Why Is Saferstein Important
CM8002 Drugs
Saferstein Chapter 8
Drugs
Natural
Used since ancient times, mostly by “medicine men”
Semi-synthetic
Modified natural compounds
Synthetic
Misuse of pharmaceutical results
Abuse of solvents
Physical and Psychological addiction www.cnb.gov.sg www.dea.gov
Drugs
“The fly agarics are dried and eaten in large pieces. After about half an hour, the person becomes completely intoxicated and experiences extraordinary visions.
CO2H
O
Those who cannot afford the high
N
NH2 price of the mushrooms drink the urine of those who have eaten,
HO
whereupon they become
Ibotenic acid - interferes intoxicated, if not more so” with neurotransmitters in the brain
Georg Steller in Siberia, 1774
Peyote and …show more content…
Mescaline
Used in Mexican religions for 1000s of years; spread to Native
Americans in the S.W. in late C19th.
Lophophora williamsii
Illegal in the USA except for religious purposes
H3C
H3C
O
NH2
O
O
CH3
mescaline
Cannabis, hemp, hashish
Widely known in China,
Central Asia, India,
Middle East since
2000BC; fibres used for rope making since Roman times Described by Marco Polo; habit brought to Europe first by Napoleon’s soldiers
Saferstein page 209-211
Cannabis, marijuana, pot, grass
Herbal material from
cannabis sativa
Usually smoked
Identified botanically
- shape of leaves
- smell
- cystolithic trichomes
- may be confused with hops
Cannabis resin and cannabis oil
Cannabis chocolate
www.usdoj.gov/dea/multimedia.html
and vodka
Cannabis
H
H
O
OH
8-tetrahydrocannabinol
multiple effects on the CNS
Reported to be effective against side effects of chemotherapy
(synthetic alternatives now available) - medical sales legal in 14
US states
(http://news.bbc.co.uk/2/hi/americas/8319950.stm)
Detect active ingredient in samples by HPLC
Plant samples can be compared by DNA
Cannabis: smuggled or grown
Gifts from the New World to the Old after 1492
“The Columbian exchange”
papaya
potato
tomato
corn
turkey
pineapple
chocolate chili quinine cocaine tobacco
syphilis
Cocaine
Used since ancient times in the Andes
(Bolivia, Peru, Ecuador, Columbia)
Strictly controlled under the Incas
Erythroxylon coca
Used for stamina, especially at high altitude
Still widely cultivated in South America
Evo Morales
President of Bolivia
Saferstein page 213-214
Cocaine
Came to Europe following the collapse of
Spanish power in South America (after
1820s)
Initially fashionable - quickly banned
Blocks action of brain neurotransmitters
Users include Sherlock Holmes and Sigmund Freud
Also used as ophthalmic anaesthetic
Cocaine, crack, coke snorted or injected
H
Cl
N
CH3
smoked or snorted or injected
N
CO2CH3
O
O
Cocaine hydrochloride
(white powder)
CH3
CO2CH3
O
O
Free base cocaine
(chunks - crack cocaine)
Often “cut”: mannitol, sugar, local anaesthetics
Cocaine: 17.4 tonnes
www.usdoj.gov/dea/multimedia.html
The Cola tree
(West Africa)
Opium, Morphine and Heroin
Opium from papaver somniferum
Known since ancient times
Opium extract in alcohol: Laudanum
(Paracelsus)
HO
O
Major illegal producer: Afghanistan
Major legal producer: Tasmania
N
HO
CH3
Morphine is the active component of opium still clinically used as a painkiller Wallabies eating poppies?
Saferstein page 207-208
Opium in art and medicine
Also used for gastrointestinal problems Samuel Taylor Coleridge:
“Xanadu”
"This fragment with a good deal more, not recoverable, composed, in a sort of Revery brought on by two grains of Opium taken to check a dysentry, at a Farm House between
Porlock and Linton, a quarter of a mile from
Culbone Church, in the fall of the year, 1797."
Opium in Art, War and Politics
Opium wars
1839-1842 and
1856-1860
Hector Berlioz:
Symphonie Fantastique
the 4th movement on U-tube
Herman Goering: morphine addict and head of the German airforce in WW2
Opium, Morphine and Heroin
Heroin was invented by the Bayer Co. It was diacetylmorphine - more potent than morphine.
Harold Shipman
215 victims?
May still be legally prescribed in the UK
Heroin - faster transport to the brain
H3C
HO
O
O
N
HO
Morphine
H3C
O
O
O
O
O
CH3
O
N
CH3
CH3 Acetic anhydride - H C
O
3 controlled in many
Diacetylmorphine
Asian countries or diamorphine
The term “heroin” now refers to the illegal drug …show more content…
which is always impure.
Rapidly metabolised to morphine - so not detected in blood or urine
Etorpine - another synthetic analog very powerful tranquiliser!
HO
O
N
HO
CH3
CH3O
O
CH3O
H3C
HO
NCH3
Opium, Morphine and Heroin
Heroin may also contain morphine, codeine, thebaine, acetyl codeine
Papaverine, noscapine
Sugar, caffeine, barbiturates
related compounds unrelated compounds cutting agents Analysis of impurities can show if two samples came from the same source
LSD (lysergic acid diethylamide)
Discovered 1943 by Albert Hofmann
NEt2
O
N
H
Semi-synthetic derivative of alkaloids from rivea corymbosa
Popular in 1960s - now unusual
NH
Potent halucinogen - disrupts communication between
neurons.
Numerous fatalities.
Saferstein page 211
Amphetamines
CH3
NH2
CH3
HN
CH3
O
O
NH2
CH3
O
O
CH3
HN
Synthetic compounds. Method of making (synthesis) leaves characteristic impurities. Precursor chemicals are controlled. CH3
Saferstein page 213
Amphetamines
Smuggling of precursor chemicals is big business
US$207,000,000 seized in March 2007 by the US DEA www.usdoj.gov/dea/multimedia.html Amphetamines - natural relatives
O
CH3
NH2
cathinone
Qat - widely chewed in the Horn of
Africa and the Middle East, especially Yemen
ketamine
O
NHCH3
Cl
Originally an anaesthetic; now veterinary use only
Typically stolen
Hallucinogen
Affects memory, sensation, mood
Delirium, amnesia, depression
Has been used for date-rape
Solid or liquid
Ingested, smoked, injected
Saferstein page 215
Drugs
Analogs “Krokodil”
CH3
HO
O iodine red phosphorus hydrochloric acid gasoline or oil
O
N
HO
CH3
codeine
codeine made from morphine or extracted from opium used in cold medicines controlled to different extents
O
+
N
?
CH3
desomorphine
desomorphine made from morphine more potent
Analogs “Designer Drugs”
H3C
O
O
not diamorphine but just as effective
O
O
CH3CH2
N
O
CH3
Legal solutions
1. Control specific compounds as they become a problem
2. Control classes of compounds
3. Control analogs
Analogs “Federal Analog Act”
H3C
N CH3
N
H
H3CH2C
H
N CH2CH3
N
H
DMT dimethyl tryptamine natural (S.America)
DET diethyltryptamine synthetic
N H
N
H
AET
-ethyltryptamine
synthetic
DMT - specifically controlled
DET - specifically controlled
AET - an analog? District Court said “no”.
- now specifically controlled
Detection and Identification
Presumptive tests
Chemical colour change: Marquis test
Heroin - red purple
Amphetamines - orange brown
Scott test for cocaine cobalt thiocyanate turns blue
Saferstein page 219-210
Detection and Identification
Thin Layer Chromatography
Detection and Identification
Quantitative tests:
GC and HPLC
Spectroscopic
identification:
IR fingerprint region Hyphenated methods: GC-MS
Detection and Identification
Immunoassay
identification of a drug in a body fluid (blood, urine)
- generate antibodies to the drug
-binding of substrate to antibody triggers colour change
- highly sensitive. Too sensitive?
Penalties in Singapore
Prison/ fines possession or consumption of cannabis, cocaine, heroin, ecstasy, ketamine
Death Penalty
Trafficking
Cannabis > 500g
Cocaine > 30g
Heroin > 15 g
Methamphetamine > 250 g
Saferstein Chapter 8
Drugs
Natural
Used since ancient times, mostly by “medicine men”
Semi-synthetic
Modified natural compounds
Synthetic
Misuse of pharmaceutical results
Abuse of solvents
Physical and Psychological addiction www.cnb.gov.sg www.dea.gov
Drugs
“The fly agarics are dried and eaten in large pieces. After about half an hour, the person becomes completely intoxicated and experiences extraordinary visions.
CO2H
O
Those who cannot afford the high
N
NH2 price of the mushrooms drink the urine of those who have eaten,
HO
whereupon they become
Ibotenic acid - interferes intoxicated, if not more so” with neurotransmitters in the brain
Georg Steller in Siberia, 1774
Peyote and …show more content…
Mescaline
Used in Mexican religions for 1000s of years; spread to Native
Americans in the S.W. in late C19th.
Lophophora williamsii
Illegal in the USA except for religious purposes
H3C
H3C
O
NH2
O
O
CH3
mescaline
Cannabis, hemp, hashish
Widely known in China,
Central Asia, India,
Middle East since
2000BC; fibres used for rope making since Roman times Described by Marco Polo; habit brought to Europe first by Napoleon’s soldiers
Saferstein page 209-211
Cannabis, marijuana, pot, grass
Herbal material from
cannabis sativa
Usually smoked
Identified botanically
- shape of leaves
- smell
- cystolithic trichomes
- may be confused with hops
Cannabis resin and cannabis oil
Cannabis chocolate
www.usdoj.gov/dea/multimedia.html
and vodka
Cannabis
H
H
O
OH
8-tetrahydrocannabinol
multiple effects on the CNS
Reported to be effective against side effects of chemotherapy
(synthetic alternatives now available) - medical sales legal in 14
US states
(http://news.bbc.co.uk/2/hi/americas/8319950.stm)
Detect active ingredient in samples by HPLC
Plant samples can be compared by DNA
Cannabis: smuggled or grown
Gifts from the New World to the Old after 1492
“The Columbian exchange”
papaya
potato
tomato
corn
turkey
pineapple
chocolate chili quinine cocaine tobacco
syphilis
Cocaine
Used since ancient times in the Andes
(Bolivia, Peru, Ecuador, Columbia)
Strictly controlled under the Incas
Erythroxylon coca
Used for stamina, especially at high altitude
Still widely cultivated in South America
Evo Morales
President of Bolivia
Saferstein page 213-214
Cocaine
Came to Europe following the collapse of
Spanish power in South America (after
1820s)
Initially fashionable - quickly banned
Blocks action of brain neurotransmitters
Users include Sherlock Holmes and Sigmund Freud
Also used as ophthalmic anaesthetic
Cocaine, crack, coke snorted or injected
H
Cl
N
CH3
smoked or snorted or injected
N
CO2CH3
O
O
Cocaine hydrochloride
(white powder)
CH3
CO2CH3
O
O
Free base cocaine
(chunks - crack cocaine)
Often “cut”: mannitol, sugar, local anaesthetics
Cocaine: 17.4 tonnes
www.usdoj.gov/dea/multimedia.html
The Cola tree
(West Africa)
Opium, Morphine and Heroin
Opium from papaver somniferum
Known since ancient times
Opium extract in alcohol: Laudanum
(Paracelsus)
HO
O
Major illegal producer: Afghanistan
Major legal producer: Tasmania
N
HO
CH3
Morphine is the active component of opium still clinically used as a painkiller Wallabies eating poppies?
Saferstein page 207-208
Opium in art and medicine
Also used for gastrointestinal problems Samuel Taylor Coleridge:
“Xanadu”
"This fragment with a good deal more, not recoverable, composed, in a sort of Revery brought on by two grains of Opium taken to check a dysentry, at a Farm House between
Porlock and Linton, a quarter of a mile from
Culbone Church, in the fall of the year, 1797."
Opium in Art, War and Politics
Opium wars
1839-1842 and
1856-1860
Hector Berlioz:
Symphonie Fantastique
the 4th movement on U-tube
Herman Goering: morphine addict and head of the German airforce in WW2
Opium, Morphine and Heroin
Heroin was invented by the Bayer Co. It was diacetylmorphine - more potent than morphine.
Harold Shipman
215 victims?
May still be legally prescribed in the UK
Heroin - faster transport to the brain
H3C
HO
O
O
N
HO
Morphine
H3C
O
O
O
O
O
CH3
O
N
CH3
CH3 Acetic anhydride - H C
O
3 controlled in many
Diacetylmorphine
Asian countries or diamorphine
The term “heroin” now refers to the illegal drug …show more content…
which is always impure.
Rapidly metabolised to morphine - so not detected in blood or urine
Etorpine - another synthetic analog very powerful tranquiliser!
HO
O
N
HO
CH3
CH3O
O
CH3O
H3C
HO
NCH3
Opium, Morphine and Heroin
Heroin may also contain morphine, codeine, thebaine, acetyl codeine
Papaverine, noscapine
Sugar, caffeine, barbiturates
related compounds unrelated compounds cutting agents Analysis of impurities can show if two samples came from the same source
LSD (lysergic acid diethylamide)
Discovered 1943 by Albert Hofmann
NEt2
O
N
H
Semi-synthetic derivative of alkaloids from rivea corymbosa
Popular in 1960s - now unusual
NH
Potent halucinogen - disrupts communication between
neurons.
Numerous fatalities.
Saferstein page 211
Amphetamines
CH3
NH2
CH3
HN
CH3
O
O
NH2
CH3
O
O
CH3
HN
Synthetic compounds. Method of making (synthesis) leaves characteristic impurities. Precursor chemicals are controlled. CH3
Saferstein page 213
Amphetamines
Smuggling of precursor chemicals is big business
US$207,000,000 seized in March 2007 by the US DEA www.usdoj.gov/dea/multimedia.html Amphetamines - natural relatives
O
CH3
NH2
cathinone
Qat - widely chewed in the Horn of
Africa and the Middle East, especially Yemen
ketamine
O
NHCH3
Cl
Originally an anaesthetic; now veterinary use only
Typically stolen
Hallucinogen
Affects memory, sensation, mood
Delirium, amnesia, depression
Has been used for date-rape
Solid or liquid
Ingested, smoked, injected
Saferstein page 215
Drugs
Analogs “Krokodil”
CH3
HO
O iodine red phosphorus hydrochloric acid gasoline or oil
O
N
HO
CH3
codeine
codeine made from morphine or extracted from opium used in cold medicines controlled to different extents
O
+
N
?
CH3
desomorphine
desomorphine made from morphine more potent
Analogs “Designer Drugs”
H3C
O
O
not diamorphine but just as effective
O
O
CH3CH2
N
O
CH3
Legal solutions
1. Control specific compounds as they become a problem
2. Control classes of compounds
3. Control analogs
Analogs “Federal Analog Act”
H3C
N CH3
N
H
H3CH2C
H
N CH2CH3
N
H
DMT dimethyl tryptamine natural (S.America)
DET diethyltryptamine synthetic
N H
N
H
AET
-ethyltryptamine
synthetic
DMT - specifically controlled
DET - specifically controlled
AET - an analog? District Court said “no”.
- now specifically controlled
Detection and Identification
Presumptive tests
Chemical colour change: Marquis test
Heroin - red purple
Amphetamines - orange brown
Scott test for cocaine cobalt thiocyanate turns blue
Saferstein page 219-210
Detection and Identification
Thin Layer Chromatography
Detection and Identification
Quantitative tests:
GC and HPLC
Spectroscopic
identification:
IR fingerprint region Hyphenated methods: GC-MS
Detection and Identification
Immunoassay
identification of a drug in a body fluid (blood, urine)
- generate antibodies to the drug
-binding of substrate to antibody triggers colour change
- highly sensitive. Too sensitive?
Penalties in Singapore
Prison/ fines possession or consumption of cannabis, cocaine, heroin, ecstasy, ketamine
Death Penalty
Trafficking
Cannabis > 500g
Cocaine > 30g
Heroin > 15 g
Methamphetamine > 250 g