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P207

Sigma-Aldrich

Philanthotoxin 433 tris(trifluoroacetate) salt

≥98% (HPLC), powder

Synonym(s):

(S)-N-[4-[[3-[(3-Aminopropyl)amino]propyl]amino]butyl]-4-hydroxy-α-[(1-oxobutyl)amino]benzenepropanamide tris(trifluoroacetate) salt, PhTX-433 tris(trifluoroacetate) salt

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About This Item

Empirical Formula (Hill Notation):
C23H41N5O3 · 3C2HF3O2
CAS Number:
Molecular Weight:
777.67
MDL number:
UNSPSC Code:
12352202
PubChem Substance ID:

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

H2O: ≥10 mg/mL

storage temp.

−20°C

SMILES string

OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.CCCC(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)NCCCCNCCCNCCCN

InChI

1S/C23H41N5O3.3C2HF3O2/c1-2-7-22(30)28-21(18-19-8-10-20(29)11-9-19)23(31)27-17-4-3-13-25-15-6-16-26-14-5-12-24;3*3-2(4,5)1(6)7/h8-11,21,25-26,29H,2-7,12-18,24H2,1H3,(H,27,31)(H,28,30);3*(H,6,7)/t21-;;;/m0.../s1

InChI key

UROZAUWUTBOQNV-YDULTXHLSA-N

Gene Information

human ... GRIN1(2902)
mouse ... GRIN1(14810)
rat ... GRIN1(24408)

Biochem/physiol Actions

Philanthotoxin 433 is a polyamine-containing toxin, which blocks NMDA-gated ion channels; originally isolated from the venom of the wasp Philanthus triangulum.

Caution

hygroscopic

Reconstitution

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

Legal Information

Sold under license from Columbia University.

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, 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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P T Brackley et al.
The Journal of pharmacology and experimental therapeutics, 266(3), 1573-1580 (1993-09-01)
Antagonism of rat excitatory amino acid receptors by a synthetic analog [philanthotoxin-343 (PhTX-343)] of a polyamine amide, wasp toxin (philanthotoxin-433) and a structurally related spider toxin, argiotoxin-636 (ArgTX-636), was examined in Xenopus oocytes injected with rat brain RNA or RNA
J A Benson et al.
Comparative biochemistry and physiology. C, Comparative pharmacology and toxicology, 102(2), 267-272 (1992-06-01)
1. The blocking action of delta-philanthotoxin (PhTX-4.3.3), a wasp toxin composed of a polyamine chain, an aromatic amino acid (tyrosyl) nucleus and an aliphatic (butanoic) acid was studied, together with 33 structural analogues, at the glutamatergic neuromuscular synapse in larvae
H Karst et al.
European journal of pharmacology, 270(4), 357-360 (1994-08-03)
The wasp venom philanthotoxin-4.3.3 (PhTX-4.3.3) is an antagonist of glutamate transmission in the insect as well as in the mammalian brain. It was recently shown that PhTX-4.3.3 inhibits the N-methyl-D-aspartate (NMDA) transmission in rat hippocampus. In this study we show
Achmed Mrestani et al.
Cell reports, 37(1), 109770-109770 (2021-10-06)
Neurotransmitter release is stabilized by homeostatic plasticity. Presynaptic homeostatic potentiation (PHP) operates on timescales ranging from minute- to life-long adaptations and likely involves reorganization of presynaptic active zones (AZs). At Drosophila melanogaster neuromuscular junctions, earlier work ascribed AZ enlargement by
Yuan Ge et al.
Nature communications, 10(1), 4089-4089 (2019-09-11)
The α-amino-3-hydroxy-5-methylisoxazole-4-propionic acid subtype glutamate receptors (AMPARs) mediate the fast excitatory synaptic transmission in the mammalian brain and are important for synaptic plasticity. In particular, the rapid insertion of the GluA1 homomeric (GluA1-homo) AMPARs into the postsynaptic membrane is considered

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