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SML1711

Sigma-Aldrich

TNCA

≥98% (HPLC)

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Synonym(s):
(3S)-2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid, L-1,2,3,4-Tetrahydronorharman-3-carboxylic acid, Lycoperodine-1
Empirical Formula (Hill Notation):
C12H12N2O2
CAS Number:
42438-90-4
Molecular Weight:
216.24
MDL number:
MFCD00272641
UNSPSC Code:
12352200
PubChem Substance ID:
329826033
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

optical activity

[α]/D -57 to -67°, c = 1 (in MeOH:1N HCl (1:1))

color

white to beige

solubility

1.5 mg/mL, clear (Solvent: 0.1N HCl:DMSO (1:1); warmed)

storage temp.

−20°C

SMILES string

O=C(O)[C@H]1NCC2=C(C3=C(N2)C=CC=C3)C1

InChI

1S/C12H12N2O2/c15-12(16)10-5-8-7-3-1-2-4-9(7)14-11(8)6-13-10/h1-4,10,13-14H,5-6H2,(H,15,16)/t10-/m0/s1

InChI key

FSNCEEGOMTYXKY-JTQLQIEISA-N

Biochem/physiol Actions

TNCA is a tryptophan derivative that binds the parathyroid Ca2+-sensing receptor (CaSR) extracellular domain (ECD) hinge region between two globular subdomains and acts as a high-affinity CaSR ligand (CaSRL) with co-agonist activity. TNCA is shown to potentiate both Mg++- and Ca++-evoked cellular calcium response (0.1-0.5 mM), as well as Mg++-evoked cellular ERK1/2 phosphorylation in CaSR-expressing HEK293 cells (0.5 mM). AC-265347 (Cat. No. SML0129), on the other hand, is a calcimimetic that functions as a CaSR agonist.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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