L-Norpseudoephedrine

L-Norpseudoephedrine
Clinical data
ATC code
  • None
Identifiers
IUPAC name
  • (1R,2R)-2-amino-1-phenyl-1-propanol
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.164.234
Chemical and physical data
FormulaC9H13NO
Molar mass151.209 g·mol−1
3D model (JSmol)
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

L-Norpseudoephedrine, or (−)-norpseudoephedrine, less commonly known as (–)-cathine or L-cathine, is a psychostimulant drug of the amphetamine family. It is the levorotary isomer of Norpseudoephedrine and is one of the 4 optical isomers of phenylpropanolamine [1] ((−)-norpseudoephedrine, (+)-norpseudoephedrine, (−)-norephedrine, & (+)-norephedrine).

L-Norpseudoephedrine is an alkaloid of Ephedra sinica, Ephedra equisetina, and Catha edulis (khat). In khat, L-norpseudoephedrine is a secondary alkaloid present alongside cathinone. It is likely responsible for some of the milder stimulant effects of the plant, while cathinone produces the stronger psychoactive effects. In the Ephedra genus, L-norpseudoephedrine is a trace alkaloid compared to the more abundant alkaloids ephedrine and pseudoephedrine. Unlike in khat, L-Norpseudoephedrine does not contribute significantly to the pharmacological actions of Ephedra, as the amount contained in stems/leaves is negligible.

Pharmacology

L-Norpseudoephedrine is a modestly selective or preferential norepinephrine releasing agent, similarly to other related compounds like ephedrine and pseudoephedrine. It acts as a releasing agent of norepinephrine (EC50 = 30 nM) and to a lesser extent of dopamine (EC50 = 294 nM).[2]

L-Norpseudoephedrine is not classified as a norepinephrine–dopamine releasing agent because of its minimal dopaminergic action and the peripheral predominance of its sympathomimetic effects.

In Germany, norpseudoephedrine is used as an alternate name to cathine, a derivative of cathinone, and is only available by prescription.

See also

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.
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