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TMPH hydrochloride

SIGMA/T5576 - solid, (Product is pure based on CHN, NMR and MS results)

Synonym: 2,2,6,6-Tetramethylpiperidin-4-yl heptanoate hydrochloride

CAS Number: 849461-91-2
Empirical Formula (Hill Notation): C16H32ClNO2
Molecular Weight: 305.88
MDL Number: MFCD08277030
Linear Formula: C16H32ClNO2
Product Type: Chemical
Catalog Number PKG Qty. Price Quantity
45-T5576-5MG 5 mg
 $199.00
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color white
form solid
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
Quality Level 100 
SMILES string Cl.CCCCCCC(=O)OC1CC(C)(C)NC(C)(C)C1
solubility H2O: 22 mg/mL at ~60 °C
storage condition under inert gas
storage temp. 2-8°C
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.
Biochem/physiol Actions: 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 .
Packaging: 5, 25 mg in glass bottle
Preparation Note: TMPH hydrochloride is soluble in water at 22 mg/ml (at approx. 60° C).
Storage Temp. 2-8°C
UNSPSC 12352200

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