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

Details

Stereochemistry ABSOLUTE
Molecular Formula C37H41N2O6.Cl.ClH
Molecular Weight 681.645
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TUBOCURARINE CHLORIDE ANHYDROUS

SMILES

Cl.[Cl-].COC1=CC2=C3C=C1OC4=CC(C[C@@H]5C6=C(OC7=CC=C(C[C@@H]3N(C)CC2)C=C7)C(O)=C(OC)C=C6CC[N+]5(C)C)=CC=C4O

InChI

InChIKey=GXFZCDMWGMFGFL-KKXMJGKMSA-N
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

HIDE SMILES / InChI

Molecular Formula C37H40N2O6
Molecular Weight 608.7233
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
MOL RATIO 2 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
2.0 µM [IC50]
9.2 µM [IC50]
24.0 nM [IC50]
84.1 nM [Ki]
27.0 µM [IC50]
17.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
TUBOCURARINE CHLORIDE

Cmax

ValueDoseCo-administeredAnalytePopulation
1.173 μg/mL
16 μg/kg/min other, intravenous
TUBOCURARINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
117 μg × min/mL
16 μg/kg/min other, intravenous
TUBOCURARINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
89 min
16 μg/kg/min other, intravenous
TUBOCURARINE plasma
Homo sapiens

Drug as perpetrator​

Drug as victim

Tox targets

Sourcing

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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
Record UNII
7BCM17J5YA
Record Status Validated (UNII)
Record Version