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Forensic Chemistry

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* Tropane alkaloids and cocaine * Tropane alkaloids and cocaine * Tropane alkaloids and cocaine * PCP and Ketamine Intended (and used) as veterinary anesthetics esp ... – PowerPoint PPT presentation

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Title: 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

3
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

4
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.

5
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
6
Toxicity v. effective doses of drugs
Gable, R.S. The Toxicity of Recreational Drugs.
American Scientist 2006, 94, 206-208
7
  • 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
8
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
9
  • 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

10
  • 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

11
  • 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

12
  • 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.

13
  • C4NH10
  • Substituted Group for
  • Triptamines, RT
  • Indole Ring System

14
  • 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

15
  • 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

16
  • 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

17
  • R1
  • R2
  • Indole Ring System

18
  • 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

19
  • JWH-018
  • JWH-122
  • JWH-210
  • AM2201
  • AM2201
  • 5F-UR-144
  • UR-144

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  • RT

21
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/
23
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
25
  • 4
  • 3
  • 5
  • 2
  • 6
  • 1
  • 7
  • Indole Ring Structure with Points of
    Substitutions 1-7.

26
  • C4NH10
  • Substituted Group for
  • Triptamines, RT
  • Indole Ring System

27
  • 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

28
  • 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

29
  • 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

31
  • Phenethylamine
  • 2
  • N

a
  • 3

b
  • 4
  • 6
  • 5

32
  • Phenethylamine
  • MDMA Molly - Ecstacy
  • MDEA Eve
  • Methamphetamine
  • Dopamine
  • Epinephrine

33
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
38
Benzodiazepaines SSRI
  • Valium (diazepam), Xanax, Prozac (Fluoxetine)

Prozac
Valium
Xanax
39
Drug analysis I acidic/neutral drugs
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