2-Amino-9H-pyrido[2,3-b]indole (CAS 26148-68-5)

2-Amino-9H-pyrido[2,3-b]indole, also known as 2-Amino-a-carboline or a-alpha-C, is an organic compound belonging to the class of alpha carbolines. It has a pyrido[2,3-b]indole core, which is a fused structure of pyridine and indole. This solid compound is practically insoluble in water and has a relatively neutral nature. It is primarily found in the cell membrane based on predictions from logP.n studies conducted on Aalpha C-treated rats, one major Aalpha C-DNA adduct and up to three minor adducts were detected in various tissues such as mammary gland epithelial cells, liver, stomach, small intestine, colon, and kidney. The adduct patterns were similar across all examined tissues. The major adduct, comprising 60-100% of the total DNA adduct levels, was identical to the principal adduct found in 3′-dGp-A C, which is synthesized by reacting 3′-phospho-2′-deoxyguanosine with N-acetoxy-A C. Among the tissues, the highest levels of Aalpha C-DNA adducts were found in the liver.It may act to be carcinogenic in mice, induce preneoplastic foci in rat liver, and form covalent DNA adducts both in vitro and in vivo. Its corresponding nitro compound, Nalpha C, was prepared and demonstrated to be a direct-acting mutagen in the Salmonella assay. However, the amino compound required external metabolic activation with rat liver homogenate (S9). When Aalpha C was incubated with S9 in the presence of calf thymus DNA, a major DNA adduct spot was detected through 32P-postlabeling analysis. This adduct shared similar characteristics in ion-exchange TLC and reversed-phase HPLC with the major adduct found in primary hepatocytes treated with Aalpha C.