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93750

Sigma-Aldrich

(+)-Tubocurarine chloride pentahydrate

≥97.0% (TLC)

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C37H42Cl2N2O6 · 5H2O
Numéro CAS:
6989-98-6
Poids moléculaire :
771.72
Numéro Beilstein :
3896374
Numéro MDL:
MFCD00150157
Code UNSPSC :
12352202
ID de substance PubChem :
57653575
Nomenclature NACRES :
NA.77

Source biologique

plant

Pureté

≥97.0% (TLC)

Forme

powder

Activité optique

[α]20/D +195±5°, c = 0.5% in H2O

Impuretés

~12% water

Pf

275-280 °C (dec.) (lit.)

Température de stockage

2-8°C

Chaîne SMILES 

[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

Clé InChI

WMIZITXEJNQAQK-GGDSLZADSA-N

Informations sur le gène

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

Actions biochimiques/physiologiques

(+)-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.

Pictogrammes

Skull and crossbones
GHS06

Mention d'avertissement

Danger

Mentions de danger

H301

Classification des risques

Acute Tox. 3 Oral

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

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

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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
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
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
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
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