Passive monitoring method for 3-Ethenylpyridine: A marker for environmental tobacco smoke

Article abstract of DOI:10.1021/es0002058

A new method was developed to assess environmental tobacco smoke in air. The method is based on passive sampling and subsequent measurement of the concentration of 3-ethenylpyridine, a vapor-phase compound specific to tobacco smoke. Air samples were collected using a 3M organic vapor monitor. Tests were carried out in a dynamic chamber to determine the sampling rate (25.7 cm³/ min). 3-Ethenylpyridine was desorbed from the sampler with 1 mL of pyridine/toluene mixture. 3-Ethenylpyridine was quantified by gas chromatography/mass spectrometry. The limit of detection was 0.01 μg/sample, corresponding to a concentration of 0.27 μg/m³ air calculated for a sampling period of 24 h. Field measurements were carried out to test the performance of the method. Mean concentrations ranging from 1.3 to 5.3μg/m³ were measured for 3-ethenylpyridine in smoking environments, but no 3-ethenylpyridine was detected in nonsmoking environments. Active sampling using charcoal tubes was used as a reference method in the chamber tests and field measurements. Individual exposures can be easily and accurately measured by means of the passive sampler. Because of simple sample treatment, the method is also well-suited for large-scale monitoring of environmental tobacco smoke.

Full text of DOI:10.1021/es0002058

Environ. Sci. Technol. 2001, 35, 1818-1822
the use of 3-EP: it is present solely in the vapor phase and
has greater stability than nicotine under ultraviolet irradiation
Passive Monitoring Method for
(
(
6). Furthermore, it decays following nearly first-order kinetics
7), whereby its concentration increases linearly with the
3
-Ethenylpyridine: A Marker for
number of cigarettes smoked (4). A good correlation with
carbon monoxide and other gas- or vapor-phase components
of ETS has been shown (8).
Environmental Tobacco Smoke
S I N I K K A V A I N I O T A L O , * ,
†
†
There is much more nicotine than 3-EP in mainstream
smoke, but the difference is much smaller in sidestream
smoke (9). As ETS is composed mainly of aged and diluted
sidestream smoke, the concentrations of 3-EP in ETS are
only slightly lower than those of nicotine. Therefore, 3-EP
can be easily measured in ETS with modern analytic
instruments (2, 8, 10, 11). In experimental conditions, an
emission factor of 660 ( 155 µg/ cigarette has been measured
R A I J A V A A R A N R I N T A ,
J A R K K O T O R N A E U S , N I N A A R E M O , ‡
T A P I O H A S E , ‡ A N D K I M M O P E L T O N E N †
†
Department of Industrial Hygiene and Toxicology, Finnish
Institute of Occupational Health, Topeliuksenkatu 41 a A,
FIN-00250 Helsinki, Finland, and Laboratory of Organic
Chemistry, Department of Chemistry, University of Helsinki,
P.O. Box 55, FIN-00014, University of Helsinki, Finland
(
2, 5).
Various methods of sampling and analysis have been used
to monitor 3-EP. ETS has been collected both by passive and
active sampling. Passive collection has been achieved with
glass fiber filters impregnated with 4% sodium bisulfate (12).
The active samplers are usually sorbent traps, such as XAD-
A new method was developed to assess environmental
tobacco smoke in air. The method is based on passive
sampling and subsequent measurement of the concentration
of 3-ethenylpyridine, a vapor-phase compound specific
to tobacco smoke. Air samples were collected using a 3M
organic vapor monitor. Tests were carried out in a
4
, Tenax/ Carbotrap, or Tenax TA (12-14). The analytic
methods are based on thermal desorption or liquid extraction
with subsequent gas chromatographic (GC) analysis using
mass spectrometric (13, 14) or nitrogen-specific detection
3
dynamic chamber to determine the sampling rate (25.7 cm /
(
12). The limits of quantification of these methods are typically
min). 3-Ethenylpyridine was desorbed from the sampler
with 1 mL of pyridine/toluene mixture. 3-Ethenylpyridine was
quantified by gas chromatography/mass spectrometry.
The limit of detection was 0.01 µg/sample, corresponding
around 0.01 µg/ sample.
In this paper, a new method for sampling and analysis of
3
-EP is introduced, and the method is also applied to field
samples. The passive sampling using a commercial device
together with simple sample treatment and specific detection
of 3-EP could open up a way to routine and inexpensive
monitoring of ETS. The easy-to-use personal sampler is well-
suited to the assessment of individual ETS exposures at
population level.
3
to a concentration of 0.27 µg/m air calculated for a
sampling period of 24 h. Field measurements were carried
out to test the performance of the method. Mean
3
concentrations ranging from 1.3 to 5.3 µg/m were measured
for 3-ethenylpyridine in smoking environments, but no
3
-ethenylpyridine was detected in nonsmoking environments.
Experimental Section
Testing of the Sam pling Method. Test samples were collected
on 3M organic vapor monitors (type 3500) (3M OH&ESD,
Active sampling using charcoal tubes was used as a
reference method in the chamber tests and field
measurements. Individual exposures can be easily and
accurately measured by means of the passive sampler.
Because of simple sample treatment, the method is also well-
suited for large-scale monitoring of environmental
tobacco smoke.
3
M Center, St. Paul, MN) containing a single charcoal
adsorbent pad. The sampling rate was determined in a
dynamic test chamber (1 m ; steel/ glass), using 4-ethenylpy-
ridine (4-EP; experiment I) or a mixture of 3-EP and 4-EP
3
(
experiment II) as test substances.
4
-EP (Aldrich Chemical Co, St. Louis, MO) or a mixture
of 3-EP and 4-EP (1:2) was vaporized under an air flow of
0.02 L/ min and fed into the chamber. In each experiment,
two sampling periods (240 and 480 min) were used, and six
samples were collected during each period. The temperature
and relative humidity (% RH) of the chamber air were
monitored during the experiments. The air velocity in the
chamber was also measured. In each experiment, 12 reference
samples (six during each period) were collected in charcoal
tubes (SKC 226-01; SKC Inc., Eighty Four, PA) with sampling
pumps (SKC-222; SKC Inc.) at an air flow rate of 0.1 L/ min
Introduction
3
-Ethenylpyridine (3-EP) is formed during pyrolytic decom-
position of nicotine and is present in the vapor phase of
tobacco smoke (1). Many researchers have proposed 3-EP as
a suitable indicator of environmental tobacco smoke (ETS).
3
-EP meets the criterion set for an ETS tracer in having a
similar emission rate across different tobacco products (2).
Three additional criteria have been set by the U.S. National
Research Council (3): uniqueness to tobacco smoke, easy
detection at low smoking rates, and consistent proportions
to other ETS compounds for different environments and
tobacco products (4, 5).
(
240 min) or 0.05 L/ min (480 min). The reference samples
were analyzed as the test samples.
The stability of samples collected with the test samplers
was investigated by spiking the sampler pads with 3 µg of
Although nicotine is widely used as a marker for vapor-
phase ETS, the recent literature lists several advantages of
3
-EP and 4-EP calibration solution. A total of 10 µL of
calibration solution in toluene was injected on each pad.
The pads were placed in Kimax tubes, and the tubes were
kept at room temperature for 2 d or in a freezer for 2 weeks.
The stability of the sample solutions (sampler pads in
desorption solution in vials; 3.7 µg of 4-EP/ sample) during
*
Corresponding author telephone: +358 9 47471; fax: +358 9
4
7472114; e-mail: Sinikka.Vainiotalo@occuphealth.fi.
†
‡
Finnish Institute of Occupational Health.
University of Helsinki.
1
8 1 8
9
ENVIRONMENTAL SCIENCE & TECHNOLOGY / VOL. 35, NO. 9, 2001
10.1021/es0002058 CCC: $20.00

2001 Am erican Chem ical Society
Published on Web 03/16/2001

TABLE 1. Sampling Rate in Chamber Testsa
sampling
period
min)
concn of 3-EP
in air (µg/m ),
mean ( SD
concn of 4-EP
in air (µg/m ),
mean ( SD
sampling rate
of 3-EP
(cm /min)
sampling rate
of 4-EP
(cm /min)
3
3
3
3
(
expt I
240
80
240
80
150 ( 7
300 ( 13
230 ( 5
320 ( 8
26.2
27.1
24.8
26.0
4
expt II
120 ( 3
160 ( 5
24.7
25.4
4
3
overall m ean ( 2 SD (cm /m in)
25.7 ( 1.8
a
SD, standard deviation.
storage was tested by keeping the vials at -20 °C for at least
evaporated. The crude product was soaked in silica and
purified by flash chromatography using hexane:EtOAc (4:1)
as eluent (yield 20%). H nuclear magnetic resonance (NMR)
3
weeks.
1
Analysis. The samples were extracted in glass vials
(
volume, 2 mL; height, 32 mm; diameter, 12 mm) with 1 mL
(200 MHz): δ 5.37 (d, J ) 11 Hz, 1H), 5.83 (d, J ) 17.8 Hz,
of toluene (Merck, Darmstadt, Germany) containing 10% (v/
v) pyridine (Pierce, Rockford, IL), shaken with a Vortex mixer,
and allowed to stand overnight in a refrigerator. A total of
1
(
chromatograph (HP 5890) equipped with a quadrupole mass-
selective detector (HP 5970 A). The separation was carried
out in an HP-INNOWax fused silica capillary column (30 m
1H), 6.71 (dd, J ) 11, 17.8 Hz, 1H), 7.23 (ddd, J ) 7.8, J )
o
4.8, J
p
) 0.4 Hz, 1H), 7.71 (ddd, J ) 7.8, 2.8, J
m
) 1.8, J
p
) 0.4
Hz, 1H), 8.49 (dd, J ) 1.8, 4.8 Hz, 1H), 8.62 (d, J ) 2 Hz, 1H).
1
3
µL of the eluate was injected with an automatic injector
HP 7673; Hewlett-Packard, Palo Alto, CA) into a gas
C NMR (50 MHz): δ 116.0, 123.2, 132.4, 132.9, 133.3, 148.2,
148.8.
The purity of the product was determined by GC-FID.
The result (77%) was obtained by comparing the intensity
of the FID response to 3-EP with that to 4-EP (known to be
95%) and by assuming equal molar responses for both
compounds.
Field Studies. Measurements were conducted in smoking
and nonsmoking environments to evaluate and verify the
utility of the method in field conditions. Parallel stationary
samples were collected for different sampling periods (4.5
h-5 d) in a home, in an office room, and in a restaurant. On
all occasions, the sampling was continuous without breaks.
Charcoal tube sampling (at 0.05 or 0.1 L/ min) was used as
a reference method for sampling periods of 2 d or less.
×
0.32 mm × 0.25 µm phase thickness). Helium was used as
a carrier gas at an inlet pressure of 45 kPa. The following
oven temperature program was used: 60 °C for 1 min,
increase to 120 °C at 6 °C/ min. The injector port was set to
a temperature of 225 °C, and a splitless injection mode was
used (valve time, 0.5 min).
The mass-selective detection was based on the electron
impact ionization mode (EI), and the ions (m/ z) 105, 79, 78,
and 51 were monitored. The area of the base peak (105) was
used for quantification. The retention time of 3-EP was 8.33
min, whereas 4-EP eluted at 8.54 min. No blank value was
detected for either 3-EP or 4-EP; therefore, the limits of
detection and quantification were determined using low-
level calibration samples.
Calibration standards were made by the phase equilibrium
method by adding a charcoal pad to a glass vial containing
1
and toluene. Subsequently, the calibration standards were
treated as samples. The stock and calibration solutions, the
latter containing both 3-EP and 4-EP, were prepared weekly.
The calibration standards were prepared daily. The external
standards method was applied: 3-EP was calibrated using
Results
Sam pling. The overall sampling rate of the passive test
3
sampler was 25.7 ( 1.8 cm / min at 22 °C and 48% RH. The
air velocity in the chamber was on average 0.1 m/ s (range
0
.09-0.2 m/ s). The overall sampling rate was calculated as
mL of calibration solution prepared in a mixture of pyridine
an arithmetic mean of the six arithmetic mean sampling
rates obtained in the chamber experiments (Table 1). The
concentrations of 3-EP and 4-EP measured by the reference
method (charcoal tube) are also shown in Table 1. No
adsorption of the test compound occurred on the plastic
surfaces of the sampler housing (data not shown).
3
-EP and 4-EP correspondingly using 4-EP.
GC using flame ionization detection (FID) presented an
No breakthrough occurred in the charcoal tubes during
the chamber tests at 320 µg/ m3 of 4-EP and 160 µg/ m of
3
alternative analytic system, but due to lack of specificity it
was not used for field samples. The equipment comprised
an HP 5890 gas chromatograph and a fused silica HP-
INNOWax column (30 m × 0.32 mm × 0.5 µm phase
thickness). The oven temperature program was as follows:
3
3
-EP (air volume 24 L) or during field sampling at 4.9 µg/ m
of 3-EP (air volume 143 L).
For the test samplers, no change in recovery was observed
after 2 d at room temperature. In the freezer, there was no
loss after 1 week of storage, but a slight loss in recovery was
seen after 2 weeks of storage. For the sample solutions, there
was no change in recovery after 2 weeks, whereas a slight
recovery loss (8%) was noted after 3 weeks of storage.
Analysis. Desorption efficiencies are shown in Table 2.
For the test samplers, the recoveries were 83% (3-EP) and
79% (4-EP) by the phase equilibrium method and 81% (3-
EP) and 76% (4-EP) by the spiking method. Compared with
the test samplers, the charcoal tubes yielded slightly higher
desorption efficiencies by both preparation methods (86%
and 89%).
5
0 °C for 1 min, increase to 140 °C at 3 °C/ min. Splitless
injection was used (valve time, 0.5 min), and the flow rate
of the carrier (helium) was 1.7 mL/ min. The retention time
of 3-EP was 25.4 min, and that of 4-EP was 25.9 min.
Synthesis of 3-EP. Triphenylmethyl phosphoniumbro-
mide (0.06 mol), sodium amide (0.07 mol), and 100 mL of
dry tetrahydrofuran were refluxed under an argon atmo-
sphere overnight. The orange-yellow reaction mixture was
cooled on an ice bath, and 3-pyridinecarboxaldehyde (0.04
mol) was added dropwise. The reaction mixture was allowed
to warm at room temperature and then was stirred for 4 h.
A total of 40 mL of diethyl ether was added, and the reaction
mixture was filtered. A 50-mL sample of water was added to
the filtered solution, which was then extracted with diethyl
ether. The water phase was saturated with NaCl. The organic
The mass spectra of 3-EP and 4-EP, derived using the EI
mode, are shown in Figure 1. The spectra of the two isomers
were similar in basic fragmentation. The ions m/ z 105 and
51 were equally abundant in the two isomers, but a difference
could be seen in the abundance of m/ z 78.
4
layer was dried with MgSO overnight, and the solvent was
VOL. 35, NO. 9, 2001 / ENVIRONMENTAL SCIENCE & TECHNOLOGY
9
1 8 1 9

limit of quantification (based on the monitoring and detection
TABLE 2. Validation Parameters Calculated for Diffusive Test
Samplers and Charcoal Tubes
of two ions) was 0.017 µg/ sample, corresponding to 0.46 µg/
3
m
calculated for an air sample of 37 L (24 h).
test concn
Overall precision values (RSDs), covering sampling and
3
-EP
4-EP
(µg/sample)
analysis, were calculated for the test samplers and charcoal
tubes on the basis of the chamber tests. These RSD values
are shown in Table 2. The precision of the tested method
varied only slightly (4.1-4.8%) between the different series.
The charcoal tube method yielded higher RSD values in
experiment I (4.7% and 5.8%) than in experiment II (2.1%
and 2.9%).
Detection Limit (µg/sample)
test sam pler
charcoal tube
0.01
0.01
0.01
0.01
Desorption Efficiency by Phase Equilibrium
Method (%), Mean ( SD (No. of Samples)
test sam pler
charcoal tube
83 ( 3 (10) 79 ( 3 (14) 3.1
89 ( 4 (8) 89 ( 4 (8)
3.1
Field Studies. The results of the field measurements are
shown in Table 3. Sampling in nonsmoking environments
Desorption Efficiency by Spiking Method
(
%), Mean ( SD (No. of Samples)
(
3
a home and an office room; n ) 6) for about 3 d yielded no
test sam pler
charcoal tube
81 ( 1 (5) 76 ( 4 (7)
86 ( 3 (6) 87 ( 4 (6)
3.1
3.1
3
-EP (<0.1 µg/ m ) or interfering substances, which produce
the specific ion used, at the retention time of 3-EP.
Precision (RSD, %)
test sam pler, 12 sam ples
test sam pler, 24 sam ples
4.5
0.7-2
The mean concentration of 3-EP in a smoker’s office room
3
4.1-4.8
0.9-3.9
2.8-3.7
3.6-7.2
ranged from 3.8 to 4.9 µg/ m (n ) 27), measured using both
charcoal tube, 12 sam ples 2.1-2.9
active and passive sampling methods and for different
sampling periods (4.5 h-5 d). The room temperature
averaged 24 °C, and the air humidity was 24% RH. The RSD
for parallel test sampler samples ranged from 2.6% to 7.8%
b
charcoal tube, 22 sam ples
2.2-5.8
a
SD, standard deviation. RSD, relative standard deviation. b Two
outliers excluded.
(
average 5.8%). The mean RSD for the charcoal tube method
was 5.1%. Although the ventilation rate was not determined,
3
the room (50 m ) was poorly ventilated judged by the slow
air flow in the room during sampling (<0.05 m/ s). In the
3
same room, a background 3-EP concentration of 1.3 µg/ m
was measured during a 24-h period when no cigarettes were
smoked. In a restaurant, concentrations ranging from 2.5 to
1
0.2 µg/ m3 (n ) 3) were measured during a 3-d sampling
period.
Discussion
3
-EP is a volatile organic compound (VOC) with a boiling
point of 162 °C (15). VOCs are generally defined as compounds
with vapor pressures in the range of 0.01-10 kPa. Airborne
compounds in this group occur in the vapor phase at room
temperature, whereas semivolatile organic compounds occur
in both particle and vapor phases. As a vapor-phase substance
of ETS, 3-EP is well-suited to monitoring using diffusive
sampling. Nicotine, although a semivolatile substance, is
known to occur almost exclusively in the vapor phase of ETS
and has also been monitored using diffusive sampling.
Unfortunately, its strong adsorption and re-emission can
cause discrepancies in the results. Compared with ethe-
nylpyridine, nicotine has been found to adsorb much more
strongly on various surfaces (16).
The present experiments indicate that the tested method
meets the criteria set for diffusive monitoring and also the
analytic requirements set for monitoring ETS (3). The
sampling method showed good precision, and the specificity
and sensitivity of the GC/ MS analysis were high enough for
reliable ETS measurements.
Com parison of 3-EP and 4-EP. The chamber test was
first carried out using 4-EP (experiment I), and the results
were confirmed in a subsequent test with a mixture of 3-EP
and 4-EP (experiment II). 4-EP was first used instead of 3-EP
because 3-EP is not commercially available, and a rather
high amount of a test chemical is needed to provide a dynamic
standard atmosphere. The physicochemical properties of
these isomers are reported to be similar (16). The charac-
teristics of 3-EP and 4-EP investigated in this study showed
close similarity. The responses of ion m/ z 105 on GC/ MS
and the slopes of the two isomers were very alike. However,
the chromatographic properties were not identical, thus
allowing separation of the isomers in the polar column used.
As no 4-EP is formed in tobacco smoke, it seems to be an
ideal candidate for an internal standard in 3-EP quantifica-
tion.
FIGURE 1. EI mass spectra of 3-EP (a) and 4-EP (b).
The calibration curves of 3-EP and 4-EP were linear in the
range of 0-10 µg/ sample. The slopes for the two isomers
were very similar, the difference being on average 1.2% with
both the test samplers and the charcoal tubes. The calibration
curves were somewhat steeper with the charcoal tube method
than with the tested sampling method (difference in slope
on average 7%). No average slope value was calculated
because the slope values were significantly changed during
the study due to servicing of the mass detector. A good
correlation coefficient (r > 0.999) was obtained for the
regression line. The detection limit was 0.01 µg/ sample. The
1
8 2 0
9
ENVIRONMENTAL SCIENCE & TECHNOLOGY / VOL. 35, NO. 9, 2001

TABLE 3. Concentrations of 3-EP in Field Measurements
measurement
method
concn of 3-EP,
mean ( SD (µg/m )
no. of
samples
sampling
period
no. of
cigarettes smoked
3
measurement site
restaurant
office (sm oker)
office (sm oker)
test sam pler
test sam pler
test sam pler
charcoal tube
test sam pler
charcoal tube
test sam pler
charcoal tube
test sam pler
charcoal tube
test sam pler
test sam pler
5.3 ( 4.2
3.8 ( 0.3
4.1 ( 0.2
4.9 ( 0.2
4.7 ( 0.3
4.9 ( 0.04
3.8 ( 0.1
3.9 ( 0.3
1.4 ( 0.1
1.3 ( 0.1
<0.1
3
3
4
4
4
4
4
4
3
3
3
3
3 d
5 d
2 d
2 d
4.5 h
4.5 h
8.5 h
8.5 h
24 h
24 h
3 d
not known
not known
60
office (sm oker)
7
12
0
office (sm oker)
office (nonsm oker)
hom e (nonsm oker)
0
0
<0.1
3 d
Evaluation of the Test Sam pler. The sampling rates of
ranging from <1.5 to 13.3 µg/ m3 have been measured in
3
3
-EP and 4-EP were very similar. The overall sampling rate
smoking areas (53-219 m ) with 21-103 smoked cigarettes/ 5
3
of 25.7 cm / min was well within the uptake range (20-48
h and air exchange rates of 3.7-21/ h (5). Although the number
of cigarettes smoked/ h was clearly higher than in our study,
poor ventilation explains the relatively high concentration
of 3-EP in the office room in our study.
3
cm / min) published for 3M organic vapor monitors (17). The
sampling rate obtained here is not inconsistent with the
3
uptake reported for styrene (28.9 cm / min), a compound
resembling ethenylpyridine in molecular structure (17). The
theoretical sampling rate was calculated according to Fick’s
We found no 3-EP in nonsmoking environments (office,
home), whereas low levels of 3-EP (mean 0.08 µg/ m ) in
nonsmoking homes have been reported by previous studies
(4, 10). However, in our study, there was a clearly detectable
background concentration of 3-EP in the office room of a
smoker. Therefore, it is useful to carry out separate mea-
surements in smoking areas during nonsmoking periods.
3
law, using the following parameters: diffusion coefficient
2
0
8
.076 cm / s (12); cross-sectional area/ diffusion length (A/ L)
3
.54 cm (18). The theoretical value obtained (38.9 cm / min)
was higher than the experimental value. This is consistent
with a previous study reporting 27-61% higher values for
theoretical sampling rates than for measured rates (18). Using
a recalculated value (5.86 cm) reported to be the “effective”
A/ L for 3M samplers (18), the calculated sampling rate 26.7
Acknowledgments
We thank Mr. Y. Peltonen for skillful technical assistance.
3
cm / min is in good agreement with the experimental rate.
Previous publications have presented passive samplers
based on impregnated glass fiber filters with sampling rates
of 23.7 (nicotine; 19), 31.5 (nicotine; 12), and 27.8 cm / min
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3
(
1) Schmeltz, I.; Wenger, A.; Hoffmann, D.; Tso, T. C. J. Agric. Food
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(
3-EP; 12). These sampling rates do not differ essentially from
those found in the present study. As the detection limits of
the previous methods appear to be adequate, the major
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house preparation of the sampler. The application is suitable
for routine surveys and also allows large-scale assessment of
individual ETS exposures. According to recent data (20),
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of individual ETS exposures.
Charcoal Tube Method. The charcoal tube method and
the passive sampling method were not identical in desorption
efficiency: a higher desorption efficiency was obtained for
the charcoal tube. The charcoal tube method can be used
as a reference method for the diffusive method. It is also
suitable for short-term monitoring of 3-EP when the detection
limit cannot be reached by the diffusive method.
Evaluation of the Field Results. The field measurements
with parallel sampling confirmed that the tested passive
method can be used with good precision (RSD 5.8%) for
monitoring low amounts of 3-EP (0.03-0.7 µg/ sample). The
difference in results between the charcoal tube method and
the passive sampler method was generally small. The largest
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sampling period (2 d). In all, a comparison of passive and
active field samples indicates that the actual sampling rate
of the office samples was slightly lower than the calculated
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1
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In this study, the average 3-EP concentration in the office
3
room during smoking was 4.3 µg/ m . This result is consistent
with previous studies. For instance, mean concentrations
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(
17) 3M Organic Vapor Monitor Sampling and Analysis Guide; 3M
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(
(
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Received for review September 4, 2000. Revised manuscript
received January 29, 2001. Accepted January 29, 2001.
(
20) Jenkins, R. A.; Counts, R. W. Environ. Health Perspect. 1999, 107
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Suppl. 2), 341.
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