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

• ChemBase ID: 174923
• Molecular Formular: C21H25NO3
• Molecular Mass: 339.4281
• Monoisotopic Mass: 339.18344367
• SMILES: c1(c2c3c(cc1)C[C@@H]1[C@]4([C@@]3([C@H](C(=C)CC4)O2)CCN1CC1CC1)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(18),8,10-triene-10,17-diol
• IUPAC Traditional name: nalmefene
• Synonyms: (5α)-17-(Cyclopropylmethyl)-4,5-epoxy-6-methylenemorphinan-3,14-diol; (-)-Nalmefene; 6-Deoxo-6-methylenenaltrexone; 6-Desoxy-6-methylenenaltrexone; JF 1; Nalmetrene; ORF 11676; Nalmefene

Database IDs

• CAS Number: 55096-26-9
• PubChem SID: 164230833
• 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

Physical Property

• Solubility: Dichloromethane
• Apperance: Off-White Solid
• Melting Point: 182-185°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - N284400

A structural analog of Naltrexone (N285780) with opiate antagonist activity used in pharmaceutical treatment of alcoholism. Other pharmacological applications of this compound aim to reduce food cravings, drug abuse and pulmonary disease in affected indiv

REFERENCES

• Brittain, H.G., et al.: Anal. Profiles Drug Subs. Excip., 24, 351 (1996)
• Anton, R., et al.: J. Clin. Psychopharmacol., 24, 421 (1996)
• Bart, G., et al.: Neuropsychopharmacol., 30, 2254 (1996)
• Wu, X., et al.: Chem. Pharmacol. Bull., 54, 977 (1996)