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[CAS NO. 549-18-8] Amitriptyline hydrochloride

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Catalog:	HY-B0527A
Brand:	MCE
CAS:	549-18-8

Overview

MDL	MFCD00012537
Molecular Weight	313.86
Molecular Formula	C20H24ClN
SMILES	CN(C)CC/C=C1C2=CC=CC=C2CCC3=C\1C=CC=C3.Cl

For research use only. We do not sell to patients.

2 Publications Citing Use of MCE

[1]PLoS Negl Trop Dis. 2019 Aug 20;13(8):e0007681.
[2]J Med Virol. 2022 Nov 1.

Summary

Amitriptyline hydrochloride is an inhibitor of serotonin reuptake transporter (SERT) and noradrenaline reuptake transporter (NET) , with K _i s of 3.45 nM and 13.3 nM for human SERT and NET, respectively. Amitriptyline hydrochloride also weakly binds to dopamine reuptake transporter (DAT) with a K _i of 2.58 μM. Amitriptyline hydrochloride also inhibits adrenergic , muscarinic , histamine and 5-HT receptors . Amitriptyline hydrochloride is a TrkA and TrkB receptors agonist with potent neurotrophic activity. Amitriptyline hydrochloride has antidepressant activity ^[1] ^[2] ^[3] .

IC50 & Target

5-HT _1A Receptor

450 nM (IC ₅₀ )

5-HT _1B Receptor

40 nM (IC ₅₀ )

5-HT _2A Receptor

4 nM (IC ₅₀ )

5-HT _2B Receptor

40 nM (IC ₅₀ )

5-HT _2C Receptor

6 nM (IC ₅₀ )

H ₁ Receptor

1.1 nM (IC ₅₀ )

H ₃ receptor

1 μM (IC ₅₀ )

H ₄ receptor

33.6 nM (IC ₅₀ )

SERT

3.45 nM (Ki)

NET

13.3 nM (Ki)

DAT

2.58 μM (Ki)

Adrenergic receptor

24 nM (IC ₅₀ )

muscarinic receptor

7.2 nM (IC ₅₀ )

TrkA

TrkB

Clinical Trial

NCT Number	Sponsor	Condition	Start Date	Phase
NCT03587025	University of Campinas, Brazil	Pain, Postoperative	June 1, 2015	Phase 3
NCT02127736	Winfried Rief\|Philipps University Marburg Medical Center	Healthy Participants		Not Applicable
NCT02256956	University Hospital Inselspital, Berne\|University of Washington\|Aalborg University\|Ludwig-Maximilians - University of Munich	Chronic Pain	November 2014	Phase 4
NCT02746250	Danish Headache Center	Tension-type Headache	March 2016	Not Applicable
NCT00766350	Universidad de Granada\|AstraZeneca\|Hospital Clinico Universitario San Cecilio	Fibromyalgia	November 2008	Phase 4
NCT01896349	Hospital de Clinicas de Porto Alegre	Treatment Resistant Depression	April 2013	Not Applicable
NCT00355277	University Hospital, Clermont-Ferrand	Healthy Volunteers	November 2005	Phase 1
NCT02195115	CAMC Health System\|University of Kentucky\|National Center for Research Resources (NCRR)\|National Institutes of Health (NIH)\|National Institute of General Medical Sciences (NIGMS)	Gallbladder Dyskinesia	February 2014	Phase 2
NCT01206478	Ann Davis, PhD, MPH, ABPP\|Eunice Kennedy Shriver National Institute of Child Health and Human Development (NICHD)\|University of Kansas Medical Center	Chronic Oral Food Refusal	August 2010	Phase 2
NCT04777838	University of Coimbra\|Instituto de Investigación Biomédica de Salamanca	Muscle Type Temporomandibular Disorders\|Myofascial Pain of the Masticatory Muscles	March 2021	Phase 2\|Phase 3
NCT02139098	Philipps University Marburg Medical Center\|Johannes Gutenberg University Mainz\|Philipps University Marburg Coordination Centre for Clinical Trials	Insomnia	May 2014	Phase 3
NCT03591458	University of Utah	Type1 Diabetes Mellitus\|Hypoglycemia Unawareness	August 1, 2018	Phase 2
NCT00000793	National Institute of Allergy and Infectious Diseases (NIAID)\|Boehringer Ingelheim	HIV Infections\|Peripheral Nervous System Disease		Phase 2
NCT00351910	AstraZeneca	Major Depressive Disorder	May 2006	Phase 3
NCT02054299	University Medical Center Goettingen	Drug Metabolism\|Membrane Transport	April 2013	Phase 1
NCT00006428	Eunice Kennedy Shriver National Institute of Child Health and Human Development (NICHD)	Spinal Cord Injuries\|Pain	August 1996	Phase 4
NCT00862095	Madigan Army Medical Center\|U.S. Army Medical Research and Development Command	Headache	June 2008	Phase 4
NCT00000817	National Institute of Allergy and Infectious Diseases (NIAID)	HIV Infections\|Peripheral Nervous System Disease	November 1994	Not Applicable
NCT00740571	Radboud University Medical Center\|Erasmus Medical Center\|University of Amsterdam	Cancer\|Neuralgia	September 2008	Phase 3
NCT00312260	The Hospital for Sick Children\|Canadian Institutes of Health Research (CIHR)	Pain	April 2006	Phase 3
NCT02552225	Boston Medical Center	Laryngeal Diseases	April 2016	Phase 2\|Phase 3
NCT02374567	Hannover Medical School	Dementia\|Depression\|Schizophrenia\|Psychosomatic Disorders\|Anxiety Disorders	January 2015	Phase 3
NCT02638870	Samsung Medical Center	Irritable Bowel Syndrome	January 2016
NCT05120934	Mayo Clinic	Interstitial Lung Disease	November 1, 2021	Phase 2
NCT02256943	University Hospital Inselspital, Berne\|University of Washington\|Ludwig-Maximilians - University of Munich\|Aalborg University	Chronic Pain	November 2014	Phase 4
NCT02014363	e-Therapeutics PLC	Major Depressive Disorder	October 2013	Phase 2
NCT01856270	University of Washington	Brain Injuries\|Post-Traumatic Headache	April 2013	Phase 2
NCT00389038	Children´s Hospital Medical Center, Cincinnati\|National Institute of Neurological Disorders and Stroke (NINDS)	Headache	October 2006	Phase 3
NCT04704453	Institut Claudius Regaud	Head and Neck Cancer	April 28, 2021	Phase 2
NCT02190526	Tehran University of Medical Sciences\|Tillotts Pharma AG	Diarrhea- Predominant Irritable Bowel Syndrome\|Quality of Life	September 2014	Phase 4
NCT01049347	Central Institute of Mental Health, Mannheim	Unipolar Depression	October 1997	Phase 3
NCT02451475	Mansoura University	Fibromyalgia	February 2013	Phase 1\|Phase 2
NCT00029497	National Center for Complementary and Integrative Health (NCCIH)	Cumulative Trauma Disorders\|Repetitive Strain Injury\|Carpal Tunnel Syndrome\|Pain		Phase 2
NCT00124306	National Institute of Diabetes and Digestive and Kidney Diseases (NIDDK)\|University of Pennsylvania	Bladder Diseases\|Interstitial Cystitis	February 2005	Phase 3
NCT02090998	Rutgers, The State University of New Jersey	Transformed Migraine\|Chronic Daily Headache	May 2014	Phase 4
NCT04750967	Dr. Lutfi Kirdar Kartal Training and Research Hospital	Migraine\|Headache	April 3, 2021	Not Applicable
NCT01357031	Hospital Israelita Albert Einstein\|Fundação de Amparo à Pesquisa do Estado de São Paulo	Migraine	May 2010	Phase 3
NCT01014520	Tabriz University	Herniated Disc\|Intervertebral Disc Displacement	May 2009	Phase 2
NCT05279963	The Third Affiliated hospital of Zhejiang Chinese Medical University	Bladder Pain Syndrome	March 16, 2022	Not Applicable
NCT00220844	Temple University	Dyspepsia	September 2005	Not Applicable
NCT00006427	Eunice Kennedy Shriver National Institute of Child Health and Human Development (NICHD)	Amputation, Traumatic\|Pain\|Postoperative Pain	August 1996	Phase 4
NCT00564525	Ann & Robert H Lurie Children´s Hospital of Chicago\|American College of Gastroenterology	Functional Gastrointestinal Disorders	October 2002	Phase 4
NCT00381199	McGill University Health Centre+Research Institute of the McGill University Health Centre	Fibromyalgia\|Sleep Initiation and Maintenance Disorders	April 2006	Not Applicable
NCT01581281	Children´s Hospital Medical Center, Cincinnati\|National Institute of Neurological Disorders and Stroke (NINDS)	Migraine\|Migraine Disorders\|Headache	June 2012	Phase 3
NCT01306708	Universidade do Sul de Santa Catarina	Adhesive Capsulitis	February 2011	Phase 2
NCT01309178	University Children´s Hospital Tuebingen\|Universität Duisburg-Essen\|University of Ulm	Cystic Fibrosis\|Pneumonia	May 2009	Phase 2
NCT02101892	Rambam Health Care Campus\|Migraine Research Foundation	Migraine\|Preventive Treatment	April 2014	Not Applicable
NCT02099006	University of Rochester\|Mae Stone Goode Foundation	Female Genital Diseases	November 2013	Phase 2\|Phase 3
NCT02237937	HolsboerMaschmeyer NeuroChemie GmbH\|Max-Planck-Institute of Psychiatry	Major Depression	September 2011	Phase 4
NCT04292470	University of California, Davis\|National Center for Complementary and Integrative Health (NCCIH)	GERD	November 5, 2020	Not Applicable
NCT00515229	University Hospital Tuebingen	Cystic Fibrosis\|Infection\|Pseudomonas Aeruginosa	October 2006	Phase 2
NCT03646526	First Affiliated Hospital of Zhejiang University\|Hunan DongtingPharm.Co.Ltd	Depressive Disorder	April 4, 2018	Phase 1
NCT00325000	German Research Foundation	Major Depression	November 2000	Not Applicable
NCT01161017	Rambam Health Care Campus	Migraine	July 2008	Not Applicable
NCT00189059	UMC Utrecht\|Utrecht University	Chronic Neuropathic Pain	October 2002	Phase 4
NCT02519400	Asan Medical Center	Depression	August 2015	Phase 1
NCT02339662	Doron Aframian\|Hadassah Medical Organization	Myofacial Pain	February 2015	Phase 4
NCT04725383	University of Missouri, Kansas City	Autism Spectrum Disorder\|Repetitive Compulsive Behavior	June 1, 2021	Phase 3
NCT02041455	Hospital de Clinicas de Porto Alegre	Fibromyalgia	June 2010	Phase 2\|Phase 3
NCT01869907	Ziekenhuis Oost-Limburg	Neuropathic Pain Caused by Lumbar Radicular Pain	September 2011	Phase 4
NCT01566825	Dieter Kunz, MD\|Charite University, Berlin, Germany	Healthy Subjects	August 2008	Not Applicable
NCT05020600	Marmara University	Central Sensitisation\|Fibromyalgia	August 19, 2021
NCT00370656	University of Surrey	Diabetes Mellitus\|Peripheral Neuropathies	February 2007	Phase 2\|Phase 3
NCT05110144	Mayo Clinic	Refractory Chronic Cough	November 1, 2021	Phase 2
NCT00798083	British Columbia Cancer Agency	Neuropathic Pain Secondary to Radiation Therapy	April 2008	Phase 3
NCT03096444	Gil Yosipovitch\|University of Miami	Pruritus	May 23, 2017	Phase 2
NCT02871661	University of Campinas, Brazil	Vulvodynia	July 2016	Phase 3
NCT02256878	Boehringer Ingelheim	Healthy	August 2004	Phase 1
NCT00248651	Mayo Clinic\|National Institute of Diabetes and Digestive and Kidney Diseases (NIDDK)	Dyspepsia and Other Specified Disorders of Function of Stomach	October 2006	Phase 2\|Phase 3
NCT03324035	University of Sao Paulo\|Cristália Produtos Químicos Farmacêuticos Ltda.	Pain, Neuropathic\|Leprosy\|Leprosy Neuropathy\|Amitriptyline	March 1, 2017	Phase 3
NCT00000428	Tufts Medical Center\|National Institute of Arthritis and Musculoskeletal and Skin Diseases (NIAMS)	Fibromyalgia	September 2000	Phase 4
NCT03472092	Children´s Hospital Medical Center, Cincinnati\|National Institute of Neurological Disorders and Stroke (NINDS)\|National Center for Complementary and Integrative Health (NCCIH)	Headache, Migraine\|Migraine\|Migraine Disorders\|Headache	October 2, 2018	Phase 2
NCT02434523	Boston Medical Center\|American Laryngological Association	Laryngeal Diseases\|Chronic Laryngeal Neuropathy	September 2013	Phase 2\|Phase 3

Appearance

Solid

Shipping

Room temperature in continental US; may vary elsewhere.

Storage

4°C, sealed storage, away from moisture

* In solvent : -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture)

Solvent & Solubility

In Vitro:

DMSO : ≥ 100 mg/mL ( 318.61 mM )

H ₂ O : ≥ 50 mg/mL ( 159.31 mM )

* "≥" means soluble, but saturation unknown.

Preparing
Stock Solutions

Concentration Solvent Mass	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

* Please refer to the solubility information to select the appropriate solvent.

In Vivo:

1.

Add each solvent one by one: PBS

Solubility: 120 mg/mL (382.34 mM); Clear solution; Need ultrasonic

* All of the co-solvents are available by MCE.

References

[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.

Synonyms

1-Propanamine, 3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N,N-dimethyl-, hydrochloride (1:1)

5H-Dibenzo[a,d]cycloheptene-Δ^5,γ-propylamine, 10,11-dihydro-N,N-dimethyl-, hydrochloride

1-Propanamine, 3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N,N-dimethyl-, hydrochloride

Amitriptyline hydrochloride

10,11-Dihydro-N,N-dimethyl-5H-dibenzo[a,d]cycloheptene-Δ⁵,γ-propylamine hydrochloride

5-(3-Dimethylaminopropylidene)dibenzo[a,d][1,4]cycloheptadiene hydrochloride

Tryptizol

Saroten

Damilen hydrochloride

Amitriptyline chloride

Lentizol

Laroxyl

Sarotex

NIH 10794

Elavil

Amineurin

Uxen

Noriline

Triptizol

Domical

Miketorin

Amilent

Endep

Amiprin

Apo-Amitriptyline

Larozyl

Amicen

Saroten Retard

Pinsaun

Amitrip

Tryptine

Etravil

Amyline

Anapsique

Tryptal

Trynol

Tridep

Amilit

Amiplin

Novoprotect

Elatrol

Tripta

Trepiline

Redomex

Elatrolet

Vanatrip

Syneudon

Trytomer

Pinsanu

Teperin

Enafon

Adepril

Tryptanol

Lantron

Amyzol

Sarotena

Euplit

Amitril

Ro 4-1575

Deprex

Sylvemid

Amitid

Amil 25

ADT

[3-(10,11-Dihydro-dibenzo[a,d]cyclohepten-5-ylidene)-propyl]-dimethyl-amine; hydrochloride

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