(1S,5R,13R,17S)-14-{2-[(1S,5R,13R,17S)-10,17-dihydroxy-4-(prop-2-en-1-yl)-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7,9,11(18)-trien-14-ylidene]hydrazin-1-ylidene}-4-(2-methylprop-2-en-1-yl)-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-triene-10,17-diol hydrate dihydrochloride

• ChemBase ID: 153424
• Molecular Formular: C39H48Cl2N4O7
• Molecular Mass: 755.72702
• Monoisotopic Mass: 754.29000526
• SMILES: CC(=C)CN1CC[C@]23c4c5ccc(c4O[C@H]2/C(=N/N=C/2\CC[C@]4([C@H]6Cc7ccc(c8c7[C@]4([C@H]2O8)CCN6CC=C)O)O)/CC[C@]3([C@H]1C5)O)O.O.Cl.Cl
• Canonical SMILES: C=CCN1CC[C@@]23[C@@]4([C@H]1Cc1c3c(O[C@H]2/C(=N/N=C/2\CC[C@@]3([C@@]56[C@H]2Oc2c6c(C[C@H]3N(CC5)CC(=C)C)ccc2O)O)/CC4)c(cc1)O)O.O.Cl.Cl
• InChI: InChI=1S/C39H44N4O6.2ClH.H2O/c1-4-15-42-16-13-36-30-22-5-7-26(44)32(30)48-34(36)24(9-11-38(36,46)28(42)18-22)40-41-25-10-12-39(47)29-19-23-6-8-27(45)33-31(23)37(39,35(25)49-33)14-17-43(29)20-21(2)3;;;/h4-8,28-29,34-35,44-47H,1-2,9-20H2,3H3;2*1H;1H2/t28-,29-,34+,35+,36+,37+,38-,39-;;;/m1.../s1
• InChIKey: FZEFFWGHDWIOOD-UPPOQGSNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5R,13R,17S)-14-{2-[(1S,5R,13R,17S)-10,17-dihydroxy-4-(prop-2-en-1-yl)-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7,9,11(18)-trien-14-ylidene]hydrazin-1-ylidene}-4-(2-methylprop-2-en-1-yl)-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 hydrate dihydrochloride
• IUPAC Traditional name: (1S,5R,13R,17S)-14-{2-[(1S,5R,13R,17S)-10,17-dihydroxy-4-(prop-2-en-1-yl)-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7,9,11(18)-trien-14-ylidene]hydrazin-1-ylidene}-4-(2-methylprop-2-en-1-yl)-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 hydrate dihydrochloride
• Synonyms: bis[(5α)-4,5-Epoxy-3,14-dihydroxy-17-(2-propenyl)morphinan-6-ylidene]hydrazone hydrate dihydrochloride; Naloxonazine dihydrochloride hydrate

Database IDs

• CAS Number: 880759-65-9(anhydrous)
• PubChem SID: 162247563; 24278602
• PubChem CID: 71311659

CALCULATED PROPERTIES

• Acid pKa: 9.873616
• H Acceptors: 10
• H Donor: 4
• LogD (pH = 5.5): -2.5840793
• LogD (pH = 7.4): 0.76380175
• Log P: 3.0579166
• Molar Refractivity: 184.2406 cm^3
• Polarizability: 71.33238 Å^3
• Polar Surface Area: 130.58 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: >2 mg/mL
• Apperance: off-white to light tan powder

Safety Information

• Storage Condition: desiccated
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Drug Control: regulated under CDSA - not available from Sigma-Aldrich Canada
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... OPRM1(4988)

Product Information

• Purity: ≥95% (HPLC)
• Empirical Formula (Hill Notation): C38H42N4O6 · 2HCl · xH2O

DETAILS

Sigma Aldrich - N176

Biochem/physiol Actions
Potent opioid antagonist that is selective for μ1 opioid receptors.