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P206

Philanthotoxin 343 tris(trifluoroacetate) salt

solid

Synonym(s):

PhTX-343, S-N-[3-[[4-[(3-Aminopropyl)amino]butyl]amino]propyl]-4-hydroxy-α-[(1-oxobutyl)amino]-benzenepropanamide tris-trifluoroacetate

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About This Item

Empirical Formula (Hill Notation):
C23H41N5O3 · 3C2HF3O2
CAS Number:
115976-93-7
Molecular Weight:
777.67
UNSPSC Code:
12352200
PubChem Substance ID:
24898266
MDL number:
MFCD00661073
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form

solid

color

light yellow-green

solubility

methanol: >8 mg/mL (solutions should be freshly prepared.)

storage temp.

−20°C

SMILES string

OS(=O)(=O)C(F)(F)F.OS(=O)(=O)C(F)(F)F.OS(=O)(=O)C(F)(F)F.CCCC(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)NCCCNCCCCNCCCN

InChI

1S/C23H41N5O3.3CHF3O3S/c1-2-7-22(30)28-21(18-19-8-10-20(29)11-9-19)23(31)27-17-6-16-26-14-4-3-13-25-15-5-12-24;3*2-1(3,4)8(5,6)7/h8-11,21,25-26,29H,2-7,12-18,24H2,1H3,(H,27,31)(H,28,30);3*(H,5,6,7)/t21-;;;/m0.../s1

InChI key

QTCLKBFOFGTNMC-YDULTXHLSA-N

Gene Information

rat ... Chrm2(81645), Chrm3(24260)

Application

Philanthotoxin 343 tris(trifluoroacetate) salt has been used as Ca2+-permeable α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptors (AMPARs) blocker. It has also been used as an effective glutamate receptors blocker in an acute homeostasis paradigm to examine the speed of the Neto-α-mediated homeostatic response in Drosophila.

Biochem/physiol Actions

Blocks NMDA-gated ion channels; synthetic analog of the wasp polyamine amide toxin δ-philanthotoxin.
Philanthotoxin 343 is a synthetic analog of the wasp polyamine amide toxin δ-philanthotoxin. It blocks the activation of ionotropic receptors such as acetylcholine receptor (AChR) or inhibitory glutamate receptors (iGluRs).

Preparation Note

Addition of 1 mL of solvent to vial yields a 1 mM solution.

Legal Information

Sold under license from Columbia University.

Disclaimer

Hygroscopic

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
021K4701

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Sidsel Frølund et al.
Journal of medicinal chemistry, 53(20), 7441-7451 (2010-09-30)
An array of analogues of the wasp toxin philanthotoxin-433, in which the asymmetric polyamine moiety was exchanged for spermine and the headgroup replaced with a variety of structurally diverse moieties, was prepared using parallel solid-phase synthesis approaches. In three analogues
A light switch controlling Ca2+-permeable AMPA receptors in the retina.
Jeffrey S Diamond
The Journal of physiology, 582(Pt 1), 3-3 (2007-04-28)
D Bowie et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 18(20), 8175-8185 (1998-10-08)
The mechanisms by which polyamines block AMPA and kainate receptors are not well understood, but it has been generally assumed that they act as open-channel blockers. Consistent with this, voltage-jump relaxation analysis of GluR6 equilibrium responses to domoate could be
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