Ipecacuanha

There is a relatively large number of alkaloids which maybe considered as simple phenethyl amine [64-04-0] (59, R = H), CgH N, or tyramine [51-67-2] (59, R = OH), CgH NO, derivatives. These iaclude mescaline (61) from the small wooly peyotyl cactus l ophophora mlliamsii (L emaire) Coult. anhalamine (62) and lophocerine (63) from other Cactaceae, and the important antamebic alkaloids (—)-protoemetiae (64), (—)-ipecoside (65), and (—)-emetine (66) from the South American straggling bush Cephaelis ipecacuanha (Brotero) Rich. AH of these bases appear to be derived from tyrosiae (25,... 

Ipecac is prepared from the dried roots and rhizomes of Cephaelis ipecacuanha (Brot.) A. Rich, and contains the alkaloids emetine [483-18-1] (17) and cephaeJine [483-17-0] (18) in a ratio between 2 1 and 4 1. It has been used extensively in cough preparations and is beheved to act by gastric reflex stimulation. Toxic effects include vomiting, irritation of the gastrointestinal tract, and cardiac arrhythmias (19). Ipecac symp is available over-the-counter in the United States only in 30-mL containers for use as an emetic in treating poisonings. 

Emetine andcephaeline, the two major alkaloids of ipecacuanha, begin to fluoresce after treatment with iodine vapor [254], The molecular iodine, which acts as a quencher, must be removed by heating in the drying cupboard or on a hotplate... 

Fig. 1 Absorption scans of the pure substances (ca. 500 ng of each) cephaeline and emetine (A) and an extract of Ipecacuanhae Radix (B) cephaeline (1), emetine (2).

The roots of Cephcelis Ipecacuanha (Brot) A. Rich constitute the Brazilian ipecacuanha of commerce and also that cultivated in the Federated Malay States, Bengal and Burma. Carthagena ipecacuanha is derived from Cephcelis acuminata Karsten collected in Colombia. Emetine, the principal alkaloid of this drug, was first obtained by Pelletier and Magendie in 1817, but was first prepared in a pure state by Paul and Cownley, who separated from commercial emetine the phenolic base, cephaeline, and later obtained a third alkaloid, psychotrine. To these Pyman added emetamine and 0-methylpsychotrine. 

A method for the estimation of the total alkaloids and of non-phenolic alkaloids (emetine fraction) is given in the British Pharmacopoeia, 1932, Addendum VI, which requires the drug to contain not less than 2 per cent, of alkaloids, of which at least 55 per cent, must be non-phenolic bases, calculated as emetine. The British Pharmacopoeia also gives an assay process for emetine in emetine bismuth iodide, the form in which the drug is chiefly used in medicine it is required to contain not less than 25 and not more than 28 per cent, of emetine. In the United States Pharmacopoeia, XIII, both Cephcelis Ipecacuanha and C. acuminata are recognised and must contain not less than 2 per cent, of ether-soluble alkaloids. 

Owing to the frequency with which the botanical attribution of ipecacuanha has been changed, and to the considerable number of substitutes which have from time to time appeared, it is difficult to summarise briefly the botanical distribution of the ipecacuanha alkaloids, and readers interested in this subject may be referred to Staub for information and references. Freise states that emetine and the allied bases are to be found in certain Rubiaceous spp. not usually regarded as sources of these alkaloids, and Orazi has stated that the roots of Bourreria... 

Two minor alkaloids of ipecacuanha, ipecamine and hydroipecamine, have been described by Hesse, and are discussed by Pyman. ... 

Ipecacuanha, alkaloids, 394 interrelationships, 397 therapeutic uses, 402 Ipecaniine, 397 Iponuea aidoefolia, 781 Isatidine, 601, 603 constitution, 612... 

Alkaloids of Curare Curine, Tubocurarine, Protocuridine, Calabash-curare I, etc., including Erythrina alkaloids Alkaloids of Ipecacuanha. ... 

Brechungs-ebene, /. (Optica) plane of refraction. -exponent, m. refractive index, -ge-setz, n. law of refraction. -Index, m. refractive index, -k effizient, m. coefficient of refraction. -kraft, /. refractive power, -messer, m. refractometer. -verhaltnis, n. refractive index, -vermfigen, n. refractive power, -winkel, m, angle of refraction, Brech-walzwerk, n. crushing rolls (or rollers), crushing mill. >weln, m. (Pharm.) wine of antimony, antimonial wine, -weiustein, m. tartar emetic, -werk, n. crusher, -wurzel, -wurz,/. ipecacuanha, ipecac. 

Note Under the conditions employed emetine and cephaeline were not well separated but there was good resolution of the subsidiary alkaloids of the ipecacuanha tincture (Fig. 1). The separation and quantitative determination of the main alkaloids (Fig. 2) can be carried out under the following conditions Ascending, one-dimensional development in a trough chamber with chamber saturation layer HPTLC plates Silica gel 60 (Merck) mobile phase dichloromethane — methanol — ammonia solution (25%) (34+6+1) migration distance 6 cm running time 13 min h/ f cephaeline 65-70 emetine 75-80. 

Fig. 2 Fluorescence scan of the chromatogram tracks of the standard substances cephaeline (A) and emetine (B) and of the ipecacuanha extract (C). Amounts applied cephaeline 0.5 pg, emetine 0.7 pg per 10 mm track length.

Iodine compounds lb 76,77 Ipecacuanha la 47 Ipecacuahna extract la 263 lb 294 Ipecacuanhae radix la 263 Ipecacuanha, tincture lb 292,293 Iprodion lb 230 Iigasan lb 227... 

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