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Jeremiah Morris Johnson County Sheriff’s Office Criminalistics Laboratory.

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1 Jeremiah Morris Johnson County Sheriff’s Office Criminalistics Laboratory

2  Review of how we got into this mess  Legislative topics  Various legislative approaches  Providing data to support control criteria  Analytical topics  Analytical standards  Types of testing  Toxicology

3  There is no value in just me talking

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5  Drug chemistry is not suppose to be this difficult  What happened to this quiet little section?

6  First appearance in 2009  JWH-018 and JWH-073  Legislative responses in 2010  Vendor responses in 2010

7  JWH-018  JWH-073  JWH-250  JWH-200  JWH-210  JWH-203  JWH-122  JWH-019  JWH-015  JWH-251  JWH-398  JWH-081  WIN-55,212-2  JWH-370  CP 47,497 (C7)  AM-630  HU-210  AM-2201 (Cl)  CP 47,497  Pravadoline  AM-1241  JWH-051  JWH-307  CP 47,497 (C9)  AM-1220  RCS-4 (2-MeO)  JWH-133  RCS-4  RCS-4 (C4)  RCS-8  AM-2201  AM-694  And so on… Over 400 compounds have been identified in the literature with potencies at least twice that of THC. This does not include the countless unpublished designer compounds which have also shown up in case submissions. 7

8 General chemical class Chemical structureCompounds currently marketed or identified in case submissions Naphthoylindoles JWH-007, JWH-015, JWH-018, JWH-019, JWH-073, JWH-081, JWH-122, JWH- 200, JWH-210, JWH-398, AM-2201, WIN , AM-2201 (Cl analog) AM-2201 (Br analog), AM-1220, 1-butyl-3-(1-(4-methyl)naphthoyl)indole; 4-methyl-AM- 2201, 4-methyl AM-2201, AM-2232, JWH-412 NaphthoylpyrrolesJWH-307, JWH-370, JWH-030, JWH-147 Phenylacetylindoles SR-18, RCS-8 (same as SR-18?), JWH-250, JWH-203, RCS-8 (C4 homolog), JWH- 251, cannabipiperidiethanone CyclohexylphenolsCP 47,497 (and homologs), cannabicyclohexanol Benzoylindoles AM-694, Pravadoline (WIN 48,098), RCS-4 (also called SR-19, BTM-4, and OBT- 199), RCS-4 (C4 homolog), AM-630, AM-1241, RCS-4 (2-methoxy isomer), AM- 2233, 3-(2-methoxybenzoyl)-1-butylindole, AM-679 Tricyclic benzopyransHU-210, JWH-051, JWH-133 8

9  The drug laws in the United Kingdom take a chemical class approach utilizing broad definitions  Tryptamines  Phenethylamines  Fentanyls  Pethidines  Barbiturates  Steroids  Piperazines  Cannabinoids  Cathinones 9

10  Any compound containing a ___________ structure with substitution at the nitrogen atom of the indole ring by a alkyl, haloalkyl, alkenyl, cycloalkylmethyl, cycloalkylethyl, 1-(N-methyl-2-piperidinyl)methyl or 2-(4-morpholinyl)ethyl group, whether or not further substituted in the indole ring to any extent and whether or not substituted in the naphthyl ring to any extent. 10

11  Initiated in 2011 by several states  Modified version used federally in 2012  Currently most common legislative approach for cannabinoids Most common controlled classes Naphthoylindoles Naphthylmethylindoles Naphthoylpyrroles Naphthylideneindenes Phenylacetylindoles Cyclohexylphenols Benzoylindoles

12  Some class definitions contain only structural requirements while others have pharmacological components:

13  Oklahoma and Texas  “Synthetic chemical compound that is a cannabinoid receptor agonist and mimics the pharmacological effect of naturally occurring substances  Minnesota  “any quantity of a substance that is a cannabinoid receptor agonist”  North Dakota  “synthetic chemicals which have similar effects on cannabinoid receptors” 13

14  What actually defines a “cannabinoid receptor agonist”?  Binding studies?  Animal studies?  Within expertise of a forensic chemist?  The answer(s) may impact the ability of the state to enforce the specific statute 14

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19 Linker Ring system B Ring system A Indole Indene Indazole Azaindole Pyrrole Pyrazole Indole Indene Indazole Azaindole Pyrrole Pyrazole Carbonyl Methylene Methine Acetyl Amide Carboxyl Carbonyl Methylene Methine Acetyl Amide Carboxyl Naphthyl Phenyl Adamantyl Tetramethylcyclopropyl Piperidinyl Quinolinyl Amino-3-methyl-1- oxobutan-2-yl Naphthyl Phenyl Adamantyl Tetramethylcyclopropyl Piperidinyl Quinolinyl Amino-3-methyl-1- oxobutan-2-yl Grand total of 252 possible cannabinoid classes

20  First appeared in 2009  Based on the chemical structure of the naturally occurring cathinone  All CNS stimulants  Act upon three different CNS receptors  Potency varies but most equal or greater than methamphetamine  No legitimate bath, beauty, or plant food purpose  No accepted medical use in the United States  Often referred to as “beta-ketones” (i.e., bk-MDMA is methylone)

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22 4-methylmethcathinone3,4-methylenedioxypyrovalerone 4-fluoromethcathinone3-fluoromethcathinone 4-methylethcathinone3,4-dimethylmethcathinone α -methylamino-butyrophenone β -keto-ethylbenzodioxolylbutanamine 3,4-methylenedioxy-N-ethylcathinone4-methoxymethcathinone  -pyrrolidinopropiophenone3,4-methlyenedioxymethcathinone  -pyrrolidinopentiophenone β -keto-N-methylbenzodioxolylpropylamine naphthylpyrovalerone 4-’methyl-  -pyrrolidinopropiophenone β -keto-methylbenzodioxolylpentanamine4’-methyl-  -pyrrolidinohexanophenone 4’-methyl-  -pyrrolidinobutyrophenone α -phthalimidopropiophenone, N-ethylcathinone4’-methyl- α -pyrrolidinohexanophenone 3,4-methylenedioxypyrrolidinobutyrophenone 22

23 23 Unsubstituted 3- or 4-methyl 3- or 4-halo (F, Cl, Br, or I) 3- or 4-ethyl 3- or 4-hydroxy 3- or 4-methoxy 3,4-methylenedioxy 3,4-dimethyl 3,4-dihalo (F, Cl, Br, or I) Replace phenyl with naphthyl Unsubstituted 3- or 4-methyl 3- or 4-halo (F, Cl, Br, or I) 3- or 4-ethyl 3- or 4-hydroxy 3- or 4-methoxy 3,4-methylenedioxy 3,4-dimethyl 3,4-dihalo (F, Cl, Br, or I) Replace phenyl with naphthyl Unsubstituted N-methyl N-ethyl N,N-dimethyl Pyrrolidine Phthalamido N-benzyl Unsubstituted N-methyl N-ethyl N,N-dimethyl Pyrrolidine Phthalamido N-benzyl Propyl Butyl Pentyl Hexyl Propyl Butyl Pentyl Hexyl Grand total of 672 possible combinations

24  Mixed approach, starting in 2011  Listing individual compounds  Chemical class approach

25  Novelty products which originally contained just substituted cathinones now include a number of additional classes:  Modified phenethylamines  Stimulants  Hallucinogenic  Arylcyclohexylamines  Tryptamines  And so on  We have no reason to believe this cycle will stop anytime soon

26  Work by Dr. Nichols et al discovered modifications of hallucinogenic phenethylamines increases potency 26

27  N-benzyl ortho- methoxy (NBOME) derivatives were the most potent 27

28  A number of these compounds are available on the web and have appeared in case submissions 28

29  Comprise the most common class of dissociatives  Complex pharmacology  CNS appears dose dependent and spans entire range 29 Methoxy Hydroxy Halo Methoxy Hydroxy Halo Carbonyl Grand total of 54 possible combinations

30  Class of highly potent hallucinogens  Present in a diverse group of botanical materials  All contain substituted indole compound 30

31 31 Hydroxyl, methoxy, acetoxy, halo Alkyl or dialkyl substitution (methyl, ethyl, propyl, isopropyl, allyl Methyl or ethyl with mono-N alkyl substitution   Grand total of 175 possible combinations

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33 The OriginalThe Original - modified

34 Fentanyl 3-Methyl Fentanyl

35  Any new substance can be considered a controlled “analog” if:  It has a substantially similar structure to a Schedule I or II hallucinogen, stimulant, or opiate, AND,  It has the same CNS effects as the related Schedule I or II hallucinogen, stimulant, or opiate, OR,  It was possessed or sold with the knowledge of being an analog  Application can be extremely difficult

36  Respective of these approaches, how effective have they been? Prosecution issues? Legal challenges? Response from chemists? Effectiveness?  Listing compounds individually  Chemical class (structure only)  Chemical class (with pharmacology)  Analog law  Emergency scheduling

37  Educating prosecutors has made all of the difference  What the law actually says  Capabilities of the drug chemistry section  How to read reports

38  Modifications to the analog law  Additional chemical classes  Broad class approach  “Synthetic drug lookalike substance” approach  FDA approach  We have to ask, “What are we trying to accomplish?”

39 "Controlled substance analog" means any of the following:  A substance that differs in its chemical structure to a controlled substance listed in or added to the scheduled designated in K.S.A or only by substituting one or more hydrogens with halogens or by substituting one halogen with a different halogen or,  A substance that is an alkyl homolog of a controlled substance listed in or added to the scheduled designated in K.S.A or or  (C) A substance intended for human consumption, and: (i) The chemical structure of which is substantially similar to the chemical structure of a controlled substance listed in or added to the schedules designated in K.S.A or , and amendments thereto; (ii) which has a stimulant, depressant or hallucinogenic effect on the central nervous system substantially similar to the stimulant, depressant or hallucinogenic effect on the central nervous system of a controlled substance included in the schedules designated in K.S.A or , and amendments thereto; or (iii) with respect to a particular individual, which the individual represents or intends to have a stimulant, depressant or hallucinogenic effect on the central nervous system substantially similar to the stimulant, depressant or hallucinogenic effect on the central nervous system of a controlled substance included in the schedules designated in K.S.A or , and amendments thereto.

40  Creates defined chemical modifications which automatically qualify compounds as an analog  Structural only, no pharmacology  Based on accepted changes in medicinal drug design  Retains previous approach for other structural modifications  Will this make the analog law more usable?

41  Draft proposed definitions for the following chemical classes are available if you’re interested:  Arylcyclohexylamines (PCP-like)  Modified tryptamines  Hallucinogenic phenethylamines (two versions)  Considerations  Same benefits and analytical issues with existing classes  Still reactionary and limited in scope

42  In addition to specific chemical classes, Kentucky has this statement:  Any other synthetic cannabinoid or piperazine which is not approved by the United States Food and Drug Administration or, if approved, which is not dispensed or possessed in accordance with state and federal law  Considerations  Catches all future “illicit” cannabinoids  But what is a “synthetic cannabinoid”? Circular definition?

43  Any compound structurally derived from (1H- indole-3-yl)(cycloalkyl, cycloalkenyl, aryl)methanone, or (1H-indole-3yl)(cycloalkyl, cycloalkenyl, aryl)methane, or (1H-indole-3- yl)(cycloalkyl, cycloalkenyl, aryl)carboxamide by substitution at the nitrogen atoms of the indole ring or carboxamide to any extent, whether or not further substituted in or on the indole ring to any extent, whether or not substituted in the naphthyl ring to any extent in or on the cycloalkyl, cycloalkenyl, aryl ring(s) (substitution in the ring may include, but is not limited to, heteroatoms such as nitrogen, sulfur and oxygen)

44  or (1H-indole-3yl)(cycloalkyl, cycloalkenyl, aryl)methane, or (1H-indole-3-yl)(cycloalkyl, cycloalkenyl, aryl)carboxamide by substitution at the nitrogen atoms of the indole ring or carboxamide to any extent

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46  Broad-based approach which attempts to pre- empt new drugs of abuse which do not fall into specific control categories  Kind of creating a “looks like a duck” law

47 (a) For the purposes of this section, "synthetic drug look-alike substance" means one or more of the following: (1) a substance that a reasonable person would believe is a synthetic drug; (2) a substance that a reasonable person would believe is being purchased or sold as a synthetic drug; or (3) a substance that a person knows or should have known was intended to be consumed by injection, inhalation, ingestion, or any other immediate means, and consumption was intended to cause or simulate a stimulant, depressant, or hallucinogenic effect on the central nervous system that is substantially similar to or greater than the stimulant, depressant, or hallucinogenic effect on the central nervous system of a controlled substance in Schedule I. ( b) Synthetic drug look-alike substance does not include: (1) food and food ingredients; (2) alcohol; (3) legend drugs; ( 4) tobacco; or (5) dietary supplements.

48 Sec (a) "Synthetic drug lookalike substance", except as provided in subsection (b), means one (1) or more of the following: (1) A substance, other than a synthetic drug, which any of the factors listed in subsection (c) would lead a reasonable person to believe to be a synthetic drug. (2) A substance, other than a synthetic drug: (A) that a person knows or should have known was intended to be consumed; and (B) the consumption of which the person knows or should have known to be intended to cause intoxication. (b) The term "synthetic drug lookalike substance" does not include the following: (1) Food and food ingredients (as defined in IC ). (2) Alcohol (as defined in IC ). (3) A legend drug (as defined in IC ). (4) Tobacco. (5) A dietary supplement (as defined in IC ).

49 (c) In determining whether a substance is a synthetic drug lookalike substance, the following factors may be considered: (1) The overall appearance of a dosage unit of the substance, including its shape, color, size, markings or lack of markings, taste, consistency, and any other identifying physical characteristics. (2) How the substance is packaged for sale or distribution, including the shape, color, size, markings or lack of markings, and any other identifying physical characteristics of the packaging. (3) Any statement made by the owner or person in control of the substance concerning the substance's nature, use, or effect. (4) Any statement made to the buyer or recipient of the substance suggesting or implying that the substance is a synthetic drug. (5) Any statement made to the buyer or recipient of the substance suggesting or implying that the substance may be resold for profit. (6) The overall circumstances under which the substance is distributed, including whether: (A) the distribution included an exchange of, or demand for, money or other property as consideration; and (B) the amount of the consideration was substantially greater than the reasonable retail market value of the substance the seller claims the substance to be.

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51  All legislative approaches based upon the controlled substance act are:  Reactionary  Restricted  In the realm of chemicals consumed by people, DEA has jurisdiction over controlled substances, FDA has everything else  FDA has provided significant assistance

52  Most states likely have FDA-like statutes modeled after Federal statutes  Meant for pharmaceuticals  Never intended for drugs of abuse  But…

53  Basis for past cases in KS  General approach  These products contain a psychoactive substance  “Not for human consumption” is a fraud  None of the packages are properly labeled  County in Florida assesses vendors a fine of $500 per pack

54  Definition for “drug”  “articles, other than food, intended to affect the structure or any function of the body of man or other animals.”  Definition for “new drug”  “any drug the composition of which is such that such drug is not generally recognized, among experts qualified by scientific training and experience to evaluate the safety and effectiveness of drugs, as safe and effective for use under the conditions prescribed, recommended, or suggested in the labeling thereof…”

55  Must be licensed to deal with “new drugs”  No person shall sell, deliver, offer for sale, hold for sale or give away any new drug unless (1) an application with respect thereto has been approved and such approval has not been withdrawn under 21 U.S.C.A. 355, or (2) when not subject to the federal act, unless such drug has been tested and has been found to be safe for use and effective in use under the conditions prescribed, recommended, or suggested in the labeling thereof  If neither of the two requirements are met, then the person can be charged with unlawful distribution of a new drug

56  Local smoke shop selling packets of “3,4-CTMP pellets”  Analysis confirms 3,4- dichloromethylphenidate  Non-controlled substance  FDA approach requirements  Meets definition of “drug”?  Meets definition of “new drug”?  Verify vendor has no license for distributing “new drugs”?

57  Laws already on the books  Broad enough to cover all future drugs of abuse  No need for pharmacological or structural comparisons  Will require more leg-work by all  Addresses dealers, not personal possession  Different application than what intended?  Violation may only be a misdemeanor

58  Legislators have controlled it  Prosecutors wish to move forward with a case  Do we have sufficient data to conclude that a compound detected in an item of evidence meets the criteria to be a controlled substance?  Primarily an issue with chemical class definitions  Also an awareness of related isomers and instrument limitations

59  The answers mean we have to talk about boring and confusing chemical technical stuff. Sorry.

60 Any compound containing a 3-(1-naphthoyl)indole structure with substitution at the nitrogen atom of the indole ring by a alkyl, haloalkyl, alkenyl, cycloalkylmethyl, cycloalkylethyl, 1-(N-methyl-2-piperidinyl)methyl or 2-(4-morpholinyl)ethyl group, whether or not further substituted in the indole ring to any extent and whether or not substituted in the naphthyl ring to any extent.

61  The supporting data is likely there.  Potentially long process between data collection and confident presentation of results  Understanding theory of instrument  Re-introduction of organic chemistry (headaches)  Knowing chemical structure of the compound  Understanding past work on structurally similar compounds  Interpretation of mass spectra (major headaches)

62 Any compound containing a 3-(1-naphthoyl)indole structure with substitution at the nitrogen atom of the indole ring by a alkyl, haloalkyl, alkenyl, cycloalkylmethyl, cycloalkylethyl, 1-(N-methyl-2-piperidinyl)methyl or 2-(4-morpholinyl)ethyl group, whether or not further substituted in the indole ring to any extent and whether or not substituted in the naphthyl ring to any extent. M

63  Confirming “AM-2201” locks in the fluorine at the 5-pentyl position 63

64 64 Do not under-estimate the value of retention times in GC/MS analyses!

65  Reporting “Confirmed AM-2201” may require purchasing multiple standards  Only one standard if reporting “Confirmed 1- fluoropentyl-3-(1-naphthoyl)indole ” 65

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68  If the compound contains a benzene ring and no other aromatic groups (e.g., indole system), di- substituted compounds can be differentiated by specific infrared absorbance bands 1,2-disubstituted cm -1 1,3-disubstituted cm cm -1 1,4-disubstituted cm -1 68

69 4-fluoromethcathinone 3-fluoromethcathinone 2-fluoromethcathinone 69

70  Schedule I reads:  Any compound structurally derived from 3-(1- naphthoyl)indole or 1H-indol-3-yl-(1-naphthyl)methane by substitution at the nitrogen atom of the indole ring by alkyl, haloalkyl, alkenyl, cycloalkyl methyl, cycloalkyl ethyl, 1-(N- methyl-2-piperidinyl)methyl or 2-(4-morpholinyl)ethyl group, whether or not further substituted in the indole ring to any extent, whether or not substituted in the naphthyl ring to any extent. Including, but not limited to:  JWH-018, or 1-pentyl-3-(1-naphthoyl)indole;  “Synthetic cannabinoid” defined as:  “any natural or synthetic material, compound, mixture, or preparation that contains any quantity of a substance that is a cannabinoid receptor agonist, including but not limited to any substance listed in paragraph (ll) of subdivision (4) of subsection 2”

71 Mass spec and retention time of single component in an item match the data for a known standard of JWH- 018

72  What do you think about the following report wording?  Analysis confirmed the presence of 1-pentyl-3- (1-naphthoyl)indole (JWH-018), a Schedule I controlled substance.

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74  Two issues:  Finding the standards (easy part)  Using the standards for casework (hard part)

75  Cayman Chemical  Most common source  ~$100 to $200 for 10 mg  “Traceable standards” are more expensive  Toronto Research Chemicals  National Measurement Institute  Cerilliant  Grace Analytical  Sigma

76  Most labs require verifying the standard prior to it being used in casework  Requires published spectra from peer-reviewed source  Generally GC/MS (sufficient for 10 mg standards)  Positional isomer determination (3- or 4- fluoroamphetamine) requires FTIR analysis (can be an issue for 10 mg standards)  Biggest obstacles are finding a reference spectrum and sufficient sample for FTIR

77  Analytical difficulties with emerging drugs of abuse are significantly greater in toxicology  Extraction from biological matrices  Multiple metabolites rather than single compounds  Little to no info on absorption, distribution, elimination  Little to no info on human pharmcokinetics  These things take time – something not afforded

78  Immunoassay screening techniques are slow to evolve  Expensive and labor intensive  Available screening kits deal with compounds long gone  GC/MS screening techniques generally developed in-house and validated too late

79  Confirmation  LC/MS/MS best option (not a routine technique)  Metabolite standards non-existent or expensive  Published data on metabolite standards?  Interpretation of any obtained results is very difficult (i.e., “Were they impaired?”)  Essentially, the compounds in these products and the resultant laws are changing faster than toxicology sections can keep up

80  If the toxicology results are critical to the case, often times the best option will be using a private laboratory.  Budget issues  Instrumentation issues  Back-log issues  Drug life-cycle issues

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