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    Chlorpheniramine molecular structure

    Chlorpheniramine Stats & Data

    Cpm Piriton Demazin Teldrin Allerest 4-cyclopropylmethoxy-3 cyclopropylmescaline
    NPS DataHub
    MW251.33
    FormulaC14H21NO3
    CAS207740-23-6
    IUPAC2-[4-(cyclopropylmethoxy)-3,5-dimethoxyphenyl]ethanamine
    SMILESNCCc1cc(OC)c(OCC2CC2)c(OC)c1
    InChIKeyLNTBHKZMYJTHTH-UHFFFAOYSA-N
    Phenethylamines; 2020/1. Von 2-Phenethylamin abgeleitete Verbindungen; 2021/1. Von 2-Phenethylamin abgeleitete Verbindungen; 2022/1. Von 2-Phenethylamin abgeleitete Verbindungen
    Chemical Class medicine
    Psychoactive Class Depressant / Psychedelic
    Half-Life 21-27 hours

    Pharmacology

    DrugBank
    Half-life 21-27 hours Protein binding 72% State Liquid

    Description

    A histamine H1 antagonist used in allergic reactions, hay fever, rhinitis, urticaria, and asthma. It has also been used in veterinary applications. One of the most widely used of the classical antihistaminics, it generally causes less drowsiness and sedation than promethazine.

    Mechanism of Action

    Chlorpheniramine binds to the histamine H1 receptor. This blocks the action of endogenous histamine, which subsequently leads to temporary relief of the negative symptoms brought on by histamine.

    Pharmacodynamics

    In allergic reactions an allergen interacts with and cross-links surface IgE antibodies on mast cells and basophils. Once the mast cell-antibody-antigen complex is formed, a complex series of events occurs that eventually leads to cell-degranulation and the release of histamine (and other chemical mediators) from the mast cell or basophil. Once released, histamine can react with local or widespread tissues through histamine receptors. Histamine, acting on H1-receptors, produces pruritis, vasodilatation, hypotension, flushing, headache, tachycardia, and bronchoconstriction. Histamine also increases vascular permeability and potentiates pain. Chlorpheniramine, is a histamine H1 antagonist (or more correctly, an inverse histamine agonist) of the alkylamine class. It competes with histamine for the normal H1-receptor sites on effector cells of the gastrointestinal tract, blood vessels and respiratory tract. It provides effective, temporary relief of sneezing, watery and itchy eyes, and runny nose due to hay fever and other upper respiratory allergies.

    Metabolism

    Primarily hepatic via Cytochrome P450 (CYP450) enzymes.

    Absorption

    Well absorbed in the gastrointestinal tract.

    Toxicity

    Oral LD50 (rat): 306 mg/kg; Oral LD50 (mice): 130 mg/kg; Oral LD50 (guinea pig): 198 mg/kg Registry of Toxic Effects of Chemical Substances. Ed. D. Sweet, US Dept. of Health & Human Services: Cincinatti, 2010. Also a mild reproductive toxin to women of childbearing age.

    Indication

    For the treatment of rhinitis, urticaria, allergy, common cold, asthma and hay fever.

    Effect Profile

    Curated + 6 Reports
    Psychedelic 3.9

    Moderate visuals with mild auditory effects and body load, low headspace

    Visual Intensity×3
    6
    Headspace Depth×3
    1
    Auditory Effects×1
    4
    Body Load / Somatic Effects×1
    4

    Tolerance & Pharmacokinetics

    drugs.wiki
    Half-Life
    21-27 hours
    Addiction Potential
    Low. Not considered habit-forming, but misuse occurs (often via combination cough/cold products) for sedative or anticholinergic effects; such misuse increases risks (confusion, delirium, overheating) without conferring reliable euphoria.

    Experience Report Analysis

    Erowid
    6 Reports
    2000–2009 Date Range
    1 With Age Data
    2 Effects Detected

    Demographics

    Gender Distribution

    Age Distribution

    Reports Over Time

    Effect Analysis

    Erowid

    Effects aggregated from 6 experience reports (6 Erowid)

    6 Reports
    2 Effects Detected
    1 Positive
    1 Adverse
    0 Neutral

    Effect Sentiment Distribution

    Confidence Distribution

    Positive Effects 1

    Anxiety Suppression 66.7% 70%

    Adverse Effects 1

    Nausea 50.0% 70%

    Real-World Dose Distribution

    62K Doses

    From 45 individual dose entries

    Oral (n=36)

    Median: 42.0mg 25th: 31.0mg 75th: 64.0mg 90th: 96.0mg
    mg/kg median: 0.634 mg/kg 75th: 1.176

    Common Combinations

    Most co-occurring substances in experience reports

    Harm Reduction

    drugs.wiki

    Harm-reduction points and cautions: 1) First-generation antihistamines have central anticholinergic effects; high doses can cause confusion, agitation, hallucinations, urinary retention, blurred vision, tachycardia, and potentially dangerous hyperthermia. Seek urgent care for severe agitation, delirium, hot/dry skin, or urinary retention. 2) Chlorpheniramine has a long elimination half-life (about 21–27 hours), so next-day drowsiness, slowed reaction time, and impaired coordination may persist beyond the 4–6 hour symptom-relief window; avoid driving or operating machinery if sedated. 3) Do not combine with dextromethorphan-containing ‘CCC/Triple C’ products: chlorpheniramine inhibits the serotonin transporter and is a CYP2D6 inhibitor/substrate; with DXM (a serotonergic CYP2D6 substrate), this raises the risk of serotonin syndrome and delirium. 4) Avoid co-use with MAOIs (or within 14 days of stopping one) due to severe interaction risk, especially if any serotonergic medicine (including DXM) is also present. 5) Additive CNS and respiratory depression occur with alcohol, opioids, benzodiazepines, and other sedatives; if accidental co-use occurs, keep doses low, avoid re-dosing, and ensure a sober monitor. 6) In hot environments or exertion (festivals, clubs), anticholinergic reduction of sweating increases overheating risk; hydrate, rest in shade, and stop use if feeling hot, confused, or unwell. 7) Older adults and those with glaucoma, prostatic hypertrophy/BPH, or a history of urinary retention are more sensitive to anticholinergic effects; consider non-sedating antihistamines instead and consult a clinician. 8) Overdose management is medical: there is no at-home antidote; in hospital, physostigmine may be considered for severe anticholinergic delirium by trained clinicians. 9) Product labels differ; many multi-symptom cold remedies already include chlorpheniramine—avoid double-dosing by checking ‘active ingredients’ on all concurrent OTCs. 10) Clinically significant hepatotoxicity is rare with chlorpheniramine-class drugs, but report unexplained jaundice, dark urine, or right-upper-quadrant pain if they occur after repeated dosing.

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