2-(3,4-dichlorophenyl)-N-methyl-N-[(1S,2S)-2-(pyrrolidin-1-yl)cyclohexyl]acetamide hydrate hydrochloride

• ChemBase ID: 133927
• Molecular Formular: C19H29Cl3N2O2
• Molecular Mass: 423.80476
• Monoisotopic Mass: 422.12946122
• SMILES: CN([C@H]1CCCC[C@@H]1N1CCCC1)C(=O)Cc1ccc(c(c1)Cl)Cl.O.Cl
• Canonical SMILES: O=C(N([C@H]1CCCC[C@@H]1N1CCCC1)C)Cc1ccc(c(c1)Cl)Cl.O.Cl
• InChI: InChI=1S/C19H26Cl2N2O.ClH.H2O/c1-22(19(24)13-14-8-9-15(20)16(21)12-14)17-6-2-3-7-18(17)23-10-4-5-11-23;;/h8-9,12,17-18H,2-7,10-11,13H2,1H3;1H;1H2/t17-,18-;;/m0../s1
• InChIKey: UWPRPWMHQDPOFR-MPGISEFESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(3,4-dichlorophenyl)-N-methyl-N-[(1S,2S)-2-(pyrrolidin-1-yl)cyclohexyl]acetamide hydrate hydrochloride
• IUPAC Traditional name: 2-(3,4-dichlorophenyl)-N-methyl-N-[(1S,2S)-2-(pyrrolidin-1-yl)cyclohexyl]acetamide hydrate hydrochloride
• Synonyms: trans-(1S,2S)-3,4-Dichloro-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]benzeneacetamide hydrochloride hydrate; (-)-trans-(1S,2S)-U-50488 hydrochloride hydrate

Database IDs

• CAS Number: 114528-79-9(anhydrous)
• MDL Number: MFCD11044455
• PubChem SID: 24278019; 162228204
• PubChem CID: 16220065

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.8841541
• LogD (pH = 7.4): 2.0654433
• Log P: 4.2984037
• Molar Refractivity: 100.2343 cm^3
• Polarizability: 39.308075 Å^3
• Polar Surface Area: 23.55 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble13 mg/mL
• Apperance: white solid
• Optical Rotation: [α]22/D -36.05°, c = 0.73 in methanol(lit.)

Safety Information

• Storage Condition: desiccated
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... OPRK1(4986)

Product Information

• Purity: ≥98% (HPLC)

DETAILS

Sigma Aldrich - U111

Biochem/physiol Actions
Potent κ opioid receptor agonist; more potent enantiomer of (±)-trans-U-50488.