(1R)-1-{[(2S,3R,11bS)-3-ethyl-9,10-dimethoxy-1H,2H,3H,4H,6H,7H,11bH-pyrido[2,1-a]isoquinolin-2-yl]methyl}-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

• ChemBase ID: 167981
• Molecular Formular: C29H40N2O4
• Molecular Mass: 480.6389
• Monoisotopic Mass: 480.29880777
• SMILES: [C@H]1([C@H](CN2[C@@H](C1)c1c(CC2)cc(c(c1)OC)OC)CC)C[C@H]1NCCc2c1cc(c(c2)OC)OC
• Canonical SMILES: CC[C@H]1CN2CCc3c([C@@H]2C[C@@H]1C[C@H]1NCCc2c1cc(OC)c(c2)OC)cc(c(c3)OC)OC
• InChI: InChI=1S/C29H40N2O4/c1-6-18-17-31-10-8-20-14-27(33-3)29(35-5)16-23(20)25(31)12-21(18)11-24-22-15-28(34-4)26(32-2)13-19(22)7-9-30-24/h13-16,18,21,24-25,30H,6-12,17H2,1-5H3/t18-,21-,24+,25-/m0/s1
• InChIKey: AUVVAXYIELKVAI-CKBKHPSWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R)-1-{[(2S,3R,11bS)-3-ethyl-9,10-dimethoxy-1H,2H,3H,4H,6H,7H,11bH-pyrido[2,1-a]isoquinolin-2-yl]methyl}-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
• IUPAC Traditional name: emetine
• Synonyms: 6',7',10,11-Tetramethoxy-emetan; Emetine; (-)-Emetine; Cephaeline Methyl Ether; Emetin; NSC 33669; (2S,3R,11bS)-3-Ethyl-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2-[[(1R)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-isoquinolinyl]methyl]-2H-benzo[a]quinolizine.; Emetine (>90%); emetine

Database IDs

• CAS Number: 483-18-1
• PubChem SID: 162262113
• PubChem CID: 10219

CALCULATED PROPERTIES

• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): -1.1466281
• LogD (pH = 7.4): 1.8145052
• Log P: 4.488257
• Molar Refractivity: 139.7507 cm^3
• Polarizability: 54.64073 Å^3
• Polar Surface Area: 52.19 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Brown Solid
• Melting Point: 89-96°C

Safety Information

• Storage Condition: -20°C Freezer

Pharmacology Properties

• Target: Others

Product Information

• Salt Data: Free Base

DETAILS

Toronto Research Chemicals - E521530

Emetine is the principal alkaloid of ipecac, the ground roots of Uragoga ipecacuanha.

REFERENCES

• Nomura, T. et. al.: J. Biol. Chem. 285, 7722 (2010)