Akuammine

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Akuammine
Akuammine.svg
Names
Other names
Vincamajoridine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
  • 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 Yes check.svgY
    Key: YILKZADAWNUTTB-OCTHBTNBSA-N Yes check.svgY
  • COC(=O)C46CO[C@]35N(C)c1ccc(O)cc1[C@]56CCN2C/C(=C\C)[C@H]4CC23
Properties
C22H26N2O4
Molar mass 382.460 g·mol−1
Melting point 225 °C (437 °F; 498 K) [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Akuammine (vincamajoridine [2] ) is an indole alkaloid. It is the most abundant alkaloid found in the seeds from the tree Picralima nitida , [3] commonly known as akuamma, comprising 0.56% of the dried powder. It has also been isolated from Vinca major . [2] 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, [3] and may be the primary constituent of P. nitida seeds responsible for this activity. [4]

Akuammine is an opioid agonist with low affinity, selective for the mu-opioid receptor, when tested in vitro . [5] [6]

References

  1. ↑ Merck Index (12th ed.). 200.
  2. 1 2 Janot MM, Le Men J, Aghoramurthy K, Robinson R (September 1955). "The identity of vincamajoridine and akuammine". Experientia. 11 (9): 343. doi: 10.1007/BF02159911 . PMID   13262018.
  3. 1 2 Kapadia GJ, Angerhofer CK, Ansa-Asamoah R (December 1993). "Akuammine: an antimalarial indolemonoterpene alkaloid of Picralima nitida seeds". Planta Medica. 59 (6): 565–6. doi:10.1055/s-2006-959764. PMID   8302957. S2CID   260253044.
  4. ↑ Neuwinger HD (1996). African Ethnobotany: Poisons and Drugs : Chemistry, Pharmacology, Toxicology. CRC Press. p. 123. ISBN   9783826100772.
  5. ↑ Menzies JR, Paterson SJ, Duwiejua M, Corbett AD (May 1998). "Opioid activity of alkaloids extracted from Picralima nitida (fam. Apocynaceae)". European Journal of Pharmacology. 350 (1): 101–8. doi:10.1016/s0014-2999(98)00232-5. PMID   9683021.
  6. ↑ Lewin G, Le Ménez P, Rolland Y, Renouard A, Giesen-Crouse E (March 1992). "Akuammine and dihydroakuammine, two indolomonoterpene alkaloids displaying affinity for opioid receptors". Journal of Natural Products. 55 (3): 380–4. doi:10.1021/np50081a017. PMID   1317407.
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