Non-isoprenoid Tryptamines

Non-isoprenoid Tryptamines.—NAT-Dimethyltryptamine (5), bufotenine (6), and bufotenine N-oxide have been found in the roots and stems of Desmodium caudatum DC. NN-Dimethyltryptamine and bufotenine have also been isolated, together with four other simple tryptamine derivatives (7)—(10), from a red-violet octocoral, Paramuricea chamaeleon, collected in the Bay of Naples.  

The pod walls of Erythrina arborescens Roxb. contain a number of alkaloids of the Erythrina group, together with hypaphorine and a new base, erysodino-phorine, which has the structure (11), since it can be hydrolysed to hypaphorine and erysodine.  

Fukushima, T. Noro, K. Morinaga, and H. Kuwano, Chem. Pharm. Bull., 1978, 26,2411. 

Cimino and S. De Stefano, Comp. Biochem. Physiol., Sect. C, 1978,61, 361. 

Three alkaloids occur in Picrasma excelsa (Swartz) Planchon, in association with bitter principles of the quassin group. Two of these were identified as canthin-6-one and 5-hydroxy-6-methoxycanthin-6-one the third is new, and was shown to be N-methoxy-l-vinyl-/8-carboline (12). The presence of an N-methoxy-group in indole alkaloids is rare, the only other examples known at present being gelsedine and 1,5-dimethoxygramine. 

One of two new alkaloids isolated from the marine bryozoan Flustra foliacea proves to be 6-bromo-Nj -formyl-Nj -methyl- 

Strychnocarpine has been found to occur in the stem bark of 

Annomontine (11a) and 6-methoxyannomontine (11b) are the first members of a new class of aminopyrimidino-6-carboline alkaloids, 

oreophila contain N,N-dimethyl-5-methoxytryptamine, 2-methyl-6-methoxy-l,2,3,4-tetrahydro-6-carboline, together with hordenine and kokusaginine, and the stem bark contains kokusaginine and three other furanoquinoline bases. The leaves of D. drupacea yielded N,N-dimethyl-5-methoxytryptamine again the stem bark contained only quinoline alkaloids. 

The root bark of Brucea antidysenterica Mill., used in folk 

The conformations of bufotenine and psilocin in solution have been studied by 360 MHz H n.m.r. spectroscopy.166 Bufotenine adopts preferentially a staggered conformation in deuteriochloroform, whereas psilocin exists mainly in the gauche conformation, presumably owing to weak hydrogen-bonding of the 4-hydroxy-group with the basic nitrogen atom. 

Cook s stereospecific synthesis19 of trans-1,3 -disubstituted tetrahydro-/ -carbolines by condensation of iVb-benzyltryptophan methyl ester with aldehydes, coupled with a simple 13C n.m.r. method for differentiating cis- and trans-tetrahydro-/ -carbolines,196 should afford a promising starting point for the synthesis of complex alkaloids. Angenot and his collaborators have also discussed the 13C n.m.r. spectra of a number of / -carboline and 3,4-dihydro-/Tcarboline derivatives.19  

The root bark of Ailanthus altissima Swingle contains the known alkaloids canthin-6-one (22), l-methoxycanthin-6-one, canthin-6-one A-oxide, and 1-acetyl-4-methoxy-/ -carboline, together with three new alkaloids, identified as 1-methoxy-canthin-6-one A-oxide, l-(2-hydroxyethyl)-4-methoxy-/ -carboline, and 1(1,2-dihydroxyethyl)-4-methoxy-/ -carboline.21 

Schmid, Arch. Pharm. (Weinheim, Ger.), 1980, 313, 990 (c) Atta-ur-Rahman and M. Ghazala, 

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Non-isoprenoid Tryptamines.—Tryptamine and Nb-methyltryptamine have been shown to be present in the inflorescences of Tachigalia paniculata (Family... 

Non-isoprenoid Tryptamines.—The structures (21) and (22) have been deduced for donaxarine and donaxaridine, the alkaloids of Arundo donax 14 the relationship between the two is confirmed by the formation of donaxarine by condensation of... 

Non-isoprenoid Tryptamines.—The tryptamide (6) of an aminoethylthiazole carboxylic acid has been isolated from a Thermoactinomyces species (strain TM-64). 

Non-isoprenoid Tryptamines. The stems of Picrasma ailanthoides, from which plant canthine derivatives had previously been obtained, has now yielded 1-methoxycarbonyl- and l-hydroxymethyl-j5-carboline. The molecular shape of eserine (= physostigmine) in the crystal has been determined. The new evidence fits in well with information, summarized previously, from n.m.r. NOE measurements. More alkylations at the C-1 methyl of harmaline have been reported.The A -methyl derivative of 1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizine has been isolated from cranberries. 

Non-isoprenoid Tryptamines.—There have been more descriptions of -carbolines and dihydro- and tetrahydro-derivatives from Virola and Phalaris species. One such compound, reported earlier as 6-methoxy-2,9-dimethyl-l,2,3,4-... 

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