| Revision as of 20:29, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 463817243 of page Akuammine for the Chem/Drugbox validation project (updated: 'ChEMBL', 'CAS_number'). |
Latest revision as of 10:26, 21 October 2024 edit JWBE (talk | contribs)Extended confirmed users10,126 edits removed Category:Phenols; added Category:Hydroxyarenes using HotCat |
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{{cs1 config|name-list-style=vanc}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Drugbox |
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{{Chembox |
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| Verifiedfields = changed |
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| Verifiedfields = changed |
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| verifiedrevid = 399379508 |
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| verifiedrevid = 477246027 |
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<!-- Images --> |
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| IUPAC_name = |
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| image = Akuammine.svg |
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| ImageFile = Akuammine.svg |
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| width = 200 |
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| ImageSize = 200px |
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| ImageAlt = |
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<!--Clinical data--> |
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<!-- Names --> |
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| tradename = |
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| IUPACName = |
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| OtherNames = Vincamajoridine |
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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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<!-- Sections --> |
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| Section1 = {{Chembox Identifiers |
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| pregnancy_category = |
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| CASNo = 3512-87-6 |
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| legal_AU = <!-- S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| legal_CA = |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| legal_UK = |
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| UNII = 0421AQV5W3 |
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| legal_US = <!-- Schedule I / Schedule II / Schedule III --> |
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| legal_status = Legal |
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| routes_of_administration = Oral, Rectal |
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<!--Pharmacokinetic data--> |
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| bioavailability = |
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| protein_bound = |
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| excretion = |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = <!-- blanked - oldvalue: 3512-87-6 --> |
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| ATC_prefix = none |
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| ATC_suffix = |
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| PubChem = 6441511 |
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| PubChem = 6441511 |
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| SMILES = COC(=O)C46CO35N(C)c1ccc(O)cc156CCN2C/C(=C\C)4CC23 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 16735645 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = <!-- blanked - oldvalue: 484665 --> |
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| C=22 | H=26 | N=2 | O=4 |
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| molecular_weight = 382.45 g/mol |
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| smiles = COC(=O)C46CO35N(C)c1ccc(O)cc156CCN2C/C(=C\C)4CC23 |
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| InChI = 1/C22H26N2O4/c1-4-13-11-24-8-7-21-16-9-14(25)5-6-17(16)23(2)22(21)18(24)10-15(13)20(21,12-28-22)19(26)27-3/h4-6,9,15,18,25H,7-8,10-12H2,1-3H3/b13-4+/t15-,18?,20?,21+,22-/m1/s1 |
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| InChIKey = YILKZADAWNUTTB-OCTHBTNBBX |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C22H26N2O4/c1-4-13-11-24-8-7-21-16-9-14(25)5-6-17(16)23(2)22(21)18(24)10-15(13)20(21,12-28-22)19(26)27-3/h4-6,9,15,18,25H,7-8,10-12H2,1-3H3/b13-4+/t15-,18?,20?,21+,22-/m1/s1 |
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| StdInChI = 1S/C22H26N2O4/c1-4-13-11-24-8-7-21-16-9-14(25)5-6-17(16)23(2)22(21)18(24)10-15(13)20(21,12-28-22)19(26)27-3/h4-6,9,15,18,25H,7-8,10-12H2,1-3H3/b13-4+/t15-,18?,20?,21+,22-/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 = YILKZADAWNUTTB-OCTHBTNBSA-N |
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| StdInChIKey = YILKZADAWNUTTB-OCTHBTNBSA-N |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| synonyms = |
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| ChemSpiderID = 16735645 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 484665 |
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}} |
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| Section2 = {{Chembox Properties |
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| C=22 | H=26 | N=2 | O=4 |
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| Appearance = |
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| Density = |
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| MeltingPtC = 225 |
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| MeltingPt_ref = <ref>{{Cite book | title = ] | id = 200 | edition = 12th}}</ref> |
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| BoilingPt = |
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| Solubility = |
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}} |
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| Section3 = {{Chembox Hazards |
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| MainHazards = |
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| FlashPt = |
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| AutoignitionPt = |
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}} |
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}} |
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}} |
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'''Akuammine''' ('''vincamajoridine'''<ref name=Janot>{{cite journal | vauthors = Janot MM, Le Men J, Aghoramurthy K, Robinson R | title = The identity of vincamajoridine and akuammine | journal = Experientia | volume = 11 | issue = 9 | pages = 343 | date = September 1955 | pmid = 13262018 | doi = 10.1007/BF02159911 | doi-access = free }}</ref>) is an ]. It is the most abundant alkaloid found in the seeds from the tree '']'',<ref name=Kapadia>{{cite journal | vauthors = Kapadia GJ, Angerhofer CK, Ansa-Asamoah R | title = Akuammine: an antimalarial indolemonoterpene alkaloid of Picralima nitida seeds | journal = Planta Medica | volume = 59 | issue = 6 | pages = 565–6 | date = December 1993 | pmid = 8302957 | doi = 10.1055/s-2006-959764 | s2cid = 260253044 }}</ref> commonly known as akuamma, comprising 0.56% of the dried powder. It has also been isolated from '']''.<ref name=Janot/> Akuammine is structurally related to ], ] and more distantly ], all of which are alkaloid plant products with pharmacological properties. |
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==Pharmacology== |
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Akuammine has ] activity,<ref name=Kapadia/> and may be the primary constituent of ''P. nitida'' seeds responsible for this activity.<ref>{{Cite book | title = African Ethnobotany: Poisons and Drugs : Chemistry, Pharmacology, Toxicology | vauthors = Neuwinger HD | publisher = CRC Press | date = 1996| isbn = 9783826100772 | page = 123}}</ref> |
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Akuammine is an ] with low affinity, selective for the ], when tested '']''.<ref>{{cite journal | vauthors = Menzies JR, Paterson SJ, Duwiejua M, Corbett AD | title = Opioid activity of alkaloids extracted from Picralima nitida (fam. Apocynaceae) | journal = European Journal of Pharmacology | volume = 350 | issue = 1 | pages = 101–8 | date = May 1998 | pmid = 9683021 | doi = 10.1016/s0014-2999(98)00232-5 }}</ref><ref>{{cite journal | vauthors = Lewin G, Le Ménez P, Rolland Y, Renouard A, Giesen-Crouse E | title = Akuammine and dihydroakuammine, two indolomonoterpene alkaloids displaying affinity for opioid receptors | journal = Journal of Natural Products | volume = 55 | issue = 3 | pages = 380–4 | date = March 1992 | pmid = 1317407 | doi = 10.1021/np50081a017 }}</ref> |
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== References == |
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{{Reflist}} |
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{{Opioidergics}} |
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