(9R,13S,14R,18S)-13-ethyl-8-methyl-8,15-diazahexacyclo[14.2.1.01,9.02,7.010,15.012,17]nonadeca-2(7),3,5-triene-14,18-diol

• ChemBase ID: 159603
• Molecular Formular: C20H26N2O2
• Molecular Mass: 326.43264
• Monoisotopic Mass: 326.19942808
• SMILES: c12c(N([C@@H]3C41CC1N5C3CC(C1[C@@H]4O)[C@@H]([C@H]5O)CC)C)cccc2
• Canonical SMILES: CC[C@H]1C2CC3N([C@@H]1O)C1C2[C@H](O)C2([C@H]3N(C)c3c2cccc3)C1
• InChI: InChI=1S/C20H26N2O2/c1-3-10-11-8-14-17-20(12-6-4-5-7-13(12)21(17)2)9-15(16(11)18(20)23)22(14)19(10)24/h4-7,10-11,14-19,23-24H,3,8-9H2,1-2H3/t10-,11?,14?,15?,16?,17-,18-,19+,20?/m0/s1
• InChIKey: CJDRUOGAGYHKKD-GNTWRGKJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (9R,13S,14R,18S)-13-ethyl-8-methyl-8,15-diazahexacyclo[14.2.1.0^1,^9.0^2,^7.0^1^0,^1^5.0^1^2,^1^7]nonadeca-2(7),3,5-triene-14,18-diol
• IUPAC Traditional name: (9R,13S,14R,18S)-13-ethyl-8-methyl-8,15-diazahexacyclo[14.2.1.0^1,^9.0^2,^7.0^1^0,^1^5.0^1^2,^1^7]nonadeca-2(7),3,5-triene-14,18-diol
• Synonyms: Takycor; Ajmaline; (17R,21α-Ajmalan-17,21-diol; (+)-Ajmaline; Cardiorythmine; Gilurytmal; Ignazin; Merabitol; NSC 15627; Raugalline; Rauwolfin; Rauwolfine; Rhytmaton; Ritmos; Rytmalin; Siddiqui; Tachmalin

Database IDs

• CAS Number: 4360-12-7
• PubChem SID: 162253738
• PubChem CID: 71313058

CALCULATED PROPERTIES

• Acid pKa: 13.280155
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.1535305
• LogD (pH = 7.4): 1.6402448
• Log P: 1.8508078
• Molar Refractivity: 92.5658 cm^3
• Polarizability: 36.288525 Å^3
• Polar Surface Area: 46.94 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO
• Apperance: White Solid
• Melting Point: 135-140°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A448000

An antiarrhythmic agent isolated from Rauwolfia serpentina.

REFERENCES

• Galarreta, B., et al.: Bioorg. Med. Chem., 16, 6689 (2008)
• Sun, L., et al.: Plant Mol. Biol., 67, 455 (2008)
• Ruiz-May, E., et al.: Mol. Biotechnol., 41, 278 (2008)