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SML2049

Sigma-Aldrich

AR-R17779 Hydrochloride

≥97% (HPLC)

Synonym(s):

(-)-AR-R 13489 HCl, (-)-AR-R13489 HCl, (-)-Spiro[1-azabicyclo[2.2. 2]octane-3,5′-oxazolidin]-2′-one hydrochloride; (3S)-Spiro[1-azabicyclo[2.2.2]octane-3,5′-oxazolidine]-2′-one hydrochloride, (S)-AR-R 13489 HCl, (S)-AR-R13489 HCl, AR-R 17779 HCl

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About This Item

Empirical Formula (Hill Notation):
C9H14N2O2 · HCl
CAS Number:
178419-42-6
Molecular Weight:
218.68
MDL number:
MFCD20926337
UNSPSC Code:
12352200
NACRES:
NA.77

assay

≥97% (HPLC)

form

powder

optical activity

[α]/D -59 to -69°, c = 1.0 in methanol

storage condition

desiccated

color

white to beige

solubility

H2O: 2 mg/mL, clear

storage temp.

−20°C

SMILES string

O=C1O[C@@]2(CN1)CN3CCC2CC3.Cl

InChI

1S/C9H14N2O2.ClH/c12-8-10-5-9(13-8)6-11-3-1-7(9)2-4-11;/h7H,1-6H2,(H,10,12);1H/t9-;/m0./s1

InChI key

XGLBLUBBDSJBIU-FVGYRXGTSA-N

Biochem/physiol Actions

AR-R17779 is a nicotinic acetylcholine receptor alpha7 full agonist that targets α7 nAChR with high affinity (Ki = 92 nM/rat α7 against 5 nM α-BTX vs.16 μM/rat α4β2 against 3 nM (-)-nicotine) and selectivity (EC50 = 6.2/10/12.7 μM using human/rat/monkey α7 nAChR-Xenopus oocyte by whole cell voltage clamp, no antagonistic activity against acetylcholine using human α4β2-, α3β4-, α3β2-, α3β2α5-expressing oocytes or antagonistic activity against 5-HT using rat 5HT3a-exxpressing oocytes). AR-R17779 exhibits cognition-improving efficacy in rats (1-20 mg/kg s.c) and mice (1-20 mg/kg i.p.) in vivo and is widely employed for studying other α7 nAChR-dependent physiological functions.

pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

Hazard Classifications

Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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E D Levin et al.
Behavioural pharmacology, 10(6-7), 675-680 (2000-04-26)
Nicotinic acetylcholine systems have been found to be important for learning and memory function. The prototypic nicotinic agonist nicotine has been shown in a variety of studies to improve aspects of cognitive function. The specific involvement of nicotinic receptor subtypes
Roger L Papke et al.
European journal of pharmacology, 524(1-3), 11-18 (2005-11-04)
An alpha7 nicotinic acetylcholine receptor sequence was cloned from Rhesus monkey (Macaca mulatta). This clone differs from the mature human alpha7 nicotinic acetylcholine receptor in only four amino acids, two of which are in the extracellular domain. The monkey alpha7
F A Koopman et al.
Oral diseases, 21(7), 858-865 (2015-06-23)
Activation of the cholinergic anti-inflammatory pathway (CAP) has been shown to reduce inflammation in animal models, while abrogation of the pathway increases inflammation. We investigated whether modulation of CAP influences inflammation in the non-obese diabetic (NOD) mouse model for Sjögren's
The α7 nicotinic acetylcholine receptor agonist tropisetron counteracts ultraviolet A-mediated oxidative stress in human dermal fibroblasts.
Agatha Stegemann et al.
Experimental dermatology, 25(12), 994-996 (2016-09-30)
R Zwart et al.
Neuropharmacology, 43(3), 374-384 (2002-09-24)
The effects of 5-hydroxyindole (5-HI) have been investigated on human alpha 7 nicotinic acetylcholine receptors (nAChRs) expressed in Xenopus oocytes and GH4 cells, on native alpha 7 nAChRs expressed by IMR-32 cells and on alpha 7 nAChR-mediated events in mossy
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