L-Norpseudoephedrine

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).

ATC code

• None

CAS Number

• 37577-07-4 ^Y

PubChem CID

• 162265

ChemSpider

• 142493

Quick facts Clinical data, ATC code ...

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)	DTXSID001045718 DTXSID20889399, DTXSID001045718
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

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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.