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Norharman indole

Figure 13.7 Mutagenic and carcinogenic heterocyclic amines of the carboline group (a) AaC (2-amino-9//-p5Tido[2,3,-i)]indole), (b) norharman (9f/-pyrido[4,3-i)]indole), (c) Trp-P-1 (3-amino-l,4-dimethyl-57/-pyrido[4,3-/)]indole), (d) Glu-P-1 (2-amino-6-methyl-dipyrido[l,2-a 3, 2 -d]imidazole). Figure 13.7 Mutagenic and carcinogenic heterocyclic amines of the carboline group (a) AaC (2-amino-9//-p5Tido[2,3,-i)]indole), (b) norharman (9f/-pyrido[4,3-i)]indole), (c) Trp-P-1 (3-amino-l,4-dimethyl-57/-pyrido[4,3-/)]indole), (d) Glu-P-1 (2-amino-6-methyl-dipyrido[l,2-a 3, 2 -d]imidazole).
Indole alkaloids, such as harmane and norharmane, were also reported to be present in tobacco but in minute quantities. [Pg.62]

PhIP 2-amino-l-methyl-6-phenylimidazo[4,5-/)]pyridine n T Vnh2 Nr" harman 1 -methyl-9H-pyrido[4,3-b]indole O7O ch3 norharman 9H-pyrido[4,3-b]indole v. L Jj... [Pg.898]

Trp-P-2 (3-amino-l-methyl-5//-pyrido[4,3-h]indole), AaC (2-amino-9//-pyrido[2,3-bJindole), MeAaC (2-amino-3-methyl-9//-pyrido[2,3- ]indole), and PhIP (2-amino-1-methyl-6-phenyl-imidazo[4,5-h]pyridine) and two /3-carbolines comutagens harman (l-methyl-9//-pyrido[4,3-h]indole) and norharman (9//-pyrido[4,3-h]indole). The optimized SPE procedure for isolation and preconcentration comprises the use of diatomaceous earth, propylsulfonyl silica gel, and C18 cartridges to separate selectively the imidazopyridine and indolpyridine derivatives from those of... [Pg.899]

Nantenine (= 0-Methyldomesticine) (aporphine isoquinoline) Norharman (P-carboline, indole)... [Pg.199]

Ephedrrne and related phenylalkyl amines (AA) reserprne, ihogaine, and related indole alkaloids (AA) cocaine (AA) armonaine and related aporphine alkaloids (AA) arecaidine (AA) norharman and related (J-carholine alkaloids (AA) salsolinol and related isoquinolines (AA)... [Pg.8]

Dimethyl 3,3 -dithiopropionate 164 can generate, in basic medium, methyl acrylate, which serves in situ as a source of a propionate moiety. This method was applied to the N-alkylation of indoles, pyrido[3,4- ]indole (Norharman) and carbazoles leading to a series of 3-(heteroaryl)propionates 165 (Scheme 34) <2000JOC3123>. KH affords slightly superior results than NaH, while other bases such as LDA, CS2CO3, or NaHMDS are generally less efficient. [Pg.69]

Tryptophan was also found to be the precursor in tobacco of two other A-heterocyclic compounds, namely harman (l-methyl-9A-pyrido[3,4-(i]indole) and norharman (9A-pyrido[3,4- ]indole), in tobacco smoke. These compounds were originally identified in tobacco and tobacco smoke by Philip Morris R D personnel in 1961 and 1962 [Poindexter and Carpenter (2972)] and in 1963 [Poindexter et al. (2972)]. That tryptophan was indeed a precursor in tobacco of the two barmans in smoke was demonstrated by addition of radiolabeled tryptophan to cigarette tobacco and identification of radiolabeled harman and norharman in the MSS. [Pg.365]

In his 1968 review of tobacco and tobacco smoke composition, Stedman (3797) discussed the identification of tumorigenic A-heterocyclic compounds [dibenz[fl,/t]acridine, dibenz[fl, ]acridine, and 7//-dibenzo[c, carbazole] reported by Van Duuren et al. (4027), as well as the identification of the following A-heterocyclic compounds 5//,10//-dipyrrolo[l,2-fl T,2 -(i]pyrazine-5,10-dione (pyrocoll), 9//-pyrido[3,4-fc] indole (norharman), l-methyl-9/f-pyrido[3,4-fc]indole (harman), and 9//-pyrido[2,3-fc]indole. [Pg.812]

In his early 1970s outline of recent research on tobacco and tobacco smoke composition, Wakeham (4103) noted the reported presence of 9//-pyrido[3,4- ]indole (norharman) and l-methyl-9//-pyrido[3,4-fc]indole (harman) in cigarette smoke and discussed their possible formation by reaction of tryptophan and an aldehyde. As noted by Rodgman (3253a), the structure of the aldehyde reacting with tryptophan ultimately dictates the structure of alkylated norharmans found in CSC (see Table XVH.E-2). [Pg.812]

Table XVII.E-7 summarizes the variation in the structures of the aza-arene compounds identified in tobacco and/ or tobacco smoke. Of particular interest with regard to the 294 aza-arenes cataloged in Table XVII.E-6 is that only twenty-three of the 294 have been identified as tobacco components. Of the twenty-three, just fifteen have been identified in both tobacco and smoke. The number of aza-arenes identified in smoke is 286. Those isolated from or identified in tobacco in greater than trace amounts include l//-indole, 2,3-dihydro-l//-indole, 9//-pyrido[3,4-/ ]indole (norharman), l-methyl-9//-pyrido[3,4-/ ]indole (harman), l//-purine, and quinoline. Table XVII.E-7 summarizes the variation in the structures of the aza-arene compounds identified in tobacco and/ or tobacco smoke. Of particular interest with regard to the 294 aza-arenes cataloged in Table XVII.E-6 is that only twenty-three of the 294 have been identified as tobacco components. Of the twenty-three, just fifteen have been identified in both tobacco and smoke. The number of aza-arenes identified in smoke is 286. Those isolated from or identified in tobacco in greater than trace amounts include l//-indole, 2,3-dihydro-l//-indole, 9//-pyrido[3,4-/ ]indole (norharman), l-methyl-9//-pyrido[3,4-/ ]indole (harman), l//-purine, and quinoline.
Although not originally classified at the time as cooked food mutagens, several amino acid-derived iV-heterocyclic compounds were identified in cigarette smoke condensate (CSC) in the early 1960s 5//,10//-Dipyrrolo[l,2-a r,2 -(i] pyrazine-5,10-dione (pyrocoll) 1 by Mold et al. (2592) and 9H-pyrido[3,4-fc]indole (norharman) 11 and l-methyl-9-H-pyrido[3,4-fc ]indole (harman) 111 by Poindexter and Carpenter (2972) (Figure XVll.F-1). [Pg.834]

Heckman and Best (1587) reported the identification of nearly 270 previously unidentified and confirmation of over 150 previously identified A-containing components in CSC. These included several components structurally similar to some of the A-heterocycfic amines 9H-pyrido[2,3- ]indole, 2-methyl-97/-pyrido[2,3- ]indole, 2-(2-methylpropyl)-9H-pyrido[2,3-fc] indole, 2-pentyl-9H-pyrido[2,3-fc]indole, l-butyl-97/-pyrido [3,4- ]indole, l-propenyl-9H-pyrido[3,4- ]indole, and a partially characterized norharman. [Pg.841]

Rodgman also discussed the already identified and other possible theoretical relationships (Figure XVII.F-5) between tryptophan XX and 9//-pyrido[3,4-( ]indole (norharman) II its methyl homolog l-methyl-9//-pyrido[3,4-fc]indole (harman) III and other substituted norharmans VI, R = C2H5, CH3CH=CH, and -C4H9, the tryptophan pyrolysis products 3-amino-1,4-dimethyl-5/7-pyrido-[4,3-( Jindole (Trp-P-1) IV and 3-amino-l-methyl-5//-pyrido[4,3-( ] indole (Trp-P-2) V the alkyl- and dialkyl-indoles indole-... [Pg.841]

Snook and Chortyk (3739, 3740) reported the cigarette mainstream smoke (MSS) yield of 9//-pyrido[3,4-fc]indole (norharman) to be 1.2 to 13.4 pg/cigarette that for 1-methyl-97/-pyrido[3,4- ]indole (harman) to be 0.3 to 3.8 pg/cigarette. They found a linear relationship between the yield of MSS tar and the yields of 97/-pyrido[3,4- ]indole (norharman) and l-methyl-9T/-pyrido[3,4-/7]indole (harman). In contrast to the 1962 findings of Poindexter and Carpenter (2972),... [Pg.842]

Poindexter and Carpenter (2972) reported the isolation and identification of 9//-pyrido[3,4-/>]indole (norharman) and l-methyl-9//-pyrido[3,4-/>]indole (barman) from CSC. They reported that the yield of the total barmans in hurley and flue-cured MSSs was between 15 and 20 xg/gram of tobacco smoked, values which were 40 to 50 times that of the barmans in the unsmoked tobacco. Since the weight of tobacco in cigarettes sold at that time approximated 1 gram, the yield of these two compounds was about 15-20 Xg/cig. Poindexter and Carpenter concluded from experiments with radiolabeled tryptophan that the barmans (found to be radiolabeled in the smoke) were generated pyrogenetically from a reaction between aldehydes (formaldehyde for norharman, acetaldehyde for barman) and the tryptophan in tobacco. [Pg.849]

In separate studies, Levitt et al. (2355a) and Nagao et al. (2667b) demonstrated the mutagenicity of 97/-pyrido[3,4-/>]indole (norharman) and l-methyl-9//-pyrido [3,4-b] indole (barman) in the Ames test. [Pg.849]

In its 1985 review, published in 1986, of the various problems from exposure to numerous components in tobacco smoke, the lARC (1870) did not designate the A-heterocyclic amines as a problem. lARC did list several tryptophan-derived tobacco smoke isolates including 9A-pyrido[3,4-f>]indole (norharman) and l-methyl-9A-pyrido[3,4-f>]indole (harman). The per cigarette MSS yields of these two components were listed as 9.5 to 14.1 and 2.5 to 5.8 xg/cig, respectively. No mention was made of the A-heterocyclic amines in CSC or the degree of evidence for their carcinogenicity in animals and humans. [Pg.850]


See other pages where Norharman indole is mentioned: [Pg.498]    [Pg.498]    [Pg.494]    [Pg.342]    [Pg.342]    [Pg.532]    [Pg.100]    [Pg.182]    [Pg.646]    [Pg.812]    [Pg.812]    [Pg.818]    [Pg.830]    [Pg.834]    [Pg.840]    [Pg.841]    [Pg.842]    [Pg.847]    [Pg.850]    [Pg.854]    [Pg.1136]   
See also in sourсe #XX -- [ Pg.899 ]




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