233 4-Aminobiphenyl 4-Aminobiphenyl is an amine derivative of biphenyl. It is used to manufacture azo dyes. It is a known human carcinogen and so it has been largely replaced by less toxic compounds. It is similar to benzidine. 92-67-1 7102 C12H11N 169.089150 White powder. 53.5°C Oral (T36) ; inhalation (T36) ; dermal (T36) 4-Aminobiphenyl requires metabolic activation in order to exert its toxicity. This is catalyzed by N-hydroxylation via cytochrome P450 1A2, then followed by O-sulfation and O-acetylation by sulfotransferase 1A1 and arylamine N-acetyltransferase 2. The metabolites of 4-aminobiphenyl may form adducts with DNA, inducing mutations. 4-Aminobiphenyl and its metabolites may also cross the placenta and have fetal effects. (A2454, A2455, A2456, A2457) 4-Aminobiphenyl exposure can be assayed by measuring the extent of adduct formation with hemoglobin. 4-Aminobiphenyl metabolism is catalyzed by N-hydroxylation via cytochrome P450 1A2. It is then followed by O-sulfation and O-acetylation by sulfotransferase 1A1 and arylamine N-acetyltransferase 2. The urinary metabolites of 4-aminobiphenyl include 4-acetylaminobiphenyl, 4'-hydroxy-4-aminobiphenyl, 2'-hydroxy-4-acetylaminobiphenyl, 4'-hydroxy-4-acetylaminobiphenyl, 3'-hydroxy, 4'-methoxy-4-acetylaminobiphenyl, 4'-hydroxy, 3'-methoxy-4-acetylaminobiphenyl, and 3',4'-dihydroxy-4-acetylaminobiphenyl. (T36, A2457) LD50: 205 mg/kg (Oral, Mouse) (T14) 1, carcinogenic to humans. (L135) 4-Aminobiphenyl is used to manufacture azo dyes and is also found in tobacco smoke. (L1654, A2455) 4-Aminobiphenyl is a known human carcinogen. It may also cause methemoglobinemia. (L135, T36) Symptoms of 4-aminobiphenyl may include dyspnea, headache, dizziness, lethargy, and ataxia. (T36) 2009-03-06T18:58:20Z 2026-04-03T01:07:18Z Cytochrome P450 1A2 (P05177) Sulfotransferase 1A1 (P50225) Arylamine N-acetyltransferase 2 (P11245) Hemoglobin subunit alpha (P69905) Hemoglobin subunit beta (P68871) Hemoglobin subunit delta (P02042) Hemoglobin subunit epsilon (P02100) Hemoglobin subunit gamma-1 (P69891) Hemoglobin subunit gamma-2 (P69892) Hemoglobin subunit mu (Q6B0K9) Hemoglobin subunit theta-1(09105) Hemoglobin subunit zeta (P02008) (A2454, A2455, A2456, A2457) http://en.wikipedia.org/wiki/4-Aminobiphenyl C10998 1784 N-HYDROXY-4-AMINOBIPHENYL C006757 4-Aminobiphenyl 70 true Cytochrome P450 1A2 (P05177) Sulfotransferase 1A1 (P50225) Arylamine N-acetyltransferase 2 (P11245) (A2454, A2455, A2456, A2457) Hemoglobin subunit alpha (P69905) Hemoglobin subunit beta (P68871) Hemoglobin subunit delta (P02042) Hemoglobin subunit epsilon (P02100) Hemoglobin subunit gamma-1 (P69891) Hemoglobin subunit gamma-2 (P69892) Hemoglobin subunit mu (Q6B0K9) Hemoglobin subunit theta-1(09105) Hemoglobin subunit zeta (P02008) (A2454, A2455, A2456, A2457) NC1=CC=C(C=C1)C1=CC=CC=C1 C12H11N InChI=1S/C12H11N/c13-12-8-6-11(7-9-12)10-4-2-1-3-5-10/h1-9H,13H2 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 169.2224 169.089149357 Exogenous Solid 2.86 HMDB13195 CHEMBL44201 6835 CHEM000203 DTXSID5020071 [1,1'-biphenyl]-4-amine