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SML0023

Sigma-Aldrich

5-Iodo-A-85380 dihydrochloride hydrate

≥98% (HPLC)

Synonym(s):

3-((2S)-2-Azetidinylmethoxy)-5-iodo-pyridine dihydrochloride hydrate

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About This Item

Empirical Formula (Hill Notation):
C9H11IN2O · 2HCl · xH2O
CAS Number:
213550-82-4
Molecular Weight:
363.02 (anhydrous basis)
MDL number:
MFCD20488048
UNSPSC Code:
12352202
PubChem Substance ID:
329825095
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to tan

solubility

H2O: ≥22 mg/mL

storage temp.

−20°C

SMILES string

O.Cl.Cl.Ic1cncc(OC[C@@H]2CCN2)c1

InChI

1S/C9H11IN2O.2ClH.H2O/c10-7-3-9(5-11-4-7)13-6-8-1-2-12-8;;;/h3-5,8,12H,1-2,6H2;2*1H;1H2/t8-;;;/m0.../s1

InChI key

DCVONLXGZUKNSI-CZDIJEQGSA-N

Application

5-Iodo-A-85380 dihydrochloride hydrate may be used in nicotinic acetylcholine receptor-mediated signaling studies.

Biochem/physiol Actions

5-Iodo-A-85380 increases the influx of extracellular Ca+2 in rat cortical neurons and exhibits protective effects against glutamate-induced neurotoxicity. Studies reveal that it also activates α6β2 nicotinic acetylcholine receptors.
5-Iodo-A-85380 is a highly selective α4β2 nicotinic receptor agonist. The Ki values for binding to the human and rat receptors are 12 and 10 pM, respectively.

Features and Benefits

This compound is featured on the Acetylcholine Receptors (Nicotinic) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302,H318

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

SML0023-25MG:4548174001868
SML0023-BULK:
SML0023-VAR:
SML0023-5MG:4548174001875

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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Adrian J Mogg et al.
Neuropharmacology, 47(6), 848-859 (2004-11-06)
The novel compound 5-iodo-A-85380 binds with higher affinity to alpha4beta2* nicotinic acetylcholine receptors (nAChR), compared with other nAChR subtypes (Mukhin et al., 2000). In the present study, we have confirmed that in competition binding assays for three major nAChR subtypes
Marwa Y Sallam et al.
European journal of pharmacology, 834, 36-44 (2018-07-17)
The cholinergic antiinflammatory pathway favorably influences end organ damage induced by inflammatory conditions. Here, we hypothesized that α7 and/or α4β2-nicotinic acetylcholine receptors (nAChRs) protect against cardiovascular and autonomic imbalances induced by endotoxemia in rats. We assessed dose-effect relationships of i.v.
Masashi Ueda et al.
Brain research, 1199, 46-52 (2008-02-14)
5-iodo-3-(2(S)-azetidinylmethoxy)pyridine (5-iodo-A-85380, 5IA) has very high affinity and selectivity to nicotinic acetylcholine receptor (nAChR) alpha 4 beta 2 subtype, and a relative safe profile. To assess whether 5IA has neuroprotective properties, we examined the effect of 5IA on glutamate (Glu)-induced
Helena Montanuy et al.
Orphanet journal of rare diseases, 15(1), 170-170 (2020-07-02)
Fanconi anemia is a rare disease clinically characterized by malformations, bone marrow failure and an increased risk of solid tumors and hematologic malignancies. The only therapies available are hematopoietic stem cell transplantation for bone marrow failure or leukemia, and surgical

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