2-(3,4-dichlorophenyl)-N-methyl-N-[(5R,7S,8S)-7-(pyrrolidin-1-yl)-1-oxaspiro[4.5]decan-8-yl]acetamide; methanesulfonic acid

• ChemBase ID: 134392
• Molecular Formular: C23H34Cl2N2O5S
• Molecular Mass: 521.49746
• Monoisotopic Mass: 520.15654856
• SMILES: CN([C@H]1CC[C@@]2(CCCO2)C[C@@H]1N1CCCC1)C(=O)Cc1ccc(c(c1)Cl)Cl.CS(=O)(=O)O
• Canonical SMILES: CS(=O)(=O)O.O=C(N([C@H]1CC[C@]2(C[C@@H]1N1CCCC1)CCCO2)C)Cc1ccc(c(c1)Cl)Cl
• InChI: InChI=1S/C22H30Cl2N2O2.CH4O3S/c1-25(21(27)14-16-5-6-17(23)18(24)13-16)19-7-9-22(8-4-12-28-22)15-20(19)26-10-2-3-11-26;1-5(2,3)4/h5-6,13,19-20H,2-4,7-12,14-15H2,1H3;1H3,(H,2,3,4)/t19-,20-,22-;/m0./s1
• InChIKey: FHEZDPDAYTVKKG-JLBKCEDKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(3,4-dichlorophenyl)-N-methyl-N-[(5R,7S,8S)-7-(pyrrolidin-1-yl)-1-oxaspiro[4.5]decan-8-yl]acetamide; methanesulfonic acid
• IUPAC Traditional name: methanesulfonic acid; spiradoline
• Synonyms: (±)-(5α,7α,8β)-3,4-Dichloro-N-methyl-N-[7-(1-pyrrolidinyl)-1-oxaspiro[4.5]dec-8-yl]benzeneacetamide mesylate salt; Spiradoline mesylate salt; U-62066

Database IDs

• CAS Number: 87151-85-7
• MDL Number: MFCD00153876
• PubChem SID: 24278071; 162228668
• PubChem CID: 55651

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 0.38058487
• LogD (pH = 7.4): 1.4838662
• Log P: 3.811584
• Molar Refractivity: 114.042 cm^3
• Polarizability: 44.807613 Å^3
• Polar Surface Area: 32.78 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble14 mg/mL; methanol: insoluble
• Apperance: white solid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... OPRK1(4986)

DETAILS

Sigma Aldrich - U105

Biochem/physiol Actions
Highly selective κ opioid receptor agonist; antitussive.