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Alkaloid Studies. I. the Isolation of Pilocereine from the Cactus Lophocereus Schottii'

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Alkaloid Studies. I. the Isolation of Pilocereine from the Cactus Lophocereus Schottii' 3632 CARLL)JEUSSI, S. FKICKAND L. E. GELLER Vol. i5 disulfide, m.p. 44-46O.3 There was no depression in melt- Detosylation of the other sulfonamides described in Table ing point when mixed with an authentic sample of di-p-tolyl I was done in identical fashion. disulfide. Ethyl N-Carboxymethyl-p-aminobenzoate.-A solution of A less soluble fraction, m.p. 132-134', was also obtained. 8.25 g. (0.05 mole) of ethyl p-aminobenzoate, 7.45 g. (0.0;i It weighed 0.250 g. Several recrystallizations from 2-pro- mole) of bromoacetic acid and 8.4 g. (0.10 mole) of sodium panol gave an analytical sample, m.p. 132-132.5". bicarbonate in 75 ml. of water and 25 id. of ethanol was Anal. Calcd. for ClsHllBrzNSOn: C, 38.45; H, 2.74; warmed on a steam-bath for 90 minutes. The mixture was Br, 39.45; S, 7.91. Found: C, 38.89, 38.92; H, 2.92, cooled, filtered and the alcohol removed under reduced prcs- 2.92: Br. 39.73. 39.46: S, 7.95, 8.02. sure. The pH of the aqueous solution was adjusted to Fi.0 This compound gave no depression of melting point wheii and the solution filtered to give 6.5 g. of product, m.p. 138- mixed with N-tosyl-2,4-dibromoaniline prepared by the 149'. An additional 1.5 g. of crystals, n1.p. 136-147', tosylation of the amine in pyridine.'* The infrared ab- was collected when the pH was lowered to 2.0. The total sorption curves of the two compounds are identical. yield was 7201,. Two recrystallizations from dilute ethanol In a similar experiment the ether precipitate of hydro- raised the melting point to 160-162". bromides was benzoylated by the method of Schotten- nnal. Calcd. for CllH13NO: C, 59.2; H, 5.9; K, 6.3; Baumann to give, after recrystallization, 0.84 g. of N-ben- neut. equjv., 223.2. Found: C, 59.6, 59.7; H, 6.2, 6.2; zoyl-p-bromoaniline, m.p. 200-201 5'. This material gave S, 5.7, 6.0; neut. equiv., 225.2. no depression of melting point when mixed with an authen- Detosylation of 3-( N- 7-Diethylaminopropyl-p-toluene- tic sample. Infrared data conhed the identity of this sulfonamido)-Q-(N-n-propyl-p- toluenesulfonamido) -anisole. derivative. There was also isolated 0.13 g. of N-benzoyl- (a).-A solution of 1.0 g. of 3-( n'-r-diethylaminopropyl-9- 2,4dibromoaniline, m.p. 136-136",11 which gave no de- toluenesulfonamido)-4-( N-n- propyl - p - toluenesulfonamid0)- pression of melting point when mixed with ail authentic anisoles and 0.9 g. of phenol in 7 ml. of 30% hydrogen bromidc sample of the benzoyl derivative of 2,4-dibromoaniline.1'2 in acetic acid after 5.5 hours at 26' was poured into 250 ml. Infrared data confirmed the identity of this compound. of anhydrous ether. The precipitate which formed was Detosylation of p-Toluenesulfonanilide in the Presence of dried under vacuum arid then dissolved by stirring with two Phenol.-A solution of 0.01 mole (2.5 8.) of p-toluenesul- 35-ml. portions of 0.05% hydrochloric acid. Neutralization, fonanilide and 0.02 mole (2.0 g.) of phenol in 23 g. of 30% followed by extraction, gave a yellow oil, a portion of hydrogen bromide in acetic acid was permitted to stand at which rapidly darkened when exposed to the air. After 26' for 16 hours. The reaction mixture was poured into dryingat 0.1 mm. for 2 hours at 60" it weighed 0.58 g. 150 ml. of anhydrous ether. The precipitate was filtered, washed with 100 ml. of ether and dried. It weighed 1.48 Anal. Calcd. for C24Ha?Na03S: C, 63.39; H, 8.33; S, g. (86% yield), m.p. 283' (dec.). 7.16. Found: C, 64.70,64.03; H,8.03,8.21; S, 7.23. Acetylation of the hydrobromide by the method of (b).-A similar experiment was permitted to stand at 26' Shotten-Baumann gave 85% yield of acetanilide, m.p. for 3.5 days. When worked up as described above there 112.5-113.5'. There was no depression of melting point was isolated 0.44 g. of a brown oil. Distillation of this when this material was mixed with an authentic sample of material gave 0.21 g., b.p. 170-176" (0.7 mm.). acetanilide. Anal. Calcd. for C17H31N30: C, 69.58; H, 10.65. Found: C, 70.27; H, 10.60; S, 0. (12) We are indebted to Prof. H. R. Snyder, of the University oi Illinois, for a sample of 2,4-dibrornoaniline. KALAMAZOO, MICHIGAN [CONTRIBUTIOS FROM THE 1)EPARTMEST OF CHEMISTRY OF WAYNE UNIVERSITY] Alkaloid Studies. I. The Isolation of Pilocereine from the Cactus Lophocereus schottii' BY CARL IIJERASSI, N. FRICK~AND L. E. GELLER3 RECEIVEDMARCH 13, 1953 Publication Date: August 1, 1953 | doi: 10.1021/ja01111a008 The isolation of a crystalline alkaloid CaoH,,OdNn, termed pilocereine, from the cactus Lophocereus Schottii and its occur- Downloaded by BIUS JUSSIEU on September 28, 2009 | http://pubs.acs.org rence in the plant tissues is described. The alkaloid has been characterized by a number of derivatives and the nature of the functional groups has been investigated. Both nitrogen atoms are tertiary, one forming part of a heterocyclic ring, while of the four oxygen atoms, two are present as methoxyl groups, one as a phenolic hydroxyl group and the fourth appears to be present in an ether linkage The hallucinatory principle (mescaline) present been this particular genus which has occupied the in certain Lophophora species first stimulated re- attention of alkaloid chemists. The giant cacti, search on cactus alkaloids4 and a whole series of which occur so widely in the southwestern United closely related alkaloids has subsequently been iso- States and particularly in the semi-arid regions of lated and identified, all of them possessing a rather Mexico, Central and South America, are encom- simple structure based on a single phenylethylam- passed in 38 genera5 of the subtribe Cerenae. With ine or tetrahydroisoquinoline nucleus. According one exception (vide infra), the few chemical studies to Britton and Rose's classification,s the genus of this subtribe have been limited to one species Lophophora (also referred to as Anhalonium) be- each of the genera Pachycereus6 and Carnegiea' longs to the subtribe Echinocactanae of the Cacta- and to Reti's4s8 investigations of Argentinian Tri- ceae family and with few exceptions, it has only chocereus species; in all instances, the alkaloids iso- (1) This work has been supported by a grant from the American lated were found to belong to the p-phenylethylam- Heart Association, Inc., to which we are greatly indebted. ine or isoquinoline group. (2) Postdoctorate Fellow, 1952-1953. In view of the fact that the giant cacti of the sub- (3) Predoctorate Fellow, 1952. tribe Cereanae are comparatively readily accessible (4) An excellent review on cactus alkaloids has been published by I.. Reti in L. Zechmeister's "Progress in the Chemistry of Organic since many of them are indigenous to Mexico, a Natural Products," Vol. VI, Springer, Vienna, 1!45IJ, pp. 242 -28Y. (1,) C; Iieyl, Arch Phorm , 239, 431 (1901). (5) N. L. Britton and J. N. Rose, "The Cactaceae." Vols. I-I\', (7) G Heyl, ibid., 266, 668 (1928) Carnegie Institution of Washington, Washington, D. C., 1919-1923. (8) L Reti and J. A. Castrillou, THISJOURNAL, 73, 1767 (1951). Aug. 5, 1953 ISOLATIONOF PILOCEREINE FROM Lophocereus schottii CACTUS 3633 - .m \- 80 %. V (0 i; 1 I- -H $60- I 2 z* 1 P VI -;; ::I 20 .la I ~ ~ 0 0 I 3 4 5 b 7 8 e 0 I1 12 13 I4 15 Ib study has been undertaken in this Laboratory of scale experiments, the complete stems were reduced some of the natural products occurring in such in size, dried and extracted exhaustively with etha- plants. Particular emphasis has been placed on nol. The crude alkaloid fraction (ca. 3.7%) ob- triterpenesg and alkaloids and the present paper tained in the conventional manner as described in deals with the isolation of an alkaloid of unknown the experimental section, was difficult to crystal- constitution from the cactus Lophocereus schottii. lize and closely followed the description given by Our attention was first directed at this plant when HeyP for his amorphous alkaloid. That this frac- it was noted that HeyP in an investigation of this tion was not homogeneous was demonstrated read- cactuslo reported the presence of 5.8% of an amor- ily by chromatography whereupon it was possible phous alkaloid, m.p. 82-86’, which he called pilo- to separate in approximately 0.5% over-all yield cereine. The alkaloid could not be crystallized (based on dry plant) a crystalline optically inactive nor could crystalline derivatives be obtained, but alkaloid with m.p. 177”. Since it is obvious that according to Hey1 it possessed the empirical form- Heyl’s L‘pilocereine’’6represents a mixture, we have ula C30H4404NZ. The significance of this observa- retained this name for the pure alkaloid which by tion was not apparent at that time, since the analysis was found to possess the empirical form- structures of the various cactus alkaloids had not ula CSOH4204N2.Titration and preparation of a yet been elucidated, and in fact it seems to have series of crystalline derivatives (hydrochloride, escaped general notice. However, if correct, this perchlorate, oxalate, methiodide) demonstrated the would indicate that a new type of alkaloid is pres- presence of two basic nitrogen atoms, which is in ent in cacti since none of the known cactus alka- marked contrast to the presently known cactus loid~~contains more than thirteen carbon atoms.
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