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Drugs and Pharmacology

Drugs and Pharmacology. Drugs Substances capable of a physiological change Swallowing, injection, inhalation, absorption “ All substances are poisons…the right dose differentiates a poison from a remedy ” (Paracelsus 1493-1541) Medicines

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Drugs and Pharmacology

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  1. Drugs and Pharmacology • Drugs • Substances capable of a physiological change • Swallowing, injection, inhalation, absorption • “All substances are poisons…the 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

  2. 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

  3. 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.

  4. Abused drugs in the USA

  5. Toxicity v. effective doses of drugs Gable, R.S. The Toxicity of Recreational Drugs. American Scientist2006, 94, 206-208

  6. 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

  7. 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

  8. Cannabinoids • 7 • 9 • 10 • 1 • 8 • 2 • 6 • 1 • 10a • 7 • 3 • 2’ • 2 • 6a • 5 • 3’ • 4 • 1’ • 6 • 3 • 4’ • 4 • 5’ • Dibenzopyran Numbering • Monoterpene Numbering • D9 – Tetrahydrocannabinol (D9-THC), Natural Product = D1-THC

  9. 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

  10. Cannabinoids • 11-Hydroxy D9-THC • 8b-Hydroxy D9-THC • 8-Keto D9-THC • 11-Nor-9-Carboxy-1’-Hydroxy D9-THC • Metabolites of D9-THC

  11. 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.

  12. C4NH10 • Substituted Group for • Triptamines, RT • Indole Ring System

  13. Bufotenin • 5-hydroxy-N,N-dimethyltryptamine • O-Acetylpsilocin • 4-acetoxy-N,N-dimethyltryptamine • Psilocybin • 4-phosphoryloxy-N,N-dimethyltryptamine • Psilocybin, Bufotenin, O-Acetylpsilocin, Zolmitriptan, and Sumatriptan • Sumatriptan • 5-(methylaminosulfonylmethylene)-N,N-dimethyltryptamine • Zolmitriptan • 5-( 4-(S)-1,3-oxazolidin-2-one)-N,N-dimethyltryptamine

  14. JWH-122 • (4-​methyl-​1-​naphthalenyl)(1-​pentyl-​1H-​indol-​3-​yl)-​methanone • JWH-018 • (1-​pentyl-​1H-​indol-​3-​yl)-​1-​naphthalenyl-​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-​naphthalenyl-​methanone

  15. UR-144 • [ 1-Pentylindo 1-3-yI]-( 2,2, 3,3-tetramethylcyclopropyl) • methanone • 5F-UR-144 • [1-(5-fluoropentyl)indol-3-yl]-(2,2,3,3-tetra-methylcyclopropyl)methanone

  16. R1 • R2 • Indole Ring System

  17. JWH-018 • (1-​pentyl-​1H-​indol-​3-​yl)-​1-​naphthalenyl-​methanone • 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 • AM2201 • [1-​(5-​fluoropentyl)-​1H-​indol-​3-​yl]-​1-​naphthalenyl-​methanone • MAM2201 • [1-​(5-​fluoropentyl)-​1H-​indol-​3-​yl](4-​methyl-​1-​naphthalenyl)-​methanone

  18. JWH-018 • JWH-122 • JWH-210 • AM2201 • AM2201 • 5F-UR-144 • UR-144

  19. RT

  20. According to Drug Data Sheet from Cayman Chemical

  21. 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/

  22. Ergot and tryptamine alkaloids and hallucinogens • Psilocybin/psilicin • From mushrooms www.drug-information-resource.com/ www.potseeds.co.uk

  23. 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

  24. 4 • 3 • 5 • 2 • 6 • 7 • 1 • Indole Ring Structure with Points of Substitutions 1-7.

  25. C4NH10 • Substituted Group for • Triptamines, RT • Indole Ring System

  26. 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-dimethyltryptamine • Sumatriptan • 5-(methylaminosulfonylmethylene)-N,N-dimethyltryptamine

  27. Bufotenin • 5-hydroxy-N,N-dimethyltryptamine • O-Acetylpsilocin • 4-acetoxy-N,N-dimethyltryptamine • Psilocybin • 4-phosphoryloxy-N,N-dimethyltryptamine • Psilocybin, Bufotenin, O-Acetylpsilocin, Zolmitriptan, and Sumatriptan • Sumatriptan • 5-(methylaminosulfonylmethylene)-N,N-dimethyltryptamine • Zolmitriptan • 5-( 4-(S)-1,3-oxazolidin-2-one)-N,N-dimethyltryptamine

  28. Tryptamines b a • 4 • 3 • 5 • 2 • 6 • 1 • 7 • Tryptophan • Tryptamine

  29. 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

  30. Phenethylamine • 2 • N a • 3 b • 4 • 6 • 5

  31. Phenethylamine • MDMA – Molly - Ecstacy • MDEA – Eve • Methamphetamine • Dopamine • Epinephrine

  32. Methamphetamine synthesis Requires Li (from batteries?) and ammonia (from fertilizers) Involves red-phosphorous (from matches) Can produce phosphine gas (PH3)

  33. Tropane alkaloids and cocaine

  34. Tropane alkaloids and cocaine

  35. Tropane alkaloids and cocaine

  36. 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

  37. Benzodiazepaines & SSRI • Valium® (diazepam), Xanax®, Prozac® (Fluoxetine) Prozac® Valium® Xanax®

  38. Drug analysis I: acidic/neutral drugs

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