Home
    Disclaimer
    Phenmetrazine molecular structure

    Phenmetrazine Stats & Data

    Preludin
    NPS DataHub
    MW177.25
    FormulaC11H15NO
    CAS134-49-6
    IUPAC3-Methyl-2-phenylmorpholine
    SMILESCC1NCCOC1c1ccccc1
    InChIKeyOOBHFESNSZDWIU-UHFFFAOYSA-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 16 to 31 hours State Solid

    Description

    A sympathomimetic drug used primarily as an appetite depressant. Its actions and mechanisms are similar to dextroamphetamine.

    Mechanism of Action

    Phenmetrazine is thought to block the reuptake of norepinephrine and dopamine into the presynaptic neuron leading to an increase in the release of these monoamines into the extraneuronal space. Dopamine integrates incoming sensory stimuli, initiates and controls fine movement (nigro-neostriatal pathway), controls emotional behavior (midbrain mesolimbic-forebrain system) and controls hypothalamic-pituitary endocrine system (tubero-infundibular system). It is this latter effect on the tubero-infundibular systm that seems to lead to reduced food intake. Phenmetrazine also acts as a monoamine oxidase inhibitor.

    Pharmacodynamics

    Phenmetrazine is a sympathomimetic drug used primarily as an appetite depressant. Its actions and mechanisms are similar to dextroamphetamine. Amphetamines are non-catecholamine sympathomimetic amines with CNS stimulant activity. Phenmetrazine was originally sold under the tradename Preludin as an anorectic. It has since been removed from the market. It is by some considered to have a greater potential for addiction than the amphetamines, and has been abused in many countries, for example Sweden.

    Metabolism

    Primarily hepatic (via CYP3A and CYP2D6). Resistant to metabolism by monoamine oxidase. Metabolism involves deamination to para-hydroxyamphetamine and phenylacetone; this latter compound is subsequently oxidize to benzoic acid and excreted as glucuronide or glycine (hippuric acid) conjugate. Smaller amounts of amphetamine are converted to norephedrine by oxidation.

    Absorption

    Readily absorbed from the gastro-intestinal tract and buccal mucosa.

    Toxicity

    Adult monkeys have an LD50 of 15 to 20 mg/kg, whereas for young monkeys the LD50 is only 5 mg/kg. Symptoms of overdose include acute central nervous system stimulation, cardiotoxicity causing tachycardia, arrhythmias, hypertension, and cardiovascular collapse. Whilst some patients show signs of toxicity at blood concentrations of 20 µg/L, chronic abusers of amphetamine have been known to have blood concentration of up to 3000 µg/L.

    Indication

    Used as an anorectic in the treatment of obesity.

    Effect Profile

    Curated
    Stimulant 4.5

    Strong anxiety/jitters and euphoria with moderate stimulation

    Stimulation / Energy×3
    6
    Euphoria / Mood Lift×2
    9
    Focus / Productivity×2
    0
    Anxiety / Jitters×1
    10

    Tolerance & Pharmacokinetics

    drugs.wiki

    Tolerance Decay

    Full tolerance 1d Half tolerance 10d Baseline ~18d
    ← Back to Phenmetrazine