Akuammine

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Akuammine
Akuammine.svg
Clinical data
Legal status
  • Legal
Routes of
administration		 Oral, Rectal
Identifiers
CAS Number 3512-87-6 N
ATC code none
PubChem CID: 6441511
ChemSpider 16735645 YesY
ChEMBL CHEMBL484665 N
Chemical data
Formula C22H26N2O4
Molecular mass 382.45 g/mol
  • COC(=O)C46CO[C@]35N(C)c1ccc(O)cc1[C@]56CCN2C/C(=C\C)[C@H]4CC23
  • InChI=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 YesY
  • Key:YILKZADAWNUTTB-OCTHBTNBSA-N YesY
 NYesY (what is this?)  (verify)

Akuammine, an indole alkaloid also known as vincamajoridine,[1] is the most abundant active alkaloid found in the seeds from the tree Picralima nitida, commonly known as Akuamma.

The dried seeds from this plant are used in traditional medicine throughout West Africa, particularly in Ghana as well as in the Ivory Coast and Nigeria. The seeds are crushed or powdered and taken orally, and are mainly used for the treatment of malaria[2] and diarrhoea, and as a painkiller. An enterprising Ghanaian hospital started manufacturing standardised 250 mg capsules of the powdered P. nitida seed, and sold them around the country where they became widely accepted as a safe and effective pain relief product. This then led researchers to try to discover the active component of the seeds.

P. nitida seeds contain a mixture of alkaloids producing antipyretic and antiinflammatory effects along with analgesia.[3][4] Several of these were shown to bind to opioid receptors in vitro, and two compounds, akuammidine and ψ-akuammigine, were found to be potent μ-opioid agonists, although not particularly selective. Surprisingly the main alkaloid from the seeds, akuammine, was found to be an opioid antagonist when tested in vitro and canceled out the effects of the active agonist components.[5] This finding contradicts the belief by some pharmacological scientists that there are no naturally occurring opioid antagonists.[6]

Given the confirmed activity of the whole seed extract in humans, this makes it likely that akuammine is in fact being metabolised once inside the body to form a metabolite acting as an opioid receptor agonist.

Akuammine is the main alkaloid found in the seeds, comprising 0.56% of the dried powder, indicating that the 250 mg "Picap Capsules" sold commercially should contain approximately 1.4 mg of akuammine, plus 0.085 mg akuammidine and 0.015 mg ψ-akuammigine. Akuammine is structurally related to both yohimbine and mitragynine, both of which are alkaloid plant products with uses in medicine.

References

  1. ↑ Janot MM, Le Men J, Aghoramuthry K, Robinson R. The identity of vincamajoridine and akuammine. Experientia. 1955;11(9):343.
  2. ↑ Kapadia GJ, Angerhofer CK, Ansa-Asamoah R. Akuammine: an antimalarial indolemonoterpene alkaloid of Picralima nitida seeds. Planta Medica. 1993 Dec;59(6):565-6.
  3. ↑ Duwiejua M, Woode E, Obiri DD. Pseudo-akuammigine, an alkaloid from Picralima nitida seeds, has anti-inflammatory and analgesic actions in rats. Journal of Ethnopharmacology. 2002; (81):73-79.
  4. ↑ Lewin G, Le Ménez P, Rolland Y, Renouard A, Giesen-Crouse E. Akuammine and dihydroakuammine, two indolomonoterpene alkaloids displaying affinity for opioid receptors. Journal of Natural Products. 1992 Mar;55(3):380-4.
  5. ↑ Menzies JRW, Paterson SJ, Duwiejua M, Corbett AD. Opioid activity of alkaloids extracted from Picralima nitida (fam. Apocynaceae). European Journal of Pharmacology. 1998 May 29;350(1):101-8.
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.


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