Chemistry:L-Norpseudoephedrine
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| Formula | C9H13NO |
| Molar mass | 151.209 g·mol−1 |
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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.
Legal Status
In Germany, norpseudoephedrine is used as an alternate name to cathine, a derivative of cathinone, and is only available by prescription.
See also
References
- ↑ Dictionary of Pharmacological Agents. CRC Press. 1997. p. 121. ISBN 978-0-412-46630-4. https://books.google.com/books?id=DeX7jgInYFMC&pg=PA121. Retrieved 18 May 2012.
- ↑ "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. October 2003. doi:10.1124/jpet.103.053975. PMID 12954796.
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