(9R)-10-propyl-10-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2(7),3,5,13,15-hexaene-3,4,15-triol hydrobromide

• ChemBase ID: 132862
• Molecular Formular: C19H22BrNO3
• Molecular Mass: 392.28688
• Monoisotopic Mass: 391.07830557
• SMILES: CCCN1CCc2cc(cc3c2[C@H]1Cc1c3c(c(cc1)O)O)O.Br
• Canonical SMILES: CCCN1CCc2c3[C@H]1Cc1ccc(c(c1c3cc(c2)O)O)O.Br
• InChI: InChI=1S/C19H21NO3.BrH/c1-2-6-20-7-5-12-8-13(21)10-14-17(12)15(20)9-11-3-4-16(22)19(23)18(11)14;/h3-4,8,10,15,21-23H,2,5-7,9H2,1H3;1H/t15-;/m1./s1
• InChIKey: KIAIFHTWTMKEDI-XFULWGLBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (9R)-10-propyl-10-azatetracyclo[7.7.1.0^2,^7.0^1^3,^1^7]heptadeca-1(17),2(7),3,5,13,15-hexaene-3,4,15-triol hydrobromide
• IUPAC Traditional name: (9R)-10-propyl-10-azatetracyclo[7.7.1.0^2,^7.0^1^3,^1^7]heptadeca-1(17),2(7),3,5,13,15-hexaene-3,4,15-triol hydrobromide
• Synonyms: R(-)-2-OH-NPA HBr; R(-)-TNPA HBr; R(-)-2,10,11-Trihydroxy-N-propyl-noraporphine hydrobromide hydrate

Database IDs

• CAS Number: 79640-85-0(anhydrous)
• MDL Number: MFCD00069241
• PubChem SID: 162227139; 24277903
• PubChem CID: 10069059

CALCULATED PROPERTIES

• Acid pKa: 8.9941
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 1.1951902
• LogD (pH = 7.4): 2.9455898
• Log P: 3.30759
• Molar Refractivity: 91.2416 cm^3
• Polarizability: 35.90176 Å^3
• Polar Surface Area: 63.93 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: alcohol: soluble (Solutions should be freshly prepared.); aqueous acid: moderately soluble (Solutions should be freshly prepared); aqueous base: insoluble; H2O: moderately soluble (dissolve in oxygen-free boiled water containing 0.1% sodium metabisulfite or other antioxidants. Solutions should be freshly prepared.)
• Apperance: light brown solid
• Optical Rotation: [α]22/D -64°, c = 7 mg/mL in methanol(lit.)

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... DRD2(1813)

DETAILS

Sigma Aldrich - D030

Biochem/physiol Actions
Potent, selective D2 dopamine receptor agonist.