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Amitriptyline

CAS No:
50-48-6 Category:
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Product Details:

  • Product Name: Amitriptyline
  • CAS #: 50-48-6
  • Mode of Action:

    Amitriptyline is metabolized to nortriptyline which inhibits the reuptake of norepinephrine and serotonin almost equally. Amitriptyline inhibits the membrane pump mechanism responsible for uptake of norepinephrine and serotonin in adrenergic and serotonergic neurons. Pharmacologically this action may potentiate or prolong neuronal activity since reuptake of these biogenic amines is important physiologically in terminating transmitting activity. This interference with the reuptake of norepinephrine and/or serotonin is believed by some to underlie the antidepressant activity of amitriptyline.

  • Pharmacodynamics:

    Amitriptyline, a tertiary amine tricyclic antidepressant, is structurally related to both the skeletal muscle relaxant cyclobenzaprine and the thioxanthene antipsychotics such as thiothixene. It is extremely sedating, and thus improvement of sleep patterns can be the first benefit of treatment. Amitriptyline exhibits strong anticholinergic activity, cardiovascular effects including orthostatic hypotension, changes in heart rhythm and conduction, and a lowering of the seizure threshold. As with other antidepressants, several weeks of therapy may be required in order to realize the full clinical benefit of amitriptyline. Although not a labelled indication, amitriptyline is widely used in the management of chronic nonmalignant pain (e.g., post-herpetic neuralgia, fibromyalgia).

  • Metabolism:

    Exclusively hepatic, with first pass effect. Amitriptyline is demethylated in the liver to its primary active metabolite, nortriptyline.

  • Toxicity:

    LD50=350 mg/kg (in mice). Symptoms of overdose include abnormally low blood pressure, confusion, convulsions, dilated pupils and other eye problems, disturbed concentration, drowsiness, hallucinations, impaired heart function, rapid or irregular heartbeat, reduced body temperature, stupor, and unresponsiveness or coma. Side effects include: sedation, hypotension, blurred vision, dry mouth, constipation, urinary retention, postural hypotension, tachycardia, hypertension, ECG changes, heart failure, impaired memory and delirium, and precipitation of hypomanic or manic episodes in bipolar depression. Withdrawal symptoms include gastrointestinal disturbances, anxiety, and insomnia.

  • IUPAC: dimethyl({3-[(2Z)-tricyclo[9.4.0.0, {3, 8}]pentadeca-1(11), 3(8), 4, 6, 12, 14-hexaen-2-ylidene]propyl})amine
  • ATC: N06AA09
  • PubChem: 2160
  • DrugBank: DB00321 (APRD00227)
  • Formula: C20H34AuO9PS
  • Molecular Mass: 277.4033
  • Synonyms: Amitriprolidine Amitriptylin Amitriptyline HCL Amitriptyline Hydrochloride Amitryptiline Amitryptyline Amytriptiline
  • SMILES: CN(C)CCC=C1C2=CC=CC=C2CCC2=CC=CC=C12
  • AHFS Code: 28:16.04.28
  • InChl: KRMDCWKBEZIMAB-UHFFFAOYSA-N
  • General Reference:

    1. Otaka M, Jin M, Odashima M, Matsuhashi T, Wada I, Horikawa Y, Komatsu K, Ohba R, Oyake J, Hatakeyama N, Watanabe S: New strategy of therapy for functional dyspepsia using famotidine, mosapride and amitriptyline. Aliment Pharmacol Ther. 2005 Jun;21 Suppl 2:42-6. Pubmed

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