(12bS)-3,4,10,11-tetramethoxy-7,8,12b,13-tetrahydro-5H-6-azatetraphene

• ChemBase ID: 177629
• Molecular Formular: C21H25NO4
• Molecular Mass: 355.4275
• Monoisotopic Mass: 355.17835829
• SMILES: c1c(c(c2c(c1)C[C@@H]1N(C2)CCc2c1cc(c(c2)OC)OC)OC)OC
• Canonical SMILES: COc1cc2CCN3[C@H](c2cc1OC)Cc1c(C3)c(OC)c(cc1)OC
• InChI: InChI=1S/C21H25NO4/c1-23-18-6-5-13-9-17-15-11-20(25-3)19(24-2)10-14(15)7-8-22(17)12-16(13)21(18)26-4/h5-6,10-11,17H,7-9,12H2,1-4H3/t17-/m0/s1
• InChIKey: AEQDJSLRWYMAQI-KRWDZBQOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (12bS)-3,4,10,11-tetramethoxy-7,8,12b,13-tetrahydro-5H-6-azatetraphene
• IUPAC Traditional name: tetrahydropalmatine
• Synonyms: (13aS)-5,8,13,13a-Tetrahydro-2,3,9,10-tetramethoxy-6H-dibenzo[a,g]quinolizine; O,O-Dimethyl-N-demethyl-cyclanoline; Gindarine; (-)-2,3,9,10-Tetramethoxyberbine; (-)-Corydalis B; (-)-S-Tetrahydropalmatine; (-)-Tetrahydropalmatine; (S)-Tetrahydropalmatine; Caseanine; Hyndarine; N-Demethyl-O,O'-dimethylcyclanoline; N-Demethyl-O,O'-dimethylsteponine; THP; Rotundine; Tetrahydropalmatine

Database IDs

• CAS Number: 483-14-7
• PubChem SID: 164233539
• PubChem CID: 72301

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 2.8399758
• LogD (pH = 7.4): 3.142365
• Log P: 3.1479747
• Molar Refractivity: 101.3555 cm^3
• Polarizability: 39.105385 Å^3
• Polar Surface Area: 40.16 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Off-White Solid; Powder
• Melting Point: 141-143°C

Safety Information

• Storage Condition: Refrigerator

Pharmacology Properties

• Target: Dopamine Receptor

Product Information

• Salt Data: Free Base

DETAILS

Toronto Research Chemicals - R700760

An analgesic drug found in Chinese herbal medicine, used to treat heart disease and liver damage.

REFERENCES

• Xi, Z., et al.: Neuropharmacol., 53, 771 (2007)
• Rao, G., et al.: J. Ethnopharmacol., 123, 1 (2007)
• Wang, C., et al.: Toxicol. Lett., 194, 8 (2007)