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SML2731

Sigma-Aldrich

alpha-NETA

≥98% (HPLC)

Synonym(s):

α-NETA, 2-(alpha-Naphthoyl)ethyltrimethylammonium iodide, N,N,N-Trimethyl-γ-oxo-1-naphthalenepropanaminium iodide, N,N,N-Trimethyl-3-(naphthalen-1-yl)-3-oxopropan-1-aminium iodide, a-NETA

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About This Item

Empirical Formula (Hill Notation):
C16H20INO
CAS Number:
115066-04-1
Molecular Weight:
369.24
MDL number:
MFCD00209857
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

O=C(C1=CC=CC2=C1C=CC=C2)CC[N+](C)(C)C.[I-]

Biochem/physiol Actions

Originally identified as a substrate (ChA or choline)-noncompetitive, slowly reversible choline acetyltransferase inhibitor (human ChAT/BuChE/AChE IC50 = 88 nM/33.3 μM/48.6 μM; does not affect mAChRs, AChE, ChE, CrAT, ganglionic or skeletal muscular nAChRs), α-NETA is a fluorescent molecule (Ex 255 & 297 nm; Em 427 nm) also known for its trace amine-associated receptor 5 (TAAR5 EC50 = 150 nM) agonist and chemokine-like receptor-1 antagonist (IC50 = 375 nM; 7 nM chemerin-induced CMKLR1 β-ARR2 recruitment) potencies both in cultures and in animal disease models in vivo (3-20 mg/kg via ip. or sc. in rats & mice).

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Justine M Abais-Battad et al.
Hypertension (Dallas, Tex. : 1979), 73(2), 440-448 (2019-01-01)
Studies from our laboratory have revealed an important role for the maternal diet and the dietary protein source in the development of hypertension and renal injury in Dahl salt-sensitive (SS) rats. The current study sought to compare salt-induced hypertension, renal
Aleksander A Aleksandrov et al.
Neurotoxicity research, 34(3), 442-451 (2018-05-02)
Mismatch negativity (MMN) is a well-defined component of human event-related potentials that reflects the pre-attentive, stimulus-discrimination process and is associated with involuntary switching of attention. MMN-like responses detected in animal models provide an opportunity to investigate the neural mechanisms of
Aleksander A Aleksandrov et al.
Neuroscience letters, 704, 208-211 (2019-04-16)
It is known that trace amine-associated receptor 5 (TAAR5) is expressed in various regions of the central nervous system. However, very limited information is available on the behavioral effects of TAAR5 activation and the TAAR5 functional role, in general. We
Kareem L Graham et al.
PloS one, 9(12), e112925-e112925 (2014-12-02)
Therapies that target leukocyte trafficking pathways can reduce disease activity and improve clinical outcomes in multiple sclerosis (MS). Experimental autoimmune encephalomyelitis (EAE) is a widely studied animal model that shares many clinical and histological features with MS. Chemokine-like receptor-1 (CMKLR1)
Vineet Kumar et al.
Scientific reports, 9(1), 7178-7178 (2019-05-11)
Small molecules that disrupt leukocyte trafficking have proven effective in treating patients with multiple sclerosis (MS). We previously reported that chemerin receptor chemokine-like receptor 1 (CMKLR1) is required for maximal clinical and histological experimental autoimmune encephalomyelitis (EAE); and identified CMKLR1
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