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469-59-0CC1=C2C(=O)[C@H]3[C@@H](CC=C4C[C@@H](O)CC[C@@]43C)[C@@H]2CC[C@]12O[C@@H]1C[C@H](C)CN[C@H]1[C@H]2CCLEXYFLHGFJONT-DNMILWOZSA-N469-59-0DTXSID70895026CHEMBL186779CHEBI:6088White Crystalline Solid
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개요First obtained from Veratrum grandiflorum by Wright and Luff, this alkaloid is also present in V. album. It was originally given the formula C26H3703N. 2H20, subsequently altered to that given above by Jacobs and Craig. The base crystallizes from aqueous EtOH in stellate groups of colourless prisms and has [α]D - 147° (EtOH). The hydrochloride (dihydrate) has m.p. 208°C (Wright and Luff) or 330-334°C (dec.) according to Jacobs and Craig, the latter finding a change in crystalline form at 280°C. The hydriodide has m.p. 302-5°C; the nitrate and aurichloride are both crystalline and the picrate melts at 278-284°C. TheN-nitroso derivative has m.p. 246-7°C; the N-acety1 compound, m.p. 161-2°C and the O,N-diacetyl derivative, m.p. 17 6-7°C.Treatment with aluminium tert-butoxide gives Δ4-jervone, m.p. 193-4°C; [α]28D + 28.3° (EtOH), giving an oxime, m.p. 287-9°C and reduced by aluminium isopropoxide to Δ4-jervine, m.p. 203- 2 11°C. Catalytic hydrogenation with Pd-C yields the dihydro derivative, m.p. 248-251°C; [α]26D - 82° (EtOH). On further hydrogenation, the tetrahydro compound is formed, m.p. 216- 221°C; [α]28D - 18° (EtOH). Jervine may be reduced by sodium in butanol to a:-dihydrojervinol, m.p. 223-5°C; [α]27D - 107° (EtOH). The similar reduction of dihydrojervine yields (3-dihydrojervino1, m.p. 286-9°C; [α]28D-4 C(EtOH). On Se dehydrogenation, the alkaloid behaves like cevine (q.v.) giving a mixture of bases and hydrocarbons from which the following have been isolated; 5-methyl- 2-ethylpyridine; 5-methyl-2-ethyl-3-hydroxypyridine; C2oH22 , m.p. 79°C; C24H30, m.p. 100- 1°C; C2l H24 , m.p. 70-8 1°C; C2oH 16 , m.p. I 25-7°C and C22H20 , m.p. I 54-5℃。In large doses, the alkaloid produces vasodilatation and a fall in blood pressure
용도Has antibacterial properties. Jervine demonstrates teratogenic properties. It is the starting material for C-nor-D-homosteroids. Jervine induces holoprosencephaly and blocks endogenous Sonic hedgehog signaling
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