Strychnine
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Basic Info
| Common Name | Strychnine(F04800) |
| 2D Structure | |
| Description | Strychnine 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. (L1230) |
| FRCD ID | F04800 |
| CAS Number | 57-24-9 |
| PubChem CID | 441071 |
| Formula | C21H22N2O2 |
| IUPAC Name | (4aR,5aS,8aR,13aS,15aS,15bR)-4a,5,5a,7,8,13a,15,15a,15b,16-decahydro-2H-4,6-methanoindolo[3,2,1-ij]oxepino[2,3,4-de]pyrrolo[2,3-h]quinoline-14-one |
| InChI Key | QMGVPVSNSZLJIA-FVWCLLPLSA-N |
| InChI | 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 |
| Canonical SMILES | C1CN2CC3=CCOC4CC(=O)N5C6C4C3CC2C61C7=CC=CC=C75 |
| Isomeric SMILES | C1CN2CC3=CCO[C@H]4CC(=O)N5[C@H]6[C@H]4[C@H]3C[C@H]2[C@@]61C7=CC=CC=C75 |
| Wikipedia | Strychnine |
| Synonyms |
UNII-H9Y79VD43J
strychnine
57-24-9
(-)-Strychnine
Strychnidin-10-one
Strychnin
[3H]strychnine
Sanaseed
Estricnina
Strychinos
|
| Classifies |
Plant Toxin
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Alkaloids and derivatives |
| Class | Strychnos alkaloids |
| Subclass | Not available |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Strychnos alkaloids |
| Alternative Parents |
|
| Molecular Framework | Aromatic heteropolycyclic compounds |
| 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 |
| Description | This compound belongs to the class of organic compounds known as strychnos alkaloids. These are alkaloids having a core structure based on the strychnan, stemmadenine (seco-curan), or the akuammicine (curan) skeleton. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 334.419 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 0 |
| Complexity | 689 |
| Monoisotopic Mass | 334.168 |
| Exact Mass | 334.168 |
| XLogP | 1.9 |
| Formal Charge | 0 |
| Heavy Atom Count | 25 |
| Defined Atom Stereocenter Count | 6 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9953 |
| Human Intestinal Absorption | HIA+ | 0.9973 |
| Caco-2 Permeability | Caco2+ | 0.8867 |
| P-glycoprotein Substrate | Substrate | 0.6362 |
| P-glycoprotein Inhibitor | Inhibitor | 0.8321 |
| Non-inhibitor | 0.9236 | |
| Renal Organic Cation Transporter | Inhibitor | 0.7052 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7080 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8894 |
| CYP450 2D6 Substrate | Non-substrate | 0.6955 |
| CYP450 3A4 Substrate | Substrate | 0.7273 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9045 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9071 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9260 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9025 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8309 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.7352 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9137 |
| Non-inhibitor | 0.7009 | |
| AMES Toxicity | Non AMES toxic | 0.7136 |
| Carcinogens | Non-carcinogens | 0.9230 |
| Fish Toxicity | High FHMT | 0.7423 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.7137 |
| Honey Bee Toxicity | Low HBT | 0.6707 |
| Biodegradation | Not ready biodegradable | 0.9963 |
| Acute Oral Toxicity | I | 0.8044 |
| Carcinogenicity (Three-class) | Non-required | 0.5487 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -3.2572 | LogS |
| Caco-2 Permeability | 1.5091 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 4.5361 | LD50, mol/kg |
| Fish Toxicity | 0.1705 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.4481 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Toxicoses of the Ruminant Nervous System. | Vet Clin North Am Food Anim Pract | 2017 Mar | 28166935 |
| Pesticide incidence in poisoned baits: A 10-year report. | Sci Total Environ | 2017 Dec 1 | 28564626 |
| Characterizing 1341 cases of veterinary toxicoses confirmed in western Canada: A 16-year retrospective study. | Can Vet J | 2016 Jan | 26740698 |
| Analysis of 32 toxic natural substances in herbal products by liquid chromatography quadrupole linear ion trap mass spectrometry. | J Pharm Biomed Anal | 2015 Nov 10 | 26210743 |
| Dual mechanism for bitter avoidance in Drosophila. | J Neurosci | 2015 Mar 4 | 25740527 |
| Cytotoxicity and DNA interaction of brucine and strychnine-Two alkaloids of semen strychni. | Int J Biol Macromol | 2015 | 25796448 |
| A study of Semen Strychni-induced renal injury and herb-herb interaction of Radix Glycyrrhizae extract and/or Rhizoma Ligustici extract on the comparative toxicokinetics of strychnine and brucine in rats. | Food Chem Toxicol | 2014 Jun | 24704041 |
| Dynamic detection of non-protein-bound strychnine and brucine in rabbit muscle and synovial fluid after topical application of total Strychnos alkaloid patches. | Drug Test Anal | 2014 Apr | 23776063 |
| Brucine, an alkaloid from seeds of Strychnos nux-vomica Linn., represses hepatocellular carcinoma cell migration and metastasis: the role of hypoxia inducible factor 1 pathway. | Toxicol Lett | 2013 Oct 24 | 23933019 |
| Brunfelsia australis (Yesterday, Today, and Tomorrow tree) and Solanum poisoning in a dog. | J Am Anim Hosp Assoc | 2012 Mar-Apr | 22267167 |
| Screening of plant toxins in food, feed and botanicals using full-scan high-resolution (Orbitrap) mass spectrometry. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2011 Oct | 22007891 |
| Use of Strychnos nux-vomica (Azraqi) seeds in Unani system of medicine: role of detoxification. | Afr J Tradit Complement Altern Med | 2010 | 21731158 |
| A simple method to identify the unprocessed Strychnos seeds used in herbal medicinal products. | Planta Med | 2008 Mar | 18484543 |
| The effect of zinc on glycinergic inhibitory postsynaptic currents in rat spinal dorsal horn neurons. | Brain Res | 2007 Aug 3 | 17604007 |
| HPLC-UV method for nicotine, strychnine, and aconitine in dairy products. | J Agric Food Chem | 2006 Oct 4 | 17002408 |
| The apoptotic effect of brucine from the seed of Strychnos nux-vomica on human hepatoma cells is mediated via Bcl-2 and Ca2+ involved mitochondrial pathway. | Toxicol Sci | 2006 May | 16443926 |
| Analysis of strychnine and brucine in postmortem specimens by RP-HPLC: a case report of fatal intoxication. | J Anal Toxicol | 2004 Mar | 15068571 |
| [Study of toxicology of strychnos]. | Fa Yi Xue Za Zhi | 2004 | 15495815 |
| Tremorgenic neuromycotoxicosis in 2 dogs ascribed to the ingestion of penitrem A and possibly roquefortine in rice contaminated with Penicillium crustosum. | J S Afr Vet Assoc | 2002 Dec | 12665136 |
| Strictly strychnine. | Anaesth Intensive Care | 1994 Apr | 8043139 |
Targets
- 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
- Mechanism of Action:
- Strychnine acts as an antagonist at the inhibitory or strychnine-sensitive glycine receptor, a ligand-gated chloride channel in the spinal cord and the brain.
References
- Wikipedia. Strychnine. Last Updated 20 July 2009. : http://en.wikipedia.org/wiki/Strychnine
- 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
- Mechanism of Action:
- Strychnine acts as an antagonist at the inhibitory or strychnine-sensitive glycine receptor, a ligand-gated chloride channel in the spinal cord and the brain.
References
- 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 ]
- 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
- Mechanism of Action:
- Strychnine acts as an antagonist at the inhibitory or strychnine-sensitive glycine receptor, a ligand-gated chloride channel in the spinal cord and the brain.
References
- Wikipedia. Strychnine. Last Updated 20 July 2009. : http://en.wikipedia.org/wiki/Strychnine
- 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
- Mechanism of Action:
- Strychnine acts as an antagonist at the inhibitory or strychnine-sensitive glycine receptor, a ligand-gated chloride channel in the spinal cord and the brain.
References
- Wikipedia. Strychnine. Last Updated 20 July 2009. : http://en.wikipedia.org/wiki/Strychnine
- 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
- Mechanism of Action:
- Strychnine acts as an antagonist at the inhibitory or strychnine-sensitive glycine receptor, a ligand-gated chloride channel in the spinal cord and the brain.
References
- Wikipedia. Strychnine. Last Updated 20 July 2009. : http://en.wikipedia.org/wiki/Strychnine
- 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
- 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
- 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 ]
- 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
- 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 ]