T5576

TMPH hydrochloride

solid, (Product is pure based on CHN, NMR and MS results)

• Synonym(s): 2,2,6,6-Tetramethylpiperidin-4-yl heptanoate hydrochloride
• Empirical Formula (Hill Notation): C₁₆H₃₂ClNO₂
• CAS Number: 849461-91-2
• Molecular Weight: 305.88
• MDL number: MFCD08277030
• UNSPSC Code: 12352200
• PubChem Substance ID: 24724633
• NACRES: NA.77

Properties

• form: solid
• storage condition: under inert gas
• color: white
• solubility: H₂O: 22 mg/mL at ~60 °C
• storage temp.: 2-8°C
• SMILES string: Cl.CCCCCCC(=O)OC1CC(C)(C)NC(C)(C)C1
• 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
• InChI key: XIDDVJIJIFWGIX-UHFFFAOYSA-N

Description

Application

Studies using TMPH have reported that it can alleviate the seizure-causing effect of levamisole. Additionally, it has been reported that TMPH does not induce behavioral changes in mice¹.

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.

Noncompetitive inhibitor of neuronal nicotinic acetylcholine receptors; potent and long-lasting inhibitor of the most abundant nAhR subtypes (α3 or α4 plus β4) with little effect on muscle type (α1β1γδ) or α7 receptors; useful tool for studying the functional roles of nAChR.

Features and Benefits

This compound is featured on the Acetylcholine Receptors (Nicotinic) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Preparation Note

TMPH hydrochloride is soluble in water at 22 mg/ml (at approx. 60° C).

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H315,H317,H319,H335
• pcodes: P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3
• target_organs: Respiratory system
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Faceshields, Gloves