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

Details

Stereochemistry ABSOLUTE
Molecular Formula C21H22N2O2
Molecular Weight 334.4116
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of STRYCHNINE

SMILES

[H][C@]12C[C@@]3([H])C4=CCO[C@@]5([H])CC(=O)N6C7=C(C=CC=C7)[C@@]1(CCN2C4)[C@]6([H])[C@@]35[H]

InChI

InChIKey=QMGVPVSNSZLJIA-FVWCLLPLSA-N
InChI=1S/C21H22N2O2/c24-18-10-16-19-13-9-17-21(6-7-22(17)11-12(13)5-8-25-16)14-3-1-2-4-15(14)23(18)20(19)21/h1-5,13,16-17,19-20H,6-11H2/t13-,16-,17-,19-,20-,21+/m0/s1

HIDE SMILES / InChI
Molecular Formula C21H22N2O2
Molecular Weight 334.4116
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including http://www.merckvetmanual.com/mvm/toxicology/strychnine_poisoning/overview_of_strychnine_poisoning.html https://www.ncbi.nlm.nih.gov/pubmed/440838

Strychnine is an indole alkaloid obtained from the seeds of the Indian tree Strychnos nux-vomica. It gets its scientific name “strychnos” from Carl Linnaeus, who classified it back in 1753, but it was known to the population of India way before then. Nux vomica originates in India. Strychnine-containing baits are currently labelled for below-ground use and are intended for the control of pocket gophers. Their use as indoor pesticides has been eliminated since 1989. In the past, strychnine has been used as a pesticide to control rats, moles, gophers, and coyotes. Strychnine is highly toxic to most domestic animals. Strychnine is a competitive antagonist at glycine receptors and thus a convulsant. It has been used as an analeptic, in the treatment of nonketotic hyperglycinemia and sleep apnea.

CNS Activity

Originator

Approval Year

1921
1467
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2778
 0.62 µM [EC50]
Antagonist
2778
 0.16 µM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Preclinical
Unknown

Approved Use

Unknown
Primary
Basic research
Unknown

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
250 mg single, oral
Dose: 250 mg
Route: oral
Route: single
Dose: 250 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/15483758
unknown, 46 years
n = 1
Health Status: unknown
Age Group: 46 years
Sex: M
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/15483758
Other AEs: Violent, Convulsions generalized...
Other AEs:
Violent (severe)
Convulsions generalized (severe)
Sources:
https://pubmed.ncbi.nlm.nih.gov/15483758
15 g single, oral
Dose: 15 g
Route: oral
Route: single
Dose: 15 g
Sources:
https://jamanetwork.com/journals/jama/article-abstract/280892
unknown, 60 years
n = 1
Health Status: unknown
Age Group: 60 years
Sex: M
Population Size: 1
Sources:
https://jamanetwork.com/journals/jama/article-abstract/280892
Other AEs: Nausea, Vomiting...
Other AEs:
Nausea (severe)
Vomiting (severe)
Sources:
https://jamanetwork.com/journals/jama/article-abstract/280892
AEs

AEs

AESignificanceDosePopulation
Convulsions generalized severe
250 mg single, oral
Dose: 250 mg
Route: oral
Route: single
Dose: 250 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/15483758
unknown, 46 years
n = 1
Health Status: unknown
Age Group: 46 years
Sex: M
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/15483758
Violent severe
250 mg single, oral
Dose: 250 mg
Route: oral
Route: single
Dose: 250 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/15483758
unknown, 46 years
n = 1
Health Status: unknown
Age Group: 46 years
Sex: M
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/15483758
Nausea severe
15 g single, oral
Dose: 15 g
Route: oral
Route: single
Dose: 15 g
Sources:
https://jamanetwork.com/journals/jama/article-abstract/280892
unknown, 60 years
n = 1
Health Status: unknown
Age Group: 60 years
Sex: M
Population Size: 1
Sources:
https://jamanetwork.com/journals/jama/article-abstract/280892
Vomiting severe
15 g single, oral
Dose: 15 g
Route: oral
Route: single
Dose: 15 g
Sources:
https://jamanetwork.com/journals/jama/article-abstract/280892
unknown, 60 years
n = 1
Health Status: unknown
Age Group: 60 years
Sex: M
Population Size: 1
Sources:
https://jamanetwork.com/journals/jama/article-abstract/280892
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
1587

substrate
1737
inhibitor
1612

OverviewOther

Other InhibitorOther SubstrateOther Inducer
P-gp
1461
UGT1A4
347

UGT2B10
127

P-gp
1537
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP3A4
1925
 yes [IC50 5.9 uM]
P-gp
1650
 yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP3A4
1737
 yes
P-gp
1537
 yes
UGT1A4
347
 yes
UGT2B10
127
 yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
1647
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:28973
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:28973
MolPort
MolPort-001-742-519
https://www.molport.com/shop/molecule-link/MolPort-001-742-519
ZINC
ZINC000000119434
http://zinc15.docking.org/substances/ZINC000000119434
eMolecules
29541143
https://www.emolecules.com/cgi-bin/more?vid=29541143
eMolecules
29909187
https://www.emolecules.com/cgi-bin/more?vid=29909187
eMolecules
510211
https://www.emolecules.com/cgi-bin/more?vid=510211
PubMed

PubMed

TitleDatePubMed
Expression and function of glycine receptors in striatal cholinergic interneurons from rat and mouse.
2001
Slow inhibitory potentials in the teleost Mauthner cell.
2001
Intracellular calcium reduces light-induced excitatory post-synaptic responses in salamander retinal ganglion cells.
2001 Apr 1
Ivermectin, an unconventional agonist of the glycine receptor chloride channel.
2001 Apr 20
Reversal of chloroquine and mefloquine resistance in Plasmodium falciparum by the two monoindole alkaloids, icajine and isoretuline.
2001 Aug
Anticonvulsant activities of the FS-1 subfraction isolated from roots of Delphinium denudatum.
2001 Aug
Biogenetically inspired approach to the Strychnos alkaloids. Concise syntheses of (+/-)-akuammicine and (+/-)-strychnine.
2001 Aug 22
Centrally administered corticotropin-releasing hormone and peripheral injections of strychnine hydrochloride potentiate the acoustic startle response in preweanling rats.
2001 Dec
Design of semicarbazones and their bio-isosteric analogues as potential anticonvulsants.
2001 Feb
The effect of proteolytic enzymes on the alpha9-nicotinic receptor-mediated response in isolated frog vestibular hair cells.
2001 Feb
Swim stress alters the behavioural response of mice to GABA-related and some GABA-unrelated convulsants.
2001 Feb
Mu opiates inhibit long-term potentiation induction in the spinal cord slice.
2001 Feb
Non-enzymatic reduction of aliphatic tertiary amine N-oxides mediated by the haem moiety of cytochrome P450.
2001 Jan
Reorganisation of respiratory network activity after loss of glycinergic inhibition.
2001 Jan
Slow dorsal-ventral rhythm generator in the lamprey spinal cord.
2001 Jan
Neither GABA(A) nor strychnine-sensitive glycine receptors are the sole mediators of MAC for isoflurane.
2001 Jan
HMSC: simultaneously detected heteronuclear shift correlation through multiple and single bonds.
2001 Jan
Autoradiographic localization of [3H]thiocolchicoside binding sites in the rat brain and spinal cord.
2001 Jun
Anticonvulsant properties and bio-guided isolation of palmitone from leaves of Annona diversifolia.
2001 Mar
Coadministration of intrathecal strychnine and bicuculline effects synergistic allodynia in the rat: an isobolographic analysis.
2001 Mar
Studies on psychopharmacological activity of Andrographis paniculata extract.
2001 May
Ionotropic histamine receptors and H2 receptors modulate supraoptic oxytocin neuronal excitability and dye coupling.
2001 May 1
Properties and interconnections of trigeminal interneurons of the lateral pontine reticular formation in the rat.
2001 Nov
Glycine receptor-mediated inhibition of dopamine and non-dopamine neurons of the rat ventral tegmental area in vitro.
2001 Nov 23
Mechanisms that initiate spontaneous network activity in the developing chick spinal cord.
2001 Sep
Iontophoresis in vivo demonstrates a key role for GABA(A) and glycinergic inhibition in shaping frequency response areas in the inferior colliculus of guinea pig.
2001 Sep 15
Approaches to the synthesis of (+/-)-strychnine via the cobalt-mediated [2 + 2 + 2] cycloaddition: rapid assembly of a classic framework.
2001 Sep 26
Glycine receptors involved in synaptic transmission are selectively regulated by the cytoskeleton in mouse spinal neurons.
2002 Jan
Synaptically evoked membrane potential oscillations induced by substance P in lamprey motor neurons.
2002 Jan
Patents

Patents

20010003799
32

Sample Use Guides

In Vivo Use Guide
daily dosage of 0.2 to 0.9 mg/kg, given orally in four doses
Route of Administration: Oral
In Vitro Use Guide
Glycine-evoked (500 um) currents were blocked by strychnine (IC50 = 630 nm) in human pluripotent stem cell-derived excitatory cortical neurones.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:00:51 GMT 2023
Edited
by admin
on Fri Dec 15 15:00:51 GMT 2023
Record UNII
H9Y79VD43J
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
STRYCHNINE
HSDB   ISO   MI   VANDF   WHO-DD  
Common Name English
STRYCHNINE [MI]
Common Name English
STRYCHNINE [ISO]
Common Name English
Strychnine [WHO-DD]
Common Name English
STRYCHNIDIN-10-ONE
Common Name English
STRYCHNINE [VANDF]
Common Name English
STRYCHNINUM
HPUS  
Common Name English
STRYCHNINE [HSDB]
Common Name English
(4bR,7aS,8aR,13S,13aR,13bS)-5,6,7a,8,8a,11,13a,13b-octahydro-13H-13,14-ethano-7,9-methanooxepino[3,4-a]pyrrolo[2,3-d]carbazol-15-one
Common Name English
STRYCHNINUM [HPUS]
Common Name English
NSC-5365
Code English
Classification Tree Code System Code
NCI_THESAURUS C737
Created by admin on Fri Dec 15 15:00:51 GMT 2023 , Edited by admin on Fri Dec 15 15:00:51 GMT 2023
CFR 21 CFR 310.528
Created by admin on Fri Dec 15 15:00:51 GMT 2023 , Edited by admin on Fri Dec 15 15:00:51 GMT 2023
EPA PESTICIDE CODE 76901
Created by admin on Fri Dec 15 15:00:51 GMT 2023 , Edited by admin on Fri Dec 15 15:00:51 GMT 2023
Code System Code Type Description
DAILYMED
H9Y79VD43J
Created by admin on Fri Dec 15 15:00:51 GMT 2023 , Edited by admin on Fri Dec 15 15:00:51 GMT 2023
PRIMARY
ALANWOOD
strychnine
Created by admin on Fri Dec 15 15:00:51 GMT 2023 , Edited by admin on Fri Dec 15 15:00:51 GMT 2023
PRIMARY
HSDB
2001
Created by admin on Fri Dec 15 15:00:51 GMT 2023 , Edited by admin on Fri Dec 15 15:00:51 GMT 2023
PRIMARY
EPA CompTox
DTXSID6023600
Created by admin on Fri Dec 15 15:00:51 GMT 2023 , Edited by admin on Fri Dec 15 15:00:51 GMT 2023
PRIMARY
SMS_ID
100000077869
Created by admin on Fri Dec 15 15:00:51 GMT 2023 , Edited by admin on Fri Dec 15 15:00:51 GMT 2023
PRIMARY
RXCUI
66422
Created by admin on Fri Dec 15 15:00:51 GMT 2023 , Edited by admin on Fri Dec 15 15:00:51 GMT 2023
PRIMARY RxNorm
DRUG CENTRAL
2484
Created by admin on Fri Dec 15 15:00:51 GMT 2023 , Edited by admin on Fri Dec 15 15:00:51 GMT 2023
PRIMARY
MERCK INDEX
m10255
Created by admin on Fri Dec 15 15:00:51 GMT 2023 , Edited by admin on Fri Dec 15 15:00:51 GMT 2023
PRIMARY Merck Index
CHEBI
28973
Created by admin on Fri Dec 15 15:00:51 GMT 2023 , Edited by admin on Fri Dec 15 15:00:51 GMT 2023
PRIMARY
CAS
57-24-9
Created by admin on Fri Dec 15 15:00:51 GMT 2023 , Edited by admin on Fri Dec 15 15:00:51 GMT 2023
PRIMARY
NCI_THESAURUS
C84183
Created by admin on Fri Dec 15 15:00:51 GMT 2023 , Edited by admin on Fri Dec 15 15:00:51 GMT 2023
PRIMARY
ChEMBL
CHEMBL227934
Created by admin on Fri Dec 15 15:00:51 GMT 2023 , Edited by admin on Fri Dec 15 15:00:51 GMT 2023
PRIMARY
MESH
D013331
Created by admin on Fri Dec 15 15:00:51 GMT 2023 , Edited by admin on Fri Dec 15 15:00:51 GMT 2023
PRIMARY
PUBCHEM
441071
Created by admin on Fri Dec 15 15:00:51 GMT 2023 , Edited by admin on Fri Dec 15 15:00:51 GMT 2023
PRIMARY
WIKIPEDIA
STRYCHNINE
Created by admin on Fri Dec 15 15:00:51 GMT 2023 , Edited by admin on Fri Dec 15 15:00:51 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-319-7
Created by admin on Fri Dec 15 15:00:51 GMT 2023 , Edited by admin on Fri Dec 15 15:00:51 GMT 2023
PRIMARY
EVMPD
SUB15411MIG
Created by admin on Fri Dec 15 15:00:51 GMT 2023 , Edited by admin on Fri Dec 15 15:00:51 GMT 2023
PRIMARY
FDA UNII
H9Y79VD43J
Created by admin on Fri Dec 15 15:00:51 GMT 2023 , Edited by admin on Fri Dec 15 15:00:51 GMT 2023
PRIMARY
NSC
5365
Created by admin on Fri Dec 15 15:00:51 GMT 2023 , Edited by admin on Fri Dec 15 15:00:51 GMT 2023
PRIMARY
Related Record Type Details
GLYCINE RECEPTOR SUBUNIT ALPHA-3
TARGET -> INHIBITOR
Binding Assay
Structure of STRYCHNINE SULFATE
SALT/SOLVATE -> PARENT
Structure of STRYCHNINE TARTRATE
SALT/SOLVATE -> PARENT
Structure of STRYCHNINE NITRATE
SALT/SOLVATE -> PARENT
Structure of STRYCHNINE HYDROCHLORIDE
SALT/SOLVATE -> PARENT
Structure of STRYCHNINE HYDROCHLORIDE DIHYDRATE
SALT/SOLVATE -> PARENT
GLYCINE RECEPTOR SUBUNIT ALPHA-1
TARGET->LIGAND
Binding Assay
Kd
Structure of STRYCHNINE ARSENATE DIHYDRATE
SALT/SOLVATE -> PARENT
Structure of STRYCHNINE HYPOPHOSPHITE
SALT/SOLVATE -> PARENT
Structure of STRYCHNINE VALERATE
SALT/SOLVATE -> PARENT
Structure of STRYCHNINE ARSENATE
SALT/SOLVATE -> PARENT
Structure of STRYCHNINE SULFATE PENTAHYDRATE
SALT/SOLVATE -> PARENT
Structure of STRYCHNINE PHOSPHATE
SALT/SOLVATE -> PARENT
Structure of STRYCHNINE SULFATE
SALT/SOLVATE -> PARENT
Structure of STRYCHNINE PHOSPHATE
SALT/SOLVATE -> PARENT
Structure of STRYCHNINE ARSENATE DIHYDRATE
SALT/SOLVATE -> PARENT
Structure of STRYCHNINE ARSENATE
SALT/SOLVATE -> PARENT
Structure of STRYCHNINE PHOSPHATE DIHYDRATE
SALT/SOLVATE -> PARENT
Structure of STRYCHNINE HYDROCHLORIDE DIHYDRATE
SALT/SOLVATE -> PARENT
Structure of STRYCHNINE VALERATE
SALT/SOLVATE -> PARENT
Structure of STRYCHNINE HYPOPHOSPHITE DIHYDRATE
SALT/SOLVATE -> PARENT
Structure of STRYCHNINE NITRATE
SALT/SOLVATE -> PARENT
Structure of STRYCHNINE SULFATE PENTAHYDRATE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of STRYCHNINE
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