(1R,6R,8R)-6-tert-butyl-3-azapentacyclo[11.8.1.03,8.09,22.016,21]docosa-9,11,13(22),16,18,20-hexaen-6-ol hydrochloride

• ChemBase ID: 134361
• Molecular Formular: C25H32ClNO
• Molecular Mass: 397.98068
• Monoisotopic Mass: 397.21724233
• SMILES: CC(C)(C)[C@]1(CCN2C[C@@H]3c4ccccc4CCc4c3c(ccc4)[C@H]2C1)O.Cl
• Canonical SMILES: O[C@@]1(CCN2[C@H](C1)c1cccc3c1[C@H](C2)c1ccccc1CC3)C(C)(C)C.Cl
• InChI: InChI=1S/C25H31NO.ClH/c1-24(2,3)25(27)13-14-26-16-21-19-9-5-4-7-17(19)11-12-18-8-6-10-20(23(18)21)22(26)15-25;/h4-10,21-22,27H,11-16H2,1-3H3;1H/t21-,22-,25-;/m1./s1
• InChIKey: QZRUMKUMFJJARD-OMMJFLKZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,6R,8R)-6-tert-butyl-3-azapentacyclo[11.8.1.0^3,^8.0^9,^2^2.0^1^6,^2^1]docosa-9,11,13(22),16,18,20-hexaen-6-ol hydrochloride
• IUPAC Traditional name: (1R,6R,8R)-6-tert-butyl-3-azapentacyclo[11.8.1.0^3,^8.0^9,^2^2.0^1^6,^2^1]docosa-9,11,13(22),16,18,20-hexaen-6-ol hydrochloride
• Synonyms: (-)-Butaclamol hydrochloride

Database IDs

• CAS Number: 55528-08-0
• MDL Number: MFCD00082308
• PubChem SID: 24893227; 162228637
• PubChem CID: 37460

CALCULATED PROPERTIES

• Acid pKa: 14.282906
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.5768733
• LogD (pH = 7.4): 2.922157
• Log P: 4.9403243
• Molar Refractivity: 112.1835 cm^3
• Polarizability: 43.63721 Å^3
• Polar Surface Area: 23.47 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble5.4 mg/mL; alcohol-water mixtures: soluble (Dissolve solid in alcohol and dilute with water.); ethanol: soluble1 mg/mL; H2O: soluble0.25 mg/mL
• Apperance: white solid
• Optical Rotation: [α]27/D -222° in methanol(lit.)

Safety Information

• RTECS: DE8039700
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

DETAILS

Sigma Aldrich - D034

Biochem/physiol Actions
Dopamine receptor antagonist; less active enantiomer.