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Record Information
Version1.0
Created at2019-05-20 17:30:31 UTC
Updated at2021-08-15 04:57:01 UTC
NP-MRD IDNP0000001
Secondary Accession NumbersNone
Natural Product Identification
Common NameStrychnine
DescriptionStrychnine, also known as strychnin, is an extremely poisonous and bitter indoline alkaloid. It 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. Strychnine is also classified as a terpene indole alkaloid belonging to the Strychnos family of Corynanthe alkaloids. In nature, strychnine is most commonly found in the seeds of the Strychnos nux-vomica tree. Strychnine is derived from two smaller, simpler compounds, tryptamine and secologanin. The enzyme, strictosidine synthase, catalyzes the condensation of tryptamine and secologanin, followed by a spontaneous reaction to form strictosidine. Several other enzymatic steps eventually lead to the conversion of strictosidine to strychnine. Strychnine is a colorless, bitter, crystalline alkaloid that is used as a pesticide, particularly for killing small vertebrates such as birds and rodents. Strychnine, when inhaled, swallowed, or absorbed through the eyes or mouth, causes poisoning which results in muscular convulsions and eventually death through asphyxia. Strychnine functions as a neurotoxin which acts as an antagonist of glycine and acetylcholine receptors. It primarily affects the motor nerve fibers in the spinal cord which control muscle contraction. Historically, strychnine has served many purposes: (1) As a medicinal remedy to treat a wide variety of ailments, (2) as an athletic performance enhancer, (3) as a recreational drug, and (4) as a pesticide for killing small vertebrates (PMID: 20810461 ).
Structure
Thumb
Synonyms
ValueSource
StrychninChEBI
Strychnidin-10-oneNP-MRD
Chemical FormulaC21H22N2O2
Average Mass334.4116 Da
Monoisotopic Mass334.16813 Da
IUPAC Name(1R,11S,18S,20R,21R,22S)-12-oxa-8,17-diazaheptacyclo[15.5.2.0^{1,18}.0^{2,7}.0^{8,22}.0^{11,21}.0^{15,20}]tetracosa-2,4,6,14-tetraen-9-one
Traditional Name(1R,11S,18S,20R,21R,22S)-12-oxa-8,17-diazaheptacyclo[15.5.2.0^{1,18}.0^{2,7}.0^{8,22}.0^{11,21}.0^{15,20}]tetracosa-2,4,6,14-tetraen-9-one
CAS Registry Number57-24-9
SMILES
[H][C@]12C[C@@]3([H])C4=CCO[C@@]5([H])CC(=O)N6C7=CC=CC=C7[C@@]1(CCN2C4)[C@]6([H])[C@@]35[H]
InChI Identifier
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
InChI KeyQMGVPVSNSZLJIA-FVWCLLPLSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50.23 MHz, CDCl3, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, simulated)V.dorna832021-08-14View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, simulated)Zinat2021-09-21View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)Zinat2021-09-21View Spectrum
Species
Species of Origin
Species NameSourceReference
Strychnos atlanticaKNApSAcK Database
Strychnos cinnamomifoliaKNApSAcK Database
Strychnos columbrinaKNApSAcK Database
Strychnos ignatiiKNApSAcK Database
Strychnos ligustrinaKNApSAcK Database
Strychnos lucida R.Br.KNApSAcK Database
Strychnos nitidaKNApSAcK Database
Strychnos nux-vomicaKNApSAcK Database
Strychnos nux-vomica L.Seed
Strychnos spinosaKNApSAcK Database
Strychnos tieuteKNApSAcK Database
Strychnos triplinerviaKNApSAcK Database
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassStrychnos alkaloids
Sub ClassNot Available
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 Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point287.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point284 °Chttps://pubchem.ncbi.nlm.nih.gov/compound/Strychnine
Water Solubility160 mg/L @ 25 °C (exp)The Good Scents Company Information System
LogP1.930The Good Scents Company Information System
Predicted Properties
PropertyValueSource
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 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity94.51 m³·mol⁻¹ChemAxon
Polarizability35.67 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
External Links
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00001770
Chemspider ID389877
KEGG Compound IDC06522
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkStrychnine
METLIN IDNot Available
PubChem Compound441071
PDB IDNot Available
ChEBI ID28973
Good Scents IDrw1137021
References
General References
  1. Parker AJ, Lee JB, Redman J, Jolliffe L: Strychnine poisoning: gone but not forgotten. Emerg Med J. 2011 Jan;28(1):84. doi: 10.1136/emj.2009.080879. Epub 2010 Sep 1. [PubMed:20810461 ]
  2. Rauramo L, Lagerspetz K, Engblom P, Punnonen R: The effect of castration and peroral estrogen therapy on some psychological functions. Front Horm Res. 1975;3:94-104. doi: 10.1159/000398269. [PubMed:1234567 ]
  3. Frederich M, Hayette MP, Tits M, De Mol P, Angenot L: In vitro activities of strychnos alkaloids and extracts against Plasmodium falciparum. Antimicrob Agents Chemother. 1999 Sep;43(9):2328-31. doi: 10.1128/AAC.43.9.2328. [PubMed:10471592 ]
  4. Frederich M, De Pauw MC, Llabres G, Tits M, Hayette MP, Brandt V, Penelle J, De Mol P, Angenot L: New antimalarial and cytotoxic sungucine derivatives from Strychnos icaja roots. Planta Med. 2000 Apr;66(3):262-9. doi: 10.1055/s-2000-8559. [PubMed:10821054 ]
  5. Narikawa K, Furue H, Kumamoto E, Yoshimura M: In vivo patch-clamp analysis of IPSCs evoked in rat substantia gelatinosa neurons by cutaneous mechanical stimulation. J Neurophysiol. 2000 Oct;84(4):2171-4. doi: 10.1152/jn.2000.84.4.2171. [PubMed:11024105 ]
  6. Wenstrup J, Leroy SA: Spectral integration in the inferior colliculus: role of glycinergic inhibition in response facilitation. J Neurosci. 2001 Feb 1;21(3):RC124. [PubMed:11157095 ]