2-(3,4-dichlorophenyl)-N-[(2S)-1-(2,5-dihydro-1H-pyrrol-1-yl)-3-methylbutan-2-yl]-N-methylacetamide hydrochloride

• ChemBase ID: 154351
• Molecular Formular: C18H25Cl3N2O
• Molecular Mass: 391.7629
• Monoisotopic Mass: 390.10324647
• SMILES: CC(C)[C@@H](CN1CC=CC1)N(C)C(=O)Cc1ccc(c(c1)Cl)Cl.Cl
• Canonical SMILES: CC([C@H](N(C(=O)Cc1ccc(c(c1)Cl)Cl)C)CN1CC=CC1)C.Cl
• InChI: InChI=1S/C18H24Cl2N2O.ClH/c1-13(2)17(12-22-8-4-5-9-22)21(3)18(23)11-14-6-7-15(19)16(20)10-14;/h4-7,10,13,17H,8-9,11-12H2,1-3H3;1H/t17-;/m1./s1
• InChIKey: WOOCHAFXTYNYQE-UNTBIKODSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(3,4-dichlorophenyl)-N-[(2S)-1-(2,5-dihydro-1H-pyrrol-1-yl)-3-methylbutan-2-yl]-N-methylacetamide hydrochloride
• IUPAC Traditional name: 2-(3,4-dichlorophenyl)-N-[(2S)-1-(2,5-dihydropyrrol-1-yl)-3-methylbutan-2-yl]-N-methylacetamide hydrochloride
• Synonyms: 2-(3,4-Dichlorophenyl)-N-methyl-N-[(1S)-1-(2-isopropyl)-2-(1-(3-pyrrolinyl))ethyl]acetamide hydrochloride; LPK-26

Database IDs

• CAS Number: 492451-07-7
• MDL Number: MFCD11114388
• PubChem SID: 162248490
• PubChem CID: 71311846

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.2469591
• LogD (pH = 7.4): 2.9948277
• Log P: 4.1378984
• Molar Refractivity: 98.3739 cm^3
• Polarizability: 37.950047 Å^3
• Polar Surface Area: 23.55 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: >10 mg/mL
• Apperance: off-white powder

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36/37
• 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

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C18H24Cl2N2O · HCl

DETAILS

Sigma Aldrich - L3669

Biochem/physiol Actions
LPK-26 is an analog of ICI-199441 and (-)U50,488H (classic kappa agonists). It has extremely high kappa affinity (0.64 nM) and low mu and delta receptor affnities (1170 and 10,000nM). LPK-26 produces an antinocicpetive effect with much higher potency in vivo than morphine or U50488. LPK-26 does not produce physical dependence in mice, but it does suppress naloxone-induced behavioral effects in mice treated with morphine.