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

• ChemBase ID: 129419
• Molecular Formular: C19H21NO4
• Molecular Mass: 327.37434
• Monoisotopic Mass: 327.14705816
• SMILES: Oc1c2c(ccc1OC)C[C@H]1c3c(cc(OC)c(O)c3)CCN1C2
• Canonical SMILES: COc1cc2CCN3[C@H](c2cc1O)Cc1c(C3)c(O)c(cc1)OC
• InChI: InChI=1S/C19H21NO4/c1-23-17-4-3-11-7-15-13-9-16(21)18(24-2)8-12(13)5-6-20(15)10-14(11)19(17)22/h3-4,8-9,15,21-22H,5-7,10H2,1-2H3/t15-/m0/s1
• InChIKey: KNWVMRVOBAFFMH-HNNXBMFYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (12bS)-3,10-dimethoxy-7,8,12b,13-tetrahydro-5H-6-azatetraphene-4,11-diol
• IUPAC Traditional name: scoulerine
• Synonyms: Discretamine; Aequaline; Scoulerin.; Scoulerine; (13aS)-5,8,13,13a-tTtrahydro-3,10-dimethoxy-6H-dibenzo[a,g]quinolizine-2,9-diol; 3,10-Dimethoxy-13aα-berbine-2,9-diol; (S)-5,8,13,13a-Tetrahydro-3,10-dimethoxy-6H-Dibenzo[a,g]quinolizine-2,9-diol; Scoulerine; (-)-Scoulerine; (S)-(-)-Scoulerine; Scoulerin; l-Scoulerine; Alkaloid HF 1, from Hunnemannia fumariaefolia; (S)-Scoulerine; (S)-(+)-5,8,13,13a-Tetrahydro-3,10-dimethoxy-6H-dibenzo[a,g]quinolizine-2,9-diol; S-(+)-Scoulerine

Database IDs

• CAS Number: 6451-73-6; 605-34-5
• PubChem SID: 162223713
• PubChem CID: 439654
• CHEBI ID: 17129
• CHEMBL: 1235966
• Chemspider ID: 388725
• Wikipedia Title: Scoulerine

CALCULATED PROPERTIES

• Acid pKa: 9.178844
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 2.070406
• LogD (pH = 7.4): 2.8212745
• Log P: 2.8561866
• Molar Refractivity: 92.3909 cm^3
• Polarizability: 35.281284 Å^3
• Polar Surface Area: 62.16 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White to Pale Pink Solid
• Melting Point: >165°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - S200805

The S-(+)-enantiomer of Scoulerine, an alkaloid found in the opium poppy.

Toronto Research Chemicals - S200800

(S)-Scoulerine is an alkaloid found in the opium poppy. (S)-Scoulerine acts as an antagonist at the α2-adrenoceptor, α1D-adrenoceptor and 5-HT receptor.

REFERENCES

• Morishige, T., et al.: Eur. J. Biochem., 269, 5659 (2002)
• Cui, W., et al.: J. Nat. Products, 70, 1771 (2002)