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    Norephedrine molecular structure

    Norephedrine Stats & Data

    NPS DataHub
    MW187.67
    FormulaC9H14ClNO
    CAS154-41-6
    IUPAC(1~{S},2~{S})-2-amino-1-phenylpropan-1-ol;hydrochloride[(1~{S},2~{S})-1-hydroxy-1-phenylpropan-2-yl]azanium;chloride(1~{S},2~{S})-2-amino-1-phenylpropan-1-ol;hydron;chloride
    SMILES[Cl-].CC(N)C(O)c1ccccc1.[H+]
    InChIKeyDYWNLSQWJMTVGJ-PRCZDLBKSA-N
    Phenethylamines; 2020/1. Von 2-Phenethylamin abgeleitete Verbindungen; 2021/1. Von 2-Phenethylamin abgeleitete Verbindungen; 2022/1. Von 2-Phenethylamin abgeleitete Verbindungen
    Psychoactive Class Stimulant

    Pharmacology

    DrugBank
    Half-life 2.1 to 3.4 hours. State Solid Metabolism Hepatic

    Description

    Phenylpropanolamine is a sympathomimetic agent that acts as a nonselective adrenergic receptor agonist and norepinephrine reuptake inhibitor. It has been used as a decongestant and appetite suppressant. Currently, it is withdrawn from the market in Canada and the United States due to the risk for hemorrahgic strokes.

    Mechanism of Action

    Phenylpropanolamine acts directly on alpha- and, to a lesser degree, beta-adrenergic receptors in the mucosa of the respiratory tract. Stimulation of alpha-adrenergic receptors produces vasoconstriction, reduces tissue hyperemia, edema, and nasal congestion, and increases nasal airway patency. PPA indirectly stimulates beta-receptors, producing tachycardia and a positive inotropic effect.

    Pharmacodynamics

    Phenylpropanolamine (PPA), a sympathomimetic agent structurally similar to pseudoephedrine, is used to treat nasal congestion. Phenylpropanolamine is found in appetite suppressant formulations and with guaifenesinin in cough-cold formulations. In 2000, the FDA requested that all drug companies discontinue marketing products containing phenylpropanolamine, due to an increased risk of hemorrhagic stroke in women who used phenylpropanolamine.

    Absorption

    Reduced bioavailability (about 38%) from gastrointestinal tract because of first pass metabolism by monoamine oxidase in the stomach and liver.

    Toxicity

    May induce ventricular extrasystoles and short paroxysms of ventricular tachycardia, a sensation of fullness in the head and tingling of the extremities; LD50=1490mg/kg (orally in rat)

    Indication

    For the treatment of nasal congestion, control of urinary incontinence, priapism and obesity.

    Effect Profile

    Curated
    Stimulant 6.5

    Strong euphoria and anxiety/jitters with moderate focus and stimulation

    Stimulation / Energy×3
    6
    Euphoria / Mood Lift×2
    10
    Focus / Productivity×2
    7
    Anxiety / Jitters×1
    10

    Tolerance & Pharmacokinetics

    drugs.wiki

    Tolerance Decay

    Full tolerance 1d Half tolerance 10d Baseline ~18d
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