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A8404

Sigma-Aldrich

Amitriptyline hydrochloride

≥98% (TLC), powder

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About This Item

Empirical Formula (Hill Notation):
C20H23N · HCl
CAS Number:
549-18-8
Molecular Weight:
313.86
EC Number:
208-964-6
MDL number:
MFCD00012537
UNSPSC Code:
12352200
PubChem Substance ID:
24278073
NACRES:
NA.77

assay

≥98% (TLC)

form

powder

color

white to off-white

solubility

H2O: soluble
ethanol: soluble

originator

Bristol-Myers Squibb

storage temp.

2-8°C

SMILES string

Cl[H].CN(C)CC\C=C1\c2ccccc2CCc3ccccc13

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

InChI key

KFYRPLNVJVHZGT-UHFFFAOYSA-N

Gene Information

human ... CHRM1(1128) , CHRM2(1129) , CHRM3(1131) , CHRM4(1132) , CHRM5(1133) , SLC6A2(6530) , SLC6A4(6532)

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Application

Amitriptyline hydrochloride has been used:
  • as an antidepressant to study its effects on social behavior and memory in transgenic for acid sphingomyelinase (t-ASM) mice
  • as a tricyclic antidepressant to analyze its effects on glucocorticoid receptor function in whole human blood
  • as an anti-depressant to study its effects on scratching and locomotion behavior in chloroquine-induced mouse

Biochem/physiol Actions

Amitriptyline hydrochloride shows therapeutic effects against anxiety, maniac depression, and involutional melancholia. It possesses antihistaminic, anticholinergic, and antiserotonimic properties. Amitriptyline hydrochloride acts as an amphiphilic agent and exhibits neuroleptic activity.
Tricyclic antidepressant; inhibits the norepinephrine and serotonin transporters with Kis of 100 nM and 14.7 nM, respectively; high in vitro affinity for α1-adrenoceptors, serotonin and muscarinic acetylcholine receptors.

Features and Benefits

Shelf-life of the powder is at least three years.

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Danger

Hazard Classifications

Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Irrit. 2 - Repr. 2

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Nadine Beckmann et al.
Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology, 43(4), 1460-1471 (2017-10-17)
Rheumatoid arthritis is a chronic autoimmune disease hallmarked by inflammation in synovial joints. Treatment is hampered by the lack of a cure and current disease-modifying drugs are associated with potentially severe toxicities. We investigated arthritis severity by measuring joint swelling
Neha Maurya et al.
Journal of biomolecular structure & dynamics, 35(6), 1367-1380 (2016-05-05)
Herein, we have explored the interaction between amitriptyline hydrochloride (AMT) and hemoglobin (Hb), using steady-state and time-resolved fluorescence spectroscopy, UV-visible spectroscopy, and circular dichroism spectroscopy, in combination with molecular docking and molecular dynamic (MD) simulation methods. The steady-state fluorescence reveals
Iulia Zoicas et al.
PloS one, 11(9), e0162498-e0162498 (2016-09-07)
Major depressive disorder is often associated with deficits in social and cognitive functioning. Mice transgenic for acid sphingomyelinase (t-ASM) were previously shown to have a depressive-like phenotype, which could be normalized by antidepressant treatment. Here, we investigated whether t-ASM mice
L A Carvalho et al.
European neuropsychopharmacology : the journal of the European College of Neuropsychopharmacology, 20(6), 379-387 (2010-03-17)
Clinical studies have demonstrated an impairment of glucocorticoid receptor (GR)-mediated negative feedback on the hypothalamic-pituitary-adrenal (HPA) axis in patients with major depression (GR resistance), and its resolution by antidepressant treatment. Recently, we showed that this impairment is indeed due to
Gema Tarrasón et al.
Experimental dermatology, 26(11), 1105-1111 (2017-06-13)
Pruritus is a major symptom of several dermatological diseases but has limited therapeutic options available. Animal models replicating the pathophysiology of pruritus are needed to support the development of new drugs. Induction of pruritus by chloroquine (CQ) in mice is
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