4-Hydroxyamphetamine

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"Hydroxyamfetamine" redirects here. For other uses, see Hydroxyamphetamine.
4-Hydroxyamphetamine
P-Hydroxyamphetamine.svg
Systematic (IUPAC) name
4-(2-aminopropyl)phenol
Clinical data
Trade names Hydroxyamfetamine
Legal status
  • Prescription only
Routes Topical (ocular)
Identifiers
CAS number 1518-86-1 YesY
ATC code None
PubChem CID 3651
ChemSpider 3525 YesY
ChEMBL CHEMBL1546 YesY
Chemical data
Formula C9H13NO 
Mol. mass 151.206 g/mol
 YesY (what is this?)  (verify)

4-Hydroxyamphetamine, also known as hydroxyamfetamine (INN and BAN), hydroxyamphetamine (USAN), oxamphetamine, norpholedrine, para-hydroxyamphetamine, and α-methyltyramine, is a sympathomimetic drug, that is, a drug that stimulates the sympathetic nervous system. When used in eye drops, it dilates the pupil. 4-Hydroxyamphetamine is sold in combination with tropicamide under the brand name Paremyd. It occurs as a metabolite of amphetamine. It is an agonist of human TAAR1.[1]

Once thought to be a human invention, 4-hydroxyamphetamine is now known to occur as an alkaloid in plants including Acacia berlandieri.[2]

In 1944, the US Naval Submarine Medical Research Laboratory researched the use of Paredrine to improve adaptation to night vision in submarine personnel. A significant improvement in adaptation was shown in the 17 subjects they tested.[3]

Metabolic pathways of amphetamine

Graphic of several routes of amphetamine metabolism
4-Hydroxyamphetamine
Para-
Hydroxylation
Para-
Hydroxylation
Para-
Hydroxylation
Beta-
Hydroxylation
Beta-
Hydroxylation
Oxidative
Deamination
Oxidation
Glycine
Conjugation
In humans, 4-hydroxyamphetamine is a metabolite of amphetamine. The aromatic hydroxylation of substituted amphetamines is mediated by CYP2D6 and dopamine β-hydroxylase.


See also[edit]

References[edit]

  1. ^ "Articleid 50034244". Binding Database. Retrieved 29 April 2014. 
  2. ^ Shulgin, Alexander (September 26, 2001). "Ask Dr. Shulgin Online: Acacias and Natural Amphetamine". Center for Cognitive Liberty & Ethics. Retrieved February 18, 2010. 
  3. ^ Verplanck, WS (1944). "The effects of paregrine on night vision performance.". US Naval Submarine Medical Research Laboratory Technical Report 42. Retrieved February 18, 2010. 

External links[edit]