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4 Gamma -Hydroxybutyric Acid: g -Hydroxybutyric Acid

4 Gamma -Hydroxybutyric Acid: g -Hydroxybutyric Acid

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17.5



Ketamine



227



Fig. 17.3 Common forms of

gamma-hydroxybutyric acid

(GHB). The popular children’s

toy “Aqua-Dots” was recalled

and cancelled when it was

discovered that 1,4-butanediol

(which metabolizes to GHB) was

used in the bead manufacturing

process.



It is a neuroprotective nutrient whose principal activity is to guard against neuron degradation. At recreational doses of

500–3,000 mg, it is a central nervous system depressant that induces euphoria.

In recent years, GHB has emerged as a significant drug of abuse throughout the United States. It is typically an odorless,

colorless liquid, and is also available as a tablet (Fig. 17.3). The production of GHB in clandestine laboratories is a relatively

simple process and local operators usually handle its distribution. It is usually mixed with alcohol for abuse and has become

popular among teens and young adults at dance clubs, bars, gyms, and “raves.” Also, it is routinely used by bodybuilders for

its anabolic effects. In low doses, GHB causes drowsiness, dizziness, nausea, and visual disturbances. In high doses, unconsciousness, seizures, severe respiratory depression, and coma can occur. GHB overdose usually requires emergency room

treatment, including intensive care for respiratory depression and coma.

GHB gained notoriety as a “date-rape” drug and has been implicated in a number of drug-related sexual assaults. It is very

difficult to establish the involvement of GHB in such cases because its detection in bodily fluids is virtually precluded by the

fact that it is quickly eliminated from the body (within 24 h). Also, the rapid onset of CNS depressant effects commonly

leaves the victim with little memory of the details of the attack. Thus, a majority of cases are unreported, and, those that are

reported, are often unsubstantiated.

Street names of GHB include lquid ecstasy, scoop, easy lay, Georgia home boy, grievous bodily harm, liquid X, and goop.



17.5



Ketamine



Ketamine (ketamine hydrochloride) is primarily used as a tranquilizer in veterinary medicine, but it also has legitimate uses in

humans as well. It is often part of the treatment for pediatric burns and has various applications in dentistry and experimental

psychotherapy. The hydrochloride salt is marketed as Ketalar for medicinal use and Ketaset to veterinarians.

Ketamine is a dissociative anesthetic that produces hallucinogenic effects similar to PCP.

O



CI



NH

CH3

Ketamine HCI

C13H16CINO

M.W. 237.7 g/mol



Structure 17.7



It blocks signals to the conscious mind from various parts of the brain and severely impairs all senses, especially sight,

balance, and sense of time. Ketamine is characterized as a “date-rape drug” and is typically abused as a “club drug” distributed at raves and parties.



228



17



Miscellaneous Controlled Substances



Fig. 17.4 Ketamine injections and tablets. Ketamine is a

powerful dissociative anesthetic that induces (among other

effects) amnesia. It is considered a “date rape” drug because

it is has no odor or taste and can be easily added to drinks

without detection.



Ketamine is a schedule III controlled substance that is generally available as a clear liquid or white (or off-white) powder. The

powder can be snorted or compressed into tablets for oral administration (Fig. 17.4). The powder or liquid can also be added to

tobacco or marijuana and smoked. Ketamine is most effective when injected either IM (intramuscular) or IV (intravenous). The

powder form of ketamine is strikingly similar to cocaine and crystal methamphetamine and careful examination is required to avoid

incorrect identification. Ketamine is sometimes sold as counterfeit MDMA (ecstasy) or as a mixture with other drugs such as

ephedrine and caffeine. Most illicit ketamine comes from diverted legitimate suppliers or theft, primarily from veterinary clinics.

Ketamine produces effects similar to PCP (phencyclidine or “Angel Dust”), including numbness, loss of coordination,

sense of invulnerability, muscle rigidity, aggressive or violent behavior, slurred or blocked speech, exaggerated sense of

strength, and a blank stare. Ketamine causes depression of respiratory functions, but, unlike most hallucinogens, the central nervous system is generally unaffected and cardiovascular function is maintained. The anesthetic properties of ketamine can relieve tension and anxiety, but inadvertent self-injury to the user is cause for great concern.

Ketamine produces a general state of dissociation that can render the user comatose. It is typically characterized by a

sense of detachment from one’s body and the external world. The effects usually last an hour but can easily extend to 4–6 h.

The effects of chronic use may take as long as 2 years to subside and flashbacks are common up to 1 year after use. Low

doses (25–100 mg) produce psychedelic effects quickly, while large doses (above 200 mg) can cause convulsions resulting

in oxygen deprivation in the brain and muscles. Long-term effects include tolerance and a high potential for both physical

and psychological dependence.

Some street names for ketamine include K, Ket, special K, vitamin K, vit K, kit kat, Keller, Kelly’s day, green, blind squid,

cat valium, purple, special la coke, super acid, and super C. Slang for the “ketamine high” include “K-hole,” “K-land,” “baby

food,” and “god.”



17.6



Lysergic Acid Diethylamide



Lysergic acid diethylamide (LSD) is a powerful psychedelic hallucinogen classified as a schedule I controlled substance.



O

CH3

N



N

H



NH

LSD

(Lysergic Acid Diethylamide)

C20H25N3O

M.W. 323.4 g/mol



Structure 17.8



17.7 Analytical Methods



229



Fig. 17.5 Common forms of LSD for distribution. Contrary to popular belief, LSD is not considered addictive because it does not produce a

compulsive need for the drug. Users can develop tolerance however, requiring progressively higher doses of the drug in order to achieve the

desired affects.



Fig. 17.6 Ergot-infected rye.

Note the dark sclerotia extending

from the base. Thousands of

pounds of ergot sclerotia are

harvested each year from

Midwestern rye farms and used

in the production of various

prescription drugs.



It is a naturally occurring alkaloid found in ergot, a fungus (Claviceps purpurea) that infects the grains of rye and

related grasses. It is also synthetically produced from the schedule III precursors lysergic acid and lysergic acid amide, and

the List I chemicals ergotamine and ergonovine. A particularly dangerous synthetic form of LSD, known as LSD-25, is

derived from natural psychoactive alkaloids found in ergot. It is roughly 4,000 times stronger than mescaline and is one of

the most powerful psychoactive drugs in existence.

LSD is available in tablet, capsule, and liquid form. It is commonly blotted on decorative paper and cut into individual

squares that are sold and ingested orally (Fig. 17.5). Naturally occurring LSD (ergine) is also found in the seeds of two species of Mexican morning glory vines that are ingested by Native Americans as part of cultural medicinal and religious

rituals.

Ergot forms a dark, compact, fungal mass called a sclerotium where the grain would normally develop. These pellet-like

structures can be seen in an infected grain spike typically extending out from the bracts (glumes) (Fig. 17.6). The sclerotia

are the source of potent alkaloids found in Claviceps purpurea. In late spring, when rye plants are in bloom, the sclerotia

from the previous year’s crop produce stalked ascocarps resembling microscopic fungal fruiting bodies. The head of each

ascocarp contains several embedded perithecia, which contain numerous saclike asci, each with eight ascospores. The

ascospores infect the young, developing grains (ovaries) of rye plants, eventually replacing them with purplish-black sclerotia. Because it produces ascospores within saclike asci, Claviceps is placed in the fungal class Ascomycetes.

The study of ergot fungus has led to several important medical discoveries. In 1935, the alkaloid ergonovine, which causes

strong muscular contractions, was isolated from ergot and used to induce labor and control hemorrhaging. Also, the alkaloid

ergotamine has been used extensively to relieve migraine headaches by causing constriction of blood vessels.



17.7



Analytical Methods



17.7.1 Visual Identification

The visual identification of this group of controlled substances is difficult because most samples are commonly submitted to

forensic laboratories in many shapes, sizes, and physical forms (Fig. 17.7).



230



17



Miscellaneous Controlled Substances



Fig. 17.7 Common forms of controlled substances submitted to forensic laboratories for analysis. (a) LSD tablets (top left and center) and

designer paper blotted with liquid LSD (top right). Fentanyl lollypops (middle), (b) barbiturate tablets (bottom left) and capsules (bottom right),

and gamma-hydroxybutyric acid (bottom center).



17.7.2 Chemical Screening Tests

The comprehensive flowchart illustrates the results of color-screening tests commonly performed on suspected samples of

LSD and barbiturates. The chart also contains tests used on a variety of other controlled substances. Ketamine is indicated

by the formation of blue color using the neutral tertiary amine test. GHB is indicated using one of the following tests: cromic

acid test (5 M H2SO4 saturated with cromic acid) produces a blood red-brown color, ferric chloride test (distilled water saturated with Iron(III) chloride-FeCl3) produces a rust brown-red color, and cobalt nitrate test (1% cobalt(II) nitrate-Co(NO3)2)

produces a violet color (Fig. 17.8).



17.7.3 Gas-Chromatography Mass

Spectrometry

GCMS is typically used to identify the controlled substances in this chapter. Sample preparation is performed using acid–base,

base, and methanol extraction. For direct extraction of suspected LSD, the paper tabs, gel tabs, or tablets are cut into small

pieces and added to the extracting solvent. The mixture is vortexed and the resulting solution is transferred (without debris) into

an autosampler vial for GCMS. Typical GCMS results for a variety of controlled substances are shown below (Fig. 17.9a–h).



17.7 Analytical Methods



Fig. 17.8 Results of presumptive color tests used to screen miscellaneous controlled substances.



231



232



Fig. 17.9 Representative GCMS spectra of miscellaneous controlled substances.



17



Miscellaneous Controlled Substances



17.7 Analytical Methods



Fig. 17.9 (continued)



233



234



Fig. 17.9 (continued)



17



Miscellaneous Controlled Substances



Fig. 17.9 (continued)



236



Fig. 17.9 (continued)



17



Miscellaneous Controlled Substances



Suggested Reading



17.8

1.

2.

3.

4.

5.

6.

7.

8.

9.

10.

11.

12.

13.

14.

15.

16.

17.

18.

19.

20.



237



Questions



Draw the structure of barbituric acid and label position five.

List three effects of barbiturate use.

Please explain to the jury how barbiturates are usually classified.

Give two examples of barbiturate use in veterinary medicine.

Cite a reason why barbiturates will eventually be replaced by benzodiazepines.

Draw the structure of fentanyl and list two legitimate uses.

What is the most potent derivative of fentanyl?

Why is fentanyl potentially hazardous in forensic investigators?

Discuss the significance of a-methylfentanyl (AMF).

Draw the structure of gamma-hydroxybutyric acid (GHB).

Briefly explain to the jury the physiological role of GHB in the body.

List three effects of GHB use.

GHB is classified as a “date-rape” drug. Explain to the jury why most sexual assault cases are unreported.

Draw the structure of ketamine and explain the term “dissociative anesthetic.”

What is the most effective method to administer ketamine?

What is a natural source for LSD?

What is the most potent derivative of LSD and how is it commonly sold in the illicit drug market?

Outline a series of color-screening tests that would indicate the presence of LSD and barbiturates.

What color-screening test could be used on GHB?

Identify the molecular ion peak (M+) and the base peak in the MS spectrum of the following:

(a) Ketamine

(b) Demerol

(c) GHB

(d) Barbital

(e) LSD

(f) Fentanyl



Suggested Reading

Andera, K. M.; Evans, H. K.; Wojcik, C. M. Microchemical Identification of Gamma Hydroxy-Butyrate (GHB). J. Forensic Sci. 2000, 45,

665–668.

ChemNet. Global Chemical Network. http://us.chemnet.com/ (accessed September 2009).

Hambling, D. Pentagon’s New Drug Weapons. http://www.wired.com/dangerroom/2007/08/drugs-r-us/?commenter (accessed September 2009).

Henderson, G. et. al. Designer Drugs: The California Experience. In Clandestinely Produced Drugs, Analogues, and Precursors. U.S. Department

of Justice, Drug Enforcement Administration: Washington, DC, 1989.

Lewis, W. H.; Elvin-Lewis, M. P. F. Medical Botany. John Wiley & Sons: New York, 1977.

Martin, W. R. The Nature of Opiate and LSD Receptors: Structural Activity Relationship Implications. In Quantitative Structure Activity

Relationships of Analgesics, Narcotic Antagonists, and Hallucinogens; Barnett, G.; Trsic, M.; Willette, R. E., Eds.; National Institute of Drug

Abuse: Rockville, MD, 1994, pp. 60–69.

National Drug Intelligence Center. Ketamine. http://www.usdoj.gov/ndic/pubs4/4769/index.htm (accessed September 2009).

Palenik, S. Particle Atlas of Illicit Drugs; Walter McCrone Associates: Chicago, 1974.

Shafer, J. Designer Drugs. Science. 1990, 85, 60–67.

United Nations. Recommended Methods for Testing Barbiturate Derivatives Under International Control. Manual for Use by National Narcotics

Laboratories; ST/NAR/18; United Nations: New York, 1989.

United Nations. Recommended Methods for Testing LSD. Manual for Use by National Narcotics Laboratories; ST/NAR/17; United Nations: New

York, 1989.

U. S. Department of Justice Drug Enforcement Administration. Symposium on Fentanyl in DEA Southwest Labs in California, USA. U. S. Drug

Enforcement Administration: Washington, DC, 2007.

U. S. Drug Enforcement Administration. Barbiturates. http://www.usdoj.gov/dea/concern/barbiturates.html (accessed September 2009).

U. S. Drug Enforcement Administration. Drug Scheduling. http://justice.gov/dea/pubs/scheduling.html (accessed September 2009).

U.S Drug Enforcement Administration. Fentanyl. http://www.usdoj.gov/dea/concern/fentanyl.html (accessed September 2009).

U. S. Drug Enforcement Administration. GHB. http://www.usdoj.gov/dea/concern/ghb_factsheet.html (accessed September 2009).

U. S. Drug Enforcement Administration. LSD. http://www.justice.gov/dea/concern/lsd.html (accessed September 2009).



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