U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C37H41N2O6.Cl.ClH.5H2O
Molecular Weight 771.722
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TUBOCURARINE CHLORIDE

SMILES

O.O.O.O.O.Cl.[Cl-].COC1=CC2=C3[C@@H](CC4=CC=C(O)C(OC5=C(OC)C=C6CCN(C)[C@@H](CC7=CC=C(OC3=C1O)C=C7)C6=C5)=C4)[N+](C)(C)CC2

InChI

InChIKey=WMIZITXEJNQAQK-GGDSLZADSA-N
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

HIDE SMILES / InChI

Molecular Formula C37H41N2O6
Molecular Weight 609.7312
Charge 1
Count
Stereochemistry EPIMERIC
Additional Stereochemistry
Defined Stereocenters 2 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Tubocurarine, a naturally occurring alkaloid, is used to treat smoking withdrawl syndrom. Tubocurarine, the chief alkaloid in tobacco products, binds stereo-selectively to nicotinic-cholinergic receptors at the autonomic ganglia, in the adrenal medulla, at neuromuscular junctions, and in the brain. Two types of central nervous system effects are believed to be the basis of Tubocurarine's positively reinforcing properties. A stimulating effect is exerted mainly in the cortex via the locus ceruleus and a reward effect is exerted in the limbic system. At low doses the stimulant effects predominate while at high doses the reward effects predominate. Intermittent intravenous administration of Tubocurarine activates neurohormonal pathways, releasing acetylcholine, norepinephrine, dopamine, serotonin, vasopressin, beta-endorphin, growth hormone, and ACTH. Tubocurarine competes with acetylcholine for post-synaptic nicotinic NM receptors and blocks them.

CNS Activity

Curator's Comment: Tubocurarine does not penetrate the normal intact blood-brain barrier.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
TUBOCURARINE CHLORIDE

Approved Use

Tubocurarine is indicated as a diagnostic aid for myasthenia gravis when the results of tests with neostigmine or edrophonium are inconclusive

Launch Date

1945
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.173 μg/mL
16 μg/kg/min other, intravenous
dose: 16 μg/kg/min
route of administration: Intravenous
experiment type: OTHER
co-administered:
TUBOCURARINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
117 μg × min/mL
16 μg/kg/min other, intravenous
dose: 16 μg/kg/min
route of administration: Intravenous
experiment type: OTHER
co-administered:
TUBOCURARINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
89 min
16 μg/kg/min other, intravenous
dose: 16 μg/kg/min
route of administration: Intravenous
experiment type: OTHER
co-administered:
TUBOCURARINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Overview

Overview

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
likely [IC50 >100 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
yes [IC50 133 uM]
yes [IC50 133 uM]
yes [IC50 133 uM]
yes [IC50 55.5 uM]
yes [IC50 62.4 uM]
yes [IC50 9.4 uM]
yes [IC50 9.6 uM]
yes [Inhibition 10 uM]
yes [Inhibition 10 uM]
Drug as victimTox targets
PubMed

PubMed

TitleDatePubMed
Monitoring neuronal calcium signalling using a new method for ratiometric confocal calcium imaging.
2003-09
GABAergic systems modulate nicotinic receptor-mediated seizures in mice.
2003-09
Curariform antagonists bind in different orientations to the nicotinic receptor ligand binding domain.
2003-08-22
Blockade of neuronal facilitatory nicotinic receptors containing alpha 3 beta 2 subunits contribute to tetanic fade in the rat isolated diaphragm.
2003-08
4-Aminopyridine inhibits the neuromuscular effects of nitric oxide and 8-Br-cGMP.
2003-07
Neuromuscular transmission of pectoral fin muscles of the goldfish Carassius auratus.
2003-07
Curariform antagonists bind in different orientations to acetylcholine-binding protein.
2003-06-20
Dopaminergic excitation of the goat carotid body is mediated by the serotonin type 3 receptor subtype.
2003-06-12
Pharmacological characterization of recombinant bovine alpha3beta4 neuronal nicotinic receptors stably expressed in HEK 293 cells.
2003-06-12
Screening procedure for eight quaternary nitrogen muscle relaxants in blood by high-performance liquid chromatography-electrospray ionization mass spectrometry.
2003-06-05
Neuromuscular effects of candoxin, a novel toxin from the venom of the Malayan krait (Bungarus candidus).
2003-06
Nicotine modulates the expression of a diverse set of genes in the neuronal SH-SY5Y cell line.
2003-05-02
Differential modulation of light-evoked on- and off-EPSCs by paired-pulse stimulation in salamander retinal ganglion cells.
2003-03-28
Task-dependent presynaptic inhibition.
2003-03-01
Chronic intraperitoneal endotoxin treatment in rats induces resistance to d-tubocurarine, but does not produce up-regulation of acetylcholine receptors.
2003-03
Bisindole alkaloids from Strychnos guianensis are effective antagonists of nicotinic acetylcholine receptors in cultured human TE671 cells.
2003-03
D-tubocurarine reduces GABA responses in rat substantia nigra dopamine neurons.
2003-03
A comparison of tubocurarine, rocuronium, and cisatracurium in the prevention and reduction of succinylcholine-induced muscle fasciculations.
2003-02
A novel class of ligand-gated ion channel is activated by Zn2+.
2003-01-10
Nicotinic activation of reticulospinal cells involved in the control of swimming in lampreys.
2003-01
Comparative fading responses induced by mivacurium, cisatracurium, and d-tubocurarine in the evoked muscular compound action potentials of the cat.
2003
Characterization of an apamin-sensitive potassium current in suprachiasmatic nucleus neurons.
2003
Synthesis and biological evaluation of 16 beta-pyrrolidinosteroidal derivatives.
2003
Impairment of synaptic vesicle exocytosis and recycling during neuromuscular weakness produced in mice by 2,4-dithiobiuret.
2002-12
Mechanism of nicotine-evoked release of 3H-noradrenaline in human cerebral cortex slices.
2002-12
Orientation of d-tubocurarine in the muscle nicotinic acetylcholine receptor-binding site.
2002-11-01
Synthesis and neuromuscular blocking activity of 16beta-N-methylpiperazino steroidal derivatives.
2002-11
Nicotinic receptors regulate the release of glycine onto lamina X neurones of the rat spinal cord.
2002-11
Sex difference in urethral response to electrical stimulation of efferent nerves in the pudendal sensory branch of rats.
2002-10
Pharmacology of nicotinic receptors in preBötzinger complex that mediate modulation of respiratory pattern.
2002-10
Nicotinic alpha 7 receptor clusters on hippocampal GABAergic neurons: regulation by synaptic activity and neurotrophins.
2002-09-15
Effects of nicotine exposure on T cell development in fetal thymus organ culture: arrest of T cell maturation.
2002-09-15
Interaction of d-tubocurarine analogs with mutant 5-HT(3) receptors.
2002-09
Neuromuscular action of Bothrops lanceolatus (Fer de lance) venom and a caseinolytic fraction.
2002-09
Electrophysiological analysis of synaptic transmission in central neurons of Drosophila larvae.
2002-08
Characterization of the interactions between volatile anesthetics and neuromuscular blockers at the muscle nicotinic acetylcholine receptor.
2002-08
Expression of soluble ligand- and antibody-binding extracellular domain of human muscle acetylcholine receptor alpha subunit in yeast Pichia pastoris. Role of glycosylation in alpha-bungarotoxin binding.
2002-07-26
Modulation by nicotine of the ionic currents in guinea pig ventricular cardiomyocytes. Relatively higher sensitivity to IKr and IKl.
2002-07
New evidence for a presynaptic action of prednisolone at neuromuscular junctions.
2002-07
Characterization of [(125) I]epibatidine binding and nicotinic agonist-mediated (86) Rb(+) efflux in interpeduncular nucleus and inferior colliculus of beta2 null mutant mice.
2002-06
Properties of nicotinic receptors underlying Renshaw cell excitation by alpha-motor neurons in neonatal rat spinal cord.
2002-06
Acetylcholine increases intracellular Ca2+ in taste cells via activation of muscarinic receptors.
2002-06
Nicotine increases hepatic oxygen uptake in the isolated perfused rat liver by inhibiting glycolysis.
2002-06
Effect of glycine on synaptic transmission at the third order giant synapse of the squids Alloteuthis subulata and Loligo vulgaris.
2002-05-31
Fm1-43 reveals membrane recycling in adult inner hair cells of the mammalian cochlea.
2002-05-15
Adenosine depresses a Ca(2+)-independent step in transmitter exocytosis at frog motor nerve terminals.
2002-04
Evaluation of the cholinomimetic actions of trimethylsulfonium, a compound present in the midgut gland of the sea hare Aplysia brasiliana (Gastropoda, Opisthobranchia).
2002-04
The nature of the acetylcholine and 5-hydroxytryptamine receptors in buccal smooth muscle of the pest slug Deroceras reticulatum.
2002-04
Peripheral site ligands accelerate inhibition of acetylcholinesterase by neutral organophosphates.
2001-12
Ketamine-pancuronium-narcotic technic for cardiovascular surgery in infants--a comparative study.
1975-11-01
Patents

Patents

Sample Use Guides

Diagnostic aid (myasthenia gravis) Intravenous, 4 to 33 mcg (0.004 to 0.033 mg) per kg of body weight. Note: It is recommended that the test be terminated within two to three minutes by intravenous injection of 1.5 mg of neostigmine, since the marked exaggeration of myasthenia gravis symptoms may result in prolonged respiratory paralysis.
Route of Administration: Intravenous
D-tubocurarine (30 uM), but not alpha-bungarotoxin (alpha-BTX, 0.1 uM), attenuated the nicotine (NIC) (100 uM)-evoked release of 3H-NA.
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:34:35 GMT 2025
Edited
by admin
on Mon Mar 31 17:34:35 GMT 2025
Record UNII
900961Z8VR
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TUBAINE
Preferred Name English
TUBOCURARINE CHLORIDE
EP   MART.   ORANGE BOOK   USP   USP-RS   VANDF   WHO-IP  
USP  
Official Name English
TUBOCURARINE CHLORIDE HYDROCHLORIDE HYDRATE
JAN  
Common Name English
TUBOCURARINE CHLORIDE PENTAHYDRATE
Common Name English
TUBOCURARINE CHLORIDE HYDROCHLORIDE HYDRATE [JAN]
Common Name English
TUBOCURARINI CHLORIDUM [WHO-IP LATIN]
Common Name English
NSC-757362
Code English
TUBARINE PENTAHYDRATE
Common Name English
D-TUBOCURARINE DICHLORIDE PENTAHYDRATE
Common Name English
TUBOCURARINE CHLORIDE [MART.]
Common Name English
TUBOCURARINE CHLORIDE [USP-RS]
Common Name English
TUBOCURARINE CHLORIDE [USP MONOGRAPH]
Common Name English
TUBOCURARINE CHLORIDE [ORANGE BOOK]
Common Name English
(+)-TUBOCURARINE CHLORIDE HYDROCHLORIDE PENTAHYDRATE
Common Name English
CURARE [HPUS]
Common Name English
TUBOCURARINE CHLORIDE [VANDF]
Common Name English
(+)-TUBOCURARINE CHLORIDE HYDROCHLORIDE, PENTAHYDRATE [WHO-IP]
Common Name English
TUBOCURARANIUM, 7',12'-DIHYDROXY-6,6'-DIMETHOXY-2,2',2'-TRIMETHYL-, CHLORIDE, HYDROCHLORIDE, PENTAHYDRATE
Common Name English
TUBOCURARINE CHLORIDE [WHO-IP]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29696
Created by admin on Mon Mar 31 17:34:35 GMT 2025 , Edited by admin on Mon Mar 31 17:34:35 GMT 2025
Code System Code Type Description
FDA UNII
900961Z8VR
Created by admin on Mon Mar 31 17:34:35 GMT 2025 , Edited by admin on Mon Mar 31 17:34:35 GMT 2025
PRIMARY
DRUG BANK
DB01199
Created by admin on Mon Mar 31 17:34:35 GMT 2025 , Edited by admin on Mon Mar 31 17:34:35 GMT 2025
PRIMARY
RS_ITEM_NUM
1702008
Created by admin on Mon Mar 31 17:34:35 GMT 2025 , Edited by admin on Mon Mar 31 17:34:35 GMT 2025
PRIMARY
WIKIPEDIA
TUBOCURARINE CHLORIDE
Created by admin on Mon Mar 31 17:34:35 GMT 2025 , Edited by admin on Mon Mar 31 17:34:35 GMT 2025
PRIMARY
DAILYMED
900961Z8VR
Created by admin on Mon Mar 31 17:34:35 GMT 2025 , Edited by admin on Mon Mar 31 17:34:35 GMT 2025
PRIMARY
RXCUI
82115
Created by admin on Mon Mar 31 17:34:35 GMT 2025 , Edited by admin on Mon Mar 31 17:34:35 GMT 2025
PRIMARY RxNorm
WHO INTERNATIONAL PHARMACOPEIA
TUBOCURARINE CHLORIDE
Created by admin on Mon Mar 31 17:34:35 GMT 2025 , Edited by admin on Mon Mar 31 17:34:35 GMT 2025
PRIMARY Description: A white to yellowish white, crystalline powder; odourless. Solubility: Soluble in 20 parts of water and 30 parts of ethanol (~750 g/l) TS; practically insoluble in acetone R and ether R. Category: Muscle relaxant. Storage: Tubocurarine chloride should be kept in a tightly closed container. Additional information: Tubocurarine chloride melts at about 270?C with decomposition. Definition: Tubocurarine chloride contains not less than 98.0% and not more than 102.0% of C37H41ClN2O6,HCl, calculated with reference to the dried substance.
NCI_THESAURUS
C47777
Created by admin on Mon Mar 31 17:34:35 GMT 2025 , Edited by admin on Mon Mar 31 17:34:35 GMT 2025
PRIMARY
SMS_ID
300000040297
Created by admin on Mon Mar 31 17:34:35 GMT 2025 , Edited by admin on Mon Mar 31 17:34:35 GMT 2025
PRIMARY
ChEMBL
CHEMBL339427
Created by admin on Mon Mar 31 17:34:35 GMT 2025 , Edited by admin on Mon Mar 31 17:34:35 GMT 2025
PRIMARY
EPA CompTox
DTXSID20930274
Created by admin on Mon Mar 31 17:34:35 GMT 2025 , Edited by admin on Mon Mar 31 17:34:35 GMT 2025
PRIMARY
CAS
6989-98-6
Created by admin on Mon Mar 31 17:34:35 GMT 2025 , Edited by admin on Mon Mar 31 17:34:35 GMT 2025
PRIMARY
NSC
757362
Created by admin on Mon Mar 31 17:34:35 GMT 2025 , Edited by admin on Mon Mar 31 17:34:35 GMT 2025
PRIMARY
PUBCHEM
23422
Created by admin on Mon Mar 31 17:34:35 GMT 2025 , Edited by admin on Mon Mar 31 17:34:35 GMT 2025
PRIMARY
Related Record Type Details
ANHYDROUS->SOLVATE
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ACTIVE MOIETY