Forensic Chemistry

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Drugs and Pharmacology

• Drugs
• Substances capable of a physiological change
• Swallowing, injection, inhalation, absorption
• All substances are poisonsthe right dose
  differentiates a poison from a remedy
• (Paracelsus 1493-1541)
• Medicines
• Mixtures of drugs and inert ingredients used to
  prevent or treat symptoms or disease
• Forensic Toxicologists
• detecting and identifying the presence of drugs
  and poisons in body fluids, tissues, and organs
  in relation to the law

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Drugs by effect

• Analgesics
• Pain relievers (at site (aspirin), or at CNS
  (morphine)
• opiates
• Depressants
• Depress CNS (slowed heart beat, reduced anxiety,
  sleep)
• Alcohol, benzodiazepines (huge class),
  barbiturates, inhalants
• Hallucinogens
• Alter mental perception of time/space/feeling
• LSD, MDMA (ecstasy), marijuana, cannabis,
  psilocybin (magic mushrooms), methamphetamine
  (high doses)
• Narcotics
• Analgesic and depress CNS
• Opiates, oxycodone, heroin
• Stimulants
• Stimulate CNS (promotes alertness, reduces
  fatigue/sleep)
• Cocaine, amphetamine, methamphetamine
• Can be hallucinogenic in high doses

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Drugs by use

• Predator drugs
• Date-rape drugs, drug-facilitated sexual assault
  (DFSA)
• Alcohol, ketamine, rohypnol, GHB (gamma
  hyrdoxybutyrate)
• Lack of memory often leads to delayed testing
• Club drugs
• Used to create highs and energy in parties and
  clubs
• Ecstasy (MDMA, methylene dioxy methamphetamine),
  LSD (lysergic acid diethylamide), psilocybin, PCP
  (phencyclidine)
• Performance-enhancing drugs
• Mostly humans and horses
• Anabolic steroids, human growth hormones
• Inhalants
• Not originally intended for drug use
• Very nasty side-effects
• Paint thinners, cleaners, solvents, butane, nail
  polish etc.

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Abused drugs in the USA
Drug  users users
Caffeine ? ?
Alcohol 53 110M users
Tobacco 26.00 55M users
Prescription drugs 0.80 1.6M users
Inhalents 1 1.6M users
Marijuana 5 10M users
Cocaine 0.80 1.6 M users
Narcotics and analgesics 0.60 1.2M users
Hallucinogens 0.40 0.8M users
Depressants 0.30 0.5M users
Stimulants 0.10 0.2M users
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Toxicity v. effective doses of drugs
Gable, R.S. The Toxicity of Recreational Drugs.
American Scientist 2006, 94, 206-208
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• Schedule I
• Have a high potential for abuse
• Have no current accepted medical use
• Examples include heroin, marijuana,
  methaqualone, LSD

Marijuana and pipes
Forms of heroin
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Marijuana and cannabis

• THC typically present at 1-5 w/w in cannabis
  sativa
• Some hybrids, such as sinsemilla, can have up to
  13 w/w
• Hashish, hash oil, cannabis resin, draw, etc has
  elevated levels
• Analysis
• Bear claws under microscope
• Acid will create bubbles

Forensic Chem Lab, 2006
G.P. Jackson, 2006
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• Cannabinoids

• 7

• 9

• 10

• 1

• 8

• 2

• 6

• 1

• 10a

• 7

• 2

• 3

• 2

• 6a

• 3

• 5

• 1

• 4

• 6

• 3

• 4

• 4

• 5

• Dibenzopyran Numbering

• Monoterpene Numbering

• D9 Tetrahydrocannabinol (D9-THC), Natural
  Product D1-THC

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• Cannabinoids

D9-THC
D6a-THC
D8-THC

• D9-THCM
• Tetrahydrocannabinol
• methylether

• D9-THCA
• Tetrahydrocannabinolic
• acid

• D9-THC acid B
• Tetrahydrocannabinolic
• acid B

• THC and Derivatives

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• Cannabinoids

• 11-Hydroxy D9-THC

• 8b-Hydroxy D9-THC

• 11-Nor-9-Carboxy-1-Hydroxy D9-THC

• 8-Keto D9-THC

• Metabolites of D9-THC

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• Synthetic cannabinoids found
• in K2 and Spice Aminoalkylindole family

• These are non-classical synthetic cannabinoids
  (cannabimimetics) because they are not
  structurally similar to THC. They are considered
  cannabinoids because they are agonists of either
  one or both cannabinoid receptors.

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• C4NH10

• Substituted Group for
• Triptamines, RT

• Indole Ring System

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• O-Acetylpsilocin
• 4-acetoxy-N,N-dimethyltryptamine

• Bufotenin
• 5-hydroxy-N,N-dimethyltryptamine

• Psilocybin
• 4-phosphoryloxy-N,N-dimethyltryptamine

• Psilocybin, Bufotenin, O-Acetylpsilocin,
  Zolmitriptan, and Sumatriptan

• Sumatriptan
• 5-(methylaminosulfonylmethylene)-N,N-dimethyltrypt
  amine

• Zolmitriptan
• 5-( 4-(S)-1,3-oxazolidin-2-one)-N,N-dimethyltrypta
  mine

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• JWH-122
• (4-?methyl-?1-?naphthalenyl)(1-?pentyl-?1H-?indol-
  ?3-?yl)-?methanone

• JWH-018
• (1-?pentyl-?1H-?indol-?3-?yl)-?1-?naphthalenyl-?me
  thanone

• JWH-210
• (4-?ethyl-?1-?naphthalenyl)(1-?pentyl-?1H-?indol-?
  3-?yl)-?methanone

• MAM2201
• 1-?(5-?fluoropentyl)-?1H-?indol-?3-?yl(4-?methyl
  -?1-?naphthalenyl)-?methanone

• AM2201
• 1-?(5-?fluoropentyl)-?1H-?indol-?3-?yl-?1-?napht
  halenyl-?methanone

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• UR-144
• 1-Pentylindo 1-3-yI-( 2,2, 3,3-tetramethylcyclo
  propyl)
• methanone

• 5F-UR-144
• 1-(5-fluoropentyl)indol-3-yl-(2,2,3,3-tetra-meth
  ylcyclopropyl)methanone

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• R1

• R2

• Indole Ring System

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• JWH-018
• (1-?pentyl-?1H-?indol-?3-?yl)-?1-?naphthalenyl-?me
  thanone

• JWH-122
• (4-?methyl-?1-?naphthalenyl)(1-?pentyl-?1H-?indol-
  ?3-?yl)-?methanone

• JWH-210
• (4-?ethyl-?1-?naphthalenyl)(1-?pentyl-?1H-?indol-?
  3-?yl)-?methanone

• MAM2201
• 1-?(5-?fluoropentyl)-?1H-?indol-?3-?yl(4-?methyl
  -?1-?naphthalenyl)-?methanone

• AM2201
• 1-?(5-?fluoropentyl)-?1H-?indol-?3-?yl-?1-?napht
  halenyl-?methanone

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• JWH-018

• JWH-122

• JWH-210

• AM2201

• AM2201

• 5F-UR-144

• UR-144

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• RT

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Affinity Affinity
CB1 CB2
nM nM
JWH-018 9.00 2.94
JWH-122 0.69 1.20
JWH-210 0.46 0.69
MAM2201 1.00 2.60
AM2201 1.00 2.60

• According to Drug Data Sheet from Cayman Chemical

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Ergot and tryptamine alkaloids and hallucinogens

• LSD derived from ergot alkaloids
• Ergot is a fungus found mostly on grains
• Difficult synthesis fewer, but more specialized
  labs
• Mescaline
• From cactus plants (peyote)
• Legal for native americans

www.aldeaeducativa.com
www.mescaline.com/exp/
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Ergot and tryptamine alkaloids and hallucinogens

• Psilocybin/psilicin
• From mushrooms

www.drug-information-resource.com/
www.potseeds.co.uk
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Ergot and tryptamine alkaloids and hallucinogens

• 5-MeO-DMT bufotoxins
• 5-methoxy-dimethyltryptamine
• from Bufo alvarius (colarado river) toads
• excreted in venum
• semi synthetic versions enhance methylation
• usually smoked, not licked!

www.eitangrunwald.com
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• 4

• 3

• 5

• 2

• 6

• 1

• 7

• Indole Ring Structure with Points of
  Substitutions 1-7.

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• C4NH10

• Substituted Group for
• Triptamines, RT

• Indole Ring System

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• O-Acetylpsilocin
• 4-acetoxy-N,N-dimethyltryptamine

• Psilocybin
• 4-phosphoryloxy-N,N-dimethyltryptamine

• Bufotenin
• 5-hydroxy-N,N-dimethyltryptamine

• Zolmitriptan
• 5-( 4-(S)-1,3-oxazolidin-2-one)-N,N-dimethyltrypta
  mine

• Sumatriptan
• 5-(methylaminosulfonylmethylene)-N,N-dimethyltrypt
  amine

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• O-Acetylpsilocin
• 4-acetoxy-N,N-dimethyltryptamine

• Bufotenin
• 5-hydroxy-N,N-dimethyltryptamine

• Psilocybin
• 4-phosphoryloxy-N,N-dimethyltryptamine

• Psilocybin, Bufotenin, O-Acetylpsilocin,
  Zolmitriptan, and Sumatriptan

• Sumatriptan
• 5-(methylaminosulfonylmethylene)-N,N-dimethyltrypt
  amine

• Zolmitriptan
• 5-( 4-(S)-1,3-oxazolidin-2-one)-N,N-dimethyltrypta
  mine

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• Tryptamines

b
a

• 4

• 3

• 5

• 2

• 6

• 1

• 7

• Tryptophan

• Tryptamine

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• Tryptamines

• LSD Lysergic Acid
• Diethylamine

• Serotonin
• 5-hydroxytryptamine

• Psilocin
• 4-hydroxy-
• N,N-dimethyltryptamine

• Psilocybin
• 4-phosphoryloxy-
• N,N-dimethyltryptamine

• DMT -
• N,N-dimethyltryptamine

• Bufotenine -
• 5-hydroxy-
• N,N-dimethyltryptamine

• Melatonin -
• N-acetyl-5-
• methoxytryptamine

• Naturally Occurring Tryptamines

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• Phenethylamine

• 2

• N

a

• 3

b

• 4

• 6

• 5

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• Phenethylamine

• MDMA Molly - Ecstacy

• MDEA Eve

• Methamphetamine

• Dopamine

• Epinephrine

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Methamphetamine synthesis
Requires Li (from batteries?) and ammonia (from
fertilizers)
Involves red-phosphorous (from matches) Can
produce phosphine gas (PH3)
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Tropane alkaloids and cocaine
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Tropane alkaloids and cocaine
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Tropane alkaloids and cocaine
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PCP and Ketamine

• Intended (and used) as veterinary anesthetics
• esp. equine
• Hallucinogenic in humans
• Both synthetic and can be produced in clandestine
  labs

Phencylcidine (PCP) Acid form angel dust
Ketamine
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Benzodiazepaines SSRI

• Valium (diazepam), Xanax, Prozac (Fluoxetine)

Prozac
Valium
Xanax
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Drug analysis I acidic/neutral drugs
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