4-[(R)-[(2S,5R)-2,5-dimethyl-4-(prop-2-en-1-yl)piperazin-1-yl](3-methoxyphenyl)methyl]-N,N-diethylbenzamide

• ChemBase ID: 177803
• Molecular Formular: C28H39N3O2
• Molecular Mass: 449.62816
• Monoisotopic Mass: 449.3042275
• SMILES: c1cc(ccc1C(=O)N(CC)CC)[C@@H](N1[C@H](CN([C@@H](C1)C)CC=C)C)c1cccc(c1)OC
• Canonical SMILES: C=CCN1C[C@H](C)N(C[C@H]1C)[C@@H](c1cccc(c1)OC)c1ccc(cc1)C(=O)N(CC)CC
• InChI: InChI=1S/C28H39N3O2/c1-7-17-30-19-22(5)31(20-21(30)4)27(25-11-10-12-26(18-25)33-6)23-13-15-24(16-14-23)28(32)29(8-2)9-3/h7,10-16,18,21-22,27H,1,8-9,17,19-20H2,2-6H3/t21-,22+,27-/m1/s1
• InChIKey: KQWVAUSXZDRQPZ-UMTXDNHDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(R)-[(2S,5R)-2,5-dimethyl-4-(prop-2-en-1-yl)piperazin-1-yl](3-methoxyphenyl)methyl]-N,N-diethylbenzamide
• IUPAC Traditional name: 4-[(R)-[(2S,5R)-2,5-dimethyl-4-(prop-2-en-1-yl)piperazin-1-yl](3-methoxyphenyl)methyl]-N,N-diethylbenzamide
• Synonyms: (+)-4-[(αR)-α-((2S,5R)-4-Allyl-2,5-dimethyl-1-piperazinyl)-3-methoxybenzyl]-N,N-diethylbenzamide; SNC 80

Database IDs

• CAS Number: 156727-74-1
• PubChem SID: 164233713
• PubChem CID: 123924

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 2.1836271
• LogD (pH = 7.4): 3.9507227
• Log P: 4.9643393
• Molar Refractivity: 137.7661 cm^3
• Polarizability: 53.162445 Å^3
• Polar Surface Area: 36.02 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Ethyl Acetate; Hexane
• Apperance: Crystalline Solid
• Melting Point: 122-123°C

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: Store in Freezer

DETAILS

Toronto Research Chemicals - S590000

A highly selective and potent non-peptide δ-agonist, 2000-fold selective over u-receptors.

REFERENCES

• Bilsky, et al.: J. Pharmacol. Exp. Ther., 273, 359 (1995)
• Knapp, et al.: J. Pharmacol. Exp. Ther., 277, 1284 (1995)
• Calderon, S.N., et al.: J. Med. Chem., 40, 695 (1997)