| Revision as of 11:53, 6 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 460121612 of page Pseudaconitine for the Chem/Drugbox validation project (updated: 'ChEMBL', 'CASNo'). |
Latest revision as of 19:11, 30 September 2023 edit Minihaa (talk | contribs)Autopatrolled, Extended confirmed users3,989 editsm →Structure and reactivity: + linkTag: Visual edit |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Chembox |
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{{Chembox |
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| verifiedrevid = 439645430 |
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| verifiedrevid = 464375777 |
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|ImageFile=Pseudaconitine.svg |
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| ImageFile=Pseudaconitine.svg |
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|ImageSize=200px |
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| ImageSize=200px |
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|SystematicName=1α,6α,14α(''E''),16β-20-Ethyl-1,6,16-trimethoxy-4-methoxymethyl-3,13-dihydroxyaconitane-8,14-diyl 8-acetate 14-(3,4-dimethoxybenzoate) |
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| IUPACName=8-(Acetyloxy)-20-ethyl-3,13-dihydroxy-1α,6α,16β-trimethoxy-4-(methoxymethyl)aconitan-14α-yl 3,4-dimethoxybenzoate |
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|OtherNames=Nepaline; Acraconitine; Feraconitine; Pseudoaconitine; Nepal aconitine; Nepaline; Veratroylaconine |
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| OtherNames=Nepaline; Acraconitine; Feraconitine; Pseudoaconitine; Nepal aconitine; Nepaline; Veratroylaconine |
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|Section1= {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 390354 |
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| ChemSpiderID = 390354 |
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| InChI = 1/C36H51NO12/c1-9-37-16-33(17-42-3)23(39)13-24(45-6)36-20-14-34(41)25(46-7)15-35(49-18(2)38,27(30(36)37)28(47-8)29(33)36)26(20)31(34)48-32(40)19-10-11-21(43-4)22(12-19)44-5/h10-12,20,23-31,39,41H,9,13-17H2,1-8H3/t20-,23-,24+,25+,26-,27+,28+,29-,30?,31-,33+,34+,35-,36+/m1/s1 |
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| InChI = 1/C36H51NO12/c1-9-37-16-33(17-42-3)23(39)13-24(45-6)36-20-14-34(41)25(46-7)15-35(49-18(2)38,27(30(36)37)28(47-8)29(33)36)26(20)31(34)48-32(40)19-10-11-21(43-4)22(12-19)44-5/h10-12,20,23-31,39,41H,9,13-17H2,1-8H3/t20-,23-,24+,25+,26-,27+,28+,29-,30?,31-,33+,34+,35-,36+/m1/s1 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = YVPYMQHYESYLIR-CERQHTHQSA-N |
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| StdInChIKey = YVPYMQHYESYLIR-CERQHTHQSA-N |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = <!-- blanked - oldvalue: 127-29-7 --> |
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| CASNo=127-29-7 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| ChEMBL = 509646 |
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| UNII = 5483BY72RT |
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| PubChem=441752 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| SMILES = O=C(O53(O)C416C2N(CC)C(1(OC)2(OC(=O)C)(C3OC)45)(COC)(O)C6OC)c7ccc(OC)c(OC)c7 |
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| ChEMBL = 509646 |
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| PubChem= 3035296 |
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| SMILES = O=C(O53(O)C416C2N(CC)C(1(OC)2(OC(=O)C)(C3OC)45)(COC)(O)C6OC)c7ccc(OC)c(OC)c7 |
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}} |
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|Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=26|H=51|N=1|O=12 |
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| C=36 | H=51 | N=1 | O=12 |
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| MeltingPtC=202 |
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| MeltingPtC=202 |
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|Section3= {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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'''Pseudaconitine''', also known as '''nepaline''' (C<sub>36</sub>H<sub>51</sub>NO<sub>12</sub>), is an extremely toxic ] found in high quantities in the ]s of '']'', also known as Indian Monkshood, which belongs to the family ]. The plant is found in East Asia, including the ]. |
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== History == |
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Pseudaconitine was discovered in 1878 by Wright and Luff. They isolated a highly toxic ] from the roots of the plant ''Aconitum ferox'' and called it pseudaconitine. The poison is also called ''bikh'', ''bish'', or ''nabee''.<ref>{{cite web |title=Monkshood |url=https://www.aacc.org/community/divisions/tdm-and-toxicology/toxin-library/monkshood |website=AACC.org |access-date=9 November 2018}}</ref> |
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== Toxicity and mechanism == |
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Pseudaconitine is a moderate ] of the ] ]. This enzyme breaks down the ] ] through ].<ref>Rahman, A, et al, ''New Norditerpenoid Alkoids from Aconitum falceroni'', 2000</ref> ] of this enzyme causes a constant stimulation of the postsynaptic ] by the neurotransmitter which it cannot cancel. This accumulation of acetylcholine may thus lead to the constant stimulation of the ], ] and ]. Furthermore, it appears the substance in small quantities also causes a tingling effect on the tongue, lips and skin.<ref name=reference1>Cash,J.T.,Dunstan,W.R., ''The Pharmacology of Pseudaconitine and Japaconitine considered in relation to that of Aconitine'', 1901</ref> |
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== Structure and reactivity == |
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Pseudaconitine is a ], with the chemical formula C<sub>36</sub>H<sub>51</sub>NO<sub>12</sub>. The ] melts at 202 °C and is moderately soluble in water, but more so in alcohol. This shows that it is a ] substance. When heated in the dry state, it undergoes ] and ] (C<sub>34</sub>H<sub>47</sub>O<sub>10</sub>N) is formed. This does not have the same tingling effect as pseudaconitine.<ref name=reference1>Cash,J.T.,Dunstan,W.R., ''The Pharmacology of Pseudaconitine and Japaconitine considered in relation to that of Aconitine'', 1901</ref><ref>Tsudaan Y., Marion L., ''Pseudaconitine, and the stereochemical relationship of the highly oxygenated aconite alkaloids'', 1963</ref> |
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== See also == |
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* ] |
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== References == |
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{{reflist}} |
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