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

• ChemBase ID: 130897
• Molecular Formular: C19H20BrNO2
• Molecular Mass: 374.2716
• Monoisotopic Mass: 373.06774089
• SMILES: C=CCN1CCc2cccc3c2[C@H]1Cc1c3c(c(cc1)O)O.Br
• Canonical SMILES: C=CCN1CCc2c3[C@H]1Cc1ccc(c(c1c3ccc2)O)O.Br
• InChI: InChI=1S/C19H19NO2.BrH/c1-2-9-20-10-8-12-4-3-5-14-17(12)15(20)11-13-6-7-16(21)19(22)18(13)14;/h2-7,15,21-22H,1,8-11H2;1H/t15-;/m1./s1
• InChIKey: LRQIVCBYMGMPLT-XFULWGLBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (9R)-10-(prop-2-en-1-yl)-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-diol hydrobromide
• IUPAC Traditional name: (9R)-10-(prop-2-en-1-yl)-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-diol hydrobromide
• Synonyms: R(-)-N-Allylnorapomorphine hydrobromide

Database IDs

• CAS Number: 18426-17-0
• MDL Number: MFCD00069247
• PubChem SID: 162225175; 24277905
• PubChem CID: 11957524

CALCULATED PROPERTIES

• Acid pKa: 9.24679
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.8602185
• LogD (pH = 7.4): 3.4791894
• Log P: 3.6865282
• Molar Refractivity: 89.1508 cm^3
• Polarizability: 35.097996 Å^3
• Polar Surface Area: 43.7 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 0.1 M HCl: soluble (Solutions should be freshly prepared.); 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble1.6 mg/mL (Solutions should be freshly prepared.); ethanol: slightly soluble (Solutions should be freshly prepared.); H2O: soluble0.29 mg/mL
• Apperance: tan
• Optical Rotation: [α]25/D -46.8°, c = 0.5 in H2O(lit.)

Safety Information

• German water hazard class: 3
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... DRD1(1812), DRD2(1813), DRD3(1814), DRD4(1815), DRD5(1816)

DETAILS

Sigma Aldrich - D042

Caution
Photosensitive. Reseal vial under argon or nitrogen to maximize stability.
Biochem/physiol Actions
Dopamine receptor agonist; intermediate for the preparation of tritium or deuterium labeled R(-)-N-propylnorapomorphine.