75195-75-4

Basic information

• Product Name: 1-nitroso-5-(3-pyridinyl)-3-pyrrolidinol
• CAS NO: 75195-75-4
• Molecular Weight: 193.205
• Mol File: 75195-75-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1-nitroso-5-(3-pyridinyl)-3-pyrrolidinol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-nitroso-5-(3-pyridinyl)-3-pyrrolidinol(75195-75-4)
• EPA Substance Registry System: 1-nitroso-5-(3-pyridinyl)-3-pyrrolidinol(75195-75-4)

Safety Data

• Hazardous Substances Data: 75195-75-4(Hazardous Substances Data)

Upstream product

• 80508-18-5 4'-hydroxynornicotine 
• 75195-85-6 1,2-epoxy-4-(N-morpholino)-4-(3-pyridyl)-4-cyanobutane 
• 75195-86-7 4'-hydroxymyosmine 
• 36740-09-7 α-(3-pyridyl)-α-(4-morpholino)acetonitrile 

Relevant articles and documents

Metabolic β-hydroxylation and N-oxidation of N'-nitrosonornicotine

3'-Hydroxy-N'-nitrosonornicotine (2), 4'-hydroxy-N'-nitrosonornicotine (3), and N'-nitrosonornicotine 1-N-oxide (4) were synthesized and identified as metabolites in the F-344 rat of the tobacco-specific carcinogen N'-nitrosonornicotine (1). For the synthesis of 2, myosmine (5) was converted to 3'-bromomyosmine (6). Displacement by acetate and hydrolysis gave 3'-hydroxymyosmine (7), which was reduced and nitrosated to give 2. 4'-Hydroxymyosmine (13), the precursor to 3, was prepared by ammonolysis of 1,2-epoxy-4-(N-morpholino)-4-(3-pyridyl)-4-cyanobutane (10). N'-Nitrosonornicotine 1-N-oxide (4) was prepared by m-chloroperbenzoic acid oxidation of 1. When 1 was incubated with liver microsomes from Aroclor-pretreated F-344 rats, trace amounts of 2 and 3 were produced and 4 was a major metabolite. The urine from rats treated with N'-nitrosonornicotine-2'-14C contained only trace amounts of 2 and 3, whereas 4 accounted for 6.7-9.7% of the dose.