L-Norpseudoephedrine

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L-Norpseudoephedrine
L-Norpseudoephedrine.svg
Systematic (IUPAC) name
(1R,2R)-2-amino-1-phenyl-1-propanol
Clinical data
Identifiers
53643-20-2
None
PubChem CID 162265
ChemSpider 142493
Chemical data
Formula C9H13NO
151.206 g/mol

L-Norpseudoephedrine, or (−)-norpseudoephedrine, also referable to as (−)-threo-β-hydroxyamphetamine, is a psychostimulant drug of the amphetamine family. It is one of the four optical isomers of phenylpropanolamine, the other three being cathine ((+)-norpseudoephedrine), (−)-norephedrine, and (+)-norephedrine; as well as one of the two enantiomers of norpseudoephedrine (the other, of course, being cathine).[1] Similarly to cathine, L-norpseudoephedrine acts as a releasing agent of norepinephrine (EC50 = 30 nM) and to a lesser extent of dopamine (EC50 = 294 nM).[2] Due to the 10-fold difference in its potency for inducing the release of the two neurotransmitters however, L-norpseudoephedrine could be called a modestly selective or preferential norepinephrine releasing agent, similarly to related compounds like ephedrine and pseudoephedrine.

See also[edit]

References[edit]

  1. ^ F.. Macdonald (1997). Dictionary of Pharmacological Agents. CRC Press. p. 121. ISBN 978-0-412-46630-4. Retrieved 18 May 2012. 
  2. ^ Rothman RB, Vu N, Partilla JS et al. (October 2003). "In vitro characterization of ephedrine-related stereoisomers at biogenic amine transporters and the receptorome reveals selective actions as norepinephrine transporter substrates". The Journal of Pharmacology and Experimental Therapeutics 307 (1): 138–45. doi:10.1124/jpet.103.053975. PMID 12954796.