Tubocurarine chloride

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MedKoo CAT#: 318962

CAS#: 57-94-3 (chloride)

Description: Tubocurarine is a toxic alkaloid historically known for its use as an arrow poison. In the mid-1900s, it was used in conjunction with an anesthetic to provide skeletal muscle relaxation during surgery or mechanical ventilation. It is now rarely used as an adjunct for clinical anesthesia because safer alternatives, such as cisatracurium and rocuronium, are available.

Chemical Structure

Tubocurarine chloride
CAS# 57-94-3 (chloride)

Theoretical Analysis

MedKoo Cat#: 318962
Name: Tubocurarine chloride
CAS#: 57-94-3 (chloride)
Chemical Formula: C37H42Cl2N2O6
Exact Mass:
Molecular Weight: 681.651
Elemental Analysis: C, 65.20; H, 6.21; Cl, 10.40; N, 4.11; O, 14.08

Price and Availability

Size Price Availability Quantity
10.0mg USD 70.0 2 Weeks
25.0mg USD 120.0 2 Weeks
50.0mg USD 150.0 2 Weeks
100.0mg USD 250.0 2 Weeks
200.0mg USD 450.0 2 Weeks
500.0mg USD 750.0 2 Weeks
1.0g USD 1250.0 2 Weeks
2.0g USD 2150.0 2 Weeks
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Related CAS #: 57-94-3 (chloride)   57-94-4 (free base)  

Synonym: Tubocurarine chloride

IUPAC/Chemical Name: (11S,51R)-36,57-dihydroxy-16,56-dimethoxy-12,52,52-trimethyl-11,12,13,14,51,52,53,54-octahydro-2,6-dioxa-1(7,1),5(1,8)-diisoquinolin-2-iuma-3(1,3),7(1,4)-dibenzenacyclooctaphane-12,52-diium chloride


InChi Code: InChI=1S/C37H40N2O6.2ClH/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/t28-,29?;;/m0../s1

SMILES Code: C[N+]1(C)[C@H](C2)C3=C(OC4=CC=C(C[C@@H]5[N+]([H])(C)CCC6=C5C=C(OC7=C(O)C=CC2=C7)C(OC)=C6)C=C4)C(O)=C(OC)C=C3CC1.[Cl-].[Cl-]

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 681.651 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Chen X, Li Y, Hollenberg M, Triggle CR, Ding H. The contribution of d-tubocurarine-sensitive and apamin-sensitive K-channels to EDHF-mediated relaxation of mesenteric arteries from eNOS-/- mice. J Cardiovasc Pharmacol. 2012 May;59(5):413-25. doi: 10.1097/FJC.0b013e318248acd9. PubMed PMID: 22217882.

2: Shafer SL. From d-tubocurarine to sugammadex: the contributions of T. Cecil Gray to modern anaesthetic practice. Br J Anaesth. 2011 Jul;107(1):97-102. doi: 10.1093/bja/aer117. Epub 2011 May 24. PubMed PMID: 21613280.

3: Brams M, Pandya A, Kuzmin D, van Elk R, Krijnen L, Yakel JL, Tsetlin V, Smit AB, Ulens C. A structural and mutagenic blueprint for molecular recognition of strychnine and d-tubocurarine by different cys-loop receptors. PLoS Biol. 2011 Mar;9(3):e1001034. doi: 10.1371/journal.pbio.1001034. Epub 2011 Mar 29. PubMed PMID: 21468359; PubMed Central PMCID: PMC3066128.

4: Su TR, Hung YS, Huang SS, Su HH, Su CC, Hsiao G, Chen YH, Lin MJ. Study of the reversal effect of NF449 on neuromuscular blockade induced by d-tubocurarine. Life Sci. 2011 Jun 6;88(23-24):1039-46. doi: 10.1016/j.lfs.2011.03.013. Epub 2011 Mar 28. PubMed PMID: 21453711.

5: Nishikawa K, Narimatsu E, Igarashi M, Namiki A. Effects of sepsis on the neuromuscular blocking actions of d-tubocurarine on rat adductor and abductor laryngeal muscles. J Anesth. 2009;23(4):520-5. doi: 10.1007/s00540-009-0816-6. Epub 2009 Nov 18. PubMed PMID: 19921361.

6: Nguyen-Huu T, Molgó J, Servent D, Duvaldestin P. Resistance to D-tubocurarine of the rat diaphragm as compared to a limb muscle: influence of quantal transmitter release and nicotinic acetylcholine receptors. Anesthesiology. 2009 May;110(5):1011-5. doi: 10.1097/ALN.0b013e31819faeaa. PubMed PMID: 19352164.

7: Hirai K, Katayama Y, Peltre G, Tsuji S. Ultrastructural visualization of the transmembranous and cytomatrix-related part of nicotinic acetylcholine receptor of frog motor endplate by means of an immunochemical avidity of IgG for d-tubocurarine. Folia Histochem Cytobiol. 2008;46(1):111-6. doi: 10.2478/v10042-008-0016-5. PubMed PMID: 18296273.

8: Poulsen H, Hougs W. The effect of some curarizing drugs in unanaesthetized man. I. d-Tubocurarine chloride, gallamonium iodide, decamethonium iodide, succinylcholine iodide and its bis-monoethyl-substituted derivative in single or repeated doses. Acta Anaesth. Scandinav. 1957, 1, 15-39. Acta Anaesthesiol Scand. 2007 Sep;51(8):1018-42; discussion 1043. PubMed PMID: 17697296.

9: Zhang R, Wen X, Militante J, Hester B, Rhubottom HE, Sun H, Leidenheimer NJ, Yan D, White MM, Machu TK. The role of loop F residues in determining differential d-tubocurarine potencies in mouse and human 5-hydroxytryptamine 3A receptors. Biochemistry. 2007 Feb 6;46(5):1194-204. PubMed PMID: 17260949.

10: Yan D, Meyer JK, White MM. Mapping residues in the ligand-binding domain of the 5-HT(3) receptor onto d-tubocurarine structure. Mol Pharmacol. 2006 Aug;70(2):571-8. Epub 2006 May 24. PubMed PMID: 16723497.

11: Rossokhin A, Teodorescu G, Grissmer S, Zhorov BS. Interaction of d-tubocurarine with potassium channels: molecular modeling and ligand binding. Mol Pharmacol. 2006 Apr;69(4):1356-65. Epub 2006 Jan 3. PubMed PMID: 16391240.

12: Nguyen-Huu T, Dobbertin A, Barbier J, Minic J, Krejci E, Duvaldestin P, Molgó J. Cholinesterases and the resistance of the mouse diaphragm to the effect of tubocurarine. Anesthesiology. 2005 Oct;103(4):788-95. PubMed PMID: 16192771.

13: Ball C, Westhorpe R. Muscle relaxants--d-tubocurarine. Anaesth Intensive Care. 2005 Aug;33(4):431. PubMed PMID: 16119481.

14: Lalo U, Pankratov Y, Krishtal O, North RA. Methyllycaconitine, alpha-bungarotoxin and (+)-tubocurarine block fast ATP-gated currents in rat dorsal root ganglion cells. Br J Pharmacol. 2004 Aug;142(8):1227-32. Epub 2004 Jul 26. PubMed PMID: 15277311; PubMed Central PMCID: PMC1575186.

15: Suzuki T, Munakata K, Watanabe N, Fukano N, Saeki S, Ogawa S. Comparative fading responses induced by mivacurium, cisatracurium, and d-tubocurarine in the evoked muscular compound action potentials of the cat. J Anesth. 2003;17(2):98-103. PubMed PMID: 12903920.

16: True CA, Carter PJ. A comparison of tubocurarine, rocuronium, and cisatracurium in the prevention and reduction of succinylcholine-induced muscle fasciculations. AANA J. 2003 Feb;71(1):23-8. PubMed PMID: 12776646.

17: Hinohara H, Morita T, Okano N, Kunimoto F, Goto F. Chronic intraperitoneal endotoxin treatment in rats induces resistance to d-tubocurarine, but does not produce up-regulation of acetylcholine receptors. Acta Anaesthesiol Scand. 2003 Mar;47(3):335-41. PubMed PMID: 12648201.

18: Caputi L, Bengtson CP, Guatteo E, Bernardi G, Mercuri NB. D-tubocurarine reduces GABA responses in rat substantia nigra dopamine neurons. Synapse. 2003 Mar;47(3):236-9. PubMed PMID: 12494406.

19: Yan D, White MM. Interaction of d-tubocurarine analogs with mutant 5-HT(3) receptors. Neuropharmacology. 2002 Sep;43(3):367-73. PubMed PMID: 12243766.

20: Willcockson IU, Hong A, Whisenant RP, Edwards JB, Wang H, Sarkar HK, Pedersen SE. Orientation of d-tubocurarine in the muscle nicotinic acetylcholine receptor-binding site. J Biol Chem. 2002 Nov 1;277(44):42249-58. Epub 2002 Aug 23. PubMed PMID: 12196523.