- INTELLIGENCE ALERT - ?SPICE? - PLANT MATERIAL(S) LACED WITH SYNTHETIC
The Customs and Border Protection (CBP) - Chicago Laboratory (Illinois) recently received five small, resealable, bright foil packets containing dull olive-colored plant material(s), labelled as ?Spice Gold,? ?Spice Silver,? ?Spice Diamond,? ?Genie,? and ?Yucatan Fire? incense (see Photo 1, right, and Photos 2 - 3, next page), all reputedly laced with various synthetic cannabinoids or synthetic cannabinoid mimicking compounds, notably ?HU-210? [(6aR,10aR)-9-(hydroxymethyl)-6,6-dimethyl-3-(2-methyloctan-2-yl)-6a,7,10,10a-tetrahydrobenzo[c]chromen-1-ol); see Figure 1, next page]. The exhibits were selected from a shipment containing approximately 1,500 such packets that were detained by a CBP agricultural specialist at an express parcel service hub in Wilmington, Ohio. The items were not smuggled but were rather part of a formal entry. Standard marijuana analyses (microscopy) of the materials were negative. Analysis of extracts by GC/MS in the scan mode with split injection indicated only the presence of a large amount of vitamin E and other, smaller amounts of various natural products. However, when the extracts were derivatized with N,O-bis(trimethylsilyl)acetamide and injected splitless with selected ion monitoring, HU-210 was found in very small but verifiable amounts in every packet (not quantitated). The results were confirmed against a standard. These were the first such submissions to the laboratory.
[Additional Laboratory and Editor?s Notes: In addition to the above-named products, there are at least two other such herbal products: ?Skunk,? and ?Sence.? These products are currently being encountered nationwide. They, and the synthetic cannabinoids and cannabinoid mimic compounds they contain, are also the subjects of widespread discussion and speculation on the Internet. Based on anecdotal reports, HU-210 is hundreds of times more potent than THC; thus, the trace amounts detected in the above case are physiologically active, and these materials may be viewed as ?stealth marijuana.? The reference standard of HU-210 used in this case was purchased from Cayman Chemical of Ann Arbor, Michigan. The ions selected for the analysis were m/z 446 (100%), 530 (molecular ion), 447, 474, and 356. Note that HU-210 is named in several different ways; for example: (6aR,10aR)-3-(1,1'-dimethylheptyl)-6a,7,10,10a-tetrahydro-1-hydroxy-6,6-dimethyl-6H-dibenzo[b,d]pyran-9-methanol. HU-210 is controlled (Schedule I) in the U.S. (See: http://www.deadiversion.usdoj.gov/drugs_concern/spice/spice_hu210.htm), and products containing it and similar cannabinoids are controlled within the U.S. and in a number of other countries, including Austria, Canada, Germany, the Netherlands, and Switzerland. In addition to HU-210, there are at least half a dozen other compounds with similar structures, plus several unrelated compounds that have cannabinoid mimicking effects (notably JWH- 018 (1-pentyl-3-(1-naphthoyl)indole)), that are being used to adulterate the plant materials in ?Spice? and similar products. An article presenting mass spectral data and background information on these compounds was recently published on line (not yet published in hard copy); see: Auwarter V, Dresen S, Weinmann W, Muller M, Putz M, Ferreiros N. ?Spice? and other herbal blends: Harmless incense or cannabinoid designer drugs? Journal of Mass Spectrometry 2009.] * * * * * - INTELLIGENCE ALERT -
BLOTTER ACID MIMIC (ACTUALLY CONTAINING A MIXTURE OF 4-CHLORO-2,5-DIMETHOXYAMPHETAMINE AND 4-BROMO-2,5-DIMETHOXYAMPHETAMINE) IN WARNER ROBINS, GEORGIA The Georgia Bureau of Investigation - Central Regional Crime Laboratory (Macon) recently received one square of tie-dyed blotter paper, suspected LSD (see Photo 4). The exhibit was seized in Warner Robins (approximately 25 miles south of Macon) by personnel from the Houston County Sheriff?s Office, pursuant to a domestic dispute call. Analysis of extracts by GC/MS and HPLC, however, indicated not LSD but rather a 2 : 1 mixture of 4-chloro-2,5- dimethoxyamphetamine (DOC) and 4-bromo-2,5-dimethoxyamphetamine (DOB) (not quantitated but a moderate loading based on the TIC). The Georgia Bureau of Investigation has previously seen blotter acid mimics that contained either DOC or DOB, but this is the first submission that contained a mixture of both compounds. * * * * * - INTELLIGENCE ALERT - "LEMMON 714" QUAALUDE MIMIC TABLETS (ACTUALLY
The DuPage County Crime Laboratory (Wheaton, Illinois) recently received one partial and five whole white, round tablets, 14 millimeters in diameter, with a ?LEMMON 714? logo on one face and single-scored on the opposite face, apparent Quaaludes (see Photo 5). The exhibits were seized by a local agency investigating a drug overdose (details sensitive). Analysis of methanol and chloroform extracts of one tablet (mass 0.88 gram) by GC/MS, however, indicated not methaqualone but rather diazepam (not quantitated, but a high loading based on the TIC). This was the first ever submission of Quaalude mimic tablets to the laboratory. [Editor?s Note: An overview of similar diazepam-containing ?LEMMON 714? Quaalude mimic tablets was presented in a recent issue; see: Microgram Bulletin 2007:40(1):5-6.]
* * * * * - INTELLIGENCE ALERT - ECSTASY MIMIC TABLETS (ACTUALLY CONTAINING DIPHENHYDRAMINE
The Lake County Crime Laboratory (Painesville, Ohio) recently received a submission of eight round, blue tablets imprinted with a logo of two females back-to-back and four round, purple-speckled tablets imprinted with a logo of an automobile (see Photos 6 and 7), and a separate submission of another one of the blue tablets, all suspected Ecstasy. The first set of tablets were acquired in Lake County (approximately 40 miles east of Cleveland) by an unnamed police department (no further details). The single tablet was also seized in Lake County, but by a different police department (also unnamed), incidental to a traffic stop. Both sets of tablets were approximately 8 millimeters in diameter and 4 millimeters thick. Analysis of the blue tablets (approximately 300 milligrams each) by color testing, GC/MS, and FTIR, however, indicated not MDMA but rather diphenhydramine. Analysis of the purple-speckled tablets (approximately 365 milligrams each) by the same techniques indicated a 3 : 1 mixture of diphenhydramine and caffeine. In both cases, the loading of the diphenhydramine was fairly high (not formally quantitated). These are the first submissions of Ecstasy mimic tablets containing only diphenhydramine or a diphenhydramine/caffeine mixture to the laboratory. * * * * * - INTELLIGENCE ALERT - ECSTASY MIMIC TABLETS (ACTUALLY CONTAINING A MIXTURE OF The Canton-Stark County Crime Laboratory (Canton, Ohio) recently received two round tablets, one small and green and the other typically sized and blue, alleged ?Triple Ecstasy? (purportedly an unusually potent form of Ecstasy; no photos). The exhibits were acquired in Alliance, Ohio (east of Canton) by an Alliance Police Department Special Investigative Unit (no further details). The green tablet was approximately 5 millimeters in diameter and 5 millimeters thick, weighed 170 milligrams, and had a 5-point star logo. The blue tablet was approximately 8 millimeters in diameter and 5 millimeters thick, weighed 270 milligrams, and had a deeply cut triangle logo. Analysis of both tablets by color testing (Marquis - negative), FTIR, and GC/MS, however, indicated not MDMA but rather a 3 : 2 mixture of 1-(3-chlorophenyl)piperazine (mCPP) and caffeine (not quantitated but a high loading based on the TIC). This is the first submission of Ecstasy mimic tablets containing mCPP, and also the first submission of a small Ecstasy mimic tablet, to the laboratory. * * * * * - INTELLIGENCE ALERT - OXYCONTIN MIMIC TABLETS (ACTUALLY CONTAINING A MIXTURE
The DEA Western Laboratory (San Francisco, California) recently received two round biconvex tablets, 9 millimeters in diameter, with ?OC? imprinted on one face and ?80? on the opposite face, apparent OxyContin (see Photos 8 and 9). The exhibit was acquired in Seattle, Washington by personnel from the DEA Seattle Field Division (no further details). The tablets had a green coating over a compressed, light brown powder (actual OxyContin tablets have a lighter green coating compressed white powder). Analysis of the tablets (total net mass 0.56 grams) by GC/MS, GC/FID, FTIR/ATR, and 1H-NMR, however, indicated not oxycodone but rather a mixture heroin (11.6 milligrams/tablet), caffeine (not quantitated), and lactose. This is the first known submission of OxyContin mimic tablets containing heroin to the Western Laboratory. * * * * * - INTELLIGENCE ALERT - ECSTASY COMBINATION TABLETS (CONTAINING MDMA,
The DEA Mid-Atlantic Laboratory (Largo, Maryland) recently received one plastic bag containing a total of 236 round blue tablets imprinted with a fly logo on one face and an indiscernible logo on the opposite face (possibly a bear or a buffalo), and 262 round blue tablets imprinted on one face only with the indiscernible (bear/buffalo) logo, both approximately 8.5 millimeters in diameter, suspected Ecstasy (see Photo 10). The exhibits were acquired in Stafford, Virginia by personnel from the Bureau of Alcohol, Tobacco, Firearms, and Explosives. Analysis of the double imprint tablets (total net mass 77.8 grams) by GC/FID, GC/MS, and LC indicated 49.7 milligrams/tablet MDMA, 14.1 milligrams/tablet methamphetamine, and caffeine (not quantitated). Analysis of the single imprint tablets (total net mass 84.7 grams) by the same techniques indicated 46.9 milligrams/tablet MDMA, 12.6 milligrams/tablet methamphetamine, and caffeine (again not quantitated). These were the first submissions of Ecstasy combination tablets with these logos, and also the first submission of Ecstasy combination tablets with logos on both faces, to the Mid-Atlantic Laboratory. * * * * * - INTELLIGENCE ALERT - l-METHAMPHETAMINE IN HAMMOND, INDIANA AND CHICAGO, ILLINOIS The DEA North Central Laboratory (Chicago, Illinois) recently received two submissions, each containing five oblong packages of yellow, crystalline materials, suspected methamphetamine (no photos). The first set was seized by DEA Chicago Field Division personnel from an impounded vehicle in Hammond, Indiana, while the second set was seized by DEA Chicago Field Division personnel pursuant to a warrant search in Chicago (no further details). All ten packages were successively wrapped in layers of clear plastic, baby wipes, and black electrical tape. Analysis of the crystalline material (total net mass 4.3 kilograms) by GC/FID, GC/MS, and IR indicated 95 - 99 % methamphetamine hydrochloride. Additional analysis following derivatization with N-trifluoroacetyl-L-prolyl chloride by GC/FID and GC/MS, however, indicated not d-methamphetamine but rather l-methamphetamine (isomer purity not determined, but high). The North Central Laboratory has received several submissions of l-methamphetamine; however, these are the first large submissions of l-methamphetamine in recent years. * * * * * - INTELLIGENCE ALERT - CAPTAGON MIMIC TABLETS (CONTAINING d,l-AMPHETAMINE, The DEA Special Testing and Research Laboratory (Dulles, Virginia) recently received two separate submissions containing a combined total of 9,382 round tablets of four different colors, all biconvex and imprinted with a Captagon-like logo on one face and a single score on the reverse side, apparent Captagon (fenethylline; no photos). The exhibits were seized in Al Anbar Province, Iraq by U.S. Department of Defense personnel (no further details). The first exhibit contained 4,860 white tablets (8.1 x 3.4 millimeters, total net mass 871 grams), all contained in a package illustrated with an ad for a Toyota SUV and containing a small packet of silica beads (as a desiccant). Analysis by color testing (Marquis, silver nitrate, and barium chloride), GC/FID, GC/MS, FTIR, NMR, and CE, however, indicated not fenethylline but rather d,l-amphetamine (20 milligrams/tablet), caffeine (39 milligrams/tablet), theophylline (14 milligrams/tablet), acetaminophen (11 milligrams/tablet), and lactose. The second exhibit contained 3 different color tablets, all contained in a package illustrated with an ad for a Mercedes-Benz SUV and again containing a small packet of silica beads. The first sub-exhibit contained 980 off-white tablets (8.2 x 3.1 millimeters, total net mass 160 grams). Analysis (same techniques) indicated d,l-amphetamine (7 milligrams/tablet), caffeine (65 milligrams/tablet), theophylline (8 milligrams/tablet), acetaminophen (9 milligrams/tablet), and lactose. The second sub-exhibit contained 2,655 tan tablets (8.3 x 3.7 millimeters, total net mass 469 grams). Analysis (same techniques) indicated d,l-amphetamine (10 milligrams/tablet), caffeine (30 milligrams/tablet), theophylline (39 milligrams/tablet), acetaminophen (21 milligrams/tablet), diphenhydramine (2.1 milligrams/tablet), quinine (2.1 milligrams/tablet), and lactose. The third sub-exhibit contained 887 dark brown tablets (8.3 x 3.4 millimeters, total net mass 156 grams). Analysis (same techniques) indicated d,l-amphetamine (10 milligrams/tablet), caffeine (30 milligrams/tablet), theophylline (38 milligrams/tablet), acetaminophen (21 milligrams/tablet), diphenhydramine (2.1 milligrams/tablet), quinine (2.1 milligrams/tablet), and lactose. In each case, the amphetamine was calculated as the sulfate, while the diphenhydramine and quinine were calculated as the hydrochlorides. All exhibits also contained varying amounts of N-formylamphetamine (not quantitated), probably present as a contaminant from a poorly executed Leuckart synthesis of amphetamine. The Special Testing and Research Laboratory has previously received Captagon mimic and counterfeit tablets, but none with these compositions. [Editor?s Notes: Fenethylline is a controlled substance in the U.S. (Schedule I). It is a CNS stimulant.] * * * * * SELECTED REFERENCES [The Selected References section is a compilation of recent publications of presumed interest to forensic chemists. Unless otherwise stated, all listed citations are published in English. Abbreviated mailing address information duplicates that provided by the abstracting service. Patents and Proceedings are reported only by their Chemical Abstracts citation number.]
Additional References of Possible Interest:
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