Tobacco and Public Health - TCSC Indonesia

168
CIGARETTE SCIENCE: ADDICTION BY DESIGN
various therapies are successful for one year or longer (National Institute on Drug
Addiction 2000).
Nicotinic pyridine alkaloids in cigarettes
Tobacco contains at least 20 different, pyridine alkaloids, 16 of which are shown in
Fig. 8.1. Of these, the dominant alkaloid is nicotine, making up nearly 88% of the total
alkaloid content of some tobaccos, and it has been reported that the average nicotine
content of tobacco is 1.5% by weight (Benowitz et al. 1983). Cigarettes can essentially
be described as nicotine delivery devices. For example, it can be seen from
chromatograms of cigarette smoke tar, that nicotine is among the few compounds that
is delivered in milligram quantities. Most of the remaining compounds in cigarette
smoke are delivered in microgram or nanogram quantities.
The relative pharmacological potency of nicotine is 1.2–2.5 times that of nornicotine
and anabasine, depending on the test system and animal model used
(U.S. Surgeon General 1988). The alkaloid profile appears to vary substantially with
N
N
CH3 N
N
N
N
H
N
N
nicotine anatabine anabasine anabaseine
N
N
N
N
N
H
N
CH3 N
CH3 N
nornicotine N-methylanatabine N-methylanabasine 2,3'-dipyridyl
N
N
N
NO
N
N
N
N
CH 3
N-nitrosonornicotine nicotyrine nornicotyrine metanicotine
O
CH3 CH3 N
O
N
N
N
H
N O
N
N
NHCH 3
NHCH3 O
nicotine N-oxide cotinine 6'-oxoanabasine pseudooxynicotine
Fig. 8.1 Chemical structures of 16 tobacco alkaloids (US Surgeon General 1988).