Akuammine

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 both yohimbine and mitragynine, both of which are alkaloid plant products with pharmacological properties.

Akuammine
Names
Other names
Vincamajoridine
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
Properties
Chemical formula
 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).
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Infobox references

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

References
  1. Merck Index (12th ed.). 200.
  2. Janot, M. M.; Le Men, J.; Aghoramurthy, K.; Robinson, R. (1955). "The identity of vincamajoridine and akuammine". Experientia. 11 (9): 343. doi:10.1007/BF02159911.
  3. Kapadia, G. J.; Angerhofer, C. K.; Ansa-Asamoah, R (1993). "Akuammine: An antimalarial indolemonoterpene alkaloid of Picralima nitida seeds". Planta Medica. 59 (6): 565–6. doi:10.1055/s-2006-959764. PMID 8302957.
  4. Hans Dieter Neuwinger (1996). African Ethnobotany: Poisons and Drugs : Chemistry, Pharmacology, Toxicology. CRC Press. p. 123. ISBN 9783826100772.
  5. Menzies, J. R.; Paterson, S. J.; Duwiejua, M; Corbett, A. D. (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 (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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