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Record Information
Version2.0
Creation Date2009-07-23 18:26:10 UTC
Update Date2014-12-24 20:25:57 UTC
Accession NumberT3D3086
Identification
Common NameStrychnine
ClassSmall Molecule
DescriptionStrychnine is a plant toxin most commonly found in the seeds of the Strychnine tree (Strychnos nux-vomica L.). It is used as a pesticide, particularly for killing small vertebrates such as birds and rodents. Strychnine causes muscular convulsions and eventually death through asphyxia or sheer exhaustion. (3)
Compound Type
  • Amide
  • Amine
  • Ether
  • Natural Compound
  • Organic Compound
  • Pesticide
  • Plant Toxin
Chemical Structure
Thumb
Synonyms
Synonym
(-)-strychnine
(−)-Strychnine
Certox
Dolco mouse cereal
Kwik-kil
Mole death
Mouse-nots
Mouse-rid
Mouse-tox
Pied piper mouse seed
Ro-dex
Sanaseed
STR
Stricnina
Strychnidin-10-one
Strychnin
Strychnos
Chemical FormulaC21H22N2O2
Average Molecular Mass334.412 g/mol
Monoisotopic Mass334.168 g/mol
CAS Registry Number57-24-9
IUPAC Name12-oxa-8,17-diazaheptacyclo[15.5.2.0¹,¹⁸.0²,⁷.0⁸,²².0¹¹,²¹.0¹⁵,²⁰]tetracosa-2,4,6,14-tetraen-9-one
Traditional Namestrychnos
SMILESO=C1CC2OCC=C3CN4CCC56C4CC3C2C5N1C1=CC=CC=C61
InChI IdentifierInChI=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
InChI KeyInChIKey=QMGVPVSNSZLJIA-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as strychnos alkaloids. These are alkaloids having a core structure based on the strychnan, stemmadenine (seco-curan), or the akuammicine (curan) skeleton.
KingdomChemical entities
Super ClassOrganic compounds
ClassAlkaloids and derivatives
Sub ClassStrychnos alkaloids
Direct ParentStrychnos alkaloids
Alternative Parents
Substituents
  • Strychnan skeleton
  • Akuammicine-skeleton
  • Stemmadenine-skeleton
  • Carbazole
  • Quinolidine
  • Indole or derivatives
  • Indolizidine
  • Aralkylamine
  • Piperidinone
  • Delta-lactam
  • Piperidine
  • Benzenoid
  • N-alkylpyrrolidine
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxamide group
  • Amino acid or derivatives
  • Lactam
  • Carboxylic acid derivative
  • Dialkyl ether
  • Ether
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Organic oxide
  • Amine
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point287°C
Boiling PointNot Available
Solubility0.16 mg/mL at 25°C [SEIDELL,A (1941)]
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.72 mg/mLALOGPS
logP1.68ALOGPS
logP0.93ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)17.24ChemAxon
pKa (Strongest Basic)9.27ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area32.78 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity94.51 m3·mol-1ChemAxon
Polarizability35.79 Å3ChemAxon
Number of Rings7ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0009000000-bbb67155f9bf87a22b0dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0009000000-2d17c0436331c78f55cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gbi-0097000000-e2bbd426370e9e71a04eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-4ff6c1229dbbcbf5de8eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0009000000-c2c0c41523f7d6fdbb43View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0007-7093000000-e83bdf997991b31eba21View in MoNA
Toxicity Profile
Route of ExposureOral (ingestion) (4) ; dermal (4)
Mechanism of ToxicityStrychnine acts as an antagonist at the inhibitory or strychnine-sensitive glycine receptor, a ligand-gated chloride channel in the spinal cord and the brain. (3)
MetabolismNot Available
Toxicity ValuesLD50: 2350 ug/kg (Oral, Rat) (1) LD50: 1100 ug/kg (Intraperitoneal, Rat) (1) LD50: 1200 ug/kg (Subcutaneous, Rat) (1) LD50: 582 ug/kg (Intravenous, Rat) (1)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesStrychnine is a plant toxin most commonly found in the seeds of the Strychnine tree (Strychnos nux-vomica L.). It is used as a pesticide, particularly for killing small vertebrates such as birds and rodents. (3)
Minimum Risk LevelNot Available
Health EffectsDeath may result from asphyxia or sheer exhaustion. (3)
SymptomsStrychnine causes muscular convulsions of increasing intensity and frequency and eventually death through asphyxia or sheer exhaustion. (3)
TreatmentTreatment of strychnine poisoning involves an oral application of an activated charcoal infusion to absorb any poison within the digestive tract that has not yet been absorbed into the blood. Anticonvulsants such as phenobarbital or diazepam are administered to control convulsions, along with muscle relaxants such as dantrolene to combat muscle rigidity. (2)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID441071
ChEMBL IDNot Available
ChemSpider IDNot Available
KEGG IDC06522
UniProt IDNot Available
OMIM ID
ChEBI ID28973
BioCyc IDNot Available
CTD IDNot Available
Stitch IDStrychnine
PDB IDNot Available
ACToR ID3106
Wikipedia LinkStrychnine
References
Synthesis ReferenceNot Available
MSDST3D3086.pdf
General References
  1. Lewis RJ (1996). Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold.
  2. Wikipedia. Strychnine poisoning. Last Updated 25 June 2009. [Link]
  3. Wikipedia. Strychnine. Last Updated 20 July 2009. [Link]
  4. Wikipedia. Phytotoxin. Last Updated 7 August 2009. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Transmitter-gated ion channel activity
Specific Function:
The glycine receptor is a neurotransmitter-gated ion channel. Binding of glycine to its receptor increases the chloride conductance and thus produces hyperpolarization (inhibition of neuronal firing).
Gene Name:
GLRA1
Uniprot ID:
P23415
Molecular Weight:
52623.35 Da
References
  1. Jensen AA, Gharagozloo P, Birdsall NJ, Zlotos DP: Pharmacological characterisation of strychnine and brucine analogues at glycine and alpha7 nicotinic acetylcholine receptors. Eur J Pharmacol. 2006 Jun 6;539(1-2):27-33. Epub 2006 May 9. [16687139 ]
  2. Wikipedia. Strychnine. Last Updated 20 July 2009. [Link]
General Function:
Transmitter-gated ion channel activity
Specific Function:
The glycine receptor is a neurotransmitter-gated ion channel. Binding of glycine to its receptor increases the chloride conductance and thus produces hyperpolarization (inhibition of neuronal firing).
Gene Name:
GLRA2
Uniprot ID:
P23416
Molecular Weight:
52001.585 Da
References
  1. Wikipedia. Strychnine. Last Updated 20 July 2009. [Link]
General Function:
Transmitter-gated ion channel activity
Specific Function:
The glycine receptor is a neurotransmitter-gated ion channel. Binding of glycine to its receptor increases the chloride conductance and thus produces hyperpolarization (inhibition of neuronal firing).
Gene Name:
GLRA3
Uniprot ID:
O75311
Molecular Weight:
53799.775 Da
References
  1. Wikipedia. Strychnine. Last Updated 20 July 2009. [Link]
General Function:
Transmitter-gated ion channel activity
Specific Function:
The glycine receptor is a neurotransmitter-gated ion channel. Binding of glycine to its receptor increases the chloride conductance and thus produces hyperpolarization (inhibition of neuronal firing).
Gene Name:
GLRA4
Uniprot ID:
Q5JXX5
Molecular Weight:
47727.92 Da
References
  1. Wikipedia. Strychnine. Last Updated 20 July 2009. [Link]
General Function:
Glycine binding
Specific Function:
The glycine receptor is a neurotransmitter-gated ion channel. Binding of glycine to its receptor increases the chloride conductance and thus produces hyperpolarization (inhibition of neuronal firing).
Gene Name:
GLRB
Uniprot ID:
P48167
Molecular Weight:
56121.62 Da
References
  1. Wikipedia. Strychnine. Last Updated 20 July 2009. [Link]
General Function:
G-protein coupled acetylcholine receptor activity
Specific Function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is adenylate cyclase inhibition. Signaling promotes phospholipase C activity, leading to the release of inositol trisphosphate (IP3); this then triggers calcium ion release into the cytosol.
Gene Name:
CHRM2
Uniprot ID:
P08172
Molecular Weight:
51714.605 Da
References
  1. Jakubik J, Krejci A, Dolezal V: Asparagine, valine, and threonine in the third extracellular loop of muscarinic receptor have essential roles in the positive cooperativity of strychnine-like allosteric modulators. J Pharmacol Exp Ther. 2005 May;313(2):688-96. Epub 2005 Jan 12. [15647330 ]
General Function:
Receptor activity
Specific Function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover.
Gene Name:
CHRM3
Uniprot ID:
P20309
Molecular Weight:
66127.445 Da
References
  1. Jakubik J, Krejci A, Dolezal V: Asparagine, valine, and threonine in the third extracellular loop of muscarinic receptor have essential roles in the positive cooperativity of strychnine-like allosteric modulators. J Pharmacol Exp Ther. 2005 May;313(2):688-96. Epub 2005 Jan 12. [15647330 ]
General Function:
Voltage-gated sodium channel activity involved in sa node cell action potential
Specific Function:
This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant Na(+) channel isoform. This channel is responsible for the initial upstroke of the action potential. Channel inactivation is regulated by intracellular calcium levels.
Gene Name:
SCN5A
Uniprot ID:
Q14524
Molecular Weight:
226937.475 Da
References
  1. Yuan C, Sun L, Zhang M, Li S, Wang X, Gao T, Zhu X: Inhibition of human Na(v)1.5 sodium channels by strychnine and its analogs. Biochem Pharmacol. 2011 Aug 15;82(4):350-7. doi: 10.1016/j.bcp.2011.05.006. Epub 2011 May 14. [21616062 ]