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Idaho State Police
Forensic Laboratory Training Manual
Cocaine

1.0.0 HISTORY
Archaeological artifacts show that the use of coca was widely accepted in ancient
cultures of South American Indians. Paintings on pottery, ornaments depicting
pictures and symbols of the coca bush and its leaves, as well as sculptured wood
and metal objects dating as far back as 3000 BC on the coast of Ecuador indicate
the use of coca in both civil and religious rituals. Relatively recent studies of the
antiquity of the use and cultivation of coca indicate that the coca plant is native to
the eastern Andes Mountains. Until this day, the natives in the area continue the
custom of chewing coca.
A French chemist, Angelo Mariani, introduced Europe to the coca leaf by
importing tons of coca leaves and using an extract from them in many products
such as his Coca Wine. Cocaine, as obtained from the coca leaves, was first
discovered by Gaedecke in 1855 and rediscovered by Niemann in 1859, at which
time he gave the compound the name cocaine. The local anesthetic properties of
cocaine were demonstrated first by Wohler in 1860; however, it was not used
medically until 1864 as a topical anesthetic in the eye.
2.0.0 TAXONOMY
The French botanist J oseph de J ussieu made the first taxonomical reference to
coca
1
in 1750. He assigned the plants to the genus Erythroxylum. Later,
Lamarck, another French botanist, published six new species, including the
famous Erythroxylum coca Lamarck, in 1786. Today, the full taxonomical
classification is:
CATEGORY TAXON
Division (phylum) Spermatophyta
Class Dicotyledons (shrubs and trees)
Order Geraniales
Family Erythroxylaceae
Genus Erythroxylum
Species One Erythroxylum coca Lamarck

1
Note that other literature sources seem to credit Patrick Brown as the founder of the
genus Erythroxylum (in 1756).
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Variety of Species One Erythroxylum coca var. ipadu (Plowman)
Species Two Erythroxylum novogranatense (Morris)
Hieronymus
Variety of Species Two Erythroxylum novogranatense var. truxillense
(Rusby) Plowman

The spelling of the genus name Erythroxylum is considered a hybrid of Greek
and Latin. Linnaeus changed the spelling of the generic name to Erythroxylon, a
pure Latin form. Nevertheless, botanists consider Erythroxylum as the proper
spelling since it was derived in accordance with the rules of nomenclature.
Excluding the wild species of coca, all cultivated coca plants are currently
considered to belong to two distinct species of Erythroxylum including one
variety within each of the species. Specific areas of cultivation for each follows:
1. Erythroxylum Coca Lam. (or E. coca) -- This is the most important species
from which almost all-commercial cocaine is derived. This species is native to
the eastern Andes extending from Ecuador south to Bolivia. This was the first
type of cultivated coca to be collected and studied by Europeans and was referred
to as Huanuco or Bolivian coca after the main areas of cultivation. Like many
plants that have been cultivated for thousands for years, E. coca is now rarely
found in a truly wild state.
A particular variety of E. coca that warrants a brief mention since it has gained
some recent notoriety is the coca of the Amazon Valley that, until today,
continues to be cultivated on a very small scale by a number of Indian tribes. It
belongs to the species of E. coca, but differs from the typical Andean species and
is described as a variety, i.e., Erythroxylum coca, var. ipadu.
2. Erythroxylum novogranatense (Morris) Hieronymus -- This is the second
species
2
of cultivated coca and is commonly known as Colombian coca. This
species is cultivated throughout the mountains of Colombia. The species name
novogranatense refers to the geographical origin of the plant, Nueva Grenad,
the old colonial name for Colombia. There appears to be little cocaine production
based upon this species.
During the early 1900s, the Europeans created a cocaine industry on one of the
major islands of Indonesia (i.e., J ava). Dutch farmers adapted the coca species
Erythroxylum novogranatense to their soil and climate using modern
agricultural techniques. Commonly referred to as J ava coca, its total alkaloidal
content was found to be higher than Colombian coca; however, its true cocaine
content was found to be much lower than Colombian coca. This variation in
alkaloidal content is attributed to changes in climate, soil, and possibly other

2
Older scientific publications (prior to 1976) refer to the studies of Morris who described
this type of coca plant as a variety of E. coca. The German botanist Hieronymus was the
first to recognize it as a distinct species.
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environmental conditions. The J ava coca industry practically collapsed just prior
to World War II because of declining prices for coca leaves from other countries.
3. Erythroxylum novogranatense var. truxillense (Rusby) Plowman -- This is
one recognized and distinct variety within the species Erythroxylum
novogranatense. It is well known as Trujillo coca
3
since it is cultivated near the
city of Trujillo in northern Peru on the slopes of the Andes (as well as the nearby
desert coast of Peru). This variety of (Colombian) coca is particularly rich in
methyl salicylate (oil of wintergreen) and other flavoring compounds that are used
in the production of coca-flavored beverages. (Coca-Cola is a popular beverage
that incorporates decocainzed extracts of Trujillo coca in its preparation.)
3.0.0 MORPHOLOGICAL AND ECOLOGICAL CHARACTERISTICS
Bolivian (or Huanuco) coca leaves are usually large and thick, broadly elliptic in
shape, pointed at the apex, and dark green in color. The underside of the leaves
has two lines (parallel) to the midrib. These leaves are not considered
characteristic of this species since they are present to a degree in the other species
of coca. The leaves are usually deciduous after the current seasons growth. The
plant grows as a small to medium size bush usually planted in rows on large,
hillside plantations. This species thrives on moist, cool mountain climates.
Colombian coca can be distinguished from Bolivian coca by its smaller, narrower,
thinner, bright yellowish-green leaves, which are usually rounded at the apex.
Contrary to the Bolivian plant, the Colombian coca plant holds its leaves on the
branches after a seasons growth. This habit gives Colombian coca a larger,
bushier, and robust appearance. In addition, Colombian coca prefers the hotter,
drier climate and thrives at lower elevations. Dried Colombian leaves also have a
more noticeable odor of methyl salicylate than Bolivian leaves.
Trujillo coca is morphologically similar to Colombian coca. Trujillo coca has
smaller, narrower, and slightly thicker leaves that are darker green at maturity.
Refer to Table 1 for additional characteristics for both varieties of Erythroxylum
coca and Erythroxylum novogranatense.
The genus Erythroxylum is the only natural source of the alkaloid cocaine and
related compounds. Almost all commercial coca leaves and cocaine are derived
from the species Erythroxylum coca Lam.; Erythroxylum novogranatense
(Morris) Hieronymus, because of its quick adaptability to different climates, is
most likely the dominant species that is illegally cultivated for the illicit drug
trade.


SPECIES OF COCA AND THEIR CHARACTERISTICS

3
Sometime referred to as Truxillo or Peruvian coca.
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Genus,
Species
ERYTHROXYLUM COCA ERYTHROXYLUM NOVOGRANATENSE
Varieties coca ipadu novogranatense truxillense
Origin montaa region of
eastern Andes;
Ecuador, Peru, and
Bolivia, mainly
between 500 -
1500m
western Amazon of
Brazil, Colombia,
and Peru
Colombia,
Venezuela and
Central America,
Sierra Nevada de
Santa Marta and
rugged mountains
of Cauca and Hucha
desert coast of Peru and in
adjacent arid valley of the Rio
Maranon, Truxillo region on
the north coast of Peru
Description of
plant and/or
leaves
pointed leaves,
parallel longitudinal
lines on leaf
undersides
tall, spindly shrub
with long weak
branches and
relatively large
elliptical leaves
which are blunt or
rounded at the
apex; flowers have
a shorter flusher
pedicel and a
markedly
denticulate staminal
tube only short
styled morphs
large bush plant
with small, narrow,
thin, and bright
yellow-green leaves
which are rounded
up to 3m tall with multiple
trunks reaching 4 cm in
diameter; branches are dense
erect and spread leaves
narrowly elliptical to oblong-
lanceolate 20-65 mm long;
medium to light green above
pale green to glossy green
beneath and midrib fluted
with slight medial ridge
Odor grassy or haylike wintergreen wintergreen
Climate favorable tropical
environment with
high rainfall,
moderate
temperatures and
well drained mineral
rich soils; moist
cool
does not like
intense heat or
poorly drained
soils, short-lived
hot, seasonably dry
habitat resistant to
drought
has been cultivated in arid,
desert climate and wet
montaa habitat of Colombia;
even more tolerant to drought;
prefers desert conditions
Adaptability very little very little will survive under a wide range of environmental
conditions; Resistant to drought
Means of
propagation
seeds cuttings seeds seeds
Commercial
uses
most important
commercial species
providing by far the
largest supply of
coca leaves and
cocaine; 95% of
Perus crop
used for chewing illegal in Colombia;
grown illegally for
coca chewing and
cocaine production
principal variety used in
beverage industry owing to its
high content of essential oils
and flavors-several hundred
tons exported to N.Y. for
preparation of extracts, used
in making Coca-Cola
% Alkaloids 0.5 - 1.0 unknown 1.0 - 2.5 1.0 - 2.5
% Cocaine of
Total alkaloid
content
70 - 90 very little 20 - 50 20 - 50
Table 1
Note that the genus Erythroxylum also includes a number of wild species of coca
(reportedly about 200), most of which contain minimal quantities of cocaine and
some of which contain no detectable quantities of cocaine.
4.4.0 CHEMISTRY
4.1.0 Coca leaves contain three basic groups of alkaloids, most of which are present in
the form of esters. The content of these alkaloids will vary depending on the
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particular species of coca used, age of the plant, where it is grown, how it was
cultivated, and when the leaves were picked. A higher total alkaloid content but
with a smaller cocaine content reportedly occurs when the leaves are picked at an
early stage of development; the reverse occurs when the leaves are picked when
fully developed. Another important factor affecting the variation of an alkaloidal
extract is the manner in which the alkaloids were refined from the leaves. Listed
in specific groups are some of the popular alkaloids found in coca leaves:
Derivatives of Ecgonine
a. l-Cocaine (Methylbenzoylecgonine)
b. cis- and/or trans-Cinnamoylcocaine
4
(cis- and/or trans-
Methylcinnamoylecgonine)
c. and/or -Truxillenes (Methyl and/or -truxilloylecgonine or
and/or -cocaine)
d. Methylecgonine (Ecgonine methyl ester)
e. Methylecgonidine
Derivatives of Tropine (and -Tropine)
5

a. Tropococaine (Benzoyl--tropeine or -tropine benzoate)
Derivatives of Hygrine
a. Cuscohygrine
b. Hygroline
c. Hygrine
In addition to l-cocaine, cinnamoylcocaine and the truxillenes are considered the
most important coca alkaloids for pharmaceutical use. Hygrine and its related
alkaloids are reported to be present in significantly large quantities in both
varieties of E. novogranatense (i.e., Colombian and Trujillo coca). Hygrine is a
tertiary aminoketone, hygroline is the secondary alcohol related to hygrine, and
cuscohygrine is a diaminoketone containing two N-methyl groups.
The pharmaceutical industry produces pure cocaine semi-synthetically. The
ecgonine conversion process employed eliminates the need to separate cocaine
from related ecgonine alkaloids and produces a much greater yield of cocaine.
Briefly, the procedure involves:
1. Extracting the coca alkaloids previously mentioned from dried coca leaves
and isolating the mixture of ecgonine alkaloids.
2. Converting the group of alkaloids to ecgonine via hydrolysis with dilute
hydrochloric acid:

4
Cinnamylcocaine and cinnamoylcocaine have been used interchangeably in the
literature.
5
Esters of tripine are called tropeines. is the Greek symbol for pseudo.
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Cocaine l-EcgonineHCl +MeOH +Benzoic Acid
Cinnamoylcocaine l-EcgonineHCl +MeOH +Cinnamic Acid
Truxillene l-EcgonineHCl +MeOH +Truxillic Acid
(Tropococaine is excluded since it would hydrolyze to pseudotropin and not
ecgonine.)
3. Isolating and purifying the ecgonine and converting it to its free base.
4. Converting the ecgonine to l-cocaine by benzoylating the ecgonine with
benzoic anhydride to benzoylecgonine followed by methylation with methyl
iodide.
An alternate commercial process converts the isolated alkaloids to ecgonine
methyl ester (or methyl ecgonine) by hydrolyzing the alkaloids in methyl alcohol-
hydrogen chloride. The ester is isolated and benzoylated directly to l-cocaine.
Either industrial process provides the following approximate yield:
Dried Coca Leaves Cocaine HCl
145 kgs 1 kg

In clandestine cocaine laboratories in South America, the crude cocaine process
also seeks to eliminate most of the coca alkaloids except cocaine. The cured
process is an extensive operation. It generally consists of:
1. a pasta laboratory where all the coca alkaloids are extracted from a batch of
coca leaves and converted to a water soluble (sulfate salt) pasty material called
pasta or sulfate or coca paste;
2. a base laboratory (optional) where the coca paste is treated to remove most
undesirable substances and to provide cocaine base;
3. a crystal laboratory where the cocaine base is converted to cocaine
hydrochloride.
Very often, however, the illicit laboratory cook abbreviates or overlooks a
critical step of the process and causes other alkaloids, impurities, and cocaine
decomposition products to become part of the final product. The approximate
yield from this illicit process can be summarized as follows:
Dried Coca Leaves Coca Paste Coca Base Cocaine HCl
240 kgs 1.4 kg 0.9 kg 1 kg
If chemical conditions become too acidic or basic, cocaine can degrade, as
illustrated in Figures 1 and 2, and the degradation products may recombine to
form new products. For example, benzoic acid and methyl alcohol will combine
to yield methyl benzoate, a sweet smelling, volatile liquid. Similarly,
cinnamoylcocaine and truxilline can decompose, producing products that can
recombine to form new products, such as
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CHEMICAL STRUCTURE OF COCAINE


Figure 1
The cocaine molecule is made up of three building blocks. If chemical conditions
become too acidic or too basic the cocaine molecule readily breaks down into
these three pieces.
DECOMPOSITION OF COCAINE
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Figure 2
methyl cinnamate and methyl truxillate. Contrary to earlier studies,
benzoylecgonine, ecgonine, pseudococaine, and cocaethylene are believed to be
produced during the refining process and are not naturally occurring in the coca
plant.
4.2.0 SYNTHESIS OF COCAINE
In 1923, using 2-carbomethoxytropanone as an intermediate, Willstatter prepared
() cocaine along with pseudococaine. At least four synthetic methods have been
reported for the synthesis of 2-carbomethoxytropanone. These syntheses range
from the difficult cyclization of 1-methyl-2,5-dicarboethoxypyrrolidine, to the
simplest, at least in principle, reaction of succindialdehyde, methylamine, and
-ketoglutaric acid to yield the target compound 2-carbomethoxytropanone.
Willstatters synthesis in 1923 involved the formation of the dipotassium salt of
monomethyl--ketoglutarate, which was then reacted with methylamine and
succinaldehyde to obtain the 2-carbomethoxytropanone. The methyl esters of ()
pseudoecgonine and () ecgonine are formed by the reduction of 2-
carbomethoxytropanone using a sodium-mercury amalgam; fractional
crystallization can be used to separate the two ecgonine methyl esters. The final
step in the reaction scheme is between the () ecgonine methyl ester and benzoyl
chloride to yield () cocaine.
4.3.0 STEREOCHEMISTRY
During the period 1898 to 1923, Willstatter and his collaborators were able to
obtain pseudococaine by transformation of (-) cocaine and by total synthesis. At
the time of this early work, stereochemistry was in its infancy. Based on chemical
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studies regarding ecgonine and tropine, Willstatter incorrectly assigned
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the C-3 pseudococaine a structure that has both the C-2 carbomethoxy group and
benzoyloxy group axial. Instead, later studies show that pseudococaine has both
the carbomethoxy group at C-2 and the benzoyloxy group at C-3 in equatorial
position.


Two other cocaines, allococaine and allopseudococaine, were synthesized and
ds.
oxy
e
5.0.0 SAMPLE ANALYSIS
ication of cocaine through acceptable analytical methods

UV
in the analysis of cocaine samples results from the
e,
cted at the ISP Laboratory
will utilize capillary GC/MS for the identification of cocaine. The high resolution
COCAINE -COCAINE ALLOCOCAINE -ALLOCOCAINE
characterized by Findley in the 1950s. Again, problems arose with the
nomenclature used in representing the stereochemistry of these compoun
Using Findleys assignments, the carbomethoxy group at C-2 and the benzoyl
group at C-3 were equatorial-axial, respectively, for allococaine and axial-axial
for allopseudococaine. More recent nomenclature places allococaine and cocain
with the same stereochemistry at the C-2 position, that is, the carbomethoxy group
is axial. Pseudococaine and allopseudococaine have the same spatial relationship
at the C-2 position; viz., the carbomethoxy group is equatorial. Thus, the cocaine
molecule has four asymmetrical centers which give rise to eight stereoisomers
arranged as four diastereoisomeric pairs -- d,l-cocaine, d,l-pseudococaine, d,l-
allococaine, and d,l-allopseudococaine.
The detection and identif
generally presents no problems; however, in most instances, pure cocaine is not
presented for analysis. Even when diluents and adulterants have not been added
to the cocaine, the sample usually contains impurities resulting from the original
isolation of the alkaloid. For example, cis- and trans-cinnamoylcocaine are
usually present in illicit cocaine samples. Benzoylecgonine may be present in
many cocaine samples and should be eliminated by a basic extraction since its
is similar to that of cocaine. Note that the detection of benzoyl ecgonine (as well
as ecgonine) by UV, GLC, or TLC can be difficult because of the polar nature of
the acid group at C-2.
A second complication
presence of adulterants. Many of the caines, such as benzocaine, lidocain
procaine, and tetracaine, are commonly encountered.
From a practical standpoint most of the analyses condu
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6.0.0
1. Prepare a sample of crack cocaine from cocaine hydrochloride.
frared
, separate
the majority of cocaine.
equatorial/axial
oup for each
re
ted to cocaine?
n of the molecule the 82,
loride.
8.0.0 REFERENCES
1. Smith RM. The Mass Spectrum of Cocaine, J ournal of Forensic Science
capabilities of capillary GC will easily separate cocaine from most common
adulterants and diluents.
EXERCISES
2. Obtain a sample of procaine base mixed with cocaine base. Via In
analysis, prove that the sample contains cocaine base. (In other words
the cocaine from the procaine without converting either to its salt.
7.0.0 DISCUSSION QUESTIONS
1. Is cocaine a stimulant or a narcotic?
2. Name the two countries that produce
3. Name one country prominent in the smuggling of cocaine.
4. Draw the structure of the four cocaine isomers and show the
relationship for the carbomethoxy group and the benzoyloxy gr
isomer.
5. Draw the structures of procaine, lidocaine, tetracaine, and benzocaine. A
they rela
6. Describe the process of preparing crack cocaine.
7. Draw the cocaine molecule and indicate what portio
182, and 272 ions arise from.
8. Describe the process by which Colombian chemists convert the crude cocaine
base to refined cocaine hydroch


,
7 42(3): 475-480, 199
2. Roberson, J .C. Legal and Analytical Aspects of Cocaine, Microgram, Vol
XI, No.3, Mar. 1978, p
.
p. 45-46
3. Allen, A.C., Cooper, D. A., et al The Cocaine Diastereoisomers, J ournal of
Forensic Science, Vol.26, No.1, J an. 1981, pp.12-26
4. Gelsomino, R., and Raney, J .K., NMR Identification of Cocaine,
Microgram, Vol. XII, Dec. 1979, pp. 222-225.
5. Sorgen, G.J ., Identification of d- and l- Cocaine, Microgram, Vol.
Aug. 1983, pp. 126-131.
XVI,
nsic Sciences
6. Siegel, J .A., Cormier, R. A., The Preparation of d-Pseudococaine from l-
Cocaine, J ournal of Fore , Vol. 25, No. 2, Apr. 1980, pp. 357-365.
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Issuing Authority: Quality Manager
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7. Hufsey, J ., and Cooper, D., Synthetic Cocaines, Microgram, Vol. XII, D
1979, pp. 231-239.
ec.
8. Kerr, K. A Simple Procedure for Separating Cocaine Base From Procaine
Base, Microgram, Vol. XXIII, No. 5, May 1990, pp. 93-95.
9. Galka, K.l., Separation of Cocaine from Benzocaine, Microgram, Vol
XXIII, May 1990, pp. 97-98.
10. Clark, C.C., and Allen, A.C., Quantitative Separation of Cocaine-Lidoca
Mixtures,
ine
Microgram, Vol. VII, 1974, pp. 96 - 99.
rensic Sciences
11. Lebelle, M., Callahan, S., etal, Comparison of Illicit Cocaine by
Determination of Minor Components, J ournal of Fo , Vol. 36, No.
Using Capillary Gas Chromatography., J ournal of
4, J ul. 1991, pp. 1102-1120.
12. Casale, J . F., Waggoner, R. W., A Chromatographic Impurity Signature
Profile Analysis for Cocaine
Forensic Sciences, Vol. 36, No.5, Sept. 1991, pp.1312-1330.
13. Casale, J . F., Methyl Esters of Ecgonine: Injection-Port Produced Artifacts
from Cocaine Base (Crack) Exhibits, J ournal of Forensic Sciences, Vol. 37, No.
5, Sept. 1992, pp. 1295-1310.
14. Ard, E., Problems With IR Spectra of Cocaine Hydrochloride Case
Samples, Microgram, Vol. XXI, No. 2, Feb. 1988, pp. 29-33.
15. Santos, N. A., Moisture Absorption Problems Associated With The
Packaging of Cocaine Hydrochloride, Microgram, Vol. XXV, No. 2, Feb. 1992,
pp. 28-32.
16. Kiser, W. O., Analysis for Cocaine Base, Microgram, Vol. XXI, No. 2, Feb.
1988, p. 28

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17. Scott, L.J ., Specific Field Test For Cocaine, Microgram, Vol. VI, 1973, pp.
179-181.
18. Fasanello, J ., Higgins, P., Modified Scott Test For Cocaine Base Or Cocaine
Hydrochloride, Microgram, Vol. XXIII, No. 4, Apr. 1990, pp. 137-138.
rior to revision 3 modules in the training manual did not have individual history
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9.0.0 HISTORY
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n # Issue or review date History Author or Reviewer

.0.0, d me reerence 3 7/08/11 Added 9 ropped so f s
David Sincerbeaux


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