(1S,5R,13S,17S)-4-(cyclopropylmethyl)-14-methylidene-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7,9,11(18)-triene-10,17-diol

• ChemBase ID: 131533
• Molecular Formular: C21H25NO3
• Molecular Mass: 339.4281
• Monoisotopic Mass: 339.18344367
• SMILES: C=C1CC[C@]2([C@@H]3Cc4ccc(c5c4[C@]2([C@H]1O5)CCN3CC1CC1)O)O
• Canonical SMILES: C=C1CC[C@@]2([C@@]34[C@H]1Oc1c4c(C[C@@H]2N(CC3)CC2CC2)ccc1O)O
• InChI: InChI=1S/C21H25NO3/c1-12-6-7-21(24)16-10-14-4-5-15(23)18-17(14)20(21,19(12)25-18)8-9-22(16)11-13-2-3-13/h4-5,13,16,19,23-24H,1-3,6-11H2/t16-,19+,20+,21-/m1/s1
• InChIKey: WJBLNOPPDWQMCH-MBPVOVBZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5R,13S,17S)-4-(cyclopropylmethyl)-14-methylidene-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7,9,11(18)-triene-10,17-diol
• IUPAC Traditional name: nalmefene
• Synonyms: (5α)-17-(Cyclopropylmethyl)-4,5-epoxy-6-methylenemorphinan-3,14-diol; Nalmefene

Database IDs

• CAS Number: 55096-26-9
• MDL Number: MFCD00133650
• PubChem SID: 162225811; 24897753
• PubChem CID: 5284594

CALCULATED PROPERTIES

• Acid pKa: 10.35208
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -1.0076869
• LogD (pH = 7.4): 0.067021266
• Log P: 1.9476479
• Molar Refractivity: 95.2095 cm^3
• Polarizability: 37.331768 Å^3
• Polar Surface Area: 52.93 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: rat ... Oprd1(24613), Oprm1(25601)

DETAILS

Sigma Aldrich - N5770

Biochem/physiol Actions
Nonselective opioid receptor antagonist.