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Merck

A3773

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

≥99%

Synonym(s):

THA hydrochloride hydrate, Tacrine hydrochloride, Tetrahydroaminacrine hydrochloride hydrate

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About This Item

Empirical Formula (Hill Notation):
C13H14N2 · HCl · xH2O
CAS Number:
206658-92-6
Molecular Weight:
234.72 (anhydrous basis)
NACRES:
NA.77
PubChem Substance ID:
24278139
UNSPSC Code:
51111800
MDL number:
MFCD00150067

Product Name

9-Amino-1,2,3,4-tetrahydroacridine hydrochloride hydrate, ≥99%

form

powder

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

SMILES string

O.Cl.Nc1c2CCCCc2nc3ccccc13

InChI key

PXGRMZYJAOQPNZ-UHFFFAOYSA-N

assay

≥99%

mp

284-286 °C (lit.)

solubility

H2O: soluble

Quality Level

100

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

signalword

Danger

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

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

wgk

WGK 3

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Certificates of Analysis (COA)

Lot/Batch Number
0000257141
0000234461
0000223246
0000223246
0000234461

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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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