Taxonomy: Physicochemical and Pharmacological Properties of Alkaloids – Tropane Alkaloids
Biological sources: Datura innoxia, D. metel, D. stramonium, Hyoscyamus niger, H. pusillus, Physochlaina alaica, Ph. orientalis, Scopolia carniolica, S. stramonifolia, S. tangutica
C17H21NO4: 303.1471
Mp: 59°C (H2O) [1], oil [2], 188°C (picrate), 194°C (hydrobromide), 200°C (hydrochloride), 210°C (dec., perchlorate), 209°C (dec., chloroaurate) [1]
[α]D −18° (EtOH), −28° (H2O) [1]
Solubility: very sol. EtOH, CHCl3, Et2O, Me2CO; spar. sol. C6H6, pet. ether [1]
UV: 253, 262, 275 [2]
IR: 3430–3370, 3020–2980, 1727, 755, 695 [2]
MS m/z: 303(M+, 100), 154(62), 138(62), 124(37), 96(25), 95(27), 94(75), 83(27), 82(37), 81(39) [2]
1 H NMR: 1.15–2.30(4H, m, H-2, H-4), 2.35(3H, s, NCH3), 2.74, 3.33(each 1H, d, J = 4, H-6, H-7), 2.85, 3.03(each 1H, m, H-1, H-5), 4.91(1H, t, H-3β), 7.22(5H, m, H–Ar) [2]
HPLC: [3]
Pharm./Biol.: (hydrobromide) causes dilatation of the pupil and an increase in the frequency of...
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References
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(2013). (−)-Scopolamine (Hyoscyne). In: Azimova, S.S., Yunusov, M.S. (eds) Natural Compounds. Springer, New York, NY. https://doi.org/10.1007/978-1-4614-0560-3_1454
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