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

• ChemBase ID: 131500
• Molecular Formular: C19H22ClNO2
• Molecular Mass: 331.83648
• Monoisotopic Mass: 331.13390663
• SMILES: CCCN1CCc2cccc3c2[C@H]1Cc1c3c(c(cc1)O)O.Cl
• Canonical SMILES: CCCN1CCc2c3[C@H]1Cc1ccc(c(c1c3ccc2)O)O.Cl
• InChI: InChI=1S/C19H21NO2.ClH/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;/h3-7,15,21-22H,2,8-11H2,1H3;1H/t15-;/m1./s1
• InChIKey: PCOQOGIDTIFQAM-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-diol hydrochloride
• 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-diol hydrochloride
• Synonyms: R(-)-10,11-Dihydroxy-N-n-propylnoraporphine hydrochloride; R(-)-NPA hydrochloride; R(-)-Propylnorapomorphine hydrochloride

Database IDs

• CAS Number: 18426-20-5
• MDL Number: MFCD00069239
• PubChem SID: 24277901; 162225778
• PubChem CID: 11957529

CALCULATED PROPERTIES

• Acid pKa: 9.313709
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.181287
• LogD (pH = 7.4): 2.938351
• Log P: 3.6735916
• Molar Refractivity: 89.2607 cm^3
• Polarizability: 35.331387 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: soluble5-10 mg/mL (Solutions should be freshly prepared); alcohol: 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.); methanol: soluble5-10 mg/mL (Solutions should be freshly prepared)
• Apperance: off-white solid
• Optical Rotation: [α]22/D -70.3°, c = 0.17 in methanol(lit.)
• Absorption Wavelength: εmax/273 nm, ethanol 17,400

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 - D027

Biochem/physiol Actions
Highly potent and selective D2 dopamine receptor agonist.
Caution
Subject to rapid oxidation.