STRYCHNINE PHOSPHATE

US Previously Marketed

First marketed in 1921

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H22N2O2.H3O4P
Molecular Weight	432.4068
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OP(O)(O)=O.O=C1C[C@@H]2OCC=C3CN4CC[C@@]56[C@@H]4C[C@@H]3[C@@H]2[C@@H]5N1C7=C6C=CC=C7

InChI

InChIKey=VNIVZTFZIJTNDV-ZEYGOCRCSA-N

InChI=1S/C21H22N2O2.H3O4P/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;1-5(2,3)4/h1-5,13,16-17,19-20H,6-11H2;(H3,1,2,3,4)/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	6 / 6
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	H3O4P
Molecular Weight	97.9952
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/mesh/68013331
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

Targets

Primary Target	Pharmacology	Condition	Potency
Glycine receptor (alpha-1/beta) 15 Target ID: CHEMBL2363052 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25146769	Antagonist 2849		0.62 µM [EC50]
Glycine receptor subunit alpha-1 24 Target ID: CHEMBL5845 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25146769	Antagonist 2849		0.16 µM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Nonketotic hyperglycinemia 11 Sources: https://www.ncbi.nlm.nih.gov/pubmed/440838 https://www.ncbi.nlm.nih.gov/pubmed/344282 https://www.ncbi.nlm.nih.gov/pubmed/541222	Primary		Preclinical	Unknown Approved Use Unknown
Sleep apnea 11 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7221350	Primary		Basic research	Unknown Approved Use Unknown

Doses

Dose	Population	Adverse 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 Health Status: unknown Age Group: 46 years Sex: M 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 Health Status: unknown Age Group: 60 years Sex: M 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

AE	Significance	Dose	Population
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 Health Status: unknown Age Group: 46 years Sex: M 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 Health Status: unknown Age Group: 46 years Sex: M 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 Health Status: unknown Age Group: 60 years Sex: M 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 Health Status: unknown Age Group: 60 years Sex: M Sources: https://jamanetwork.com/journals/jama/article-abstract/280892

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252 substrate 1946			inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1741	UGT1A4 399 UGT2B10 131 P-gp 2052

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A4 2633	inhibitor 4027 Sources: https://www.sciencedirect.com/science/article/abs/pii/S1674638412600057	yes [IC50 5.9 uM]
P-gp 1932	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/29883892/	yes

Drug as victim

Target	Modality	Activity
CYP3A4 1946	substrate 4014 Sources: https://www.sciencedirect.com/science/article/abs/pii/S1674638412600057	yes
P-gp 2052	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/29234368/ \| https://pubmed.ncbi.nlm.nih.gov/21351573/	yes
UGT1A4 399	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/28803208/ \| https://issx.confex.com/issx/ap11/webprogram/Paper23904.html	yes
UGT2B10 131	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/28803208/	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubmed.ncbi.nlm.nih.gov/30545237/ \| https://pubmed.ncbi.nlm.nih.gov/30282042/

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:28973	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:28973
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
MolPort	MolPort-001-742-519	https://www.molport.com/shop/molecule-link/MolPort-001-742-519
ZINC	ZINC000000119434	http://zinc15.docking.org/substances/ZINC000000119434

PubMed

Title	Date	PubMed
Identification of two novel Drosophila melanogaster histamine-gated chloride channel subunits expressed in the eye.	2002-01-18	11714703
Fluorescent labeling of drugs and simple organic compounds containing amine functional groups, utilizing dansyl chloride in Na(2)CO(3) buffer.	2002-01-05	11755390
Glycine receptors involved in synaptic transmission are selectively regulated by the cytoskeleton in mouse spinal neurons.	2002-01	11784780
Synaptically evoked membrane potential oscillations induced by substance P in lamprey motor neurons.	2002-01	11784734
A role for the human sperm glycine receptor/Cl(-) channel in the acrosome reaction initiated by recombinant ZP3.	2002-01	11751269
Centrally administered corticotropin-releasing hormone and peripheral injections of strychnine hydrochloride potentiate the acoustic startle response in preweanling rats.	2001-12	11770058
IgG isolated from LP-BM5 infected mouse brain activates ionotropic glutamate receptors.	2001-12	11741402
Strychnine alters response properties of trigeminal nociceptive neurons in the rat.	2001-12	11731563
NMDA receptor-dependent periodic oscillations in cultured spinal cord networks.	2001-12	11731558
GABAergic and glycinergic neural inhibition in excitatory frequency tuning of bat inferior collicular neurons.	2001-12	11715077
Glycine receptor-mediated inhibition of dopamine and non-dopamine neurons of the rat ventral tegmental area in vitro.	2001-11-23	11701143
Role of protein kinase C in opioid modulation of glycine-gated Cl(-) current in rat periaqueductal gray neuron.	2001-11-16	11728420
Glycine activates myenteric neurones in adult guinea-pigs.	2001-11-01	11691868
Enzymatic and non-enzymatic reduction of brucine N-oxide by aldehyde oxidase and catalase.	2001-11	11765140
Properties and interconnections of trigeminal interneurons of the lateral pontine reticular formation in the rat.	2001-11	11698544
Modulation of excitatory synaptic transmission by GABA(C) receptor-mediated feedback in the mouse inner retina.	2001-11	11698519
Anticonvulsant activities of ethanolic extract and aqueous fraction isolated from Delphinium denudatum.	2001-11	11585691
[Arsenic and strychnine against tired eyes].	2001-10-10	11699263
[Are homeopathic studies better-fated in India?].	2001-10	11760717
Subunit composition of strychnine-sensitive glycine receptors expressed by adult rat basolateral amygdala neurons.	2001-10	11683900
Characterization of the spontaneous synaptic activity of amacrine cells in the mouse retina.	2001-10	11600626
Excitatory synaptic currents in lumbosacral parasympathetic preganglionic neurons elicited from the lateral funiculus.	2001-10	11600622
The central nervous effects of Mitragyna africanus (Willd) stembark extract in rats.	2001-10	11535357
Synchronization of an embryonic network of identified spinal interneurons solely by electrical coupling.	2001-09-27	11580902
Approaches to the synthesis of (+/-)-strychnine via the cobalt-mediated [2 + 2 + 2] cycloaddition: rapid assembly of a classic framework.	2001-09-26	11562215
A novel generation of coupling reagents. Enantiodifferentiating coupling reagents prepared in situ from 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) and chiral tertiary amines.	2001-09-21	11559174
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.	2001-09-15	11549740
Osmoregulation of vasopressin secretion via activation of neurohypophysial nerve terminals glycine receptors by glial taurine.	2001-09-15	11549721
Sensitive and specific multiresidue methods for the determination of pesticides of various classes in clinical and forensic toxicology.	2001-09-15	11516896
Homeostatic plasticity induced by chronic block of AMPA/kainate receptors modulates the generation of rhythmic bursting in rat spinal cord organotypic cultures.	2001-09	11595029
[Effects of enflurane on respiratory neurons of the pre-Bötzinger complex in medullary slices of neonatal rats].	2001-09	11593718
Mechanisms that initiate spontaneous network activity in the developing chick spinal cord.	2001-09	11535692
Electrophysiological evidence for vasopressin V(1) receptors on neonatal motoneurons, premotor and other ventral horn neurons.	2001-09	11535670
The release of spinal prostaglandin E2 and the effect of nitric oxide synthetase inhibition during strychnine-induced allodynia.	2001-09	11524348
Biogenetically inspired approach to the Strychnos alkaloids. Concise syntheses of (+/-)-akuammicine and (+/-)-strychnine.	2001-08-22	11506556
IPSC kinetics at identified GABAergic and mixed GABAergic and glycinergic synapses onto cerebellar Golgi cells.	2001-08-15	11487628
Dermal exposure to strychnine.	2001-08-14	11499889
Determination of berberine and strychnine in medicinal plants and herbal preparations by pressurized liquid extraction with capillary zone electrophoresis.	2001-08	11545398
Reversal of chloroquine and mefloquine resistance in Plasmodium falciparum by the two monoindole alkaloids, icajine and isoretuline.	2001-08	11509972
Anticonvulsant activities of the FS-1 subfraction isolated from roots of Delphinium denudatum.	2001-08	11507736
Developmental changes in 5-hydroxytryptamine-induced rhythmic activity in the spinal cord of rat fetuses in vitro.	2001-07-06	11516560
The generation of rhythmic activity in dissociated cultures of rat spinal cord.	2001-07	11553272
Spatiotemporal characterization of rhythmic activity in rat spinal cord slice cultures.	2001-07	11553271
Enflurane actions on spinal cords from mice that lack the beta3 subunit of the GABA(A) receptor.	2001-07	11465553
Intraspinal amino acid neurotransmitter activities are involved in the generation of rhythmic sympathetic nerve discharge in newborn rat spinal cord.	2001-06-15	11516417
Interactions between allosteric modulators and 4-DAMP and other antagonists at muscarinic receptors: potential significance of the distance between the N and carboxyl C atoms in the molecules of antagonists.	2001-04	11495349
Early expression of glycine and GABA(A) receptors in developing spinal cord neurons. Effects on neurite outgrowth.	2001	11738262
Is the vertebrate respiratory central pattern generator conserved? Insights from in-vitro and in-vivo amphibian models.	2001	11729866
The neuropharmacology of upper airway motor control in the awake and asleep states: implications for obstructive sleep apnoea.	2001	11686898
AMPA-evoked acetylcholine release from cultured spinal cord motoneurons and its inhibition by GABA and glycine.	2001	11564428

Patents

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 `Mon Mar 31 19:51:58 GMT 2025` Edited by `admin` on `Mon Mar 31 19:51:58 GMT 2025`
Record UNII	09703TJV4U
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

STRYCHNINE PHOSPHATE

Common Name

English

STRYCHNIDIN-10-ONE, PHOSPHATE (1:1)

Preferred Name

English

STRYCHNINE, PHOSPHATE (1:1)

Common Name

English

Strychnine phosphate [WHO-DD]

Common Name

English

Code System Code Type Description

PUBCHEM

20841677