Lecture 1 Flashcards
herbal cannabis)
K
cannabis resin), t
K
• In the plants material, resin and “hash oil” the main active ingredient is
G
The greatest concentration of glandular trichomes is in the
Y
Material prepared from the flowering
tops or leaves is commonly called
N
Cannabis plants grown
under controlled..
I
manufactured product of cannabis produced by extracting the whole plant material using an
organic solvent (usually alcohol, ether or benzene).
G
There is a large number of known cannabinoids that can be divided into
Y
The main cannabinoids ar
U
cannabinol
Y
CBN
G
cannabidiol
V
CBD
L
two isomers of tetrahydrocannabinol (Δ8
and Δ9-THC)
G
tetrahyrdocannininolic acid
Y
THCOOH
H
is the cannabinoid that has the greatest pharmacological activity
I
is this cannabinoid that
needs to be detected to demonstrate that a sample is legally cannabis.
I
the precursor of THC
U
the decomposition product of THC.
Y
converted to THCOOH on smoking.
U
Long-term storage of resin and plant extracts cause
U
can be used to identify which drug is present within a drug class,
I
are also used as confirmatory analysis.
U
are deemed sufficient for court purposes.
U
weakly acidic compounds because of the
J
undergoing ionization in aqueous media forming compounds that will strongly interact with the stationary
phase in HPLC analysis, causing tailing of the peaks when analyzed using liquid chromatographic methods
U
Because of this, ionization is suppressed by the presence of acetic acid in the mobile phase.
Y
tends to be favored over HPLC.
T
suffer
severely from thermal decomposition and, as a result, do not chromatograph well.
T
belong to a family of compounds known as narcotic analgesics,
T
extracted from the opium poppy and its acetylation affords the semi-synthetic opiate
diacetylmorphine (diamorphine).
G
crude mixture of opium alkaloids obtained from the extraction of morphine from opium and the
acetylation reaction.
T
was found to have narcotic and addictive properties far
exceeding those of morphine.
H
the air-dried milky latex, obtained by cutting unripe pods of the opium poppy Papaver somniferum (Papaveraceae).
I
used as an analgesic, sleep-inducer (narcotic), and for the treatment of coughs.
L
is standardized to contain 10% of anhydrous morphine, usually by dilution with an approved diluent, e.g. lactose or cocoa
husk powder.
U
meconic acid (poppy acid
H
display acidic properties as well as the basic properties due to the tertiary amine.
P
arboxylic acid function, whilst morphine is acidic due to its phenolic hydroxyl. This acidity can be exploited for the preferential
U
powerful analgesic and narcotic, and remains one of the most valuable analgesics for relief of severe
pain.
U
induces a state of euphoria and mental detachment, together with nausea, vomiting, constipation,
tolerance, and addiction.
P
withdrawal symptoms,
H
which may last for 10–14 days
Y
3-O-methyl ether of morphine and is the most widely used of the opium alkaloids.
K
Because of the
relatively small amounts found in opium, almost all of the material prescribed is manufactured by semi-synthesis
from morphine.
U
action is dependent on partial demethylation in the liver to produce morphine,
U
so it produces morphine-like
analgesic effects, but little if any euphoria.
8
As an analgesic, codeine has about one-tenth the potency of morphine.
U
It is a
relatively safe non-addictive medium analgesic, but is still too constipating for long-term use.
U
antitussive action, helping to relieve and prevent coughing. It effectively depresses the
cough centre, raising the threshold for sensory cough impulses.
I
Thebaine
D
Papaverine
E
Noscapine
E
Pholcodine
E
Dihydrocodeine
E
hydromorphone
E
Heroin
E
differs structurally from morphine/codeine mainly by its possession of a conjugated diene ring system.
V
almost devoid of analgesic activity,
but may be used as a morphine antagonist. Its main value is as substrate for the semi-synthesis of other drugs.
V
benzylisoquinoline alkaloid, and is structurally very different from the morphine, codeine, thebaine group of alkaloids (
morphinans). It has little or no analgesic or hypnotic properties, but it relaxes smooth muscle in blood vessels.
F
member of the phthalideisoquinoline alkaloids and provides a further structural variant in the opium alkaloids.
V
antitussive and cough suppressant activity comparable to that of codeine, but no analgesic or narcotic action.
I
Despite many years of use as a cough suppressant, the finding that noscapine may have teratogenic properties (i.e.
may deform a fetus)
V
effective and reliable antitussive, can be obtained by alkylation with N-(chloroethyl)morpholine.
C
is a reduced form of codeine with similar analgesic properties.
D
double bond of morphine has been reduced, and in addition the 6-hydroxyl has been oxidized to a ketone.
,
This increases the
analgesic effects, but also the side-effects; the drug is used for severe pain associated with cancer.
B
diacetate of morphine; it is a highly addictive analgesic and hypnotic.
K
The increased lipophilic character of heroin over morphine results in
improved solubility, with better transport and absorption, though the active agent is probably the 6-acetate, the 3-acetate group being hydrolysed by
M
synthesized originally as a cough suppressant; and though most effective in this role, it has unpleasant addictive properties, with users
developing a psychological craving for the drug. It is widely used for terminal care, e.g. cancer sufferers, both as an analgesic and cough suppressant.
L
obtained from salutaridine by stereospecific reduction of the carbonyl group. Ring closure
to form the ether linkage in thebaine would be the result of nucleophilic attack of the phenol group onto the dienol
system and subsequent displacement of the hydroxyl.
D
treatment of salutaridinol with acid. In vivo, however, an
additional reaction is used to improve the nature of the leaving group, and this is achieved by acetylation with acetyl
-CoA. The cyclization then occurs readily, and without any enzyme participation.
C
The conversion of thebaine into codine and morphine, involves a process which modifies the oxidation state of the
diene ring, removing two O-methyl groups.
D
The enzymic demethylations of both the enol ether (in thebaine) and the phenol ether (in codeine) involve
hydroxylation followed by loss of the methyl groups as formaldehyde.
D
Opioid Analysis
S
often used as a simple and rapid screening technique to identify the opiate alkaloids and other
components that may be present in heroin samples prior to examination by other methods.
G
Examples of solvent systems are cyclohexane/toluene/diethylamine (75:15:10) and
toluene/acetone/ethanol/ammonia (45:45:7:3)
S
generates highly specific mass spectral
data enabling the definitive identification of both known and unknown components within heroin samples.
H
Heating the heroin street samples from 250 to 400°C produced substantial diamorphine degradation,
whereas morphine, codeine, acetylcodeine, papaverine and caffeine were heat stable.
H
generates highly specific mass spectral
data enabling the definitive identification of both known and unknown components within heroin samples.
S
bicyclic structure of the tropane skeleton in cocaine is achieved by a repeat of the Mannich-like
reaction.
E
new 1-pyrrolinium cation,
K
intramolecular Mannich reaction on the R enantiomer accompanied by decarboxylation
generates tropinone,
U
stereospecific reduction of the carbonyl yields tropine with a 3α-hydroxyl, or the
isomeric ψ-tropine, the precursor of the calystegines.
U
is the ester of tropine with (S)-tropic acid, which is derived from l-phenylalanine via phenyl-
lactic acid.
C
carboxyl carbon from the acetoacetyl side-chain not be lost as it was in the formation of tropine, then
the subsequent intramolecular Mannich reaction will generate a tropane skeleton with an additional carboxyl
substituent.
D
diester of ecgonine, the benzoyl moiety arising from phenylalanine via cinnamic acid and
benzoyl-CoA. It found in Erythroxylum coca (coca) and is used medicinally as a local anesthetic, and as an
illicit drug for its euphoric properties.
D
The First Total Synthesis of Cocaine
D
cycloheptanone
D
bromination
followed by an intramolecular
transannular SN2 to form the
tropane skeleton (Chem. Ber.
1901, 34, 129).
D
chewing has been practiced by South American Indians for many years and has been an integral
part of the native culture pattern.
J
Leaf is mixed with lime, thus liberating the principal alkaloid cocaine as the free base, and the combination
is then chewed. Cocaine acts as a potent antifatigue agent, and allows laborers to ignore hunger, fatigue,
and cold, enhancing physical activity and endurance. It is estimated that 25% of the harvest is consumed in
this way by the local workers, who may each use about 50 g of leaf per day (≡ 350 mg cocaine).
H
are extracted from crushed leaf using alkali (lime) and petrol.
D
The petrol extract is then re-
extracted with aqueous acid, and this alkaloid fraction is basified and allowed to stand, yielding the free
alkaloid as a paste.
F
are often diluted with carrier to give a preparation with 10–12% of cocaine.
F
Regular usage induces depression, dependence, and damage to the nasal membranes.
D
For inhalation,
D
local anesthetic for
topical application. It is rapidly absorbed by
mucous membranes and paralyses peripheral
ends of sensory nerves.
D
This is achieved by blocking ion channels in
neural membranes. It was widely used in
dentistry, and is still used in ear, nose and throat
surgery.
C
Cocaine Derivatives
S
Procaine
Q
Benzocaine
S
Lidocaine
J
lignocaine
V
local anesthetics for eye
surgery.
F
the most widely used local
anesthetic.
F
Amphetamine-type stimulants
L
methylamphetamine
9
ecstasy
J
β-phenethylamine derivatives and totally synthetic drugs and, as such, are very different
in terms of the potential for analysis, as in all cases there are many synthetic by-products carried through
each stage of the synthetic process.
9
amphetamine sulfate,
7
methylamphetamine hydrochloride or
free base
0
methylenedioxymethylamphetamine hydrochloride (ecstasy).
I
Analysis of Amphetamine-type stimulants
J
are used when quantification of amphetamines is required.
9
generally chromatograph well on both systems
J
There can be some co-elution of amphetamine,
methylamphetamine, MDA and MDMA occurring.
U
contain caffeine, which has a much greater molar absorptivity coefficient
than amphetamine and, as such, will have a much greater peak area than amphetamine, even though the
concentration of both within the sample may be similar. • Amphetamines generally chromatograph well underivatized using GCMS instruments, though many
I
trifluoroacetic acid (TFA)
U
Phenylalanine-derived Alkaloids
J
the main alkaloid in species of Ephedra (Ephedraceae) and a valuable nasal
decongestant and bronchial dilator.
U
major constituent of the leaves of khat (Catha edulis; Celastraceae),
chewed in African and Arab countries as a stimulant. Its traditional use alleviates hunger and fatigue
, but also gives a sensation of general well-being. Users become cheerful and talkative, and khat
has become a social drug.
U
Norpseudoephedrine
U
Prolonged usage can lead to hypertension, insomnia, or even mania.
I
may lead to pyschological dependence, but not normally physical dependence.
I
Most of the central nervous system stimulant action comes from the more active
J
New psychoactive substances
O
legal highs, designer drugs or bath salts or spice.
J
Synthetic cannabinoids
H
compounds that have been prepared to have the same functionality as Δ9-
tetrahydrocannabinol (THC) in terms of their interactivity with the cannabinoid receptors in the brain. I
I
Many of the synthetic cannabinoids are structurally unrelated to
U
however, they do often contain a side
chain containing between four and nine carbon atoms.
H
The synthetic cannabinoids can be classified into six major structural groups:
U
Naphthoylindolesu
O
Naphthylmethylindoles
K
Naphthoylpyrroles
Y
Naphthylmethylindenes
U
Phenylacetylindoles
P
Cyclohexylphenols
7
The synthetic cathinone most reported to the United Nations Office on Drugs and Crime
Y
4-
methylmethcathinone
7
mephedrone
8
was viewed as a legal alternative to illicit substances, meaning it was also viewed as being
safer.
U
The decreasing purity in ecstasy and cocaine also led to an increase in …… consumption,
as it was seen as a cheaper, more potent alternative.
L
The synthesis of cathinones is a two-step synthesis process
7
α-bromoketone
6
hydrochloride or hydrobromide salt:
K
Analysis of cathinones and synthetic cannabinoids
I
The greatest challenge in the analysis of both cathinones and synthetic cannabinoids is the
J
consistently effective at detecting a range of cathinone derivatives.
J
Zimmerman test,
H
Both the cathinones and cannabinoids are readily resolved using………, but their
identification and quantitative analysis is limited by the …..
M
is used to identify the structures of the
target molecules.
I
FTIR and Raman are
H
used in identifying compounds once standards are available.
H
