Resins and Resins

Combinations

Eyael Tewelde (MSC)

Objectives

At the end of this chapter students will be able to:

• define and classify resins

• identify resins

• mention their use

• describe their physical and chemical characteristics

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Contents

Introduction

Properties

Classification

Drugs Containing Resins

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Introduction
• The term ‘resin’ is applied to more or less solid, amorphous
products of complex chemical nature
• Resins commonly used in pharmacy are derived from natural
sources
• Almost all are plant products products except Shellac, which is an
insect secretion

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Physical Properties
• are insoluble in water and usually insoluble in petroleum ether

• dissolve more or less completely in alcohol, chloroform and ether

• are hard, transparent or translucent

• are amorphous and brittle

• upon heating they soften and finally melt

• produce smoky flame on burning

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Chemical Properties

Resins are complex mixtures of :

• resin acids,

• resin alcohols (resinols),

• resin phenols (resinotannols),

• esters

• resenes 6
Resin Acids

• are mixtures of large proportion of diterpenoid oxyacids, carboxylic acids and

phenolic acids

• occur in free State or as esters

• are soluble in aqueous alkali solutions

• usually forming soap like froth on shaking

used extensively in the manufacture of cheap soaps and varnishes

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Resin Alcohols
• These are complex alcohols of high molecular weights
• present in free state or as ester of simple aromatic acids like
benzoic acid, cinnamic acid, and salicylic acid
• Resin alcohols are further subdivided into:
I. Resinotannols (resin phenols)
• have tannin like properties and form blue color with ferric
chloride
Example: Aloeresinotannol from aloe
II. Resinols
• are high molecular weight non phenolic alcohols which do
not give tannin reaction with iron salts
Example: Benzoresinol from benzoin

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Resenes

• are complex neutral substances that do not respond to any chemical

reactions

• are insoluble in alkalis and acids,

• do not form salts or esters and resist hydrolysis by alkalis

Example: Alban and fluvial from Gutta percha

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Classification
On the basis of their occurrence in combination with other
compounds, resins are classified as:

a) Balsams

b) Oleoresin

c) Gum resin

d) Oleo-gum resin

e) Glycoresins (glucoresin)

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a) Balsams

• Resinous substances containing high proportions of balsamic acid

(benzoic acid, cinnamic acid etc) either in free or in combination or their
esters
• Tolu balsam

• Benzoin

• Peru balsam

• Storax
• Read their Chemistry and Pharmacology

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b) Oleoresin
• resins that occur in combination with volatile oils

• Volatile oil is removed by steam distillation

• Turpentine

• Ginger

• Capsicum

• Male fern

• Copaiba …
Read their Chemistry and Pharmacology
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c) Gum resin

• Resins that occur in combination with gums

• Dissolving the associated gums in water can purify these resins

• Asafoetida

• Gamboge

• Myrrh

Read their Chemistry and Pharmacology

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d) Oleo-gum resin

• Resins associated with both gums and volatile oils

• The volatile oil is removed by steam distillation

• Dissolving in water separates the gum

• Myrrh
• Ipomoea

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e) Glycoresins (glucoresin)

• Resins found in combination with sugars are called glycoresins

• On hydrolysis they produce sugars and complex resins as aglycones

• Ipomoea

• Jalap

• Podophyllum

Read their Chemistry and Pharmacology

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Preparation of resins
• Two general classes of resinous substances are recognized based on the
method used in preparing them:

1. Natural resins, occur as exudates from plants, produced normally or as

result of pathogenic conditions
• artificial punctures e.g. mastic
• deep cuts in the wood of the plant e.g. turpentine
• hammering and scorching e.g. balsam of Peru

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2. Prepared resins; are obtained by different methods
• The drug containing resins is powdered and extracted with alcohol till
exhaustion
• The concentrated alcoholic extract is either evaporated, or poured into
water and the precipitated resin is collected, washed and carefully dried
• In the preparation of oleoresins; ether or acetone having lower boiling
point are used
• The volatile oil portion is removed through distillation
• When the resin occurs associated with gum (gum-resins), the resin is
extracted with alcohol leaving the gum insoluble

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Drugs Containing Resins
1. Podopyllum
• The term is derived from ancient Greek word means
`foot leaf'
• also known as Mayapple because of its fruits ripen in spring
• The genus Podophyllum is generally represented by
two species:
• P. hexandrum - Himalayan Mayapple
• P. peltatum - American Mayapple
• P. peltatum contains lower amounts of resin in
comparison to P. hexandrum

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P. hexandrum P. peltatum

• Podophyllum is an endangered but high value medicinal

plant from temperate and cold climatic zones of the globe
• It has wide scope of organized scientific study on its
different aspects
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Uses
• The rhizome, which is about a metre in length, is dug
up, cut into pieces about 10 cm in length, and dried
Uses :
• Podophyllin (a crude resin)
• vermifuge and emetic
• purgative
• treatment of venereal warts
• antitumour properties
• developed to be anticancer agents

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 Chemical constituents

Podophyllotoxin -Peltatin, R = CH3

topically to treat
-Peltatin, R = H
venereal warts

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Derivatives of Podophylotoxin

1. Etoposide
• Lignan derivative obtained semi-synthetically from
podophyllotoxin
• Used in the treatment of small-cell lung cancer,testicular
cancer, lymphomas and leukaemias

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2. Teniposide
• Thenylidene derivative
• Used in the treatment of paediatric cancer: lymphocytic leukaemia,
brain tumours

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2. Ginger
Constituents
• Volatile oils (1 – 2%)
• Camphene
• Cineole
• Citral
• Borneol
• Sesquiterpene HC’s
• Zingiberene & Zingiberol (Sesquiterpene alcohol)
• Resins
• Gingerols – pungent component – Anti-inflammatory
• Shogaols – increases bile secretion
• Starch
• Mucilage
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Constituents
• Volatile oils (1 – 2%)
• Camphene
• Cineole
• Citral
• Borneol
• Sesquiterpene HC’s
• Zingiberene & Zingiberol (Sesquiterpene alcohol)
• Resins
• Gingerols – pungent component – Anti-inflammatory
• Shogaols – increases bile secretion
• Starch
• Mucilage

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• Gingerols are a homologous series of phenols
• The most abundant is [6]-gingerol
• The pungency of dry ginger mainly results from shogaols
which are dehydrated forms of gingerols
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Uses

• ACTIONS
• Carminative
• Stimulant
• Anti-emetic
• Anti-bacterial & Anti-fungal
• Gingerol – pungent component – Anti-inflammatory
• Shogaols– increases bile secretion & enhanced GIT activity
• Motion Sickness
• Morning Sickness

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3. Capsicum
• is the dried ripe fruit of Capsicum frutenscens, known in commerce
African chilies, C. annum, known in commerce Tabasco pepper
• Constiuents
capsaicinoids
volatile oils (1.5%)
fixed oil
carotenoids
ascorbic acid

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Capsaicinoids
• cause the spicy flavor (pungency) of chili pepper fruit
• The primary capsaicinoid in chili pepper is capsaicin, followed by
dihydrocapsaicin, nordihydrocapsaicin, homodihydrocapsaicin and
homocapsaicin
• Capsaicin and dihydrocapsaicin:
• account for approximately 90% of capsaicinoids in chili pepper fruit,
• are the two most potent capsaicinoids
• their molecules differ only in the saturation of the acyl group

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Uses
• culinary importance

• used medicinally in creams to counter neuralgia and in other topical pain-

relieving preparations
• The initial burning effect of capsaicin is found to affect the pain receptors, making
them less sensitive

• antioxidant, anti carcinogenic , promotion of energy metabolism and

suppression of fat accumulation , and anti-inflammatory
However, the potential applications are limited by the irritation caused by their
pungency
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 4. Myrrh
• is oleo-gum resin exudates obtained from several species in
the genus Commiphora
• it contains :
• 57–61% water-soluble gum
• 7–17% volatile oils
• 25–40% alcohol-soluble resins and
• 3–4% impurities
• it was one of the three gifts believed to have been offered to
the infant Jesus by Magi
• The name myrrh is derived from the Arabic and Hebrew word
mur, which means bitter
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Occurrence

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• The alcohol-soluble resins of myrrh consist of:
• commiphoric acids

• commiphorinic acid

• heeraboresene

• heerabomyrrhols

• Commiferin……

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• The water-soluble gum fraction is composed mainly of acidic
polysaccharide with galactose, xylose, 4-0-methyl-glucuronic acid and
arabinose

• It’s characteristic odor is due to the furanosesquiterpenes

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Uses

• food, flavour, liqueur and beverage, cosmetics, perfumery and others.

Moreover,

• frankincense and myrrh have several local applications in medicinal,

hygienic, and insecticide areas that could be developed through
research

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Pharmacology

• The anti-inflammatory, antipyretic and …

Myrrh has been shown to work in two ways:

• it stimulates the production of white blood corpuscles (with their anti-

pathogenic actions)

• it has a direct anti-microbial effect

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 4. Cannabis

• is the general name given to a variety of substances prepared

from the plant Cannabis sativa
• In small doses, it is classified as a depressant

• In larger doses, it can be an hallucinogen

• The dried plant, resin or oil is commonly smoked for

recreational purposes

• can also be ingested by cooking it in food

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History
• Cannabis is among the very oldest of economic plants,
providing fiber, edible seed, and drug resin

1st archaeological evidence Used in Europe

of hemp use Ritual use
in India Used semi-
Medical use Hashish use in legal in
in China Arab world CA/AZ

8000 BC 2700 BC 2000 BC 1000 AD 1850s 1996

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Why do people use cannabis?

• To experience euphoria or perceptual distortions

• To relieve mental symptoms

• negative symptoms of schizophrenia

• anxiety

• To relieve physical symptoms

• eg nausea, anorexia
Forms and Preparations
Marijuana
• mixture of leaves, stems, tops
• 1960’s: 1-3% THC; up to 8-10%

“Bubble Gum” “Big Bud” “Dutch Northern Lights”

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Hashish
• dried resin from top of female plant

• THC usually 2-5%, but up to 15%

Hash Oil
• organic extraction
from hashish
• THC usually ~ 10-20% up to 70%

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Effects on Behavior
Low - moderate doses
• disinhibition, relaxation, drowsiness
• feeling of well being, exhileration, euphoria
• sensory - perceptual changes
• recent memory impairment
• balance/stability impaired
• decreased muscle strength, small tremor
• poor on complex motor tasks (e.g., driving)

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High doses
• pseudohallucinations
• synesthesias
• impaired judgement, reaction time
• pronounced motor impairment
• increasingly disorganized thoughts, confusion, paranoia, agitation

Not lethal even at very high doses

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Repeated Administration
Long-term effects - Amotivational syndrome?

Tolerance
3
H-CP-55,940 Binding
Chronic THC Control

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17.9
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Cannabinoids
• a group of terpenophenolics compounds that are pharmacologically
active compounds
• over 60 (delta-9-tetrahydrocannabinol (Δ9-THC), Δ8-THC,
cannabinol, etc.)

CH 3

OH

H 3C
CH 2 CH 2
H 3C O CH 2 CH 2 CH 3
9-Tetrahydrocannabinol

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Some Common Cannabinoids

In the plant: In your body Synthetic:

(endogenous):
Δ9 – THC 2-arichidonyl glycerol (2 CP 55,940
– AG)

Δ8 – THC anandamide HU – 210

cannabidiol and
cannabinol

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Mode of Cannabis Action
• Two specific cannabinoid receptors
• CB1 - brain and peripheral tissues
• CB2 - immune system

• Linked to G-proteins with diverse downstream signalling pathways

• Euphoria results from stimulation of mesolimbic dopaminergic

neurons, like other drugs of abuse

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Potential medical uses

• Glaucoma (increased intraocular pressure)

• Antiemetic (reduce nausea and vomiting)

• Anticonvulsant

• Enhance appetite (e.g., AIDS patients)

• Analgesic

THC versus marijuana controversy?

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