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This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License rensic use of organic compoun University of Lincoln presentation

Organic Chemistry: Forensic use of organic compounds

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Lecture materials for the Introductory Chemistry course for Forensic Scientists, University of Lincoln, UK. See http://forensicchemistry.lincoln.ac.uk/ for more details.

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Page 1: Organic Chemistry: Forensic use of organic compounds

This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License

Forensic use of organic compounds

University of Lincoln presentation

Page 2: Organic Chemistry: Forensic use of organic compounds

This work is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 2.0 UK: England & Wales License

Fire accelerants Drugs

Petrol: It is petroleum-derived, and consists mostly of aliphatic hydrocarbons enhanced with iso-octane or the aromatic hydrocarbons toluene and benzene to increase its octane rating.Diesel:Diesel is produced from oil and is a hydrocarbon mixture, obtained in the fractional distillation of crude oil between 200 °C and 350 °C at atmospheric pressure

Butane Gas:consumedfrom lighters

Carbon tetrachloride:Used for solvent abuse

Hydrocarbons

Cl

Cl Cl

Cl

CH3

CH3

C4H10

CCl4

Page 3: Organic Chemistry: Forensic use of organic compounds

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Aromatic compounds

Fire accelerants

Toluene Benzene

Drugs

Explosives

Tri-Nitro Toluene (TNT)

Dyes

Alizarin

Benzodiazepines:Psychoactive drugs with varying hypnotic, sedative, anxiolytic, anticonvulsant, muscle relaxant and amnesic properties

CH3

CH3

N+

O-

O

N+

O-

O

N+

O-

O

NH N

O

O

O

OH

OH

Page 4: Organic Chemistry: Forensic use of organic compounds

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Alcohols

Fire accelerants Drugs

Explosives Dyes

4-hydroxybutanoic acid (GHB):Date rape drug. GHB has been used in cases of drug-related sexual assault

Ethyl Alcohol – Ethanol:(C2H5OH), flash point 13 oC; ignition temp. 365 oC; explosive limits 3.5%-19.0%

Glycerol or glycerine: Used as starting material for nitro-glycerine

BTTN :Military propellant for missiles: the mixturecan be made by co-nitration of butanetriol and glycerol

Sudan Red G: It is considered carcinogenic andgenotoxic

CH3 OH

OH

OH

OH

O

OH

OH

NN

OHO

CH3

Page 5: Organic Chemistry: Forensic use of organic compounds

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Aldehydes

Drugs Dyes

4-amino-3-nitrobenzaldehyde: Hair dye

O

O

O

NH2

O

N+

O-

OPiperonal: Precursor of MDMA (Ecstasy: 3,4-methylenedioxy-N-methylamphetamine)

Page 6: Organic Chemistry: Forensic use of organic compounds

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KetonesFire accelerants Drugs

Explosives Dyes

Acetone:(Dimethyl ketone)flash point -20 degrees C; ignition temperature 465.4 degrees C; explosive limits 2.6%-13.0%

ACETONE: precursor of TATP.TATP: The synthesis of the explosive is made through oxidation of acetone using hydrogen peroxide

Methcathinone: 2-(methylamino)-propiophenone.Psychoactive stimulant. Addictive. Can be smoked, injected, or taken orally .

9,10-dioxoanthracene

CH3 CH3

O CH3

NH

CH3

O

O

O

Page 7: Organic Chemistry: Forensic use of organic compounds

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Ethers

Fire accelerants Drugs

Dyes

Ethyl Ether - diethyl ether: flash point -45 degrees C; ignition temperature 180 degrees C; explosive limits 1.9% - 36%

Codeine: Opiate alkaloid

Rhodamine 123

CH3 O CH3 NCH3

O

OH

OH

OCH3

O

NH2

N+

H

H

O

Cl-

Page 8: Organic Chemistry: Forensic use of organic compounds

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Carboxylic acids

Drugs

Benzoylecgonine (ecgonine benzoate) is the primary metabolite of cocaine. It is formed in the liver by the metabolism of cocaine

O

O

N

CH3

OOH

Page 9: Organic Chemistry: Forensic use of organic compounds

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Esters

Fire accelerants Drugs

Explosives

Biodiesel refers to a non-petroleum-based diesel fuel consisting of short chain alkyl (methyl or ethyl) esters

Dibutylphatalate:Plasticizer used in explosives. Plasticizersare additives that increase the plasticity orfluidity.

Benzocaine (local anaesthetic) : Benzocaine is often favoured by drug dealers to bulk out their cocaine supplies.while many dealers use the cheaper paracetamol or corn flour, Benzocaine givesa numbing effect (like purer cocaine should have).

OCH3

O

CH3

OO

NH2

O CH3

O

Page 10: Organic Chemistry: Forensic use of organic compounds

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Amides

Drugs

Dyes Yellow 13: pigment

Fraud between drug dealers Lidocaine is often added to cocaine asa diluent because it numbs the gums when applied,giving the impression of higher cocaine purity

NN

NH

CH3

CH3O

CH3O

CH3

CH3

NH

O

O CH3

NN

ClCl

CH3

CH3

NHN CH3

CH3

O

Page 11: Organic Chemistry: Forensic use of organic compounds

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Amines

DrugsExplosives

Dyes

Indigo: found in foodstuff and textiles (jeans)

Hexanitrodiphenylamine: 40% part of an explosive called hexanite; rest 60% TNT. Obsolete explosive from WWII

Ephedrine: found in cold remedies, but used to Enhance performance. Overdose can lead to death.Similar chemical structure than methamphetamine

NH

N+

O-

O

N+

O-

O

N+

O-

ON

+O

-

O

N+

O-

O

N+

O-

O

NH

NH

O

O

NHCH3

CH3

OH

Page 12: Organic Chemistry: Forensic use of organic compounds

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Nitro-compounds

Explosives

2,3-dimethyl-2,3-dinitrobutane: used as a detection taggant for explosives. Added in C-4

RDX or cyclonite: main explosive In C-4.Military explosive

Picric acid:2,4,6-trinitrophenol (TNP): Like other highly nitrated compounds such as TNT, picric acid is an explosive

CH3

CH3

CH3

CH3

N+

O-

O

N+

O-

O

OH

N+

O-

O

N+

O-

O

N+

O-

ON

N

NN

+

O-

O

N+

O-

O

N+

O-

O

Page 13: Organic Chemistry: Forensic use of organic compounds

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Functional groups

Link to “Functional

Groups” video

Page 14: Organic Chemistry: Forensic use of organic compounds

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Acknowledgements

• JISC• HEA• Centre for Educational Research and Developmen

t• School of Natural and Applied Sciences• School of Journalism• SirenFM• http://tango.freedesktop.org