Amitriptyline

Amitriptyline is an orally active tricyclic antidepressant (TCA) . Amitriptyline mainly exerts its antidepressant effect by blocking SERT (Ki = 3.45 nM) and NET (Ki = 13.3 nM), thereby increasing the concentrations of 5-hydroxytryptamine (5-HT) and norepinephrine (NE) in the synaptic cleft. Amitriptyline is also an agonist at α2A and TrkA/TrkB receptors, thereby exerting analgesic and neurotrophic activities (inhibiting cell apoptosis) . Amitriptyline can reduce inflammation, angiogenesis and fibrosis. Amitriptyline binds to DAT (with Ki = 2.58 μM) . Amitriptyline has high affinity for a series of receptors and can antagonize muscarinic cholinergic receptors (M1/M2/M3/M4/M5 receptors) (Ki = 11-24 nM), H1 receptors (Ki = 0.5-1.1 nM), adrenergic α1 receptors (Ki = 4.4 nM), etc., resulting in a series of side effects. Amitriptyline can block sodium channels and hERG potassium channel (IC50 = 4.78 μM) and it has cardiotoxicity[1][2][3][4][5].

Product Specifications

CAS Number

[50-48-6]

UNSPSC

12352005

Hazard Statement

H302-H315-H319-H335

Target

5-HT Receptor; Adrenergic Receptor; Apoptosis; Dopamine Transporter; Histamine Receptor; mAChR; Potassium Channel; Serotonin Transporter; Sodium Channel; Trk Receptor

Type

Reference compound

Related Pathways

Apoptosis; GPCR/G Protein; Immunology/Inflammation; Membrane Transporter/Ion Channel; Neuronal Signaling; Protein Tyrosine Kinase/RTK

Applications

Metabolism-protein/nucleotide metabolism

Field of Research

Endocrinology; Inflammation/Immunology; Neurological Disease

Assay Protocol

https://www.medchemexpress.com/amitriptyline.html

Concentration

10mM

Purity

99.94

Solubility

DMSO : 100 mg/mL (ultrasonic)

Smiles

CN(CC/C=C1C2=CC=CC=C2CCC3=C\1C=CC=C3)C

Molecular Formula

C20H23N

Molecular Weight

277.40

Precautions

P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

References & Citations

[1]Kim Lawson. A Brief Review of the Pharmacology of Amitriptyline and Clinical Outcomes in Treating Fibromyalgia. Biomedicines. 2017 Jun; 5 (2) : 24. |[2]S Neil Vaishnavi , et al. Milnacipran: a comparative analysis of human monoamine uptake and transporter binding affinity. Biol Psychiatry. 2004 Feb 1;55 (3) :320-2.|[3]Jang, S.W., et al., Amitriptyline is a TrkA and TrkB receptor agonist that promotes TrkA/TrkB heterodimerization and has potent neurotrophic activity. Chem Biol, 2009. 16 (6) : p. 644-56.|[4]Ghelardini C, et al. Antinociception induced by amitriptyline and imipramine is mediated by alpha2A-adrenoceptors. Jpn J Pharmacol. 2000 Feb;82 (2) :130-7. |[5]Scheuermann K, et al. Amitriptyline efficacy in decreasing implant-induced foreign body reaction. IUBMB Life. 2023 Sep;75 (9) :732-742.