イボゲイン 化学特性,用途語,生産方法
解説
C20H26N2O(310.43)．キョウチクトウ科Tabernanthe ibogaに含まれるインドールアルカロイドの一つ．この植物は西アフリカの赤道地域に限られて生育し，原住民は，通称，イボガ(iboga)とよんで，根皮のエキスを疲労防止，あるいは特有の幻覚，恍惚感を得るのに用いている．この作用は，成分として含まれるアルカロイドのためである．このアルカロイドをイボガアルカロイドとよぶ．
"主アルカロイドがイボガインで，虹色の斜方晶系の針状晶．融点152～153 ℃．d420"－53°(95％ エタノール)．λmax 226，298 nm(log ε 4.39，3.93．メタノール)．水に不溶，エタノール，エーテル，クロロホルム，アセトン，ベンゼンに可溶．イボガアルカロイドには，ほかに，イボガミン，タベルナンチンなどがあり，類似の構造のアルカロイドがVoacanga属からも得られている．[CAS 83-74-9]
森北出版「化学辞典（第2版）
説明
This indole alkaloid occurs in the root of Tabernanthe iboga Baill. It was first
examined in detail by Raymond-Hamet who assigned to it the empirical formula
C19H24(26)ON2, now altered to that given above. The base forms colourless
crystals from EtOH and is laevorotatory with [Q1D - 53° (EtOH). It is insoluble
in Et20, slightly so in Me2CO or CHC1 3 but dissolves freely in MeOH, EtOH or
H20. The alkaloid yields a hydrochloride, m.p. 299°C (dec.); lQlhs - 67°
(MeOH) or - 37.3° (H20). It contains one methoxyl group and gives the typical
indole reactions. On distillation with Zn dust or soda-lime it furnishes products
which are indole derivatives with the ~-position free.
In a manner similar to that of cocaine, the alkaloid potentiates the pressor
action of adrenaline and abolishes the sino-carotid reflexes. Unlike cocaine,
however, it also augments the action of tyramine and that of dl-ephedrine to a
slight extent. Vincent and Sero have reported that it inhibits the action of serum
cholinesterase.
純化方法
Crystallise it from EtOH or aqueous EtOH and sublime it at 150o/0.01mm. It is soluble in organic solvents but insoluble in H2O. The hydrochloride, m 299-300o(dec), is soluble in H2O and alcohols. [Büchi et al. J Am Chem Soc 88 3099 1866, Rosenmund Chem Ber 108 1871 1975, Beilstein 23 III/IV 2742.]
参考文献
Raymond-Hamet., Bull. Soc. Chirn. Fr., 9,620 (1942)
Delourme-Houde., Chern. Abstr., 41, 1390 (1947)
Bartlett, Dickel, Taylor.,J. Arner. Chern. Soc., 80, 126 (1958)
Arai, Coppola, Jeffery., Acta Cryst., 13, 553 (1960)
Shamma, Soyster., Experientia, 20,36 (1964)
Synthesis:
Buchi et ai., f. Arner. Chern. Soc., 88,3099 (1966)
Pharmacology:
Raymond-Hamet, Rothlin., C.R. Soc. Bioi., 127,592 (1938)
Raymond-Hamet, Rothlin., Arch. inst. Pharrnacodyn., 63, 27 (1939)
Raymond-Hamet., Cornpt. rend., 201,285 (1940)
Raymond-Hamet., C.R. Soc. Bioi., 135, 176 (1941)
Raymond-Hamet, Perrot., Bull. Acad. Med., 24,423 (1941)
Vincent, Sero., C.R. Soc. Bioi., 136,612 (1942)
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