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CICAD/Doc.1733/09 Washington, DC 5 May 2009 Original: English ORGANIZATION OF AMERICAN STATES INTER-AMERICAN DRUG ABUSE CONTROL COMMISSION FORTY-FIFTH REGULAR SESSION OEA/Ser.L/XIV.2.45 May 6 - 8, 2009 CICAD/doc.1733/09 Washington, DC 5 May 2009 Original: English DR. STEVEN G. TOSKE SPECIAL TESTING AND RESEARCH LABORATORY U.S. DEPARTMENT OF JUSTICE DRUG ENFORCEMENT ADMINISTRATION (DEA) GENERAL SECRETARIAT OF THE ORGANIZATION OF AMERICAN STATES, WASHINGTON, D.C. 20006 ExtractionExtraction ofof MethamphetamineMethamphetamine PrecursorPrecursor MaterialMaterial fromfrom MedicinalMedicinal PreparationsPreparations andand MethamphetamineMethamphetamine ProfilingProfiling ResultsResults Dr. Steven G. Toske Special Testing and Research Laboratory CommonCommon MethamphetamineMethamphetamine PrecursorsPrecursors EphedrineEphedrine oror PseudoephedrinePseudoephedrine PhenylPhenyl--22--PropanonePropanone (P2P)(P2P) Pseudoephedrine/EphedrinePseudoephedrine/Ephedrine (Sources)(Sources) Ephedrine/PseudoephedrineEphedrine/Pseudoephedrine areare naturalnatural productsproducts thatthat cancan bebe isolatedisolated individuallyindividually fromfrom thethe EphedraEphedra plantplant commonlycommonly cultivatedcultivated inin ChinaChina andand India.India. EphedraEphedra productsproducts cancan bebe obtainedobtained inin tablettablet oror capsulecapsule formform asas partpart ofof dietdiet pills..pills.. Ephedra Plant Pseudoephedrine/EphedrinePseudoephedrine/Ephedrine (Sources)(Sources) PseudoephedrinePseudoephedrine HClHCl andand EphedrineEphedrine HClHCl cancan bebe producedproduced syntheticallysynthetically EphedrineEphedrine HClHCl isis usedused asas aa stimulant/decongestantstimulant/decongestant toto controlcontrol asthmaasthma PseudoephedrinePseudoephedrine HClHCl isis aa commoncommon ingredientingredient inin OverOver--thethe--CounterCounter decongestantdecongestant tabletstablets SimpleSimple ExtractionExtraction ofof TabletsTablets Grind Tablets Alcohol Filter Evaporate Resulting Powder Contains Pseudoephedrine or Ephedrine TabletTablet BinderBinder ExtractionExtraction WasteWaste ColdCold andand FluFlu PreparationsPreparations ContainingContaining PseudoephedrinePseudoephedrine HydrochlorideHydrochloride Soft Liquid Filled Gel Capsules Liquid Tablets Coated Tablets ColdCold andand FluFlu PreparationsPreparations ContainingContaining PseudoephedrinePseudoephedrine HydrochlorideHydrochloride Pseudoephedrine HCl Product Form Co-Ingredients per dose (mg) 1 tablets 30 acetaminophen (500 mg) acetaminophen (500 mg) coated tablets 30 2 diphenhydramine HCl (25 mg) acetaminophen (250 mg) soft gelatin 30 dextromethorphan HBr (10mg) 3 capsules guaifenesin (100 mg) soft gelatin acetaminophen (325 mg) 30 4 capsules dextromethorphan HBr (15 mg) 30 acetaminophen (500 mg) 5 liquid dextromethorphan HBr (15 mg) (15 mL) doxylamine succinate (7.25 mg) Acid/BaseAcid/Base TabletTablet ExtractionExtraction Grind Tablets Add Powder into Hot Water Coated Tablet Powder Passed through and Stir Sieve to Remove Large Pieces of Coating Adjust pH to 1 with HCl Extract 3 Times with Ether (Muriatic Acid Can Be Used) (Starter Fluid Can Be Used) AAcid/Basecid/Base TabletTablet ExtractionExtraction Discard Ether Washes Adjust pH to 12 with NaOH (Common Drain Cleaner Can Be Used) Extract 3 Times with Ether Collect Ether Containing Pseudoephedrine Acid/BaseAcid/Base TabletTablet ExtractionExtraction Wash Ether with Water then Pour or Filter Ether to Another Dry Using Sodium Sulfate Beaker for Evaporation Final Pseudoephedrine Powder ColdCold andand FluFlu PreparationsPreparations ExtractionExtraction ResultsResults Purity of Recovered Yield* Other Drugs Product Form Pseudoephedrine (%) Still Present Base (%) 1 tablets 99 58 None acetaminophen coated 46 40 2 tablets diphenhydramine dextromethorphan soft gelatin 51 45 3 capsules guaifenesin soft gelatin dextromethorphan 4 capsules 90 46 dextromethorphan liquid 66 75 5 doxylamine *Percentage of Pseudoephedrine Recovered, Calculated as Pseudoephedrine HCl AllergyAllergy andand DecongestantDecongestant PreparationsPreparations ContainingContaining PseudoephedrinePseudoephedrine Pseudoephedrine Additional Drugs Product Form per dose (mg) Present 6 12 Hour tablets 120* loratadine (5mg) Release 7 24 Hour tablets 240* loratadine (10mg) Release 8 guaifenesin tablets 60** Extended (600mg) Release *Pseudoephedrine Sulfate **Pseudoephedrine HCl ExtractionExtraction ResultsResults Extraction Dosage Purity of Recovered Yield Product Procedure Units Used Pseudoephedrine Base (%) (%) 6 (12 hour) 1 20 95 60 6 1 10 96 62 7 (24 hour) 1 20 43 3 7 2 10 25 8 7 3 5 70 38 7 4 5 46 10 7 5 10 66 26 7 6 10 89 22 7 7 10 71 9 Loratadine was present in all pseudoephedrine extracts Product 8 ExtractionExtraction ResultsResults Dosage Theoretical Amount Purity of Recovered Units Weight Pseudoephedrine Yield Pseudoephedrine Used Pseudoephedrine Recovered (mg) (%) Base (%) (800 mg) Base (mg) (as base) 4 41* 196.5 98.3 50** *Extract also contained 56% guaifenesin. **Best Result after Several Poor Yielding Attempts Using Procedure 1. ExtractionExtraction ConclusionsConclusions InIn allall cases,cases, pseudoephedrinepseudoephedrine waswas extractedextracted outout withwith varyingvarying degreesdegrees ofof successsuccess (3%(3% toto 75%75% yields).yields). TheThe selectedselected acid/baseacid/base extractionextraction workedworked wellwell onon thethe pseudoephedrine/acetaminophenpseudoephedrine/acetaminophen tablets.tablets. Also,Also, extractionextraction ofof thethe 12h12h timetime releaserelease tabletstablets waswas efficient.efficient. LowerLower pseudoephedrinepseudoephedrine puritiespurities werewere observedobserved whenwhen otherother activeactive drugsdrugs werewere present.present. TheThe selectedselected extractionextraction methodsmethods usedused areare notnot amenableamenable forfor scalingscaling upup forfor thethe extendedextended releaserelease formulations.formulations. However,However, therethere areare otherother extractionextraction methodsmethods availableavailable onon thethe internetinternet whichwhich maymay bebe effective.effective. MethamphetamineMethamphetamine ProfilingProfiling ProgramProgram SelectedSelected samplessamples fromfrom thethe sevenseven U.S.U.S. regionsregions areare suppliedsupplied byby sevenseven DEADEA regionalregional labs.labs. SamplesSamples representingrepresenting thethe MexicoMexico andand CanadaCanada regionsregions areare obtainedobtained fromfrom borderborder oror PortPort--ofof--EntryEntry seizures.seizures. ForeignForeign samplessamples havehave beenbeen obtainedobtained mainlymainly fromfrom supportsupport toto otherother governments.governments. SinceSince 4Q4Q--2004:2004: Purity,Purity, Isomer,Isomer, CuttingCutting Agent,Agent, OTCOTC Impurity,Impurity, andand SyntheticSynthetic RouteRoute TrendsTrends havehave beenbeen establishedestablished andand monitored.monitored. MPP Regions 4Q4Q--20082008 PurityPurity TrendsTrends (162(162 Samples)Samples) MPP Overall Small Medium Large Region Purity Seizures Seizures Seizures Northwest 63.6 46.3 73.5 88.1* Southwest 76.5 66.7 71.8 91.4 North Central 51.2 44.1 59.0* 100* South Central 52.2 44.9 35.3 80.1 Northeast 73.0 68.1 NA 79.6 Southeast 50.4 47.0 49.9 82.3 Pacific 97.0 96.7* 97.2* NA Mexico 97.0 99.1* 94.7 97.4 Canada NA NA NA NA Foreign 97.5 97.5* NA NA Average Purity 71.4 54.7 68.2 92.7 Small Seizure: 6 g to 100g Medium Seizure: 101 g to 999 g Large Seizure: > 1000 g * Only one sample was available in this category for the purity calculation. 100 d d- 95 Isomer Trend Line 90 85 Percent80 75 70 65 60 U.S. Combat Meth Act Signed into Law 4Q-2004 1st Half-2005 2nd Half-2005 1st Half-2006 2nd Half-2006 1Q through 3Q-2007 4Q-2007 1Q-2008 2Q-2008 d-isomer 3Q-2008 4Q-2008 PercentagePercentage ofof AntihistamineAntihistamine DrugsDrugs DetectedDetected asas TraceTrace ComponentsComponents 4Q4Q--20082008 (162(162 Samples)Samples) ChlorpheniramineChlorpheniramine 46%46% TriprolidineTriprolidine 35%35% LoratadineLoratadine 17%17% BrompheniramineBrompheniramine 10%10% DextromethorphanDextromethorphan 5%5% CarbinoxamineCarbinoxamine 1%1% Triprolidine/ChlorpheniramineTriprolidine/Chlorpheniramine 23%23% AntihistamineSamples ContainingImpurities 70 65 60 55 50 45 Percentage of Samples 40 35 30 2nd Half-2006 1Q through 3Q-2007 4Q-2007 1Q-2008 2Q-2008 Q 2 0 Antihistamine 3 - 0 8 Impurities 4Q-2008 SyntheticSynthetic RouteRoute DeterminationDetermination (4Q(4Q--2008)2008) 78% - Showed Evidence of Being Prepared from Formulated Pseudoephedrine or Ephedrine Precursor 32% Phosphorus- Iodine Method 47% P2P Method Mixed Methods <1% Birch Method Unknown 8% Method 12% Questions???Questions??? Contact Information: Dr. Steven G. Toske Senior Research Chemist DEA Special Testing and Research Laboratory 22624 Dulles Summit Ct. Dulles, VA 20166 U.S.A. (703) 668-3332 Email: [email protected].
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