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Details

Stereochemistry UNKNOWN
Molecular Formula C21H22N2O3.3H2O
Molecular Weight 404.4568
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of STRYCHNINE-N-OXIDE TRIHYDRATE

SMILES

O.O.O.[H][C@]12C[C@@]3([H])C4=CCO[C@@]5([H])CC(=O)N6C7=C(C=CC=C7)[C@@]1(CC[N+]2([O-])C4)[C@]6([H])[C@@]35[H]

InChI

InChIKey=LUWMGCJFSHDFTH-JAIAZADYSA-N
InChI=1S/C21H22N2O3.3H2O/c24-18-10-16-19-13-9-17-21(6-7-23(17,25)11-12(13)5-8-26-16)14-3-1-2-4-15(14)22(18)20(19)21;;;/h1-5,13,16-17,19-20H,6-11H2;3*1H2/t13-,16-,17-,19-,20-,21+,23?;;;/m0.../s1

HIDE SMILES / InChI

Molecular Formula C21H22N2O3
Molecular Weight 350.411
Charge 0
Count
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 5 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Strychnine-N-oxide is the major metabolite of Strychnine. Strychnine, the major alkaloid present in $trychnos:nuxypmicagseeds has been reported to stimulate the entire central nervous system with preference for the spinal cord. It is a powerful convulsant and because of this property, it is an important pharmacological tool as it plays a unique role as an inhibitor of post synaptic inhibitory impulses. It is useful to study inhibitory transmitter and receptor types. However, because of its extreme toxicity, strychnine does not have any therapeutic application in the Western system of medicine. Strychnine-N-oxide is less toxic and less convulsive than strychnine itself. However, strychnine N-oxide is not being used as a therapeutic agent now probably because of the threat of convulsions at higher doses. Strychnine-N-oxide is a muscarinic allosteric agent.

Originator

Curator's Comment: Isolation of strychnine from the beans of Strychnos ignatii was performed by Pierre Joseph Pelletier and Joseph Bienaimé Caventou in 1818.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Metabolism of strychnine in vitro.
1985 Nov-Dec
Concise Syntheses of bis-Strychnos Alkaloids (-)-Sungucine, (-)-Isosungucine, and (-)-Strychnogucine B from (-)-Strychnine.
2016 Aug 8
Determination of strychnine, brucine, strychnine N-oxide, and brucine N-oxide in plasma samples after the oral administration of processed semen strychni extract by high-performance liquid chromatography with ultrasound-assisted mixed cloud point extraction.
2016 Jul
Patents

Patents

Sample Use Guides

TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE: Subcutaneous SPECIES OBSERVED: Rodent - mouse DOSE/DURATION: 24500 ug/kg
Route of Administration: Other
In Vitro Use Guide
Binding affinity at the NMS liganded human muscarinic acetylcholine receptor M1 was estimated as log affinity (log1/M) = 3.8.
Substance Class Chemical
Created
by admin
on Sat Dec 16 09:49:35 GMT 2023
Edited
by admin
on Sat Dec 16 09:49:35 GMT 2023
Record UNII
6VN99G6GMU
Record Status Validated (UNII)
Record Version
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Name Type Language
STRYCHNINE-N-OXIDE TRIHYDRATE
Common Name English
STRYCHNIDIN-10-ONE, 19-OXIDE, HYDRATE (1:3)
Common Name English
STRYCHNINE-N6-OXIDE TRIHYDRATE
Common Name English
Code System Code Type Description
FDA UNII
6VN99G6GMU
Created by admin on Sat Dec 16 09:49:35 GMT 2023 , Edited by admin on Sat Dec 16 09:49:35 GMT 2023
PRIMARY
CAS
1089312-01-5
Created by admin on Sat Dec 16 09:49:35 GMT 2023 , Edited by admin on Sat Dec 16 09:49:35 GMT 2023
PRIMARY
PUBCHEM
90479189
Created by admin on Sat Dec 16 09:49:35 GMT 2023 , Edited by admin on Sat Dec 16 09:49:35 GMT 2023
PRIMARY
Related Record Type Details
ANHYDROUS->SOLVATE