9-butyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-yl (2S)-3-hydroxy-2-phenylpropanoate hydrochloride

• ChemBase ID: 163477
• Molecular Formular: C20H28ClNO4
• Molecular Mass: 381.89362
• Monoisotopic Mass: 381.17068606
• SMILES: Cl.O(C(=O)[C@@H](c1ccccc1)CO)C1CC2C3C(C(N2CCCC)C1)O3
• Canonical SMILES: CCCCN1C2CC(CC1C1C2O1)OC(=O)[C@@H](c1ccccc1)CO.Cl
• InChI: InChI=1S/C20H27NO4.ClH/c1-2-3-9-21-16-10-14(11-17(21)19-18(16)25-19)24-20(23)15(12-22)13-7-5-4-6-8-13;/h4-8,14-19,22H,2-3,9-12H2,1H3;1H/t14?,15-,16?,17?,18?,19?;/m1./s1
• InChIKey: SSLCPCNDUBUVAN-FDOJSRBYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 9-butyl-3-oxa-9-azatricyclo[3.3.1.0^2,^4]nonan-7-yl (2S)-3-hydroxy-2-phenylpropanoate hydrochloride
• IUPAC Traditional name: 9-butyl-3-oxa-9-azatricyclo[3.3.1.0^2,^4]nonan-7-yl (2S)-3-hydroxy-2-phenylpropanoate hydrochloride
• Synonyms: [7(S)-(1α2β,4β,5α,7β)]-α-(Hydroxymethyl)benzeneacetic Acid; 9-Butyl-3-oxa-9-azatricyclo[3.3.1.02,4]non-7-yl Ester Hydrochloride; 8-Butyl-6β,7β-epoxy-1αH,5αH-nortropan-3α-ol (-)-Tropate Ester Hydrochloride; N-Butylnorhyoscine Hydrochloride; N-Butylnorscopolamine Hydrochloride; N-Butyl Nor Scopolamine Hydrochloride

Database IDs

• CAS Number: 22235-98-9
• PubChem SID: 162257612
• PubChem CID: 71314450

CALCULATED PROPERTIES

• Acid pKa: 15.14574
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 0.0479939
• LogD (pH = 7.4): 1.7501806
• Log P: 2.2188513
• Molar Refractivity: 93.5949 cm^3
• Polarizability: 37.528797 Å^3
• Polar Surface Area: 62.3 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - B693580

An N-alkyl derivatives of (-)-Norscopolamine, useful as central anticholinergics and spasmolytics.

REFERENCES

• Banholzer, R., et al.: Arzneim.-Forsch., 35(1A), 217 (1985)