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Details

Stereochemistry ABSOLUTE
Molecular Formula C9H13NO
Molecular Weight 151.2056
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NORPSEUDOEPHEDRINE, (-)-

SMILES

C[C@@H](N)[C@H](O)C1=CC=CC=C1

InChI

InChIKey=DLNKOYKMWOXYQA-APPZFPTMSA-N
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

HIDE SMILES / InChI

Molecular Formula C9H13NO
Molecular Weight 151.2056
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

L-Norpseudoephedrine is a psychostimulant drug of amphetamine family, first isolated from an Ephedra species. It is one of the two enantiomers of norpseudoephedrine, less potent that D-Norpseudoephedrine. L-Norpseudoephedrine is a norepinephrine and dopamine releasing agent, and has thermogenic and anorectic effect.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Comparison of brown adipose tissue thermogenesis induced by congeners and isomers of phenylpropanolamine.
1985 Sep 16
(-)-Norpseudoephedrine, a metabolite of cathinone with amphetamine-like stimulus properties, enhances the analgesic and rate decreasing effects of morphine, but inhibits its discriminative properties.
1998 Apr
In vitro characterization of ephedrine-related stereoisomers at biogenic amine transporters and the receptorome reveals selective actions as norepinephrine transporter substrates.
2003 Oct
Patents

Sample Use Guides

L-Norpseudoephedrine induces drown adipose tissue thermogenesis when administered intraperitoneally at .0223 mMol/kg to male rats.
Route of Administration: Intraperitoneal
For the NE release assay, whole rat brain minus cerebellum and caudate was homogenized in ice-cold 10% sucrose containing 1 uM reserpine. 50 nM GBR12935 and 100 nM citalopram were added to block [3H]MPP uptake into DA and 5-HT nerves. After 12 strokes with a Potter-Elvehjem homogenizer, brain homogenates were centrifuged at 1,000g for 10 min at 0–4°C, and the supernatants were retained on ice. Synaptosomal preparations were incubated to steady state with 5 nM [3H]MPP in a Krebs-phosphate buffer. After incubation to steady state, 850uL of synaptosomes preloaded with 3H ligand was added to test tubes that contained 150 uL of test drug. The release reaction was terminated by dilution with 4 ml of wash buffer followed by rapid vacuum filtration over GF/B filters. Retained tritium was counted by a liquid scintillation counter. L-Norpseudoephedrine was able to evoke NE release with EC50 of 30 nM.
Substance Class Chemical
Created
by admin
on Sat Dec 16 09:12:10 UTC 2023
Edited
by admin
on Sat Dec 16 09:12:10 UTC 2023
Record UNII
QQ0FVC4PXS
Record Status Validated (UNII)
Record Version
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Name Type Language
NORPSEUDOEPHEDRINE, (-)-
Common Name English
(1R,2R)-PSEUDONOREPHEDRINE
Common Name English
NORPSEUDOEPHEDRINE, L-
Common Name English
L-PSEUDONOREPHEDRINE
Common Name English
(1R,2R)-2-AMINO-1-PHENYL-PROPAN-1-OL
Systematic Name English
(-)-THREO-2-AMINO-2-METHYL-1-PHENYLETHANOL
Common Name English
(-)-NORPSEUDOEPHEDRINE
Common Name English
L-NORPSEUDOEPHEDRINE
Common Name English
(R,R)-(-)-NORPSEUDOEPHEDRINE
Common Name English
BENZENEMETHANOL, .ALPHA.-((1R)-1-AMINOETHYL)-, (.ALPHA.R)-
Systematic Name English
Code System Code Type Description
FDA UNII
QQ0FVC4PXS
Created by admin on Sat Dec 16 09:12:10 UTC 2023 , Edited by admin on Sat Dec 16 09:12:10 UTC 2023
PRIMARY
EPA CompTox
DTXSID001045718
Created by admin on Sat Dec 16 09:12:10 UTC 2023 , Edited by admin on Sat Dec 16 09:12:10 UTC 2023
PRIMARY
PUBCHEM
162265
Created by admin on Sat Dec 16 09:12:10 UTC 2023 , Edited by admin on Sat Dec 16 09:12:10 UTC 2023
PRIMARY
CAS
37577-07-4
Created by admin on Sat Dec 16 09:12:10 UTC 2023 , Edited by admin on Sat Dec 16 09:12:10 UTC 2023
PRIMARY
WIKIPEDIA
L-Norpseudoephedrine
Created by admin on Sat Dec 16 09:12:10 UTC 2023 , Edited by admin on Sat Dec 16 09:12:10 UTC 2023
PRIMARY 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, of course, being cathine).[1] Similarly to cathine, L-norpseudoephedrine acts as a releasing agent of norepinephrine (EC50 = 30 nM) and to a lesser extent of dopamine (EC50 = 294 nM).[2] Due to the 10-fold difference in its potency for inducing the release of the two neurotransmitters however, L-norpseudoephedrine could be called a modestly selective or preferential norepinephrine releasing agent, similarly to related compounds like ephedrine and pseudoephedrine.