Record Information |
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Version | 1.0 |
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Created at | 2019-05-20 17:30:31 UTC |
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Updated at | 2024-09-03 04:21:43 UTC |
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NP-MRD ID | NP0000001 |
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DOI | https://doi.org/10.57994/2582 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Strychnine |
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Description | Strychnine, 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 ). |
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Structure | [H]C1=C([H])C([H])=C2C(=C1[H])N1C(=O)C([H])([H])[C@]3([H])OC([H])([H])C([H])=C4C([H])([H])N5C([H])([H])C([H])([H])[C@]22[C@]5([H])C([H])([H])[C@]4([H])[C@]3([H])[C@]12[H] 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 |
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Synonyms | Value | Source |
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Strychnin | ChEBI | Strychnidin-10-one | NP-MRD |
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Chemical Formula | C21H22N2O2 |
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Average Mass | 334.4116 Da |
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Monoisotopic Mass | 334.16813 Da |
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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 |
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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 |
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CAS Registry Number | 57-24-9 |
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SMILES | [H]C1=C([H])C([H])=C2C(=C1[H])N1C(=O)C([H])([H])[C@]3([H])OC([H])([H])C([H])=C4C([H])([H])N5C([H])([H])C([H])([H])[C@]22[C@]5([H])C([H])([H])[C@]4([H])[C@]3([H])[C@]12[H] |
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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 |
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InChI Key | QMGVPVSNSZLJIA-FVWCLLPLSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 1H NMR Spectrum (1D, 700 MHz, CDCl3, simulated) | Varshavi.d26 | | | 2021-12-06 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, CDCl3, experimental) | Varshavi.d26 | | | 2021-12-06 | View Spectrum | HMBC NMR | [1H, 13C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental) | john.cort@pnnl.gov | Not Available | Not Available | 2024-05-13 | View Spectrum | HSQC NMR | [1H, 13C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental) | john.cort@pnnl.gov | Not Available | Not Available | 2024-05-13 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, CD3OD, experimental) | john.cort@pnnl.gov | Not Available | Not Available | 2024-05-13 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50.23 MHz, CDCl3, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 1H NMR Spectrum (1D, 400 MHz, CDCl3, simulated) | v.dorna83@yahoo.com | Not Available | Not Available | 2021-08-14 | View Spectrum |
| Species |
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Species of Origin | |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Alkaloids and derivatives |
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Class | Strychnos alkaloids |
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Sub Class | Not Available |
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Direct Parent | Strychnos alkaloids |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Solid |
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Experimental Properties | |
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Predicted Properties | |
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General References | - 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- Poleksic J: [Epidemiological research on alcoholism in the industry and mining in our country]. Nar Zdrav. 1975 Jul-Aug;31(7-8):224-30. [PubMed:1234321 ]
- Metaxas AE, Cort JR: Counterion influence on chemical shifts in strychnine salts. Magn Reson Chem. 2013 May;51(5):292-8. doi: 10.1002/mrc.3945. Epub 2013 Mar 11. [PubMed:23495106 ]
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