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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
L-Norpseudoephedrine induces drown adipose tissue thermogenesis when administered intraperitoneally at .0223 mMol/kg to male rats.
Route of Administration: Intraperitoneal
In Vitro Use Guide
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
Record UNII
QQ0FVC4PXS
Record Status Validated (UNII)
Record Version