2-Nitroso-1-phenylpropane

2-nitrosopropylbenzene 2-Nitroso-1-phenylpropane.svg 55941-34-9 124315 110742 CC(CC1=CC=CC=C1)N=O 1S/C9H11NO/c1-8(10-11)7-9-5-3-2-4-6-9/h2-6,8H,7H2,1H3 JNWJQOCPCZKSQI-UHFFFAOYSA-N 9 11 1 1 2-Nitroso-1-phenylpropane, also known as N-nitrosoamphetamine, is a product of the oxidation of N-hydroxyamphetamine, which is formed during the metabolism of amphetamine and methamphetamine and plays a role in their potential toxicity.Powell Samantha M. Thomas Leonard M. Richter-Addo George B. 2020 The nitrosoamphetamine metabolite is accommodated in the active site of human hemoglobin: Spectroscopy and crystal structure Journal of Inorganic Biochemistry 213 111262 10.1016/j.jinorgbio.2020.111262 1873-3344 7686107 33049600 2020JIBio.21311262P Wang Bing Powell Samantha M. Guan Ye Xu Nan Thomas Leonard M. Richter-Addo George B. 2017-07-01 Nitrosoamphetamine binding to myoglobin and hemoglobin: Crystal structure of the H64A myoglobin-nitrosoamphetamine adduct Nitric Oxide: Biology and Chemistry 67 26–29 10.1016/j.niox.2017.04.012 1089-8611 5548592 28450187 Toxicology Toxicodynamics N-Nitrosoamphetamine is capable of binding strongly to the heme sites of various proteins (such as microperoxidase 8, prostaglandin H synthase, nitric oxide synthase, as well as hemoglobin and myoglobin). By interacting with the divalent iron of heme, it forms stable nitrosoenzyme derivatives of the form FeII-N(O)amphetamine. Such derivatives inhibit the normal function of these proteins. Toxicokinetics The compound is oxidized (specifically, the beta-carbon is oxidized to nitrogen), forming what is known as a “beta-hydroxylated nitrosodimer.” Nitroso compounds, ketones, and alcohols are also formed during this process. However, the formation of ketones and alcohols depends on the presence of cofactors (special auxiliary molecules necessary for enzyme activity). Under these conditions, N-nitrosoamphetamine was not reduced back; that is, the reaction proceeded toward oxidation and structural modification rather than reduction.Beckett A. H. Jones G. R. 1977 The in vitro metabolism of 2-nitroso-1-phenylpropane dimer by fortified 9000g supernatants from rabbit liver The Journal of Pharmacy and Pharmacology 29 6 350–354 10.1111/j.2042-7158.1977.tb11333.x 0022-3573 18571 References Category:Substituted amphetamines Category:Nitroso compounds