Amitriptyline HCl (Elavil)

Alias: trade names: Elavil; Amitriptylin; Tryptanol; Damilen; Triptanol; Amitriptyline HCl; Amitriptyline hydrochloride
Cat No.:V0992 Purity: ≥98%
Amitriptyline (Elavil; Tryptanol; Amitriptylin; Damilen; Triptanol),a tricyclic antidepressant (TCA), is an inhibitor of serotonin receptor, norepinephrine receptor, 5-HT4, 5-HT2 and sigma 1 receptor with potential anti-depressive activity.
Amitriptyline HCl (Elavil) Chemical Structure CAS No.: 549-18-8
Product category: 5-HT Receptor
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1g
5g
10g
Other Sizes

Other Forms of Amitriptyline HCl (Elavil):

  • Amitriptyline-d3 hydrochloride
  • Amitriptyline-d6 hydrochloride (amitriptyline d6 hydrochloride)
  • Amitriptyline (Elavil)
Official Supplier of:
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Amitriptyline (Elavil; Tryptanol; Amitriptylin; Damilen; Triptanol), a tricyclic antidepressant (TCA), is an inhibitor of serotonin receptor, norepinephrine receptor, 5-HT4, 5-HT2 and sigma 1 receptor with potential anti-depressive activity. It inhibits the sigma 1 receptor, 5-HT4, 5-HT2, norepinephrine receptor, and serotonin receptor with IC50s of 3.45 nM, 13.3 nM, 7.31 nM, 235 nM and 287 nM, respectively.

Biological Activity I Assay Protocols (From Reference)
Targets
5-HT1A Receptor ( IC50 = 450 nM ); 5-HT1B Receptor ( IC50 = 40 nM ); 5-HT2A Receptor ( IC50 = 4 nM ); 5-HT2B Receptor ( IC50 = 40 nM );
5-HT2C Receptor ( IC50 = 6 nM ); H1 Receptor ( IC50 = 1.1 nM ); H3 Receptor ( IC50 = 1 μM ); H4 Receptor ( IC50 = 33.6 nM );
SERT ( Ki = 3.45 nM ); NET ( Ki = 13.3 nM ); DAT ( Ki = 2.58 μM ); Adrenergic receptor ( IC50 = 24 nM ); muscarinic receptor ( IC50 = 7.2 nM ); TrkA; TrkB
ln Vitro

In vitro activity: Amitriptyline inhibits the accumulation of cyclic AMP stimulated by forskolin with EC50 values as low as 16.2 μM in intact CHO/DOR cells. In CHO/DOR cells, amitriptyline stimulates phosphorylation of GSK-3β and ERK1/2 in a concentration-dependent manner, with EC50 values of 9.0 μM. In C6 cells, amitriptyline (15 μM) stimulates phosphorylation of ERK1/2. Amitriptyline (30 μM) counteracts the (−)-U50,488 inhibitory effect in the rat nucleus accumbens and inhibits adenylyl cyclase activity stimulated by forskolin.[5] Amitriptyline stimulates TrkA-TrkB receptor heterodimerization by binding to the extracellular domains of both TrkA and TrkB. In PC12 cells, amitriptyline (< 500 nM) stimulates neurite outgrowth and increases TrkA autophosphorylation in primary neurons. With an EC50 of 50 nM, amitriptyline specifically prevents T17 cells from dying.[6]

ln Vivo
Amitriptyline (15 mg/kg, i.p.) dramatically lessens the death of neurons caused by kainic acid by activating TrkA and TrkB receptors in mice.[6] In the forced swimming test (FST), amitriptyline (15 mg/kg and 30 mg/kg, i.p.) reduces immobility time in a dose-dependent manner in mice. In the forced swimming test (FST) of mice, amitriptyline (15 mg/kg, i.p.) exhibits a significant 24-h rhythm in the immobility time.[7] Mice in new cages travel a significantly greater total distance when given amitriptyline (1 mg/kg and 3 mg/kg). Mice's hypothermic response to 8-OHDPAT and mCPP is significantly reduced by amitriptyline (10 mg/kg p.o., twice daily). In the cortex of mice, amitriptyline (10 mg/kg p.o., twice daily) dramatically lowers serotonin transporter density by about 20%. [8]
Cell Assay
Cell Line: hippocampal neurons
Concentration: 0.5 μM
Incubation Time: 30 min
Result: Induced TrkA phosphorylation. Induced Erk 1/2 and Akt signalings activation.
Animal Protocol
15, 30 mg/kg, i.p.; 10 mg/kg p.o.
Mice
References

[1]. Biol Psychiatry . 2004 Feb 1;55(3):320-2.

[2]. Mol Pharmacol . 2001 Mar;59(3):427-33.

[3]. J Pharmacol Exp Ther . 2001 Oct;299(1):83-9.

[4]. Exp Neurol . 2007 Oct;207(2):248-57.

[5]. J Pharmacol Exp Ther . 2010 Jan;332(1):255-65.

[6]. Chem Biol . 2009 Jun 26;16(6):644-56.

[7]. J Pharmacol Exp Ther . 2005 Nov;315(2):764-70.

[8]. Psychopharmacology (Berl) . 2005 Oct;181(4):741-50.

[9]. Bioorg Med Chem . 2006 Oct 1;14(19):6640-58.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C20H24CLN
Molecular Weight
313.86
Exact Mass
277.18
Elemental Analysis
C, 76.54; H, 7.71; Cl, 11.29; N, 4.46
CAS #
549-18-8
Appearance
Solid powder
SMILES
CN(C)CCC=C1C2=CC=CC=C2CCC3=CC=CC=C31.Cl
InChi Key
KFYRPLNVJVHZGT-UHFFFAOYSA-N
InChi Code
InChI=1S/C20H23N.ClH/c1-21(2)15-7-12-20-18-10-5-3-8-16(18)13-14-17-9-4-6-11-19(17)20;/h3-6,8-12H,7,13-15H2,1-2H3;1H
Chemical Name
N,N-dimethyl-3-(2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaenylidene)propan-1-amine;hydrochloride
Synonyms
trade names: Elavil; Amitriptylin; Tryptanol; Damilen; Triptanol; Amitriptyline HCl; Amitriptyline hydrochloride
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: ~63 mg/mL (~200.7 mM)
Water: ~15 mg/mL (~47.8 mM)
Ethanol: ~63 mg/mL (~200.7 mM)
Solubility (In Vivo)
5%DMSO + Corn oil: 4.0mg/ml (12.74mM) (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.1861 mL 15.9307 mL 31.8613 mL
5 mM 0.6372 mL 3.1861 mL 6.3723 mL
10 mM 0.3186 mL 1.5931 mL 3.1861 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT06158230 Active
Recruiting
Drug: Pizotifen
Drug: Amitriptyline-propranolol
Migraine Bangabandhu Sheikh Mujib Medical
University, Dhaka, Bangladesh
March 19, 2023 Phase 2
NCT03324035 Active
Recruiting
Drug: Amitriptyline
Drug: Tramadol
Pain, Neuropathic
Leprosy
University of Sao Paulo March 1, 2017 Phase 3
NCT04725383 Recruiting Drug: amitriptyline Autism Spectrum Disorder
Repetitive Compulsive Behavior
University of Missouri, Kansas City November 1, 2023 Phase 3
NCT06162819 Not yet recruiting Drug: Amitriptyline
Drug: Flunarizine 5mg
Migraine
Prophylaxis
Shalamar Institute of Health Sciences January 1, 2024 Not Applicable
NCT05889624 Recruiting Drug: Amitriptyline
Behavioral: CBT
Headache
Migraine
Children's Hospital Medical
Center, Cincinnati
August 22, 2023 Not Applicable
Biological Data
  • Amitriptyline activates the TrkA receptor and its downstream signaling cascades. Chem Biol . 2009 Jun 26;16(6):644-56.
  • Amitriptyline provokes neurite outgrowth in PC12 cells. Chem Biol . 2009 Jun 26;16(6):644-56.
  • Amitriptyline prevents neurons from apoptosis in a TrkA-dependent manner. Chem Biol . 2009 Jun 26;16(6):644-56.
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