(1S,5R,13R,17S)-4-[(1-2H)cyclopropyl(2H2)methyl]-10,17-dihydroxy-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-trien-14-one

• ChemBase ID: 174948
• Molecular Formular: C20H23NO4
• Molecular Mass: 341.40092
• Monoisotopic Mass: 341.16270822
• SMILES: c1(c2c3c(cc1)C[C@@H]1[C@]4([C@@]3([C@H](C(=O)CC4)O2)CCN1CC1CC1)O)O
• Canonical SMILES: O=C1CC[C@@]2([C@@]34[C@H]1Oc1c4c(C[C@H]2N(CC3)CC2CC2)ccc1O)O
• InChI: InChI=1S/C20H23NO4/c22-13-4-3-12-9-15-20(24)6-5-14(23)18-19(20,16(12)17(13)25-18)7-8-21(15)10-11-1-2-11/h3-4,11,15,18,22,24H,1-2,5-10H2/t15-,18+,19+,20-/m1/s1
• InChIKey: DQCKKXVULJGBQN-XFWGSAIBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5R,13R,17S)-4-[(1-^2H)cyclopropyl(^2H₂)methyl]-10,17-dihydroxy-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7(18),8,10-trien-14-one
• IUPAC Traditional name: (1S,5R,13R,17S)-4-[(1-^2H)cyclopropyl(^2H₂)methyl]-10,17-dihydroxy-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7(18),8,10-trien-14-one
• Synonyms: (5α)-17-(Cyclopropyl-methyl-d3)-4,5-epoxy-3,14-dihydroxymorphinan-6-one; Antaxone-D3; Depade-D3; EN 1639A-D3; NIH 8503-D3; Nalorex-D3; Trexan-D3; Naltrexone-d3

Database IDs

• PubChem SID: 164230858
• PubChem CID: 45039987

CALCULATED PROPERTIES

• Acid pKa: 10.106068
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -1.4911842
• LogD (pH = 7.4): 0.13493212
• Log P: 1.3626752
• Molar Refractivity: 91.5015 cm^3
• Polarizability: 35.902298 Å^3
• Polar Surface Area: 70.0 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Water
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 161-166°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - N285752

Nonselective opioid receptor antagonist; congener of Naloxone.

REFERENCES

• Maickel, R.P., et al.: Ann. N.Y. Acad. Sci., 281, 321 (1976)
• Gritz, E.R., et al.: Clin. Pharmacol. Ther., 19, 773 (1976)
• Gonzales, J.P., et al.: Drugs, 35, 192 (1976)
• Berg, B.J., et al.: Drug Saf., 15, 274 (1976)