynorephedrine, p-}}

[[Category:Amphetamine]]
[[Category:Beta-Hydroxyamphetamines]]
[[Category:Human drug metabolites]]
[[Category:Recreational drug metabolites]]
[[Category:Sympathomimetics]]

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