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T5576 Sigma-Aldrich

TMPH hydrochloride

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

  •  PubChem Substance ID 24724633

  •  NACRES NA.77

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Properties

Related Categories Antagonists, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cell Biology, Cell Signaling and Neuroscience,
Quality Level   100
assay   (Product is pure based on CHN, NMR and MS results)
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.

Packaging

5, 25 mg in glass bottle

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.

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

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).

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

Acetylcholine Receptors (Nicotinic)

Nicotinic acetylcholine receptors (nAChRs) constitute a family of ligand-gated channels, originally classified on the basis of their activation by the alkaloid nicotine, with acetylcholine (ACh) bein...
Keywords: Analgesics, Diseases, Dopamine agents, Gene expression, Genetic, Inflammation, Ligands, Microscopy, Neurotransmission, Neurotransmitters, Scanning electron microscopy, Schizophrenia, Tissue microarrays, Transduction

Peer-Reviewed Papers
15

References

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