Akuammicine

Akuammicine
Identifiers
CAS Number	639-43-0 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:70499;
ChemSpider	8489522;
PubChem CID	10314057;
UNII	RG055O00BG ;
CompTox Dashboard (EPA)	DTXSID30903914 ;
	InChI InChI=1S/C20H22N2O2/c1-3-12-11-22-9-8-20-14-6-4-5-7-15(14)21-18(20)17(19(23)24-2)13(12)10-16(20)22/h3-7,13,16,21H,8-11H2,1-2H3/b12-3-/t13-,16-,20+/m0/s1 Key: YZOMNXCYSIYMOX-UHFFFAOYSA-N;
	SMILES C123C(=C(C4CC1N(CC3)CC4=CC)C(OC)=O)Nc1c2cccc1;
Properties
Chemical formula	C20H22N2O2
Molar mass	322.408 g·mol−1
Appearance	White solid[1]
Melting point	182 °C (360 °F; 455 K)[2]
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Akuammicine is an alkaloid found in Vinca minor and Aspidosperma.[3] It is a μ-opioid receptor agonist while also agonizing (but to a much lower, clinically insignificant degree) the κ and δ-opioid receptors. Agonistic activity at both human variants of the σ-sigma receptors has been indicated but is not yet proven, so have possible mechanisms of action at the NMDA receptor (antagonist) and glycine receptor.

References

Shittu, Hafsat; Gray, Alexander; Furman, Brian; Young, Louise (2010). "Glucose uptake stimulatory effect of akuammicine from Picralima nitida (Apocynaceae)". Phytochemistry Letters. 3 (1): 53–55. doi:10.1016/j.phytol.2009.11.003. ISSN 1874-3900.
Robinson, Robert; Thomas, A. F. (1955). "The Alkaloids of Picralima nitida, Stapf, Th. and H. Durand. Part III. A Note on Akuammicine and pseudoAkuammicine". Journal of the Chemical Society (Resumed): 2049. doi:10.1039/jr9550002038. ISSN 0368-1769.
Mitaine, A. C.; Mesbah, K; Richard, B; Petermann, C; Arrazola, S; Moretti, C; Zèches-Hanrot, M; Men-Olivier, L. L. (1996). "Alkaloids from Aspidosperma species from Bolivia". Planta Medica. 62 (5): 458–61. doi:10.1055/s-2006-957939. PMID 17252481.

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[ShittuGray2010-1] Shittu, Hafsat; Gray, Alexander; Furman, Brian; Young, Louise (2010). "Glucose uptake stimulatory effect of akuammicine from Picralima nitida (Apocynaceae)". Phytochemistry Letters. 3 (1): 53–55. doi:10.1016/j.phytol.2009.11.003. ISSN 1874-3900.

[OsdeneTimmis1955-2] Robinson, Robert; Thomas, A. F. (1955). "The Alkaloids of Picralima nitida, Stapf, Th. and H. Durand. Part III. A Note on Akuammicine and pseudoAkuammicine". Journal of the Chemical Society (Resumed): 2049. doi:10.1039/jr9550002038. ISSN 0368-1769.

[3] Mitaine, A. C.; Mesbah, K; Richard, B; Petermann, C; Arrazola, S; Moretti, C; Zèches-Hanrot, M; Men-Olivier, L. L. (1996). "Alkaloids from Aspidosperma species from Bolivia". Planta Medica. 62 (5): 458–61. doi:10.1055/s-2006-957939. PMID 17252481.