ethyl 4-({2-[(2-methylphenyl)formamido]ethyl}amino)piperidine-1-carboxylate hydrochloride

• ChemBase ID: 154719
• Molecular Formular: C18H28ClN3O3
• Molecular Mass: 369.88622
• Monoisotopic Mass: 369.18191945
• SMILES: CCOC(=O)N1CCC(CC1)NCCNC(=O)c1ccccc1C.Cl
• Canonical SMILES: CCOC(=O)N1CCC(CC1)NCCNC(=O)c1ccccc1C.Cl
• InChI: InChI=1S/C18H27N3O3.ClH/c1-3-24-18(23)21-12-8-15(9-13-21)19-10-11-20-17(22)16-7-5-4-6-14(16)2;/h4-7,15,19H,3,8-13H2,1-2H3,(H,20,22);1H
• InChIKey: XKJQVUIXSBOCPP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 4-({2-[(2-methylphenyl)formamido]ethyl}amino)piperidine-1-carboxylate hydrochloride
• IUPAC Traditional name: ethyl 4-({2-[(2-methylphenyl)formamido]ethyl}amino)piperidine-1-carboxylate hydrochloride
• Synonyms: 4-[[2-[(2-Methylbenzoyl)amino]ethyl]amino]-1-piperidinecarboxylic Acid Ethyl Ester Hydrochloride; VU 0357017 Hydrochloride; 4-[[2-[(2-Methylbenzoyl)amino]ethyl]amino]-1-piperidinecarboxylic acid ethyl ester monohydrochloride; CID 25010775; ML071 hydrochloride; SID 56353039; VU0357017 monohydrochloride

Database IDs

• CAS Number: 1135242-13-5
• MDL Number: MFCD17215959
• PubChem SID: 162248857
• PubChem CID: 25010775

CALCULATED PROPERTIES

• Acid pKa: 15.316934
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -1.7647622
• LogD (pH = 7.4): -0.78148925
• Log P: 1.4263797
• Molar Refractivity: 93.8932 cm^3
• Polarizability: 36.0474 Å^3
• Polar Surface Area: 70.67 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥10 mg/mL
• Apperance: white to off-white powder

Safety Information

• European Hazard Symbols: Nature polluting (N)
• German water hazard class: 2
• Risk Statements: 52/53
• Safety Statements: 61
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C18H27N3O3 · HCl

DETAILS

Sigma Aldrich - V4640

Biochem/physiol Actions
VU0357017 is a subtype-selective M1 muscarinic acetylcholine allosteric agonist. VU0357017 has a potency of 200 nM and Achmax of 81% and had no activity at M2-M5 up to the highest concentrations tested and also had little or no detectable antagonist activity at any other mAChR subtype at concentrations over 2 orders of magnitude higher than those required to activate M1 or activity at a large panel of GPCRs, ion channels, and transporters. In contrast, TBPB inhibited responses to ACh at each of the other mAChR subtypes. VU0357017 was active in reversing cognitive deficits induced by scopolamine in a preclinical rodent model.

Toronto Research Chemicals - V787500

VU0357017 is a subtype-selective M1 muscarinic acetylcholine allosteric agonist. VU0357017 has a potency of 200 nM and Achmax of 81% and had no activity at M2-M5 up to the highest concentrations tested and also had little or no detectable antagonist activ

REFERENCES

• Bridges, et al.: Bioorg. Med. Chem. Lett., 20, 1972 (2010)
• Lebois, et al.: ACS Chem. Neurosci., 1, 104 (2010)