Akuammine
{{cs1 config|name-list-style=vanc}}
{{Chembox
| Verifiedfields = changed
| verifiedrevid = 477246027
| ImageFile = Akuammine.svg
| ImageSize = 200px
| ImageAlt =
| IUPACName =
| OtherNames = Vincamajoridine
| Section1 = {{Chembox Identifiers
| CASNo = 3512-87-6
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 0421AQV5W3
| PubChem = 6441511
| SMILES = COC(=O)C46CO[C@]35N(C)c1ccc(O)cc1[C@]56CCN2C/C(=C\C)[C@H]4CC23
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = YILKZADAWNUTTB-OCTHBTNBSA-N
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 16735645
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 484665
}}
| Section2 = {{Chembox Properties
| C=22 | H=26 | N=2 | O=4
| Appearance =
| Density =
| MeltingPtC = 225
| MeltingPt_ref = {{Cite book | title = Merck Index | id = 200 | edition = 12th}}
| BoilingPt =
| Solubility =
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| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt =
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Akuammine (vincamajoridine{{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 }}) is an indole alkaloid. It is the most abundant alkaloid found in the seeds from the tree Picralima nitida,{{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 }} commonly known as akuamma, comprising 0.56% of the dried powder. It has also been isolated from Vinca major. Akuammine is structurally related to yohimbine, mitragynine and more distantly Voacangine, all of which are alkaloid plant products with pharmacological properties.
Pharmacology
Akuammine has antimalarial activity, and may be the primary constituent of P. nitida seeds responsible for this activity.{{Cite book | title = African Ethnobotany: Poisons and Drugs : Chemistry, Pharmacology, Toxicology | vauthors = Neuwinger HD | publisher = CRC Press | date = 1996| isbn = 9783826100772 | page = 123}}
Akuammine is an opioid agonist with low affinity, selective for the mu-opioid receptor, when tested in vitro.{{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 }}{{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 }}