Chemical Control Actions
Liqun L. Wong
Chief
Data Analysis Unit
Drug & Chemical Evaluation Section
Office of Diversion Control
Drug Enforcement Administration
10th DEA Chemical Industry Conference
Atlanta, Georgia
September 17-18, 2008
Chemical Control
• Controlled Substances Act (1970)
the principal federal law directed at combating the illicit manufacture and
distribution of controlled drugs in the United States. Since its passage
in 1970, the CSA has been amended on a number of occasions
• Chemical Diversion and Trafficking Act (CDTA, 1988)
¾ regulated 12 precursor chemicals, eight essential chemicals, tableting
machines, and encapsulating machines
¾ resulted in the incorporation of Article 12 into the U.N. Convention
Against Illicit Drug Traffic of 1988 (the Vienna Convention)
2.
Chemical Control
• Domestic Chemical Diversion Control Act (DCDCA,1993)
¾ Eliminated single entity ephedrine tablet loophole
¾ No controls on Combination EPH, PSE, PPA
• Comprehensive Methamphetamine Control Act
(MCA1996)
¾ Control drug products containing EPH, PSE, PPA
• Methamphetamine Anti-Proliferation Act (MAPA, 2000)
¾ Reduce transaction threshold from 24g to 9g of PSE and PPA
¾ Blister pack exempted
• Combat Methamphetamine Epidemic Act (CMEA, 2005)
Chemical Control Background
• Total of 40 List I and List II chemicals
• List I chemical handlers (Importers/Exporters/
Manufacturers/Distributors) must:
– registration
– maintain records
– report suspicious orders
• Through industry outreach and voluntary
compliance measures, DEA strives to
control chemical diversion in partnership
with industry and the public.
• DEA routinely inspects records and
required controls
3.
Examples of List I and List II Chemicals
• List I
– Acetic anhydride → heroin synthesis
– Benzaldehyde → amphetamine synthesis
– Ergotamine → LSD synthesis
– Phenylacetic acid → P2P synthesis
– Hypophosphorus acid → am/meth synthesis
– Safrole → MDA/MDMA synthesis
• List II
– Potassium permanganate → cocaine purification
4.
Recent Chemical Controls Actions
• Removal of Ephedrine/Pseudoephedrine Mixture
Exemptions
• Recent Controls Fentanyl Precursors
¾ NPP (List I, April 23, 2007)
¾ ANPP (proposed Schedule II, comment period ended June 9,
2008)
• Iodine and Mixture Regulations
• Under consideration:
¾ Ergocristine LSD
¾ L-Phenylacetylcarbinol Ephedrine
¾ Acetylpseudoephedrine Meth
¾ Isopropylbenzylamine Fake Meth
7.
Ephedrine/ Pseudoephedrine Exemptions
Final Rulemaking [68 FR 23195] published on May 1, 2003-
• created an exemption for all chemical mixtures containing
five percent or less total ephedrine/pseudoephedrine.
• created an exemption for chemical mixtures consisting of
unaltered harvested plant material containing ephedrine
alkaloids (e.g. ephedra).
Ephedrine/ Pseudoephedrine Concerns
¾ Ephedra and dietary supplements containing ephedra
used as the source of the precursor material for the illicit
production of methamphetamine.
¾ FDA has taken action to eliminate ephedra dietary
supplements from the U.S. market
¾ increase in importation of below 5% ephedra chemical
mixtures from China to circumvent regulations
Changes in
Ephedrine/Pseudoephedrine Controls
Implement the CMEA, Interim Final Rule effective August
24, 2007:
¾ originally set at 5% to capture bulk ephedra (ma
huang) that historically at concentration of 6-8%
ephedrine
¾ Chemical Mixtures containing <5% total ephedrine
/pseudoephedrine become regulated
Number of Deaths
0
20
40
60
80
100
120
140
160
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Time (Months)
6
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Illicit Fentanyl Death Database
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Illicitly Manufactured Fentanyl-Related Deaths in U.S.
Fentanyl Lab in Toluca, Mexico
Sunday, May 21, 2006 PGR/SIEDO and AFI
LA Area Fentanyl / MDA Lab
¾ November 2005, law
enforcement seized a lab in
the LA area suspected to be
Fentanyl lab.
¾ Chemists analyzed the
samples submitted and
confirmed fentanyl and MDA
present.
¾ A 5 kilogram bag of “NPP” (1-
phenethyl-4 piperidone)
precursor was seized.
Fentanyl Synthesis - Siegfried Method
N O N N
NPP NPP imine
O
H
N N N N
HCl
Fentanyl hydrochloride ANPP
N-Phenethyl-4-piperidone (NPP)
77 FR20039 effective April 23, 2007
¾ NPP becomes List I chemical
¾ Chemical mixtures containing NPP are not exempt from
regulatory requirements at any concentration
¾ All transactions (domestic & International) involving NPP,
regardless of size, shall be regulated
ANPP Federal Register
¾ Federal Register Notice of Proposed
Rulemaking closed June 9, 2008
¾ Designates 4-anilino-N-phenethyl-4-piperidine
(ANPP) as an immediate precursor to a
schedule II controlled substance
¾ ANPP controlled as schedule II substance,
subject to quota requirement
Legitimate Uses of Iodine
¾In medicine, iodine tincture is used as a
disinfectant
¾In the manufacture of compounds used
in photography (e.g. silver iodide which
is a light sensitive material used in film)
¾In the manufacture of dyestuffs and
drugs
¾as a reagent in analytical chemistry and
precursor in organic synthesis
Production of Iodine
¾ from the liquor remaining after the extraction of
potassium nitrate from saltpeter found in deposits in
Chile,
¾ by extraction from the ash from the combustion of
seaweed. In the process, the sea-weeds are burnt in
shallow pits and the resulting kelp (i.e. the ash from the
process) contains potassium salts and from 0.4 per
cent to 1.3 per cent of iodine in the form of iodide salts
(e.g. potassium iodide),
¾ in a wet extraction of the seaweed with sodium
carbonate solution is prepared and an organic adhesive
is precipitated on acidifying of this solution, and
¾ by extraction from salt brine
Iodine Diversion
• Widely used in clandestine laboratories with
application in large-scale methamphetamine synthesis
• 7% tincture - a source of iodine and was exempted
Meth Lab Seizures
Year I2 HI Labs
1999 2232 637 7446
2000 2751 652 9112
2001 3952 716 13460
2002 4421 743 16241
2003 5098 655 17615
2004 5140 581 17774
2005 3261 338 12626
2006 1760 157 7177
Source: NSS
Iodine and the Clandestine
Methamphetamine Laboratory
Iodine is added to a solution of ephedrine or
pseudoephedrine with phosphorus to
produce methamphetamine
Ephedrine Iodine
or and
Pseudoephedrine Phosphorus
Heat
Methamphetamine
Chemicals from a Lab Seizure
Iodine Seized in Clan Labs
Veterinary products from clan labs, source of iodine
More Iodine in Clan Labs
Iodine at clandestine lab Iodine at a dumpsite
Internet Procedure –
Extraction of Iodine from Tincture
Recent Controls Iodine
¾ Moved from List II to List I
¾ Impose registration requirements
¾ Capture 7% iodine tincture
¾ Zero threshold - Control imports and exports
¾ Control chemical mixtures containing >2.2%
¾ Exemption of iodophors/organically bound
compounds
7.
Comparison of Iodine Regulations
Past Current
List II Chemical List I Chemical
0.4 Kilogram
No Threshold
Threshold
Domestic Transactions All
Regulated Transactions
Chemical Mixtures Chemical Mixtures
Not Regulated <2.2% Exempt
Iodine Product Exemptions
¾1 package of Lugol’s Solution (30 mL)
per transaction
¾Chemical Mixtures below 2.2%
2% Iodine Tincture
¾Iodophors
¾Organic bonded Iodine
What is an Iodophor?
• Carrier of iodine generally consisting of a
complex with a polymer or surfactant
• Provides a sustained release of iodine
• Primarily used as a disinfectant
I3
H
O O O
N N N
HC CH CH
C C ...........
C
H2 H2 H2
Example of an Iodophor: PVP-Iodine Complex
Common Iodophor Products
¾ Betadine
¾ Biopal CVL-10
¾ Idonxy
¾ Kleenodyn
¾ Wescodyne
¾ Westamine X
Iodophor as a Source of Iodine
¾It has been demonstrated that betadine
can be used as a source for I2
¾By heating of the solution and trapping
the vapors
¾Method requires a large amount of
iodophor and is a lengthy process
Extraction of Iodine from Iodophor
Discussion forums describe the extraction of
iodine from betadine by sublimation
1. The iodophor solution is heated to dryness
1. Continued heating of the solid and the presence
of a cold surface (cold finger, condenser, etc.)
results in the collection of iodine crystals
Potassium Iodide - Source of Iodine
Beginning to see the use of KI as a source
of iodine
2KI + 2HCl + H2O2 Æ I2 + 2H2O + 2KCl
2KI + MnO2 + 3H2SO4 Æ I2 + MnSO4 + 2H2O + 2KHSO4
2KI + Cl2 Æ I2 + 2KCl
Fake Methamphetamine - Benzylamines
• Numerous evidence samples testing positive for
amphetamines
– Las Vegas, NV; Phoenix, AZ; Nogales, AZ; San
Diego, CA, DC
• benzylmethylamine, benylethylamine, and
isopropylbenzylamine
• Available chemical suppliers
• Believed to be counterfeit Meth because:
– show positive for meth field test
– have a similar crystalline structure/ appearance
• Pure, cut and mixed with methamphetamine
• Can be synthesized to methamphetamine
• Gathering data and under evaluation
Benzylamines
1
R
N
H
R = methyl; benzylmethyamine
R = ethyl; benzylethylamine
R = isopropyl; benzylisopropylamine
1
2
HN
methamphetamine
L-Phenylacetylcarbinol (L-PAC)
• Molasses-based fermentation by yeast used to make ephedrine
• Specialized Process: Difficult in Clan Lab Setting (However one
lab in Australia)
Benzaldehyde
biotrans
+ L-PAC Ephedrine
Pyruvate
¾ L-PAC production is the difficult step
¾ Final step in ephedrine production easy
(same as producing meth from P2P using methylamine)
N-Acetylpseudoephedrine (APSE)
• Not Controlled under the CSA
• Pseudoephedrine with an attached acetyl group
OH OH
N N NH
H
O
Pseudoephedrine APSE Meth
• Acetyl group can be added and removed with acid or base
(also, formyl and benzoyl group)
• Can convert to Pseudoephedrine first or run reaction via HI/Red
P directly to meth with 44% yield
Contact Us
Drug Enforcement Administration
Office of Diversion Control
Drug & Chemical Evaluation Section
(202) 307-7183
Christine A. Sannerud, PhD, Chief
[Link]@[Link]
