L-Norpseudoephedrine

L-Norpseudoephedrine, or (−)-norpseudoephedrine, 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 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.

L-Norpseudoephedrine

Clinical data
ATC code	None
Identifiers
IUPAC name (1R,2R)-2-amino-1-phenyl-1-propanol
CAS Number	37577-07-4^Y
PubChem CID	162265
ChemSpider	142493
UNII	QQ0FVC4PXS
CompTox Dashboard (EPA)	DTXSID20889399
ECHA InfoCard	100.164.234
Chemical and physical data
Formula	C9H13NO
Molar mass	151.209 g·mol^−1
3D model (JSmol)	Interactive image
SMILES O[C@H](c1ccccc1)[C@H](N)C
InChI InChI=1S/C9H13NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7,9,11H,10H2,1H3/t7-,9+/m1/s1 Key:DLNKOYKMWOXYQA-APPZFPTMSA-N

See also

• Cathine
• Phenylpropanolamine
• Cathinone
• Pseudoephedrine
• Ephedrine

References

1. Macdonald F (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, Roth BL, Hufeisen SJ, Compton-Toth BA, 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. S2CID 19015584.