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A5861

Sigma-Aldrich

A-61603 hydrate

≥98% (HPLC)

Synonym(s):

N-[5-(4,5-dihydro-1H-imidazol-2yl)-2-hydroxy-5,6,7,8-tetrahydronaphthalen-1-yl]methanesulphonamide hydrobromide

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About This Item

Empirical Formula (Hill Notation):
C14H19N3O3S·HBr · xH2O
CAS Number:
107756-30-9
Molecular Weight:
390.30 (anhydrous basis)
MDL number:
MFCD16875412
UNSPSC Code:
12352200
PubChem Substance ID:
329770878

assay

≥98% (HPLC)

form

powder

color

off-white

solubility

H2O: >5 mg/mL

originator

Abbott

storage temp.

2-8°C

SMILES string

O.Br.CS(=O)(=O)Nc1c(O)ccc2C(CCCc12)C3=NCCN3

InChI

1S/C14H19N3O3S.BrH.H2O/c1-21(19,20)17-13-10-3-2-4-11(14-15-7-8-16-14)9(10)5-6-12(13)18;;/h5-6,11,17-18H,2-4,7-8H2,1H3,(H,15,16);1H;1H2

InChI key

PRYXREGSOWDDDR-UHFFFAOYSA-N

Application

A-61603 is an α1A agonist and has been studied to understand the functional roles of α(1)-adrenoceptor subtypes in mouse carotid arteries. A-61603 stimulated phosphoinositide hydrolysis In fibroblast cells transfected with α1a receptors.

Biochem/physiol Actions

A-61603 is an α1A agonist. In radioligand binding assays, A-61603 was at least 35-fold more potent at α1A receptors than at α1b or α1d sites. In fibroblast cells transfected with α1a receptors, A-61603 more potently stimulated phosphoinositide hydrolysis than norepinephrine, and was antagonized by prazosin. A-61603 is less potent in cells transfected with α1b or α1d receptors. It is a potent agonist at α1A receptors in rat vas deferens (200- to 300-fold more potent than norepinephrine or phenylephrine, respectively) and in isolated canine prostate strips (130- to 165-fold more potent than norepinephrine or phenylephrine, respectively). In contrast, it is only 40-fold more potent than phenylephrine at α1B sites in rat spleen and 35-fold less potent at rat aortic, α1D sites. A-61603 induces a pressor response in conscious rats at doses 50- to 100-fold lower than phenylephrine.

Features and Benefits

This compound is featured on the α1-Adrenoceptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Abbott. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - 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)

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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Clare Deighan et al.
British journal of pharmacology, 144(4), 558-565 (2005-01-19)
1. alpha(1)-Adrenoceptor (AR) subtypes in mouse carotid arteries were characterised using a combination of agonist/antagonist pharmacology and knockout (KO) mice. 2. Phenylephrine (PE) was most potent in the alpha(1B)-KO (pEC(50)=6.9+/-0.2) followed by control (pEC(50)=6.3+/-0.06) and alpha(1D)-KO (pEC(50)=5.5+/-0.07). Both N-[5-(4,5-dihydro-1H-imidazol-2yl)-2-hydroxy-5,6,7,8-tetrahydronaphthalen-1-yl] methanesulphonamide

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