Volume 19, Issue 2
Natural Products
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ChemInform Abstract: Synthesis of 5′-Carboxy-N′-nitrosonornicotine and 5′-((14C)Carboxy)-N′-nitrosonornicotine.

A. ABBASPOUR

A. ABBASPOUR

Naylor Dana Inst. Dis. Preven., American Health Found., Valhalla, NY 10595, USA

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S. S. HECHT

S. S. HECHT

Naylor Dana Inst. Dis. Preven., American Health Found., Valhalla, NY 10595, USA

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D. HOFFMANN

D. HOFFMANN

Naylor Dana Inst. Dis. Preven., American Health Found., Valhalla, NY 10595, USA

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First published: January 12, 1988

Abstract

5'-Carboxy-N'-nitrosonornicotine (IX) is prepared as shown in the reaction scheme.

ChemInform Abstract

5'-Carboxy-N'-nitrosonornicotine (IX) is prepared as shown in the reaction scheme. The key step is the cyclization of the γ-keto aldehyde (IV) with potassium cyanide (V) and ammonia. (IX) and its 14C-labeled derivative mentioned in the title are synthesized in order to study the metabolism of N'-nitrosonornicotine compounds which are assumed to be responsible for cancer-inducing effect of tobacco products.

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