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L-Norpseudoephedrine

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
L-Norpseudoephedrine
Clinical data
ATC code
  • None
Identifiers
  • (1R,2R)-2-amino-1-phenyl-1-propanol
CAS Number
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
ECHA InfoCard100.164.234Edit this at Wikidata
Chemical and physical data
FormulaC9H13NO
Molar mass151.209 g·mol−1
3D model (JSmol)
  • O[C@H](c1ccccc1)[C@H](N)C
  • 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 orL-cathine, is apsychostimulantdrug of theamphetamine family. It is thelevorotary isomer ofNorpseudoephedrine and is one of the 4optical isomers ofphenylpropanolamine[1] ((−)-norpseudoephedrine,(+)-norpseudoephedrine,(−)-norephedrine, &(+)-norephedrine).

L-Norpseudoephedrine is analkaloid ofEphedra sinica,Ephedra equisetina, andCatha edulis (khat). In khat,L-norpseudoephedrine is a secondary alkaloid present alongsidecathinone. It is likely responsible for some of the milder stimulant effects of the plant, whilecathinone produces the stronger psychoactive effects. In theEphedra genus,L-norpseudoephedrine is a trace alkaloid compared to the more abundant alkaloidsephedrine andpseudoephedrine. 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

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L-Norpseudoephedrine is a modestlyselective or preferentialnorepinephrine releasing agent, similarly to other related compounds likeephedrine andpseudoephedrine. It acts as areleasing agent ofnorepinephrine (EC50 = 30 nM) and to a lesser extent ofdopamine (EC50 = 294 nM).[2]

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

Legal Status

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

See also

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References

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  1. ^Macdonald F (1997).Dictionary of Pharmacological Agents. CRC Press. p. 121.ISBN 978-0-412-46630-4. Retrieved18 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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