Annonamine

Annonamine is a benzylisoquinoline alkaloid isolated from Annona muricata[1] (commonly known as soursop, graviola, guanabana, paw-paw and sirsak), a plant commonly used in folk medicine by indigenous communities in Africa and South America.[2] Structurally, it contains an aporphine core featuring a quaternary ammonium group.

Annonamine

Names
Systematic IUPAC name (R)-2-Hydroxy-1-methoxy-6,6-dimethyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-6-ium
Identifiers
CAS Number	1404308-11-7
3D model (JSmol)	Interactive image
ChemSpider	28289744
PubChem CID	56929881
InChI InChI=1S/C19H21NO2/c1-20(2)9-8-13-11-16(21)19(22-3)18-14-7-5-4-6-12(14)10-15(20)17(13)18/h4-7,11,15H,8-10H2,1-3H3/p+1/t15-/m1/s1 Key: WWSQXPANNACSIL-OAHLLOKOSA-O InChI=1S/C19H21NO2/c1-20(2)9-8-13-11-16(21)19(22-3)18-14-7-5-4-6-12(14)10-15(20)17(13)18/h4-7,11,15H,8-10H2,1-3H3/p+1/t15-/m1/s1 Key: WWSQXPANNACSIL-XRLFSOBABS
SMILES C[N+]1(C)CCC2=CC(O)=C(OC)C3=C2[C@H]1CC4=C3C=CC=C4
Properties
Chemical formula	C19H22NO2
Molar mass	296.390 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

See also

• Asimilobine - amine not quaternized
• Anonaine
• Pukateine

References

1. Matsushige, A; Kotake, Y; Matsunami, K; Otsuka, H; Ohta, S; Takeda, Y (2012). "Annonamine, a new aporphine alkaloid from the leaves of Annona muricata". Chemical & Pharmaceutical Bulletin. 60 (2): 257–9. doi:10.1248/cpb.60.257. PMID 22293487.
2. Moghadamtousi, Soheil; Fadaeinasab, Mehran; Nikzad, Sonia; Mohan, Gokula; Ali, Hapipah; Kadir, Habsah (10 July 2015). "Annona muricata (Annonaceae): A Review of Its Traditional Uses, Isolated Acetogenins and Biological Activities". International Journal of Molecular Sciences. 16 (7): 15625–15658. doi:10.3390/ijms160715625. PMC 4519917.