3- Amino-1,4-dimethyl-5//-pyrido indole

FIGURE 9.3 Total gas chromatogram obtained from standard heterocyclic amines (containing 5 ng of each amine). GC conditions-peaks 1. 2-amino-9H-pyrido[2,3-b]indole (AaC) + 2-aminodipyrido [l,2-a 3 2Cd]imidazole (Glu-p-2) 2. 2-amino-6-methyldipyrido[l,2-a 3 2Cd]imidazole (Glu-P-1) 3. 3-amino-l,4-dimethyl-5H-pyrido[3,4-b]indole (Trp-P-1) 4. 3-amino-l-methyl-5H-pyrido[3,4-b]indole (Trp-P-2) ... 

Yamashita et al. (4367, 4368) identified and quantitated the following /V-heterocyclic amines in mainstream CSC 2-amino-3-methylimidazo[4,5-/]quinoline (IQ) (0.3 ng/cigarette), 3-amino-l,4-dimethyl-57/-pyrido[4,3-/>]mdole (Trp-P-1) (0.3 ng/cigarette), 3-amino-l-methyl-5//-pyrido[4,3-fc]indole (Trp-P-2) (0.2 ng/cigarette), 2-amino-9//-pyrido[2,3-fc]indole (AaC) (16.9 ng/cigarette), and 2-amino-3-methyl-9//-pyrido [2,3- ]indole (MeAaC) (1.6 ng/cigarette). 

AaC = 2-amino-9Tf-pyrido[2,3-fe]indole MeAaC = 2-amino-3-methyl-9Tf-pyrido[2,3-fe]indole Glu-P-1 = 2-amino-6-methyldipyrido[l,2-a 3 ,2 -ai] imidazole Glu-P-2 = 2-aminodipyrido[l,2-a 3 ,2 -ii]imidazole PhIP = 2-amino-l-methyl-6-phenyl-lH-imidazo[4,5-i)]pyridine IQ = 2-amino-3-methyl-3//-imidazo[4,5-/ quinoline MelQ = 2-amino-3,4-dimethyl-3Tf-imidazo[4,5-/ quinoline Trp-P-1 = 3-amino-l,4-dimethyl-5Tf-pyrido[4,3-i)]indole Trp-P-2 = 3-amino-l-methyl-5//-pyrido[4,3-I>]indole. 

In an in-house presentation, Rodgman (3253a) discussed the already identified and other possible theoretical relationships between tryptophan and the substituted norharmans, the tryptophan pyrolysis products 3-amino-l,4-dimethyl-5//-pyrido[4,3-/ ]indole (Trp-P-1) and 3-amino-l-methyl-5A-pyrido[4,3-/7]indole (Trp-P-2), the 2-amino-9A-pyrido[2,3-f>] indoles (AaC and MeAaC), indole-3-acetonitrile, and the alkyl- and dialkylindoles. 

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).

Z-aminO 1 -methy 1 6 phenylimidazo [4,5-b]-pyridine 2 aminO 3,7,8 trimethylimidazo[4,5 f]quinoxaline 2 aminO 3,4,7,8 tetramethyl 3H imidazO [4,5 f]quinoxaline inoxaline 3 aminO l,4 dimethyl SH pyrid [4,3 b] indole (Trp P I) and 3 aminO l methyl 5H pyrido [4,3 b]indole induced mutagenesis. Metabolic activation was required for positive results b... 

DiMeIQx 2-amino-3,4,8-trimethylimidazo-[/] quinoxaline nh2 Trp-P-1 3-amino-l,4-dimethyl-5H-pyrido[4,3-/)Jindole CH3 0X1. CH3 Trp-P-2 3-amino-l-methyl-5H-pyrido[4,3-/)]indole ch3 f S X" N... 

Galceran et al. (199) developed an SPE-HPLC method for the determination in beef extract of five mutagenic amines, namely Trp-P-1 (3-amino-1,4-dimethyl-5//-pyrido[4,3-fc]indole),... 

Both 3-amino-l-methyl-5 -pyrido[4,3-6]indole and 3-amino-l,4-dimethyl-5//-pyrido[4,3-ijindole were found to possess potent convulsant activity <90Mi 706-oi>. 

SYNS 3-. UvtINO-l,4-DIMETHYL-Y-CARBOLINE 3-AMINO-l,4-DIMETHYL-5H-PYRIDO(4,3-b)INDOLE 1,4-DIMETHYL-5H-PYRIDO(4,3-b)lNDOL-3-AMlNE TRP-P-1 dl-TRYPTOPHAN, pyrolyzate 1... 

AMINO-l,4-DIMETHYL-5H-PYRIDO(4,3-b)INDOLE ACETATE see AJR500... 

PHAs identified in cooked foods that are of concern to human health include 2-amino-3-methylimidazo[4,5-/Iquinoline (IQ), 2-amino-3,4-dimethyl-3H-imidazo[4,5-/ quinoline (MelQ), 2-amino-3,8-dimethylimidazo[4,5-/Iquinoxaline (MelQx), 2-amino-2,4,8 (or 3,7,8)-trimethylimidazo[4,5-/Iquinoxaline (diMelQx), 2-amino-iV-methyl-5-phenylimidazopyridine (PhIP), 3-amino-l,4-dimethyl-5/f-pyrido[4,3-fe]indole (Trp-P-1), 3-amino-l-methyl-5H-... 

In relation to food intake, pyrolysis products of L-tryptophan in which highly mutagenic y-carboline, tryptophan-P-1 (3-amino-l, 4-dimethyl-5H-pyrido[4,3-b] indole and tryptophan-P-2 (3-amino-l-methyl-5H-pyrido[4,3-b] indole are formed and can be activated to mutagens in liver. Implications of such events in liver carcinogenesis are discussed in Chapter 6. 

In the late 1970s, Japanese investigators, in their detailed studies of components of various cooked foods, isolated and identified the first of a series of Af-heterocyclic amines as pyrolysis products of several amino acids. Sugimura et al. (3829) reported the isolation and identification of 3 -am ino-1,4-dimethyl-5//-py rido[4,3 -fcjindole (designated as Trp-P-1) IV and 3-amino-l-methyl-5//-pyrido[4,3-fc] indole (Trp-P-2) V (Figure XVII.F-2) from tryptophan pyrolysates. 

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