CAS Registry Number: 475-83-2
Taxonomy: Physicochemical and Pharmacological Properties of Alkaloids – Isoquinoline Alkaloids – Aporphine Alkaloids
Biological sources: Papaver orientale
C19H21NO2: 295.1572
Mp: 164–165°C (EtOH)
[α]D −164° (MeOH) [1]
UV: 230, 274, 312 [1]
IR: 1600, 1500, 1425, 1375, 1250 [1]
MS m/z: 295(M+, 100), 294, 280, 252, 237, 221 [1]
1 H NMR: 2.54(3H, s, NCH3), 3.66, 3.88(each 3H, s, 2 × OCH3), 6.66(1H, s), 7.15–7.35(3H, m), 8.33(1H, m) [1]
13 H NMR(DMSO-d6): [2]
Table 1
C-1 |
144.3 |
C-5 |
52.3 |
C-10 |
127.1 |
1a |
125.7 |
6a |
61.9 |
11 |
126.6 |
1b |
128.6 |
7 |
34.3 |
 11a |
131.5 |
2 |
151.4 |
7a |
136.2 |
NCH3 |
43.6 |
3 |
111.8 |
8 |
127.9 |
1-OCH3 |
59.6 |
3a |
127.5 |
9 |
127.5 |
2-OCH3 |
55.6 |
4 |
28.6 |
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References
H. Guinaudeau, A. Cave, R.R. Paris, Phytochemistry 10, 1963 (1971)
E. Wenkert, B.L. Buckwalter, I.R. Burfitt, M.J. Gasic, H.E. Gottlieb, E.W. Hagaman, F.M. Schell, P.M. Wovkulich, in Topics in 13 C NMR Spectroscopy, ed. by G.C. Levy, 2nd edn. (Wiley, New-York, 1976), p. 81
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(2013). Nuciferine (1,2-Dihydroxyaporphine). In: Azimova, S.S., Yunusov, M.S. (eds) Natural Compounds. Springer, New York, NY. https://doi.org/10.1007/978-1-4614-0560-3_651
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