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93750

Sigma-Aldrich

(+)-Tubocurarine chloride pentahydrate

≥97.0% (TLC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C37H42Cl2N2O6 · 5H2O
CAS Number:
6989-98-6
Molecular Weight:
771.72
Beilstein:
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

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

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

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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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
Xiufang Guo et al.
Biomaterials, 32(36), 9602-9611 (2011-09-29)
Functional in vitro models composed of human cells will constitute an important platform in the next generation of system biology and drug discovery. This study reports a novel human-based in vitro Neuromuscular Junction (NMJ) system developed in a defined serum-free
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
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