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93750

Sigma-Aldrich

(+)-Tubocurarine chloride pentahydrate

≥97.0% (TLC)

Sinónimos:

(+)-Tubocurarine chloride hydrochloride pentahydrate, D-Tubocurarine dichloride pentahydrate, Tubarine pentahydrate

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About This Item

Fórmula empírica (notación de Hill):
C37H42Cl2N2O6 · 5H2O
Número de CAS:
6989-98-6
Peso molecular:
771.72
Beilstein/REAXYS Number:
3896374
MDL number:
MFCD00150157
UNSPSC Code:
12352202
PubChem Substance ID:
57653575
NACRES:
NA.77

biological source

plant

assay

≥97.0% (TLC)

form

powder

optical activity

[α]20/D +195±5°, c = 0.5% in H2O

impurities

~12% water

mp

275-280 °C (dec.) (lit.)

storage temp.

2-8°C

SMILES string

[Cl-].Cl[H].[H]O[H].[H]O[H].[H]O[H].[H]O[H].[H]O[H].COc1cc2CCN(C)[C@H]3Cc4ccc(Oc5c(O)c(OC)cc6CC[N+](C)(C)[C@H](Cc7ccc(O)c(Oc1cc23)c7)c56)cc4

InChI

1S/C37H40N2O6.2ClH.5H2O/c1-38-14-12-24-19-32(42-4)33-21-27(24)28(38)16-22-6-9-26(10-7-22)44-37-35-25(20-34(43-5)36(37)41)13-15-39(2,3)29(35)17-23-8-11-30(40)31(18-23)45-33;;;;;;;/h6-11,18-21,28-29H,12-17H2,1-5H3,(H-,40,41);2*1H;5*1H2/t28-,29+;;;;;;;/m0......./s1

InChI key

WMIZITXEJNQAQK-GGDSLZADSA-N

Gene Information

human ... CHRNA1(1134) , CHRNB1(1140) , CHRND(1144) , CHRNE(1145) , CHRNG(1146)

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Application

(+)-Tubocurarine chloride pentahydrate has been used:
  • as an acetylcholine receptor antagonist in synapse blocking experiment to study its effect on neuromuscular junction formation (NMJ) formation in a co-culture system of human skeletal muscles and human stem cell-derived motoneurons
  • to induce paralysis in zebrafish larvae to study whole-brain imaging of seizures by two-photon light-sheet microscopy
  • to block NMJ to study its role in myotube contraction

Biochem/physiol Actions

(+)-Tubocurarine chloride pentahydrate serves as a neuromuscular blocker.
Classical competitive antagonist of the nicotinic acetylcholine receptor. Structure-activity relationships and conformational studies for tubocurarine binding at the nicotinic AChR.

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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R V Papineni et al.
The Journal of biological chemistry, 272(40), 24891-24898 (1997-10-06)
The binding of d-tubocurarine and several of its analogs to the mouse nicotinic acetylcholine receptor (AChR) was measured by competition against the initial rate 125I-alpha-bungarotoxin binding to BC3H-1 cells. The changes in affinity due to methylation or halogenation at various
J W Karpen et al.
Biochemistry, 25(7), 1786-1792 (1986-04-08)
The issue of whether d-tubocurarine, the classical acetylcholine receptor inhibitor, inhibits the receptor by a competitive or noncompetitive mechanism has long been controversial. d-Tubocurarine, in this study, has been found to be both a competitive (KC = 120 nM) and
Fast whole-brain imaging of seizures in zebrafish larvae by two-photon light-sheet microscopy
de Vito G, et al.
Biomedical Optics Express, 1516-1536 null
Richard Mills et al.
Molecular metabolism, 7, 12-22 (2017-11-22)
We examined whether skeletal muscle overexpression of PGC-1α1 or PGC-1α4 affected myokine secretion and neuromuscular junction (NMJ) formation. A microfluidic device was used to model endocrine signaling and NMJ formation between primary mouse myoblast-derived myotubes and embryonic stem cell-derived motor
Pietro Ricci et al.
Journal of biophotonics, 15(4), e202100256-e202100256 (2022-01-10)
Two-photon (2P) excitation is a cornerstone approach widely employed in neuroscience microscopy for deep optical access and sub-micrometric-resolution light targeting into the brain. However, besides structural and functional imaging, 2P optogenetic stimulations are less routinary, especially in 3D. This is
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