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T5576

Sigma-Aldrich

TMPH hydrochloride

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

Synonym(s):

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

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About This Item

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

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

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.

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).

pictograms

Exclamation mark
GHS07

signalword

Warning

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Ashish K Rehni et al.
Naunyn-Schmiedeberg's archives of pharmacology, 382(3), 279-285 (2010-08-10)
Levamisole produces seizures in man and is also known to activate the neuronal nicotinic acetylcholine receptors, which are further known to elicit seizure activity. Therefore, the present study has been designed to investigate the role of nicotinic acetylcholine receptor activation
Feifei Ge et al.
Molecular psychiatry, 26(3), 941-954 (2019-04-14)
Sleep is essential to emotional health. Sleep disturbance, particularly REM sleep disturbance, profoundly impacts emotion regulation, but the underlying neural mechanisms remain elusive. Here we show that chronic REM sleep disturbance, achieved in mice by chronic sleep fragmentation (SF), enhanced
Asami Tanimura et al.
Neuron, 101(3), 444-458 (2019-01-20)
The motor symptoms of Parkinson's disease (PD) are thought to stem from an imbalance in the activity of striatal direct- and indirect-pathway spiny projection neurons (SPNs). Disease-induced alterations in the activity of networks controlling SPNs could contribute to this imbalance.

Articles

Acetylcholine Receptors (Nicotinic)

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