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Merck

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:
Molecular Weight:
771.72
Beilstein:
3896374
MDL number:
UNSPSC Code:
12352202
PubChem Substance ID:
NACRES:
NA.77

form:
powder
Assay:
≥97.0% (TLC)

biological source

plant

Quality Level

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

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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[1]
  • to induce paralysis in zebrafish larvae to study whole-brain imaging of seizures by two-photon light-sheet microscopy[2]
  • to block NMJ to study its role in myotube contraction[3]

Biochem/physiol Actions

(+)-Tubocurarine chloride pentahydrate serves as a neuromuscular blocker.[4]
Classical competitive antagonist of the nicotinic acetylcholine receptor[5]. Structure-activity relationships and conformational studies for tubocurarine binding at the nicotinic AChR.[6]

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

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

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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
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

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