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A3773

Sigma-Aldrich

9-Amino-1,2,3,4-tetrahydroacridine hydrochloride hydrate

≥99%

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Synonym(s):
THA hydrochloride hydrate, Tacrine hydrochloride, Tetrahydroaminacrine hydrochloride hydrate
Empirical Formula (Hill Notation):
C13H14N2 · HCl · xH2O
CAS Number:
206658-92-6
Molecular Weight:
234.72 (anhydrous basis)
MDL number:
MFCD00150067
UNSPSC Code:
12352200
PubChem Substance ID:
24278139
NACRES:
NA.77

Quality Level

100

Assay

≥99%

form

powder

mp

284-286 °C (lit.)

solubility

H2O: soluble

SMILES string

O.Cl.Nc1c2CCCCc2nc3ccccc13

InChI

1S/C13H14N2.ClH.H2O/c14-13-9-5-1-3-7-11(9)15-12-8-4-2-6-10(12)13;;/h1,3,5,7H,2,4,6,8H2,(H2,14,15);1H;1H2

InChI key

PXGRMZYJAOQPNZ-UHFFFAOYSA-N

Gene Information

human ... ACHE(43)

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Features and Benefits

This compound is featured on the Acetylcholine Synthesis and Metabolism and Histamine Synthesis and Metabolism pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Oral - Carc. 2 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Certificates of Analysis (COA)

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M Harel et al.
Proceedings of the National Academy of Sciences of the United States of America, 90(19), 9031-9035 (1993-10-01)
Binding sites of Torpedo acetylcholinesterase (EC 3.1.1.7) for quaternary ligands were investigated by x-ray crystallography and photoaffinity labeling. Crystal structures of complexes with ligands were determined at 2.8-A resolution. In a complex with edrophonium, and quaternary nitrogen of the ligand
Go Koganemaru et al.
Pharmacology, biochemistry, and behavior, 126, 103-108 (2014-09-30)
We examined the effects of two dopamine agonists, cabergoline and rotigotine, on tacrine-induced tremor and c-Fos expression in rats. Rats received intraperitoneal injection of cabergoline (0.5, 1.0, or 5.0mg/kg), rotigotine (1.0, 2.5, or 10.0mg/kg), or vehicle 30min before intraperitoneal injection
Dietrich E Lorke et al.
Molecules (Basel, Switzerland), 25(7) (2020-04-02)
Organophosphates (OPCs), useful agents as pesticides, also represent a serious health hazard. Standard therapy with atropine and established oxime-type enzyme reactivators is unsatisfactory. Experimental data indicate that superior therapeutic results can be obtained when reversible cholinesterase inhibitors are administered before
Jinggong Liu et al.
Biochimica et biophysica acta, 1840(9), 2886-2903 (2014-05-14)
Alzheimer's disease (AD) is a progressive neurodegenerative brain disorder that is characterized by dementia, cognitive impairment, and memory loss. Diverse factors are related to the development of AD, such as increased level of β-amyloid (Aβ), acetylcholine, metal ion deregulation, hyperphosphorylated
Satish N Dighe et al.
ACS omega, 5(48), 30971-30979 (2020-12-17)
Cholinesterases (ChE) are well-known drug targets for the treatment of Alzheimer's disease (AD). In continuation of work to develop novel cholinesterase inhibitors, we utilized a structure-based scaffold repurposing approach and discovered six novel ChE inhibitors from our recently developed DNA
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