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

• ChemBase ID: 153217
• Molecular Formular: C14H22BrN3O4S
• Molecular Mass: 408.31118
• Monoisotopic Mass: 407.0514392
• SMILES: CS(=O)(=O)Nc1c(ccc2c1CCCC2C1=NCCN1)O.O.Br
• Canonical SMILES: Oc1ccc2c(c1NS(=O)(=O)C)CCCC2C1=NCCN1.O.Br
• InChI: 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
• InChIKey: PRYXREGSOWDDDR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[5-(4,5-dihydro-1H-imidazol-2-yl)-2-hydroxy-5,6,7,8-tetrahydronaphthalen-1-yl]methanesulfonamide hydrate hydrobromide
• IUPAC Traditional name: N-[5-(4,5-dihydro-1H-imidazol-2-yl)-2-hydroxy-5,6,7,8-tetrahydronaphthalen-1-yl]methanesulfonamide hydrate hydrobromide
• Synonyms: N-[5-(4,5-dihydro-1H-imidazol-2yl)-2-hydroxy-5,6,7,8-tetrahydronaphthalen-1-yl]methanesulphonamide hydrobromide; A-61603 hydrate

Database IDs

• MDL Number: MFCD16875412
• PubChem SID: 162247356
• PubChem CID: 57370119

CALCULATED PROPERTIES

• Acid pKa: 8.161993
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.3385881
• LogD (pH = 7.4): -0.11702238
• Log P: 0.27670437
• Molar Refractivity: 80.1479 cm^3
• Polarizability: 31.341185 Å^3
• Polar Surface Area: 90.79 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: >5 mg/mL
• Apperance: off-white powder

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C14H19N3O3S·HBr · xH2O

DETAILS

Sigma Aldrich - A5861

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.