This presentation is about natural products

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2. Osama Khawaja
University of aj&k
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3. Contents
 Introduction
 Types of Tertiary Amines
 Natural Tertiary Amines
 Synthetic Tertiary Amines
 Analytical Methods
 Visual Inspections
 Chemical screening of Tertiary Amines
 Confirmatory Examination
• Fourier Transform Infrared Spectroscopy
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4. Introduction
 Amines are organic derivatives of ammonia (NH3) produced by
replacing the hydrogen atoms (H) with various alkyl groups (R).
 Tertiary amines contain nitrogen bound to three alkyl groups.
 There are no limitations on the alkyl substitutions: they may be identical
or different, straight chains, branched chains, or cyclic, including
aromatic rings.
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Ammonia tertiary Amine

5. Natural Tertiary Amines
Cocaine
Opiates
• Morphine
• Codeine
• Heroin
Synthetic Tertiary Amines
Phenylcyclohexylpiperidine
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6. Natural Tertiary Amines
Cocaine
 Cocaine is a potent stimulant that is highly addictive. In pure form, it is either a
powdered hydrogen-chloride salt or a rockcrystal free base (crack).
 The acid form (salt) is typically either snorted or dissolved in water and injected, while
the base form (free base) is usually vaporized and inhale.
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Cocaine

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• The term “crack cocaine” originates from the characteristic “crackling” sound that is heard when the free-base
form is heated.
• Cocaine is a Schedule II controlled substance that has a high potential for addiction.
• Cocaine is known by the street names blow, nose candy, snowball, tornado, and wicky sticks.
• Coca typically thrives in warm, moist, frost-free valleys between 1,500 and 6,000 m above sea level. The plant can
grow to heights exceeding 8 ft. with leaves rich in vitamins, proteins, calcium, iron, and fiber. The cocaine content in
leaves range from 0.1 to 0.9% . Diurnal fluctuations of cocaine within the leaf occur in 24-h cycles.
Cocaine is naturally occurring stimulant
found in the leaves of coca plant

8. The Short And Long Term Effects of Cocaine
use
The short- and long-term effects of cocaine use are usually related to the
inhibition of dopamine reabsorption by nerve cells in the brain. Elevated levels of
dopamine produce a variety of physical and psychological effects including
increased body temperature, heart rate and blood pressure, constriction of blood
vessels, dilated pupils, tremors, muscle twitches, vertigo, paranoia, and anxiety.
Excessive use can cause irritability, erratic or violent behavior, periods of
paranoid psychosis including auditory hallucinations, seizures resulting in
respiratory failure, and death from cardiac arrest.
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9. History of Cocaine
 Cocaine is arguably the oldest known drug of abuse, with a documented history dating back thousands of years. It is extracted
from the coca plant, a member of the order Geraniales and the family Erythroxylaceae . There are four genera with an
estimated 200 species in Erythroxylaceae.
 Early botanists believed that all coca plants belonged to a single species. However, subsequent research revealed two species
of domesticated coca: Erythroxylum coca Lam. and Erythroxylum novogranatense. The two species have two varieties
each: Erythroxylum coca Lam . var. coca and var. Lpuda Plowman and Erythroxylum novogranatense var.
novogranatense , and var. truxillense Plowman .
 Coca is grown in South America, Africa, Ceylon, Taiwan, and Indonesia. But it is most commonly associated with its center
of origin, the South-American Montana zone of the eastern Andes below 2,000 m.
 Huánuco, or Bolivian coca ( E. coca var. coca ), is an ancestral variety that grows in the moist tropical forests of the eastern
Andes of Peru and Bolivia.
 Amazon Coca ( E. coca var. lpuda ) is cultivated in the lowland areas of the Amazon.
 Trujillo coca ( E. novogranatense var. truxillense ) is a hardy, drought-resistant variety found in the river valleys of coastal
Peru and surrounding regions.
 Colombian coca ( E. novogranatense var. novogranatense) is cultivated in the moist, dry areas of the Colombian mountains.
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Huánuco, or Bolivian coca
( E. coca var. Coca )
Amazon Coca ( E. coca var. Ipuda )
Colombian coca
( E. novogranatense var. novogranatense)
Trujillo coca
( E. novogranatense var. Truxillense)
Four taxa of domesticated coca

11. Opiates
 Opiates refer to any of the naturally occurring narcotic alkaloids found in the latex( is a milky, sap-like
emulsion containing proteins, alkaloids, sugars, oils, and resins that are commonly used in rubber
manufacturing (i.e., latex gloves) of opium poppy plants as well as synthetic derivatives of the natural
alkaloid.
 Morphine and codeine are naturally occurring alkaloids.
 Heroin is the synthetic alkaloid.
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Morphine Codeine
Heroin

12. Morphine
 Morphine is the most prevalent alkaloid in latex, often representing 10–15% of the total mass. It
crystallizes as morphine sulfate, a salt that is usually either a white powder or white silky crystals.
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Morphine structure White powered form of Morphine
Uses
It is a potent narcotic that directly affects the central nervous system and gastrointestinal tract. It
is primarily used as an analgesic and sedative to relieve pain.
Side effects
Side effects include euphoria, alteration in mood, impairment of mental and physical
performance, reduced fear and anxiety, decreased hunger, renal failure, and depression of
respiratory functions.

13.  Morphine is highly addictive and can cause physical and
psychological dependence as well as tolerance and withdrawal.
Withdrawal symptoms typically develop just before the next scheduled
dose include watery eyes, irritability, runny nose, sweating, severe
headaches, and depression. In extreme cases, heart attack, stroke, and
blood clotting can occur.
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Morphine sulphate structure

14. Codeine
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Codeine is structurally similar to morphine and close examination of the two reveals a single
difference in the aromatic substituted group: the H in the hydroxyl group on morphine is replaced with
a methyl group (CH3 ).
CodeineMorphine
Although codeine can be isolated as a natural product from latex, it is usually synthetically produced
using O-methylation (adding a methyl group to oxygen) of morphine . Codeine is Schedule II controlled
substance. Codeine is typically used as an analgesic, cough suppressant, or antidiarrheal agent. The short-
and long-term side effects, including symptoms of withdrawal, are very similar to those associated with
morphine but are less severe in nature.

15. Heroin15
HeroinMorphine
Heroin (diacetylmorphine) is synthetically produced from morphine using a chemical process
called acetylation in which the hydroxyl groups on morphine are replaced with acetyl groups.
Heroin is typically a white crystalline solid in both the hydrogen-chloride salt and free-base forms. It
can be administered orally, by inhalation, by snorting (rarely), or by intravenous injection. Injecting or
“shooting up,” a solution of heroin is the preferred method of illicit use.
Heroin’s potential for addiction is much greater than most narcotics.

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The short- and long-term side effects of heroin use
 The short- and long-term side effects of heroin use, including symptoms of withdrawal, are very
similar to those associated with morphine. However, they are often complicated by the fact that
heroin is often used in combination with other drugs.
 Cocaine can be fatal when used in combination with heroin. Speedballs (when injected) and
moonrocks (when smoked) are popular combinations, but mixing stimulants and depressants can
have unpredictable effects that are often fatal.

17. Poppy
 Poppy ( Papaver somniferum L .), or opium poppy, is a plant native to southeastern Europe and western
Asia. The species is cultivated extensively in many countries, including Iran, Turkey, Holland, Poland,
Romania, and India.
 The erect plant can have white, pink, red, or purple flowers and can grow to heights exceeding 4 ft.
 Seeds range in color from white to purple-gray and grow best at temperatures between 7 and 23°C.
 Latex is obtained from immature seed capsules 1–3 weeks after flowering. Incisions are made in the
walls of the green seed pods, and the milky, sap-like liquid is collected and dried.
 Opium and the alkaloids morphine, codeine, noscapine, papaverine, and thebaine are subsequently
isolated from the dried material.
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18.  Poppy is used for medicinal purposes, dry opium poppy is considered an astringent,,
antispasmodic, aphrodisiac, diaphoretic, expectorant, hypnotic, narcotic, and sedative. It is
commonly used to treat toothaches and coughs, but opium, and its derivatives, are highly
addictive and can have toxicological effects.
 All opiates except heroin and opium are prescribed and regulated in tablet, caplet, or liquid
form (for injection). Therefore, they are easily distinguished from heroin, which is often
submitted to crime laboratories as a white powder.
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Poppy seed capsule prior to alkaloid extraction (left).Poppy
plant(mid).Sliced seed capsule oozing latex (right).

19. Synthetic Tertiary Amines
Phenylcyclohexylpiperidine or phencyclidine or PCP
 PCP is a Schedule II controlled substance that produces hallucinogenic and neurotoxic effects.
 PCP blocks neurological signals from the brain to the conscious mind, resulting in dream-like states
of sensory deprivation and dissociation.
 It is a general depressant that produces euphoria, sedation, respiratory depression, analgesia, and
amnesia.
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 PCP is a yellow oil in its pure base form and appears as a white-tan crystals or powder in pure
hydrogen- chloride-salt form (PCP hydrochloride).
 The primary effects typically last 8–10 h, but complete removal from the body can exceed 7 days.
 PCP is an extremely powerful hallucinogen that alters the mind in an unpredictable fashion. It
causes some users to become detached from reality, while others become animated.
PCP Structure

20. PCP exist in either pure base
form(left)or pure hydrogen
chloride-salt form(right)
Cigarette dipped
in PCP
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21. Analytical Methods
Visual inspections
 Visual inspections are an integral part of the identification process. Generally, they are
used to determine subsequent testing methods, but it is very important to recognize
their limitations. Tertiary amine controlled substances are submitted to forensic
laboratories in many forms and shapes. Therefore, visual inspection should only be
used to formulate a preliminary opinion on the basic nature of the substance. They are
not a confirmatory method and should never be used to render a final judgment.
Chemical Screening of Tertiary Amines
 A comprehensive flowchart for the color screening of tertiary amines is illustrated
below. The chart contains testing methods and results for commonly encountered
controlled substances in this category.
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22. A Flowchart for color Screening of Tertiary Amines
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Tertiary Amines
Test (neutral)
purple
purple
green
Marquis’ test Froehde Test
Mecke’s Test
Indication of
cocaine,
PCP, ketamine,
methadone
No color
Tertiary Amines
Test (acidic)
No color change or
appearance of any other color
indicates the absence of this
family of controlled substances
Indication of
opiate family of
Controlled
substances
including heroin
Indication of cocaine
base, crystal PCP, TCP,
methadone
No color

23. Confirmatory Examination
Fourier Transform Infrared Spectroscopy
 Fourier transform infrared spectroscopy (FTIR) is often used to identify
controlled substances in the tertiary amine class.
 Band at 600–900 cm −1 resulting from out-of-plane bending of aromatic C–H
bonds.
 Bands at 1,585–1,600 cm −1 result from aromatic carbon-to-carbon bond
stretching.
 Band at 3,000– 3,100 cm −1 resulting from aromatic C-H bond stretching .
 A broad band at 2,400–2,700 cm −1 region resulting from Amine salts.
 Bands at 1,250–1,300 cm −1 resulting from C–N bond stretching .
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24. FTIR SPECTRA OF COCAINE HCL AND COCAINE BASE24