| Revision as of 14:42, 1 December 2010 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: InChI1->InChI StdInChI StdInChIKey.← Previous edit |
Latest revision as of 11:47, 15 January 2024 edit undoMaxim Masiutin (talk | contribs)Extended confirmed users, IP block exemptions, Pending changes reviewers31,043 edits Added s2cid. Added the cs1 style template to denote Vancouver ("vanc") citation style, because references contain "vauthors" attribute to specify the list of authors. |
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{{Short description|Chemical compound}} |
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{{drugbox |
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{{cs1 config|name-list-style=vanc}} |
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| IUPAC_name = 21-methyl-3,13,21-triazapentacyclohenicosa-2(10),4,6,8,15,17,19-heptaen-14-one |
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{{Drugbox |
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| Verifiedfields = changed |
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| verifiedrevid = 399926864 |
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| IUPAC_name = 21-Methyl-3,13,21-triazapentacyclohenicosa-2(10),4,6,8,15,17,19-heptaen-14-one |
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| image = Evodiamine.svg |
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| image = Evodiamine.svg |
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| alt = Skeletal formula |
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| width = 250 |
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| ChemSpiderID = 133343 |
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| width = 220 |
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| image2 = Evodiamine-3D-spacefill.png |
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| InChI = 1/C19H17N3O/c1-21-16-9-5-3-7-14(16)19(23)22-11-10-13-12-6-2-4-8-15(12)20-17(13)18(21)22/h2-9,18,20H,10-11H2,1H3 |
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| alt2 = Space-filling model |
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| InChIKey = TXDUTHBFYKGSAH-UHFFFAOYAJ |
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<!--Clinical data--> |
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| smiles = O=C4N3CCc2c(nc1ccccc12)C3N(c5ccccc45)C |
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| tradename = |
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| StdInChI = 1S/C19H17N3O/c1-21-16-9-5-3-7-14(16)19(23)22-11-10-13-12-6-2-4-8-15(12)20-17(13)18(21)22/h2-9,18,20H,10-11H2,1H3 |
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| StdInChIKey = TXDUTHBFYKGSAH-UHFFFAOYSA-N |
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| CAS_number = 518-17-2 |
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| ATC_prefix = none |
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| PubChem = 151289 |
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| C = 19 | H = 17 | N = 3 | O = 1 |
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| molecular_weight = 303.36 g/mol |
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| bioavailability = |
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| protein_bound = |
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| metabolism = |
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| elimination_half-life = |
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| excretion = |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| pregnancy_category = |
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| legal_AU = <!-- Unscheduled / S2 / S4 / S8 --> |
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| legal_AU = <!-- Unscheduled / S2 / S4 / S8 --> |
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| legal_UK = <!-- GSL / P / POM / CD --> |
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| legal_UK = <!-- GSL / P / POM / CD --> |
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| legal_US = <!-- OTC / Rx-only --> |
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| legal_US = <!-- OTC / Rx-only --> |
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| legal_status = |
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<!--Identifiers--> |
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| routes_of_administration = |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 518-17-2 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = C01825BVNL |
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| ATC_prefix = none |
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| PubChem = 442088 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 133343 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 486598 |
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<!--Chemical data--> |
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| C=19 | H=17 | N=3 | O=1 |
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| smiles = O=C4N3CCc2c(c1ccccc12)C3N(c5ccccc45)C |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C19H17N3O/c1-21-16-9-5-3-7-14(16)19(23)22-11-10-13-12-6-2-4-8-15(12)20-17(13)18(21)22/h2-9,18,20H,10-11H2,1H3 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = TXDUTHBFYKGSAH-UHFFFAOYSA-N |
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'''Evodiamine''' is a chemical which is extracted from the ''] spp'' family of plants which has been shown to reduce fat uptake in mouse studies.{{Fact|date=February 2007}} Its method is believed to be similar to ], but retains none of the "hot" taste.{{Fact|date=February 2007}} |
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'''Evodiamine''' is a ] extracted from the plant genus '']'', which has been shown to reduce fat uptake in mouse studies. It is suspected that its ] is similar to that of ].<ref name="Kobiyashi2001">{{cite journal | vauthors = Kobayashi Y, Nakano Y, Kizaki M, Hoshikuma K, Yokoo Y, Kamiya T | s2cid = 19937385 | title = Capsaicin-like anti-obese activities of evodiamine from fruits of Evodia rutaecarpa, a vanilloid receptor agonist | journal = Planta Medica | volume = 67 | issue = 7 | pages = 628–33 | date = October 2001 | pmid = 11582540 | doi = 10.1055/s-2001-17353 }}</ref> As such, it has been included in some dietary supplements. Neither its fat-burning effects in humans nor any potential side effects have been empirically established. |
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Evodiamine acts primarily as a ] and ].<ref name="Wang2008">{{cite journal | vauthors = Wang T, Wang Y, Kontani Y, Kobayashi Y, Sato Y, Mori N, Yamashita H | title = Evodiamine improves diet-induced obesity in a uncoupling protein-1-independent manner: involvement of antiadipogenic mechanism and extracellularly regulated kinase/mitogen-activated protein kinase signaling | journal = Endocrinology | volume = 149 | issue = 1 | pages = 358–66 | date = January 2008 | pmid = 17884939 | doi = 10.1210/en.2007-0467 | doi-access = free }}</ref> |
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== References == |
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Evodiamine may also act by increasing the number of ]s available in the brain, enhancing the reuptake of serotonin.<ref>{{cite journal | vauthors = Hu Y, Ehli EA, Hudziak JJ, Davies GE | title = Berberine and evodiamine influence serotonin transporter (5-HTT) expression via the 5-HTT-linked polymorphic region | journal = The Pharmacogenomics Journal | volume = 12 | issue = 5 | pages = 372–8 | date = October 2012 | pmid = 21647174 | doi = 10.1038/tpj.2011.24 | doi-access = | s2cid = 11148104 }}</ref> |
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*Kobayashi, Y. ''et al.'' (2001): ''Capsaicin-like anti-obese activities of evodiamine from fruits of Evodia rutaecarpa, a vanilloid receptor agonist''. In: ''Planta Med.'' '''67'''(7); 628–33; PMID 11582540 |
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*Wang, T. ''et al.'' (2008): ''Evodiamine improves diet-induced obesity in an uncoupling protein-1-independent manner: involvement of antiadipogenic mechanism and extracellularly regulated kinase/mitogen-activated protein kinase signaling''. In: ''Endocrinology'' '''149'''(1); 358–66; PMID 17884939 |
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== References == |
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{{Reflist}} |
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{{Transient receptor potential channel modulators}} |
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] |
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{{gastrointestinal-drug-stub}} |
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] |
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] |
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] |