(1S,5R,13R,14R,17S)-14-[bis(2-chloroethyl)amino]-4-(cyclopropylmethyl)-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-triene-10,17-diol dihydrochloride

• ChemBase ID: 131241
• Molecular Formular: C24H34Cl4N2O3
• Molecular Mass: 540.35036
• Monoisotopic Mass: 538.13235368
• SMILES: c1cc(c2c3c1C[C@H]1[C@]4([C@]3(CCN1CC1CC1)[C@@H](O2)[C@@H](CC4)N(CCCl)CCCl)O)O.Cl.Cl
• Canonical SMILES: ClCCN([C@@H]1CC[C@@]2([C@@]34[C@H]1Oc1c4c(C[C@@H]2N(CC3)CC2CC2)ccc1O)O)CCCl.Cl.Cl
• InChI: InChI=1S/C24H32Cl2N2O3.2ClH/c25-8-11-27(12-9-26)17-5-6-24(30)19-13-16-3-4-18(29)21-20(16)23(24,22(17)31-21)7-10-28(19)14-15-1-2-15;;/h3-4,15,17,19,22,29-30H,1-2,5-14H2;2*1H/t17-,19-,22+,23+,24-;;/m1../s1
• InChIKey: JJZDLJGFHABVOM-QNWHWJQFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5R,13R,14R,17S)-14-[bis(2-chloroethyl)amino]-4-(cyclopropylmethyl)-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7(18),8,10-triene-10,17-diol dihydrochloride
• IUPAC Traditional name: chlornaltrexamine dihydrochloride
• Synonyms: β-CNA; β-Chlornaltrexamine dihydrochloride

Database IDs

• CAS Number: 67025-98-3
• PubChem SID: 162225519; 24897920
• PubChem CID: 5746034

CALCULATED PROPERTIES

• Acid pKa: 10.33189
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -0.6858119
• LogD (pH = 7.4): 0.9899718
• Log P: 2.8522837
• Molar Refractivity: 122.8123 cm^3
• Polarizability: 48.299725 Å^3
• Polar Surface Area: 56.17 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: ethanol: soluble (is stable for ca. 1 month in the freezer.); H2O: soluble (use aqueous solutions immediately.); polar organic solvents: soluble
• Apperance: white solid

Safety Information

• RTECS: QC7792000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

DETAILS

Sigma Aldrich - O001

Biochem/physiol Actions
Irreversible μ, δ and κ opioid receptor antagonist.
Caution
Hygroscopic, photosensitive.