L-Norpseudoephedrine

{{Short description|Chemical compound}}

{{DISPLAYTITLE:{{sc|L}}-Norpseudoephedrine}}

{{Drugbox

| drug_name = L-Norpseudoephedrine

| IUPAC_name = (1R,2R)-2-amino-1-phenyl-1-propanol

| image = L-Norpseudoephedrine.svg

| image_class = skin-invert-image

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 37577-07-4

| CAS_supplemental =

| ATC_prefix = None

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = QQ0FVC4PXS

| ATC_suffix =

| PubChem = 162265

| ChemSpiderID = 142493

| C = 9

| H = 13

| N = 1

| O = 1

| smiles = O[C@H](c1ccccc1)[C@H](N)C

| StdInChI = 1S/C9H13NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7,9,11H,10H2,1H3/t7-,9+/m1/s1

| StdInChIKey = DLNKOYKMWOXYQA-APPZFPTMSA-N

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| pregnancy_category =

| legal_status =

| routes_of_administration =

}}

{{sc|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).{{cite book | vauthors = Macdonald F| title = Dictionary of Pharmacological Agents | url = https://books.google.com/books?id=DeX7jgInYFMC&pg=PA121 | access-date = 18 May 2012 | year = 1997 | publisher = CRC Press | isbn = 978-0-412-46630-4 | page = 121}} Similarly to cathine, {{sc|L}}-norpseudoephedrine acts as a releasing agent of norepinephrine (EC₅₀ = 30 nM) and to a lesser extent of dopamine (EC₅₀ = 294 nM).{{cite journal|author4-link=Bryan Roth| vauthors = Rothman RB, Vu N, Partilla JS, Roth BL, Hufeisen SJ, Compton-Toth BA, Birkes J, Young R, Glennon RA | display-authors = 6 | title = In vitro characterization of ephedrine-related stereoisomers at biogenic amine transporters and the receptorome reveals selective actions as norepinephrine transporter substrates | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 307 | issue = 1 | pages = 138–45 | date = October 2003 | pmid = 12954796 | doi = 10.1124/jpet.103.053975 | s2cid = 19015584 }} Due to the 10-fold difference in its potency for inducing the release of the two neurotransmitters however, {{sc|L}}-norpseudoephedrine could be called a modestly selective or preferential norepinephrine releasing agent, similarly to related compounds like ephedrine and pseudoephedrine.