2,2,6,6-tetramethylpiperidin-4-yl heptanoate hydrochloride

• ChemBase ID: 153937
• Molecular Formular: C16H32ClNO2
• Molecular Mass: 305.88378
• Monoisotopic Mass: 305.21215695
• SMILES: CCCCCCC(=O)OC1CC(NC(C1)(C)C)(C)C.Cl
• Canonical SMILES: CCCCCCC(=O)OC1CC(C)(C)NC(C1)(C)C.Cl
• InChI: InChI=1S/C16H31NO2.ClH/c1-6-7-8-9-10-14(18)19-13-11-15(2,3)17-16(4,5)12-13;/h13,17H,6-12H2,1-5H3;1H
• InChIKey: XIDDVJIJIFWGIX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,2,6,6-tetramethylpiperidin-4-yl heptanoate hydrochloride
• IUPAC Traditional name: 2,2,6,6-tetramethylpiperidin-4-yl heptanoate hydrochloride
• Synonyms: 2,2,6,6-Tetramethylpiperidin-4-yl heptanoate hydrochloride; TMPH hydrochloride

Database IDs

• CAS Number: 849461-91-2
• MDL Number: MFCD08277030
• PubChem SID: 162248076; 24724633
• PubChem CID: 16079014

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.20716822
• LogD (pH = 7.4): 0.6453654
• Log P: 3.4394205
• Molar Refractivity: 78.7141 cm^3
• Polarizability: 31.763924 Å^3
• Polar Surface Area: 38.33 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble22 mg/mL at ~60 °C
• Apperance: white solid

Safety Information

• Storage Condition: under inert gas
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38-43
• Safety Statements: 26-36/37
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H317-H319-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: (Product is pure based on CHN, NMR and MS results)
• Empirical Formula (Hill Notation): C16H32ClNO2

DETAILS

Sigma Aldrich - T5576

Biochem/physiol Actions
2,2,6,6-tetramethylpiperidin-4-yl heptanoate (TMPH) is a potent inhibitor of neuronal nicotinic receptors. Evaluation of nicotinic acetylcholine receptor (nAChR) subunits expressed in Xenopus laevis oocytes indicated that TMPH can produce a potent and long-lasting inhibition of neuronal nAChR formed by the pairwise combination of the most abundant neuronal alpha (i.e., alpha3 and alpha4) and beta subunits (beta2 and beta4), with relatively little effect, because of rapid reversibility of inhibition, on muscle-type (alpha1beta1gammadelta) or alpha7 receptors. However, the inhibition of neuronal beta subunit-containing receptors was also decreased if any of the nonessential subunits alpha5, alpha6, or beta3 were coexpressed. This decrease in inhibition is shown to be associated with a single amino acid present in the second transmembrane domain of these subunits. TMPH abilitty to relate the diverse central nervous system effects to specific nAChR subtypes makes it a useful tool for studying the functional roles of nAChR.