(1S,9S,10S)-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2,4,6-trien-4-ol

• ChemBase ID: 130356
• Molecular Formular: C17H23NO
• Molecular Mass: 257.37062
• Monoisotopic Mass: 257.17796436
• SMILES: Oc1ccc2C[C@@H]3N(C)CC[C@]4(CCCC[C@H]34)c2c1
• Canonical SMILES: Oc1ccc2c(c1)[C@@]13CCCC[C@@H]3[C@H](C2)N(CC1)C
• InChI: InChI=1S/C17H23NO/c1-18-9-8-17-7-3-2-4-14(17)16(18)10-12-5-6-13(19)11-15(12)17/h5-6,11,14,16,19H,2-4,7-10H2,1H3/t14-,16+,17+/m1/s1
• InChIKey: JAQUASYNZVUNQP-PVAVHDDUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,9S,10S)-17-methyl-17-azatetracyclo[7.5.3.0^1,^1^0.0^2,^7]heptadeca-2,4,6-trien-4-ol; (1S,9S,10S)-17-methyl-17-azatetracyclo[7.5.3.0^1,^1^0.0^2,^7]heptadeca-2(7),3,5-trien-4-ol
• IUPAC Traditional name: dextrorphan; dextrorfano
• Synonyms: Dextrorphan; (+)-3-Hydroxy-17-methylmorphinan; 1,3,4,9,10,10a-Hexahydro-6-hydroxy-2H-10,4a-(iminoethano)-11-methylphenanthrene; Dextrorphan

Database IDs

• CAS Number: 125-73-5
• EC Number: 204-754-3
• MDL Number: MFCD00864199
• PubChem SID: 162224635; 24724648
• PubChem CID: 5360697
• CHEMBL: 341216
• Chemspider ID: 10489895
• Unique Ingredient Identifier: 04B7QNO9WS
• Wikipedia Title: Dextrorphan

CALCULATED PROPERTIES

• Acid pKa: 10.461597
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -0.095644645
• LogD (pH = 7.4): 0.9349801
• Log P: 2.9030437
• Molar Refractivity: 78.0809 cm^3
• Polarizability: 30.3868 Å^3
• Polar Surface Area: 23.47 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: white to off-white
• Melting Point: ≥195 °C
• Optical Rotation: [α]/D ≥+54°

Safety Information

• RTECS: QD1832000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Legal Status: unscheduled (US)
• Gene Information: human ... GRIN2A(2903)rat ... Grin2a(24409)

Product Information

• Empirical Formula (Hill Notation): C17H23NO

DETAILS

Sigma Aldrich - UC205

Application
CYP2D6 O-Demethyl metabolite of dextromethorphan