Akuammicine

Akuammicine

Identifiers
CAS Number	639-43-0
ChemSpider	8489522
Jmol interactive 3D	Image
PubChem	10314057
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	322.40
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. It is a μ-opioid receptor agonists which is also agonizes (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.

Notes

• Alkaloids from Aspidosperma species from Bolivia

References

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.
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.