Peter T. AusiliPeter T. AusiliForensic Chemist, Drug Enforcement AdministrationForensic Chemist, Drug Enforcement Administration

North Central Laboratory North Central Laboratory

(Presented to September 19, 2006)(Presented to September 19, 2006)

Forensic ChemistryForensic Chemistry

The following presentation does not reflect the The following presentation does not reflect the commentscommentsand/or opinions of the Drug Enforcement and/or opinions of the Drug Enforcement Administration or the U.S. Department of Administration or the U.S. Department of Justice.Justice.

usajobs.govusajobs.gov

Forensic: Application of Forensic: Application of Science to Assist Legal Science to Assist Legal DecisionsDecisions

Rules of engagement:Rules of engagement:

You must ask questions – or I willYou must ask questions – or I willI am not here to lecture about drugs-I am not here to lecture about drugs-unfortunately, I can’t avoid the unfortunately, I can’t avoid the subject completely subject completely Learn something and have FUNLearn something and have FUN

IntroductionIntroductionChemistry Chemistry Legal IssuesLegal Issues

CapacitiesCapacitiesBicarb ?Bicarb ?

Pharmacology-Drug actionPharmacology-Drug actionMiscellaneousMiscellaneousAbout DEAAbout DEA

CHEMISTRYCHEMISTRY

Responsibility: Responsibility: Analysis and identification of ALL CONTROLLED Analysis and identification of ALL CONTROLLED SUBSTANCESSUBSTANCESIdentify all substances greater than 1%Identify all substances greater than 1%Determine Salt, Isomer and Purity as appropriateDetermine Salt, Isomer and Purity as appropriateIdentify Adulterants and DiluentsIdentify Adulterants and Diluents

Chemical AnalysisChemical Analysis::Sampling plan ?Sampling plan ?

Preliminary ScreeningPreliminary ScreeningConfirmation:Confirmation:

GC/MSGC/MSFTIRFTIRNMRNMRLC, LCMSLC, LCMSCE, CD-ORDCE, CD-ORDPurityPurity

LegalLegal Production CapacityProduction Capacity

Clandestine LaboratoriesClandestine Laboratories Theoritical YieldTheoritical Yield Substance containing vs. actualSubstance containing vs. actual

Why analyze Sodium Bicarbonate?Why analyze Sodium Bicarbonate? Sentencing commission guidelinesSentencing commission guidelines

(Cure for insomnia)(Cure for insomnia)

PharmacologyPharmacology Why do people use drugsWhy do people use drugsEffects mimic natural chemicals in the Effects mimic natural chemicals in the

bodybodySimilar chemical structure act on the same Similar chemical structure act on the same

receptor sites---with effects of different receptor sites---with effects of different intensity and durationintensity and duration

KHAT (Catha Edulis)KHAT (Catha Edulis)

CathineCathine

CathinoneCathinone

BackgroundBackground

•Primarily cultivated in East Africa and the Arabian Peninsula

•Legal throughout most of Europe and Africa

•Used since antiquity as a recreational and religious drug

• Used by Alexander the Great

• First historical reference in early 14th century

•Important to the economies of Somalia, Yemen, Kenya and Ethiopia

•More than 37 tons seized in the US in 2001 (EPIC)

Legal StatusLegal Status

- Cathinone- Schedule I Final Action 2/93 - Produces a euphoric effect similar to amphetamine in that it stimulates the Central nervous system - Begins to degrade 48 hours after harvesting

- Proper handling can prolong potency

- Cathine- Schedule IV Final action 6/88

Produces a much less stimulant effect that cathinone

Structural SimilaritiesStructural Similarities

Cathinone - I Cathinone - I

NH2

O

Cathine - IVCathine - IV

NH2

OH

Natural breakdownNatural breakdown

Structural SimilaritiesStructural Similarities

CathinoneCathinone

NH2

OCathineCathine

NH2

OH

AmphetamineAmphetamine

NH2

MethamphetamineMethamphetamine

NHCH3

Pharmacological SimilaritiesPharmacological Similarities

CathineCathine

NH2

OHPseudoephedrinePseudoephedrine

NHCH3

OH

AdrenalineAdrenaline

NHCH3

OH

OH

OH

Laboratory ConcernsLaboratory Concerns

•Handling and preservation of samples in the field

•Storage space in the laboratory

•Analysis-preservation-judicial integrity

•Since cathinone is labile (likely to undergo

chemical change) the preservation of the sample

after analysis is critical.

Historical CommentaryHistorical Commentary

..

KHAT is used in relatively poor regions, where the frequent KHAT is used in relatively poor regions, where the frequent lack of food encourages deficiency diseases. Consequently, lack of food encourages deficiency diseases. Consequently, in view of its stimulating effect, it is often not unnaturally in view of its stimulating effect, it is often not unnaturally regarded as a regarded as a divine blessing. divine blessing. For populations with relatively For populations with relatively few sources of distraction it constitutes a simple and few sources of distraction it constitutes a simple and convenient form of escapism.convenient form of escapism.

Since khat is regarded as an excitant and stimulant like Since khat is regarded as an excitant and stimulant like coffee, tea and the like, it is generally not considered coffee, tea and the like, it is generally not considered prohibited by Koranic law and consequently there is no moral prohibited by Koranic law and consequently there is no moral objection in Moslem countries against its abuse.objection in Moslem countries against its abuse. - Bulletin on Narcotics, 1956- Bulletin on Narcotics, 1956

Web sitesWeb siteswww.ncstl.orgwww.ncstl.orgwww.ussc.gov www.ussc.gov LycaeumLycaeumErowidErowid

ReferencesReferences

•PIHKALPIHKAL•TIHKALTIHKAL

CourtCourt• As experts, we are not advocates As experts, we are not advocates we can only seek scientific truthwe can only seek scientific truth• Unusual casesUnusual cases

• Ayahuasca > DMTAyahuasca > DMT

Drug mixturesDrug mixtures•Synergistic effectsSynergistic effects

•MDMAMDMA•MDAMDA•CaffeineCaffeine•LidocaineLidocaine•ProcaineProcaine•DiphenhydramineDiphenhydramine•DimethylsulfoneDimethylsulfone

About DEAAbout DEA

We are responsible for only 1 law We are responsible for only 1 law • Eight Chemical Analysis LabsEight Chemical Analysis Labs• One Computer Forensics LabOne Computer Forensics Lab• 200 Chemists/6000 Agents200 Chemists/6000 Agents• North Central Lab covers 13 StatesNorth Central Lab covers 13 States

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Abundance

Scan 622 (5.779 min): PMA.D44

122

789151 10765 134 16515011530 5837 98

4-Methoxyamphetamine (PMA) M. W. 165

CH2

N

CH CH3

HH

CH3O

Spectrum 33

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Abundance

Scan 685 (6.149 min): PMMA.D58

1217830 42 9151 65 148 164106 134 17811498

4-Methoxymethamphetamine (PMMA) M. W. 179

CH2

N

CH CH3

CH3H

CH3O

Spectrum 34