Akuammine

Akuammine
Names
	Other names Vincamajoridine
Identifiers
CAS Number	3512-87-6 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL484665 ;
ChemSpider	16735645 ;
PubChem CID	6441511;
UNII	0421AQV5W3 ;
	InChI 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 Key: YILKZADAWNUTTB-OCTHBTNBSA-N ;
	SMILES COC(=O)C46CO[C@]35N(C)c1ccc(O)cc1[C@]56CCN2C/C(=C\C)[C@H]4CC23;
Properties
Chemical formula	C22H26N2O4
Molar mass	382.460 g·mol−1
Melting point	225 °C (437 °F; 498 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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.

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

^ Merck Index (12th ed.). 200.
^ ^a ^b 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.
^ ^a ^b 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.
^ Neuwinger HD (1996). African Ethnobotany: Poisons and Drugs : Chemistry, Pharmacology, Toxicology. CRC Press. p. 123. ISBN 9783826100772.
^ 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.
^ 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.

[1] Merck Index (12th ed.). 200.

[Janot-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.

[Kapadia-3] 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.

[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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