CAS Registry Number: 18063-21-3
Taxonomy: Physicochemical and Pharmacological Properties of Alkaloids – Quinoline Alkaloids
Biological sources: Haplophyllum perforatum
C18H23NO4: 317.1627
Mp: 110–111°C (pet. ether), 148°C (O–Ac), 136°C (tetrahydro) [1]
[α]D −16° (Me2CO) [1]
Solubility: very sol. MeOH, EtOH, Me2CO, C6H6, CHCl3, EtOAc [1]
UV: 258 (4.18) [2]
MS m/z: 317(M+, 4), 302(2), 287(14), 285(22), 270(72), 248(68), 216(100), 188(94), 173(12), 69(6) [3]
1 H NMR(CCl4): 1.67, 1.73(each 3H, s, 2 × CH3), 3.05, 4.21(each 3H, s, 2 × OCH3), 4.00(1H, m, O–CH–), 5.25(1H, t, J = 7, =CH), 6.86, 7.48(each 1H, J = 3, H-3, H-2) [3]
13 C NMR: [4]
Table 1
C-2 |
142.0 |
C-5 |
18.4 |
C-10 |
119.5 |
 2a |
161.5 |
 6 |
23.9 |
 11 |
133.2 |
 3 |
104.3 |
 7 |
69.4 |
 12 |
25.8 |
 3a |
116.8 |
 8 |
78.8 |
 13 |
17.8 |
 4 |
157.9 |
 8a |
150.1 |
4-OCH3 |
58.1 |
 4a |
104.7 |
 9 |
29.7 |
8-OCH3 |
50.3 |
Pharm./Biol.: LD50600, 500, 750, 160 mg/kg (per os, s/c, i/p, i/v, mice). Sedative, soporific, analgetic, tranquilizing, and estrogenic...
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References
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(2013). Haplophyllidine. In: Azimova, S.S., Yunusov, M.S. (eds) Natural Compounds. Springer, New York, NY. https://doi.org/10.1007/978-1-4614-0560-3_1159
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