         Case: 15-14599   Date Filed: 08/11/2017   Page: 1 of 42


                                                    [DO NOT PUBLISH]



          IN THE UNITED STATES COURT OF APPEALS

                  FOR THE ELEVENTH CIRCUIT
                    ________________________

                           No. 15-14599
                     ________________________

               D.C. Docket No. 1:14-cr-20926-KMM-1



UNITED STATES OF AMERICA,

                                            Plaintiff - Appellee,


                                versus


RONEN NAHMANI,

                                            Defendant - Appellant.

                     ________________________

              Appeal from the United States District Court
                  for the Southern District of Florida
                    ________________________

                           (August 11, 2017)
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Before MARCUS, JILL PRYOR and SILER, * Circuit Judges.

JILL PRYOR, Circuit Judge:

       After a six-day trial, a jury convicted defendant Ronen Nahmani of one

count of conspiring to possess with intent to distribute controlled substances and

controlled substance analogues. The district court sentenced him to 240 months’

imprisonment, the statutory maximum. On appeal, Nahmani challenges his

conviction and sentence on numerous grounds.

       Nahmani’s challenges include whether: (1) the indictment was defective

because it alleged Nahmani conspired to possess with intent to distribute controlled

substances and controlled substance analogues but failed to identify the specific

substances that were the object of the conspiracy; (2) evidence seized from his

automobile should be suppressed on the basis that there was no probable cause at

the time of the search to believe that he was engaged in illegal conduct;

(3) cumulative errors warranted a new trial; (4) the district court erred in applying

a 20 year, as opposed to one year, statutory maximum when the indictment

explicitly alleged a conspiracy to possess with intent to distribute a controlled

substance analogue; and (5) the district court clearly erred in finding that the most

closely related substance referenced in the drug equivalency tables in the United

States Sentencing Guidelines was THC, not marijuana. After careful consideration
       *
        Honorable Eugene E. Siler, Jr., United States Circuit Judge for the Sixth Circuit, sitting
by designation.

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and with the benefit of oral argument, we conclude that there was no reversible

error and thus affirm.

                        I.      STATUTORY BACKGROUND

       We begin with an overview of the law regarding controlled substances and

their analogues. The Controlled Substances Act prohibits possession with intent to

distribute a controlled substance, as well as conspiring to possess with intent to

distribute a controlled substance. 21 U.S.C. §§ 841(a)(1), 846. A controlled

substance is any drug or other substance listed in five schedules, I through V,

which were established by the Controlled Substances Act. 1 Id. §§ 802(6), 812(a).

       The maximum sentence for a controlled substance offense depends on which

schedule lists the controlled substance. The maximum sentence for an offense

involving a schedule I substance generally is 20 years’ imprisonment. 2 See id.

§§ 841(b)(1)(C), 846. In contrast, the maximum sentence for an offense involving

a schedule V substance is one year of imprisonment. Id. § 841(b)(3).

       The Controlled Substances Analogue Enforcement Act (“Analogue Act”),

21 U.S.C. §§ 802(32), 813, prohibits the possession with intent to distribute a


       1
         The Attorney General has the authority to add or remove substances from the schedules
by rule. 21 U.S.C. § 811(a). The current schedules are set forth in the Code of Federal
Regulations. See 21 C.F.R. §§ 1308.11-1308.15.
       2
        If the indictment alleges and the government proves to a jury that the quantity of drugs
exceeded certain amounts, the maximum sentence of imprisonment increases to 40 years or life.
See 21 U.S.C. § 841(b)(1)(A), (B); United States v. Sanders, 668 F.3d 1298, 1309 (11th Cir.
2012). No such enhanced maximum sentence was imposed in this case.

                                                3
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controlled substance analogue, as well as conspiring to possess with intent to

distribute a controlled substance analogue. Congress passed the Analogue Act “to

prevent underground chemists from altering illegal drugs in order to create new

drugs that are similar to their precursors in effect but are not subject to the

restrictions imposed on controlled substances.” United States v. Klecker, 348 F.3d

69, 70 (4th Cir. 2003).

      The Analogue Act defines a controlled substance analogue as a substance:

      (i) the chemical structure of which is substantially similar to the
      chemical structure of a controlled substance in schedule I or II;

      (ii) which has 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 or II; or

      (iii) with respect to a particular person, which such person represents
      or intends to have 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 or II.

21 U.S.C. § 802(32)(A). We have not previously decided whether this definition

should be read disjunctively, meaning a substance that satisfies any one of the

three criteria qualifies as a controlled substance analogue, or conjunctively,

meaning that a substance must (1) have a chemical structure substantially similar

to a controlled substance in schedule I or II and (2) either a substantially similar

effect on the central nervous system or be purported or intended to have such an


                                           4
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effect. See United States v. Brown, 415 F.3d 1257, 1261 (11th Cir. 2005). Here,

the district court read the definition conjunctively, and neither party challenges this

reading. Because Nahmani’s challenge fails even under the conjunctive reading of

the Analogue Act—which places a more demanding burden on the government—

we assume for our purposes here that the district court’s reading was correct.3

       A substance that qualifies as a controlled substance analogue, when intended

for human consumption, is treated as a schedule I controlled substance. 21 U.S.C.

§ 813. Accordingly, an offense involving a conspiracy to possess with intent to

distribute a controlled substance analogue is generally punishable by up to 20

years’ imprisonment.

                            II.     FACTUAL BACKGROUND

A.     The Indictment

       A federal grand jury indicted Nahmani of one count of conspiring to possess

with intent to distribute controlled substances and controlled substance analogues

during the period from approximately April 1 through July 28, 2014. More

specifically, the indictment provided that:

             From on or about April 1, 2014, the exact date being unknown
       to the Grand Jury, through on or about July 28, 2014 . . . Ronen
       Nahmani[] did knowingly and willfully combine, conspire,

       3
          A number of our sister circuits have adopted a conjunctive reading of the definition.
See, e.g., United States v. Makkar, 810 F.3d 1139, 1146 (10th Cir. 2015); Klecker, 348 F.3d at
71; United States v. Hodge, 321 F.3d 429, 435-36 (3d Cir. 2003); United States v. Washam,
312 F.3d 926, 930 n.2 (8th Cir. 2002).

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        confederate, and agree with others known and unknown to the Grand
        Jury, to

                  a. possess with intent to distribute controlled substances, in
                     violation of Title 21, United States Code, Section 841(a)(1),
                     and Title 18, United States Code, Section 2.

                  b. possess with intent to distribute               controlled substance
                     analogues as defined in Title 21,               United States Code,
                     Section 802(32)(A), knowing that                the substances were
                     intended for human consumption as               provided in Title 21,
                     United States Code, Section 813.

                  All in violation of Title 21, United States Code, Section 846.

               The controlled substances involved in the conspiracy
        attributable to the defendant as a result of his own conduct, and the
        conduct of other conspirators reasonably foreseeable to him, include
        Schedule I controlled substances, that is, AB-FUBINACA, PB-22,
        and XLR11, in violation of Title 21, United States Code, Section
        841(a)(1).

               The controlled substance analogues involved in the conspiracy
        attributable to the defendant as a result of his own conduct, and the
        conduct of other conspirators reasonably foreseeable to him, include
        THJ-2201, 5-Chloro-UR-144, and 5-Bromo-UR-144, which are
        analogues of Schedule I controlled substances, in violation of Title 21,
        Untied States Code, Section 841(a)(1), 802(32)(A), and 813.

Indictment (Doc. 3). 4 Nahmani raised no objection to the indictment prior to trial.

B.      The Trial

        During a six-day trial, the government presented evidence that Nahmani

operated a business importing synthetic cannabinoids5 from China and Hong Kong


        4
            Citations to “Doc.” refer to numbered docket entries in the district court record in this
case.
                                                    6
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that he sold throughout the United States. The government presented to the jury

testimony and evidence about its investigation of Nahmani, which showed that he

acted essentially as a wholesale distributor for synthetic cannabinoids. In addition,

the government introduced expert testimony to establish that the items seized from

Nahmani included the chemicals listed in the indictment, and that three of these

chemicals, which were not listed on the schedules at the time of the conspiracy—

THJ-2201, 5-Bromo-UR-144, and 5-Chloro-UR-144—qualified as controlled

substance analogues.

       1.      Nahmani’s Business 6

       Nahmani imported synthetic cannabinoids in powder form from suppliers in

China and Hong Kong who shipped the substances to Nahmani by UPS and other

international carriers. He paid these suppliers through wire transfers, which

sometimes were sent by his brother, Israel Nahmani. At times, Nahmani discussed

in emails with his suppliers the specific chemicals they were sending him, showing

that he knew the chemicals included AB-Fubinaca and THJ-2201.7


       5
         Synthetic cannabinoids are manmade chemicals that mimic the effect of THC, the
psychoactive chemical in marijuana. These chemicals may be smoked with plant material or in
e-cigarettes.
       6
         We have set forth the facts viewing the evidence in the light most favorable to the
government and drawing all reasonable inferences and credibility choices in favor of the jury’s
guilty verdict, as we are required to do. See United States v. Boffil-Rivera, 607 F.3d 736, 740
(11th Cir. 2010).
       7
        At the time the foreign suppliers sent Nahmani AB-Fubinaca and THJ-2201, the
substances were not listed on schedule I.
                                                7
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      Nahmani operated as a wholesaler, selling to others around the country the

synthetic cannabinoids in powder and smokeable forms. He sold large quantities

of synthetic cannabinoids in powder form, including more than 40 kilograms of

powder to a single purchaser. He also set up in a storage space a laboratory to turn

the powder into consumable products that could be smoked with plant material or

in e-cigarettes. To create a smokeable product, Nahmani mixed the powder with

liquid acetone and coated plant material with the mixture, which he packaged into

small bags. Nahmani also mixed the powder with tobacco gel to create a product

to be smoked in e-cigarettes.

      Nahmani marketed his products under a variety of names. Some names,

such as Scooby Snax and Mary Joy, conveyed that the products were related or

similar to marijuana. Nahmani labeled some of the products as “potpourri” or “not

for human consumption,” but the government presented testimony that the

products were intended to be consumed and that these labels were included to

avoid detection by the Food and Drug Administration.

      Nahmani distributed the products with assistance from his brother, Israel.

Sometimes Nahmani or others would deliver the products in person. Other times

Nahmani or Israel would ship the products through UPS, using aliases to make it

more difficult to tie the packages to them.




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      At trial, the government presented testimony from Kyle Hurley, who

purchased large quantities of AB-Fubinaca in powder form from Nahmani for

approximately a one-year period.8 In February 2014, Hurley asked Nahmani if

AB-Fubinaca was banned, and Nahmani responded that the product was banned in

Florida but not in other states. In fact, though, AB-Fubinaca had been added to

schedule I earlier that month. The next month, Hurley arranged to sell his

remaining supply of AB-Fubinaca, which consisted of plant material weighing

more than one ton, to a prospective purchaser. Preparing to sell his entire supply,

Hurley contacted Nahmani to purchase more chemicals and began to negotiate a

price. The purchase was never completed, however, because Hurley was arrested

when his prospective purchaser turned out to be a law enforcement officer.

      2.       The Investigation

      In spring 2014, the Drug Enforcement Agency (DEA) began to investigate

Nahmani after receiving a tip from a confidential informant that Nahmani was

selling “spice”—synthetic cannabinoids. In the investigation, the officers observed

Nahmani selling spice. After the informant told the DEA that Nahmani planned to

sell spice to a convenience store, law enforcement officers observed Nahmani

drive into the store’s parking lot. From his car, Nahmani briefly spoke to a man.

Then, the officers saw Nahmani drive out of the convenience store parking lot to

      8
          Nahmani’s sales to Hurley occurred before the conspiracy period began.

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another parking lot across the street where he met with the same man for a few

minutes. At the end of the meeting, the man took a box from Nahmani’s car and

returned with it to the convenience store. An undercover officer entered the store

and observed the man removing vials of liquid from the box and placing them in a

display case. The man told the officer that the liquid in the vials was for smoking.

Other officers followed Nahmani; they watched him go to a storage facility. About

ten minutes later, Nahmani drove away from the storage facility. The officers

witnessed Nahmani make multiple u-turns, possibly in an attempt to evade

surveillance.

       A few weeks later, the informant reported to the DEA that he was

accompanying Nahmani on a road trip so that Nahmani could collect money for a

previous spice transaction. During the trip, the informant reported to the DEA that

Nahmani had received a phone call and then directed Israel to ship a package from

a local UPS store. Based on this tip, the DEA alerted UPS, which found a powder

substance inside the package.9

       While Nahmani was driving back from collecting the money, the DEA

contacted a local law enforcement officer to watch for Nahmani, who would be

traveling with a large amount of currency. The officer followed Nahmani in an


       9
          When Nahmani learned from a UPS employee that the package had been seized, he
asked the employee whether there was any way to change the shipping information on the receipt
of the seized package.

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unmarked vehicle and saw him speeding. The officer pulled Nahmani over for

violating the traffic laws and then searched the vehicle. Inside the vehicle, the

officer found cash, business records, and packages containing a green, leafy

substance.

       When DEA agents arrived on the scene, they informed Nahmani that they

had a warrant to search his storage space. Nahmani agreed to go to the DEA

agents’ office. During the drive to the office, Nahmani asked if he could call his

wife. The agents permitted the call but instructed Nahmani not tell his wife that he

was with the DEA. Nahmani nonetheless immediately told his wife that he was

with the DEA, which caused the DEA to send other officers to Nahmani’s home.

       The officers arrived to find Israel removing boxes from Nahmani’s

apartment and loading them into Israel’s vehicle. Israel allowed the officers to

search the car where they found several boxes containing chemicals. Israel also

admitted to the officers that he had additional chemicals at his house.

       When law enforcement searched Nahmani’s storage space under the

warrant, they found materials used to manufacture synthetic cannabinoids,

including kilograms of powder chemicals and bales of plant material, as well as

packaging supplies and labels.10



       10
          Before trial, Nahmani sought to suppress the evidence that was found in the searches of
his vehicle and storage space; the district court denied these motions.

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       3.     The Substances at Issue

       At trial, the government also presented scientific evidence about the powder

and plants it had seized from Nahmani. A government witness testified that

chemical testing showed the powder and plants seized from Nahmani contained the

chemicals AB-Fubinaca, PB-22, XLR-11, THJ-2201, and 5-Bromo-UR-144.11 At

the time of the conspiracy alleged in the indictment, AB-Fubinaca, PB-22, and

XLR-11 were listed as controlled substances on schedule I.

       Because THJ-2201, 5-Bromo-UR-144, and 5-Chloro-UR-144 were not listed

as controlled substances, the government had to prove that they qualified as

controlled substance analogues. To meet this burden, the government introduced

expert testimony about these chemicals. A DEA chemist testified that the chemical

structure of each potential analogue was substantially similar to a controlled

substance listed on schedule I. Dr. Jordan Trecki, a DEA pharmacologist, testified

that each substance had (or was likely to have) a substantially similar effect on the

       11
            This government witness did not testify that any of the materials seized from Nahmani
contained the chemical 5-Chloro-UR-144. In its brief to this Court, the government explains that
the witness apparently misspoke when identifying the chemical compounds in a particular
sample. The government asserts that the witness testified that the sample included XLR-11, 5-
Fluoro-UR-144, and 5-Bromo-UR-11 when she meant to state that the sample included XLR-11,
5-Chloro-UR-144, and 5-Bromo-UR-11. To show that the witness misspoke, the government
points out that other testimony established that XLR-11 and 5-Fluoro-UR-144 were alternate
names for the same chemical and that the underlying laboratory report, which was produced to
Nahmani in discovery, reflected that the chemicals in the sample included XLR-11, 5-Chloro-
UR-144, and 5-Bromo-UR-144. Nahmani does not challenge on appeal that the witness
misspoke or argue on the basis of this misstatement that the government failed to prove that 5-
Chloro-UR-144 was a substance that he conspired to possess with intent to distribute. Because
Nahmani raises no challenge based on the witness’s apparent misstatement, we need not discuss
it further.
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central nervous system as a controlled substance listed on schedule I. His opinion

was based on his analysis of the chemical structure of the substances; in vitro

testing, which showed the attraction each drug had to a molecular receptor for

cannabinoids; in vivo testing in rodents, which showed the efficacy or potency of

the substances; and case reports that contained accounts from physicians about

substances’ effect on individuals who had consumed them. Trecki testified that

these methods were accepted ways to determine the effect a chemical would have

on the human central nervous system. He explained there were no scientific

studies using humans to determine the effect of the substances on the human

central nervous system because scientists ethically could not run a trial on humans

for a drug with no known benefits that had potentially serious adverse effects.

      4.     Closing Arguments and Jury Instructions

      In closing arguments, Nahmani’s counsel argued to the jury that the

government had failed to carry its burden to prove that the plants and powder

seized from Nahmani in fact contained AB-Fubinaca, PB-22, XLR-11, THJ-2201,

5-Bromo-UR-144, and 5-Chloro-UR-144 because the government’s process for

collecting and testing samples was unreliable. In response, the government argued

that its witnesses had provided two days of testimony describing the testing that

confirmed the identity of the substances, expressing disbelief that Nahmani was

challenging the identity of the substances after that extensive testimony and


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Nahmani’s failure to present any expert evidence of his own establishing that the

substances were something else.

      The court then instructed the jury. The jury instructions described the

knowledge element for conspiracy to possess with intent to distribute a controlled

substance and a controlled substance analogue. For the controlled substance

conspiracy, the government had to prove that the defendant knew the conspiracy

involved some controlled substance. For the analogue-to-a-controlled-substance

conspiracy, the government had to prove, through circumstantial or direct

evidence, that the defendant knew the conspiracy involved a substance (1) with a

chemical structure was structurally similar to a controlled substance or (2) that had

a stimulant, depressant, or hallucinogenic effect on the central nervous system that

was substantially similar to or greater than the effect of a controlled substance in

schedule I or II.

      During deliberations, the jury sent a note asking, “Does the defendant have

to be in possession of all three substances mentioned in the indictment or is one

enough? In regards to the controlled substance analogues, does the defendant have

to be in possession of all three substances mentioned in the indictment or is one

enough?” In response to the jury’s questions, the district court explained that

because Nahmani was charged with conspiracy, not possession, he did not have to

possess anything. The court also reminded the jury that it was to consider the


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court’s previous instructions as a whole. And the court repeated to the jury its

instruction regarding conspiracy to possess with intent to distribute a controlled

substance. The district court explained that the knowledge requirement could be

met by showing that the defendant knew “that the conspiracy involved some

controlled substance.” Trial Tr. at 70 (Doc. 173). But the court did not repeat its

explanation of the knowledge required for conspiracy to possess with intent to

distribute a controlled substance analogue. Instead, it simply stated that the

“instruction is the same for conspiracy with respect to controlled substance

analogues.” Id. at 71.

      The jury returned a verdict finding that Nahmani had engaged in a

conspiracy to possess with intent to distribute both a controlled substance and a

controlled substance analogue. The verdict form did not require the jury to specify

the amount or substances involved in the conspiracy.

C.    Post-Trial Motions

      After the guilty verdict, Nahmani filed several post-trial motions. First, he

filed a motion for judgment of acquittal and a new trial, contending that the jury’s

verdict was not supported by substantial evidence and that the district court had

erred in admitting certain testimony, refusing to suppress evidence, and improperly

instructing the jury. Second, Nahmani filed a motion to dismiss the indictment,

arguing that the indictment was defective because it failed to identify the specific


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substances that were the object of the conspiracy. He further argued that because

the indictment failed to identify the substances that were the object of the

conspiracy, the court had to assume that the object of the conspiracy was a

schedule V substance, making the statutory maximum sentence only one year. The

district court denied the motions.

D.    Sentencing

      Before Nahmani’s sentencing, the probation office issued a presentence

investigation report (“PSR”). In calculating Nahmani’s base offense level under

the Sentencing Guidelines, the PSR found that Nahmani was responsible for a total

of 1,200 kilograms of a mixture or substance containing a detectible amount of

synthetic marijuana. This total included (1) 1,100 kilograms of plant material that

Hurley tried to sell to an undercover officer in late March 2014, (2) 40 kilograms

of powder seized from Nahmani in July 2014, and (3) 60 kilograms of powder that

Nahmani had ordered from China from late 2012 through early 2014.

      Because the Sentencing Guidelines set forth no marijuana equivalence ratio

for any of the synthetic cannabinoids in this case, the PSR calculated the base

offense level using the marijuana equivalency of the most closely related

controlled substance in the Guidelines’ equivalency table. See U.S.S.G. § 2D1.1,

cmt. n.6. The PSR found that THC was the most closely related controlled

substance in the table and applied a conversion ratio of 1 gram of synthetic


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cannabinoids to 167 grams of marijuana. 12 U.S.S.G. § 2D1.1, cmt. n.8(D). The

1,200 kilograms of a mixture containing a detectable amount of synthetic

cannabinoids thus converted to 200,400 kilograms of marijuana. 13 The PSR

calculated Nahmani’s base offense level as 38, the level applicable to any offense

involving 90,000 kilograms or more of marijuana. The PSR then applied a two-

level increase because Nahmani maintained a premises for the purpose of

manufacturing or distributing a controlled substance and a four-level increase

because Nahmani was an organizer or leader of criminal activity that involved five

or more participants or was otherwise extensive. See U.S.S.G. §§ 2D1.1(b)(12),

3B1.1(a). Under the Guidelines, Nahmani’s offense level and criminal history

category of I resulted in a term of life imprisonment, which the PSR reduced to the

statutory maximum of 240 months’ imprisonment.

       Before sentencing, Nahmani filed written objections to the PSR, raising

several arguments including that (1) marijuana, not THC, was the most closely

related substance in the Guidelines’ drug equivalency table; (2) the PSR should not

have included the weight of the plant material in calculating the total weight of

drugs seized from Hurley; and (3) Nahmani was ineligible for the enhancement for



       12
            The PSR applied this conversion ratio with respect to both the powder and plant
material.
       13
         Put another way, Nahmani was held responsible for the equivalent of more than 220
tons of marijuana.

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an organizer or leader of criminal activity that involved five or more participants or

was otherwise extensive.

      At the sentencing hearing, the government and Nahmani presented evidence

about whether the synthetic cannabinoids at issue were most closely related to

THC or marijuana. Trecki, the DEA pharmacologist, again testified for the

government, explaining that the substances were more similar to THC than

marijuana. He identified two key differences between marijuana and synthetic

cannabinoids. First, he explained that although marijuana contains THC,

marijuana plants contain other naturally occurring chemicals that mediate and

reduce the effects of THC. But the synthetic cannabinoids here, whether in powder

or plant form, contained no such moderating chemicals. Second, he described the

severe adverse effects of the synthetic cannabinoids that were not seen after the

ingestion of marijuana, like loss of consciousness, psychomotor agitation,

hallucinations, and seizures.

      Trecki also explained that the synthetic cannabinoids had hallucinogenic

effects on the central nervous system that were substantially similar or likely to be

substantial similar to THC. He offered this opinion based on his analysis of the

chemical structure of the substances; in vitro testing, which showed the substances’

attraction to a molecular receptor; and in vivo testing in rodents, which showed the




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efficacy or potency of the substances. He opined that most of the synthetic

cannabinoids at issue were at least as potent as THC.14

       In response, Nahmani presented testimony from his expert—Dr. Daniel

Buffington, a pharmacologist—challenging Trecki’s opinions. Buffington

criticized Trecki for offering an opinion on the effect of synthetic cannabinoids on

the human central nervous system without human studies. Because there were no

studies showing the effects of these cannabinoids on humans, Buffington stated

that the appropriate equivalency ratio should be 1:1, not 1:167.

       After considering this evidence, the district court found Nahmani

responsible for a total weight of 1,200 kilograms of synthetic cannabinoids. The

district court found that THC was the most closely related substance and applied a

1:167 marijuana equivalence ratio. The district court further found that Nahmani

was an organizer or leader of criminal activity that involved five or more

participants or was otherwise extensive and applied the enhancement. Because the

sentencing range under the Guidelines was 360 months to life, which exceeded the

statutory maximum, the court reduced the range to the statutory maximum of 240

months. After considering the factors set forth in 18 U.S.C. § 3553(a), the district




       14
           Trecki offered no opinion about whether 5-Bromo-UR-144 and 5-Chloro-UR-144 were
at least as potent as THC because there had been no in vivo testing involving the substances from
which he could draw conclusions about their potency.

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court sentenced Nahmani to 240 months’ imprisonment to be followed by three

years of supervised release. This is Nahmani’s appeal.

                                III.     LEGAL ANALYSIS

A.     The District Court Properly Denied Nahmani’s Motion to Dismiss the
       Indictment.

       Nahmani argues that the district court should have dismissed the indictment

because the indictment had a jurisdictional defect in failing to identify the specific

controlled substance or controlled substance analogues that were the object of the

conspiracy. 15 To begin, we must identify the relevant standard of review.

Nahmani claims that we must apply de novo review because his challenge is

jurisdictional. See United States v. Sperrazza, 804 F.3d 1113, 1119 (11th Cir.

2015). But if the challenge is non-jurisdictional, we must review for plain error

unless Nahmani can show that the basis for his motion was not “reasonably

available” before trial or could not have been “determined without a trial on the

merits.” Id. (internal quotation marks omitted).

       We conclude that Nahmani raises a non-jurisdictional challenge to the

indictment and so plain error review applies. We have explained that “an omission

of an element from an indictment does not deprive the district court of


       15
          Although a latter portion of the indictment identified the substances “involved in” the
conspiracy, the parties agree that the portion of the indictment setting forth the substantive
criminal offense alleged a generic conspiracy because it failed to identify the specific substances
that were the object of the conspiracy.

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jurisdiction.” United States v. Brown, 752 F.3d 1344, 1351 (11th Cir. 2014). 16

Nahmani argues that the indictment was defective because it omitted an element of

offense; his challenge thus is non-jurisdictional. Nahmani failed to challenge the

indictment prior to trial or show that the basis of his motion was unavailable prior

to trial,17 and therefore we review for plain error. See Sperrazza, 804 F.3d at 1119.

       There was no error, let alone plain error, here. Nahmani asserts that the

indictment was defective because it failed to identify the specific controlled

substances and controlled substance analogues that were the object of the

conspiracy to possess with intent to distribute. But our precedent recognizes that

an indictment may charge a generic conspiracy to possess with intent to distribute a

controlled substance and need not identify the specific drug that was the object of

the conspiracy. See United States v. Sanders, 668 F.3d 1298, 1311 (11th Cir.

2012) (explaining that an indictment may charge “a generic violation of §§ 841(a)

and 846 in which [the defendant] conspired to knowingly and intentionally


       16
           By contrast, we have explained that an indictment contains a jurisdictional defect when
(1) “the Government affirmatively alleged a specific course of conduct that is outside the reach
of the [] statute”; (2) the indictment alleged “conduct that was not a crime against the laws of the
United States,” such as charging a conspiracy to attempt to import marijuana when there was no
such crime in the United States Code; or (3) the indictment alleged the defendant violated a
regulation that carried only civil penalties and did not impose criminal liability. Brown, 752 F.3d
at 1352-53.
       17
          Nahmani argues that he could not bring the motion prior to trial because the full extent
of the prejudice he experienced was not revealed until trial when the government constructively
amended the indictment by making his lawful dealing with Hurley the focus of the trial. We are
unpersuaded. After all, Nahmani’s argument that the indictment failed to allege an element of
the offense is based on the face of the indictment, which was available to him before trial.

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distribute ‘a controlled substance’”). We reject Nahmani’s argument that the

indictment was insufficient.

      Nahmani relies on our decision in United States v. Narog, 372 F.3d 1243

(11th Cir. 2004), to argue that an indictment must allege the drug involved in the

conspiracy. His reliance on Narog is misplaced. In Narog, the indictment alleged

that the defendants possessed pseudoephedrine knowing that it would be used to

manufacture methamphetamine. Id. at 1246. Despite the indictment’s specificity,

the district court instructed that the jury need not find the defendants knew that the

pseudoephedrine would be used to make methamphetamine specifically, as

opposed to some other drug. Id. at 1247. We reversed the defendants’ convictions

because the district court’s instruction constructively amended the indictment when

it removed the requirement that the defendants had to know the pseudoephedrine

would be used to make methamphetamine. Id. at 1248-49. Narog is unhelpful

here because it did not address whether an indictment may allege a generic

conspiracy involving controlled substances.

      We conclude that there was no defect in the indictment. The district court

properly denied Nahmani’s motion to dismiss.

B.    The District Court Properly Denied Nahmani’s Motion to Suppress.

      Nahmani next challenges the district court’s denial of his motion to suppress

the evidence found in the search of his vehicle. In reviewing a district court’s


                                          22
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denial of a motion to suppress, we apply a mixed standard of review. United States

v. Boyce, 351 F.3d 1102, 1105 (11th Cir. 2003). We review the district court’s

findings of fact for clear error and its application of the law to those facts de novo.

Id. Additionally, we construe all facts in the light most favorable to the prevailing

party, which in this case is the government. Id.

      To evaluate the search, we must consider separately whether the initial stop

and subsequent search of the vehicle each were lawful. On the first inquiry, we

conclude that the officer validly stopped Nahmani. A police officer may stop a

vehicle if he has “probable cause to believe that a driver is violating any one of the

multitude of applicable traffic and equipment regulations relating to the operation

of motor vehicles.” United States v. Strickland, 902 F.2d 937, 940 (11th Cir. 1990)

(internal quotation marks omitted). Here, the officer observed Nahmani speeding

in violation of Florida law, see Fla. Stat. § 316.183(1), making the initial stop

lawful.

      Second, we determine that the warrantless search of the vehicle was justified

under the automobile exception. Under the automobile exception, police may

conduct a warrantless search of a vehicle “if (1) the vehicle is readily mobile; and

(2) the police have probable cause for the search.” United States v. Lindsey,

482 F.3d 1285, 1293 (11th Cir. 2007). Probable cause “exists when under the

totality of the circumstances, there is a fair probability that contraband or evidence


                                           23
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of a crime will be found in the vehicle.” Id. (internal quotation marks omitted).

Here, there is no question that Nahmani’s vehicle was readily mobile. And there

was probable cause, as there was a fair probability that his vehicle contained

contraband or evidence of a crime. At the time of the stop, the confidential

informant, who had provided law enforcement with reliable information in the

past, had told law enforcement that Nahmani was traveling with the proceeds from

a sale of spice.

      Nahmani argues that the officer lacked probable cause because law

enforcement had no basis for concluding that the spice he was selling was illegal.

But even if the informant’s tip that Nahmani was selling “spice” was insufficient

alone to create probable cause that the substances were illegal, law enforcement’s

surveillance of Nahmani was sufficient to raise a fair probability that the

substances were illegal. When Nahmani sold spice to the convenience store, he

went to a nearby parking lot instead of the store’s premises for the transaction.

This conduct supports an inference that Nahmani was trying to hide the transaction

because he knew the substance was illegal. And after Nahmani sold the spice to

the convenience store, he went to the storage facility; upon leaving the storage

facility, he made multiple u-turns in an apparent attempt to avoid being followed.

This evasive driving supports the inference that Nahmani was trying to escape

surveillance because he knew he was violating the law.


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       Despite this evidence, Nahmani argues that the officer lacked probable cause

for the search because the spice he sold to the convenience store had not been

tested to determine whether it contained illegal substances. He relies for this

argument on our decision in Kingsland v. City of Miami, 382 F.3d 1220 (11th Cir.

2004). In Kingsland, we explained that law enforcement may not turn “a blind eye

to immediately available exculpatory information” when conducting an

investigation. Id. at 1229 n.10 (emphasis added). But Nahmani has identified no

immediately available information to which law enforcement turned a blind eye, so

we conclude that Kingsland is inapplicable here. The district court properly denied

the motion to suppress the search of the vehicle because there was probable cause

for the search and the automobile exception applied.18

C.     There Was No Cumulative Error Requiring a New Trial.

       Nahmani argues he is entitled to a new trial because of the cumulative effect

of errors at trial—including, but not limited to, the district court’s erroneous

       18
           Nahmani also argues that the district court erred when it declined to suppress evidence
found in the search of the storage space. Although law enforcement obtained a warrant for the
search, Nahmani contends that the search was improper because the information in the warrant
was insufficient to establish probable cause. Again, Nahmani’s argument is based on the
assumption that law enforcement lacked sufficient information to conclude that the spice he was
selling was illegal. We disagree because as we explained above, law enforcement had a
sufficient basis to conclude that the substances were illegal. We further note that, because the
confidential informant had told law enforcement that Nahmani kept his supply of spice in the
storage space and law enforcement had observed Nahmani frequently visit the storage space,
there was a “fair probability that contraband or evidence of a crime” would be found there.
United States v. Lebowitz, 676 F.3d 1000, 1010-11 (11th Cir. 2012) (internal quotation marks
omitted). The district court thus properly denied Nahmani’s motion to suppress the search of
the storage space.

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evidentiary rulings, the prosecutor’s improper statement in closing arguments, and

the district court’s misleading response to a question from the jury—deprived him

of a fair trial. We disagree.

       We review for abuse of discretion the district court’s evidentiary rulings,

overruling of Nahmani’s objection to the closing argument, and response to the

jury’s questions. See United States v. Augustin, 661 F.3d 1105, 1123 (11th Cir.

2011); United States v. Lopez, 590 F.3d 1238, 1247 (11th Cir. 2009); United States

v. Calderon, 127 F.3d 1314, 1338 (11th Cir. 1997). Even if a ruling was an abuse

of discretion, “it will result in reversal only if the . . . error was not harmless.”

Augustin, 661 F.3d at 1123. When a defendant raises an evidentiary challenge for

the first time on appeal, we review for plain error. United States v. Eduoard,

485 F.3d 1324, 1343 (11th Cir. 2007). Under the plain error standard, there must

be (1) error, (2) that is plain, (3) that affects the defendant’s substantial rights, and

(4) that seriously affected the fairness, integrity or public reputation of judicial

proceedings. Id. at 1343 n.7. But even when an individual error alone is

insufficient to warrant reversal, we must also consider the cumulative effect of the

errors to determine whether the defendant was denied a fair trial. See Calderon,

127 F.3d at 1333.

       To review Nahmani’s cumulative error argument, we must first assess

whether Nahmani’s individual claims of error are correct and then determine the


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combined effect of any erroneous rulings. We conclude that there is no reversible

error here because Nahmani was afforded “a fundamentally fair trial.” Id.

      1.     The District Court Did Not Abuse Its Discretion in Admitting
             Hurley’s Testimony.

      Nahmani argues that the district court erred in permitting Hurley to testify

for the government. He contends that the district court should have excluded

Hurley’s testimony because the testimony was (1) about conduct that occurred

before the conspiracy period, (2) inadmissible character evidence that should have

been excluded under Federal Rule of Evidence 404(b), and (3) included

inadmissible hearsay about separate investigative findings and judicial

proceedings. We conclude that the district court did not abuse its discretion in

permitting Hurley to testify.

      First, Nahmani asserts that Hurley’s testimony should have been excluded

because it related to conduct that occurred before the conspiracy period alleged in

the indictment. By allowing Hurley to testify, Nahmani contends, the district court

let the government constructively amend the indictment by changing the time

period of the conspiracy. Although Nahmani is correct that he last sold AB-

Fubinaca to Hurley in late January or early February 2014, before the conspiracy

period, the evidence showed that Nahmani also tried to sell synthetic cannabinoids

to Hurley on March 28, which is “on or about April 1,” as the indictment alleged.



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Indictment (Doc. 3). Thus, we reject Nahmani’s assertion that Hurley’s testimony

only covered acts that occurred outside the conspiracy period.19

       Second, Nahmani argues that Hurley’s testimony should have been excluded

under Federal Rule of Evidence 404(b). Rule 404(b) prohibits the use of

“[e]vidence of a crime, wrong, or other act . . . to prove a person’s character in

order to show that on a particular occasion the person acted in accordance with that

character.” Fed. R. Evid. 404(b). But evidence “pertaining to the chain of events

explaining the context, motive and set-up of the crime[] is properly admitted if

linked in time and circumstances with the charged crime, or forms an integral and

natural part of an account of the crime, or is necessary to complete the story of the

crime for the jury.” United States v. McLean, 138 F.3d 1398, 1403 (11th Cir.

1998) (internal quotation marks omitted).

       The district court properly admitted Hurley’s testimony because it was

intrinsic evidence that completed the story of Nahmani’s crime. Hurley’s

testimony showed that Nahmani knew he was selling AB-Fubinaca and tried to sell

Hurley AB-Fubinaca even after it was listed as a schedule I controlled substance.

Hurley also testified that he paid Nahmani $100,000 in cash several times and that

Nahmani directed him to send other payments to several bank accounts. This
       19
          For similar reasons, we reject Nahmani’s argument that Hurley’s testimony was
irrelevant because when Nahmani sold substances to Hurley, AB-Fubinaca was not listed as a
controlled substance on schedule I. Even though all the completed transactions occurred before
AB-Fubinaca was added to schedule I, the evidence shows that Nahmani tried to sell AB-
Fubinaca to Hurley after the substance was listed as a schedule I compound in February 2014.
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testimony showed that Nahmani was trying to conceal the transactions and

supported an inference that he knew the spice that he was importing and selling

was illegal. Because Hurley’s testimony completed the story of the crime, we

cannot say that Rule 404(b) required the district court to exclude it.

       Third, Nahmani argues that Hurley should not have been permitted to testify

about investigative or judicial findings—more specifically, that Hurley’s testimony

that he had pled guilty and the substances seized from him tested positive for AB-

Fubinaca should have been excluded. But Hurley was permitted to disclose his

guilty plea to the jury to blunt the attack on Hurley’s credibility during cross-

examination. See United States v. DeLoach, 34 F.3d 1001, 1004 (11th Cir.

1994). 20 And even assuming that permitting Hurley’s testimony about testing

performed by the government and by Hurley showing the substances seized

contained AB-Fubinaca was error, any error was harmless given the other evidence

that Nahmani sold Hurley AB-Fubinaca, including Hurley’s testimony that

Nahmani told him that the substance was AB-Fubinaca.




       20
          Nahmani contends that the district court should have given an instruction to identify
the limited purpose for which the jury could consider Hurley’s guilty plea. But because
Nahmani never requested such a limiting instruction, there can be no error. See United States v.
Miranda, 197 F.3d 1357, 1360 (11th Cir. 1999) (“The failure to give a limiting instruction is
error only when such an instruction is requested.”).
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      2.     The District Court Did Not Abuse Its Discretion in Admitting
             Trecki’s Expert Testimony.

      Next, Nahmani argues that the district court erred when it admitted expert

testimony from Trecki about the effect that the three alleged analogues, THJ-2201,

5-Bromo-UR-144, and 5-Chloro-UR-144, have on the human central nervous

system. Nahmani contends that Trecki’s opinions should have been excluded as

unreliable because they were not based on research performed on humans. We

discern no abuse of discretion.

      Under Federal Rule of Evidence 702, a district court acts as a gatekeeper to

keep out irrelevant or unreliable testimony. See Daubert v. Merrell Dow, 509 U.S.

579, 593 (1993). To evaluate the reliability of scientific expert testimony, a district

court must assess “whether the reasoning or methodology underlying the testimony

is scientifically valid and . . . whether that reasoning or methodology properly can

be applied to the facts in issue.” Id. at 592-93. In Daubert, the Supreme Court

identified the following factors as ones that could assist in determining whether an

expert’s methodology was sufficiently reliable: (1) whether it can and has been

tested, (2) whether it has been subjected to peer review and publication, (3) what

its known or potential rate of error is, and (4) whether it is generally accepted in

the field. Id. at 593-94. Because the inquiry is flexible, “expert testimony that

does not meet all or most of the Daubert factors may sometimes be admissible.”

Brown, 415 F.3d at 1268.
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        We have emphasized that the district court’s gatekeeping role “is not

intended to supplant the adversary system or the role of the jury.” United States v.

Ala. Power Co., 730 F.3d 1278, 1282 (11th Cir. 2013) (internal quotation marks

omitted). After all, vigorous cross-examination, presentation of contrary evidence,

and careful instruction on the burden of proof “are the traditional and appropriate

means of attacking shaky but admissible evidence.” Id. (internal quotation marks

omitted).

        Here, Nahmani claims that Trecki’s opinions were insufficiently reliable

because they were not based on human testing. But we cannot say that district

court abused its discretion when it allowed Trecki to testify. Trecki explained that

his opinions about what effect the alleged analogues would have on the human

central nervous system were based on the structure of the chemicals, in vitro

testing, in vivo testing in rodents, and case reports. Importantly, Trecki had

testified that each method was a scientifically accepted way to determine what

effect a drug would have on the human central nervous system. Because

Nahmani’s objections go to the weight, not the admissibility, of Trecki’s

testimony, the district court acted within its discretion in allowing the expert to

testify. 21



        21
         Nahmani also argues that the district court should have barred the government from
cross examining his expert witness, Buffington, about a medical report showing that an infant
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            3. The District Court Did Not Abuse Its Discretion When
               Responding to a Jury Question.

       Nahmani also argues that he should get a new trial because the district court

gave a misleading answer to the jury’s questions when the court failed to describe

the knowledge required to convict Nahmani of conspiracy to possess with intent to

distribute a controlled substance analogue.22 Viewing the instructions as a whole,

though, we cannot say that the jury was misled.



died after ingesting a synthetic cannabinoid. Nahmani has failed to show that the district court
abused its discretion.
        First, the testimony was relevant. Buffington had testified that there was insufficient
evidence about the effect synthetic cannabinoids on humans and specifically asserted that there
was no human data on any synthetic cannabinoids. To demonstrate that Buffington’s assertion
about the lack of human data was inaccurate, the prosecutor asked Buffington on cross
examination if he was familiar with a New England Journal of Medicine article that discussed a
case study in which a 10-month-old died after ingesting synthetic cannabinoids. The question
was relevant to refute Buffington’s testimony that there was no human data about synthetic
cannabinoids and to undermine his opinion there was insufficient evidence on the effect of
synthetic cannabinoids on the human central nervous system. See Fed. R. Evid. 401 (“Evidence
is relevant if: (a) it has any tendency to make a fact more or less probable than it would be
without the evidence; and (b) the fact is of consequence in determining the action.”)
         Second, Nahmani failed to show that question was unfairly prejudicial. A district court
may exclude relevant evidence “if its probative value is substantially outweighed by a danger of
. . . unfair prejudice.” Fed. R. Evid. 403. But this “extraordinary remedy . . . must be used
sparingly because it results in the exclusion of concededly probative evidence.” United States v.
US Infrastructure, Inc., 576 F.3d 1195, 1211 (11th Cir. 2009). Accordingly, we have explained
that evidence is properly excluded as unfairly prejudicial when it is “dragged in by the heels
solely for prejudicial impact.” Id. (internal quotation marks omitted). Here, the cross
examination of Buffington was probative, as it was connected to whether it was possible to
determine the effect of synthetic cannabinoids on the human central nervous system. Because
we cannot say that the evidence was presented solely for prejudicial impact, the district court did
not err in allowing the cross examination.
       22
          Nahmani also argues that the district court erred in denying his request to use a verdict
form that would have required the jury to find the specific weight of each drug involved in the
conspiracy. But under Supreme Court precedent, a jury is required to find drug weights only
when the government seeks to exceed the statutory maximum of 20 years for controlled
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       Although a district court has considerable discretion regarding supplemental

jury instructions, it may not misstate the law or confuse the jury. See Lopez,

590 F.3d at 1247-48. We review a challenged supplemental jury instruction “as

part of the entire jury charge, in light of the indictment, evidence presented[,] and

argument of counsel to determine whether the jury was misled.” United States v.

Johnson, 139 F.3d 1359, 1366 (11th Cir. 1998) (internal quotation marks omitted).

We will reverse the district court because of an erroneous instruction only “when

we are left with a substantial and ineradicable doubt as to whether the jury was

properly guided in its deliberations.” Brown, 590 F.3d at 1247. When the

instructions as a whole accurately convey the applicable law, “there is no reason

for reversal even though isolated clauses may, in fact, be confusing, technically

imperfect, or otherwise subject to criticism.” United States v. Beasley, 72 F.3d

1518, 1525 (11th Cir. 1996).

       In its initial instructions to the jury, the district court properly explained the

government’s burden in establishing Nahmani’s knowledge of the conspiracy. The

court instructed that to convict Nahmani of conspiracy to possess with intent to

distribute a controlled substance analogue, the jury had to find, among other things,

that Nahmani knew that the purpose of the conspiracy was to possess with intent to


substance offenses. Apprendi v. New Jersey, 530 U.S. 466, 490 (2000) (holding that “any fact
that increases the penalty for a crime beyond the prescribed statutory maximum must be
submitted to a jury”). Because the government did not seek to exceed the statutory maximum
here, no special verdict form was needed.
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distribute analogues. The government could prove that Nahmani knew the

substances were analogues by proving through direct or circumstantial evidence

that he knew that the substances either had (1) a chemical structure similar to a

controlled substance or (2) a stimulant, depressant, or hallucinogenic effect on the

central nervous system that was substantially similar to or greater than the effect of

a controlled substance in schedule I or II.

        In response to the jury’s questions asking whether Nahmani had to possess

the controlled substances and controlled substance analogues, the district court

explained that because the charged offense was conspiracy, the government need

not prove that Nahmani had possessed controlled substances or controlled

substance analogues. The district court also repeated to the jury a portion of its

earlier instruction about conspiracy. With respect to the conspiracy to possess with

intent to distribute a controlled substance, the district court explained that Nahmani

needed to know that the conspiracy involved a controlled substance. But the

district court did not repeat its earlier instruction about what knowledge Nahmani

needed to have about the substances for the controlled substance analogue

conspiracy. Instead, the district court stated that the “instruction is the same for

conspiracy with respect to controlled substance analogues.” Trial Tr. at 71 (Doc.

173).




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      Even if the supplemental instruction was technically imperfect, we cannot

say that the jury was misled. The jury’s question was about whether, to convict, it

had to find the Nahmani had possessed the substances. The district court directly

answered this question by stating that possession was not required. To provide

context, the district court repeated its initial instruction about conspiracy.

Although the court omitted the instruction specific to knowledge about analogues,

it reminded the jury to consider the supplemental instruction in connection with the

earlier instructions. Because “[t]he jury could refer to the initial jury instructions,

which correctly stated the” knowledge requirement for the controlled substance

analogue conspiracy offense, the district court did not abuse its discretion. United

States v. Baston, 818 F.3d 651, 662 (11th Cir. 2016), cert. denied, 137 S. Ct. 850

(2017).

      4.     There Was No Cumulative Error.

      Having reviewed each error Nahmani argues, we conclude that there is no

cumulative error. At most, Nahmani has shown that the trial court erred in

permitting Hurley to testify about the results of chemical testing showing the

substances that were seized from him were AB-Fubinaca. But as we explained

above, any error was harmless, and Nahmani is not entitled to a new trial.




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D.    The Evidence Was Sufficient to Support Nahmani’s Conviction.

      Nahmani next argues that we must reverse his conviction because there was

insufficient evidence for a jury to find that he conspired with another person. We

disagree because there was sufficient circumstantial evidence for a jury to find that

Nahmani agreed with his brother, Israel, to possess with intent to distribute

controlled substances and controlled substance analogues.

      We review de novo the district court’s denial of a judgment of acquittal on

sufficiency of evidence grounds, considering the evidence in the light most

favorable to the government and drawing all reasonable inferences as well as

credibility determinations in the government’s favor. United States v. Capers,

708 F.3d 1286, 1296-97 (11th Cir. 2013). We may not overturn a jury’s verdict “if

any reasonable construction of the evidence would have allowed the jury to find

the defendant guilty beyond a reasonable doubt.” Id. at 1297 (internal quotation

marks omitted).

      Here, the jury could have inferred from circumstantial evidence that

Nahmani and Israel conspired. To establish a conspiracy, “the government must

prove (1) an agreement between the defendant and one or more persons, (2) the

object of which is to do either an unlawful act or a lawful act by unlawful means.”

United States v. Garcia, 405 F.3d 1260, 1269 (11th Cir. 2005) (internal quotation




                                         36
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marks omitted). The government may rely on circumstantial evidence to prove the

existence of such an agreement. Id.

      There was ample circumstantial evidence that Nahmani and Israel agreed to

distribute illegal substances. Nahmani does not challenge that there was ample

evidence that he and Israel had agreed to work together, but he argues that Israel

cannot qualify as a conspirator because Israel was unaware that the object of their

agreement was to do an unlawful act. But viewing the evidence in the light most

favorable to the government, a jury could find that Israel was aware that he and

Nahmani were distributing illegal substances. This evidence included that Israel

used an alias to ship a package containing powder at Nahmani’s direction and went

to Nahmani’s house to remove chemicals that contained synthetic cannabinoids

after Nahmani alerted his wife that he was with the DEA. This is sufficient

evidence to support Nahmani’s conviction.

E.    The District Court Did Not Err in Applying a 20-Year Statutory
      Maximum.

      Nahmani also challenges his 20-year sentence, arguing that under the

conspiracy charged in the indictment the maximum sentence of imprisonment he

could receive was one year. He claims that because the indictment alleged only a

generic conspiracy to possess with intent to distribute controlled substances and

controlled substance analogues, the indictment gave him no notice that schedule I

substances were the object of the conspiracy. In the absence of such notice,
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Nahmani contends, he was subject to the one-year statutory maximum that applies

to conspiracies involving schedule V substances. We review de novo whether

Nahmani’s sentence exceeded the statutory maximum. See United States v.

Mazarky, 499 F.3d 1246, 1249 (11th Cir. 2007) (“We review de novo the legality

of a sentence . . . .” (internal quotation marks omitted)).

      Nahmani’s position rests on the assumption that nothing in the indictment

notified him that the substances involved in the conspiracy were controlled

substances listed on schedule I or II and thus subject to a 20-year statutory

maximum. See 21 U.S.C. § 841(b)(1)(C). Not so. The indictment alleged that

Nahmani conspired to possess with intent to distribute controlled substance

analogues. The Analogue Act makes clear that all controlled substance analogues

are treated as schedule I substances. Id. § 813 (“A controlled substance analogue

shall, to the extent intended for human consumption, be treated, for the purposes of

any Federal law as a controlled substance in schedule I.”); see McFadden v. United

States, 135 S. Ct. 2298, 2302 (2015). The indictment therefore gave Nahmani

notice that a 20-year statutory maximum applied, and the district court did not err

in applying a 20-year statutory maximum sentence.

F.    The District Court Did Not Err in Applying a 1:167 Equivalency Ratio
      for Purpose of Calculating the Relevant Weight of Drugs.

      Finally, Nahmani challenges the district court’s calculation of his offense

level under the Sentencing Guidelines, arguing that the district court improperly
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calculated his base offense level. He claims that in determining the equivalent

weight of marijuana the district court erred in finding that THC, not marijuana, was

the most closely related substance referenced in the Guidelines to the synthetic

cannabinoids and thus should not have applied the 1:167 equivalency ratio that

applies when the most closely related substance is THC. 23 But we cannot say that

the district court’s factual finding was clearly erroneous.

       The synthetic cannabinoids at issue in this case do not appear in § 2D1.1 of

the Guidelines, which provides the base offense level for drug offenses. When a

substance is not listed in § 2D1.1, the district court must “determine the base

offense level using the marihuana equivalency of the most closely related

       23
          Nahmani also argues that the district court erred at sentencing by (1) including in the
weight of drugs for which Nahmani was responsible the 1,100 kilograms of plant material seized
from Hurley and (2) applying a four-level increase in offense level under § 3B1.1 of the
Guidelines because Nahmani was an organizer or leader of criminal activity that involved five or
more participants or was otherwise extensive.
       First, even if the district court erred in attributing the weight of the plant material seized
from Hurley to Nahmani in calculating his sentence, any error was harmless and does not
warrant resentencing. See United States v. Mathenia, 409 F.3d 1289, 1292 (11th Cir. 2005).
Resentencing is unnecessary because if the district court excluded the weight of the plant
material seized from Hurley, the sentence calculated under the Guidelines would remain the
same. Nahmani did not challenge the portions of the PSR attributing to him 40 kilograms of
powder seized from him in July 2014, 60 kilograms of powder that he ordered from China, and
150 kilograms of powder that he sold to Hurley. Even if the district court had used 250
kilograms of a mixture containing synthetic cannabinoids as the relevant drug quantity,
Nahmani’s sentence would have remained the same. His guideline range still would have been
360 months to life, and the statutory maximum of 240 months would have become his sentence.
       Second, we cannot say that the district court erred in applying a four-level increase to the
offense level because Nahmani was an organizer or leader of criminal activity that involved five
or more participants or was otherwise extensive. See U.S.S.G. § 3B1.1. The district court’s
finding that the criminal activity was extensive was not clearly erroneous given the evidence that
Nahmani was acting as a wholesale distributor importing and selling large quantities of synthetic
cannabinoid powder to suppliers across the country.

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substance referenced in this guideline.” U.S.S.G. § 2D1.1 cmt. n.6. Because the

identification of the most closely related substance is a fact question, we review for

clear error. See United States v. Clarke, 562 F.3d 1158, 1165 (11th Cir. 2009).

      To identify the most closely related substance under the Guidelines, the

district court must consider “to the extent practicable,” the following three factors:

      (A) Whether the controlled substance not referenced in this guideline
      has a chemical structure that is substantially similar to a controlled
      substance referenced in this guideline.

      (B) Whether the controlled substance not referenced in this guideline
      has a stimulant, depressant, or hallucinogenic effect on the central
      nervous system that is substantially similar to the stimulant,
      depressant, or hallucinogenic effect on the central nervous system of a
      controlled substance referenced in this guideline.

      (C) Whether a lesser or greater quantity of the controlled substance
      not referenced in this guideline is needed to produce a substantially
      similar effect on the central nervous system as a controlled substance
      referenced in this guideline.

U.S.S.G. § 2D1.1 cmt. n.6. The Guidelines explicitly provide that each factor must

be considered only “to the extent practicable,” so the district court need not

consider a factor if there is no available evidence about it. Id.; see United States v.

Novak, 841 F.3d 721, 730 (7th Cir. 2016) (concluding that absence of evidence

about chemical structure meant that the court would consider only the two other

factors); United States v. Chowdhury, 639 F.3d 583, 586 (2d Cir. 2011) (holding

that district court’s determination about the most similar controlled substance was



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not clearly erroneous even in the absence of evidence about chemical structure and

potency).

       At sentencing, the government produced reliable and specific evidence, in

the form of Trecki’s testimony, that THC was the most closely related substance in

the Guidelines. The government produced no evidence at sentencing showing that

the synthetic cannabinoids had chemical structures that were substantially similar

to a controlled substance in the Guidelines, because no such evidence was

available. Given the lack of evidence about the chemical structure, the Guidelines

direct that we must consider only the two other factors. See U.S.S.G. § 2D1.1 cmt.

n.6. Trecki’s testimony supported the conclusion that each of the synthetic

cannabinoids at issue had (or was likely to have) a stimulant, depressant, or

hallucinogenic effect on the central nervous system that was substantially similar

to THC. Trecki explained that the synthetic cannabinoids and THC had similar

hallucinogenic effects on the brain. In contrast, although marijuana contained

THC, marijuana plants contained other chemicals that moderated the effect of the

THC. 24 He further testified that most of the synthetic cannabinoids were at least as

potent as an equivalent quantity of THC. 25


       24
          Nahmani argues that Trecki’s opinions were unreliable because he had no human
studies showing the effects of the synthetic cannabinoids. But for the reasons set forth in Section
III.C.2, we conclude that Trecki’s opinions were sufficiently reliable.
       25
           Trecki offered no opinion about whether 5-Bromo-UR-144 and 5-Chloro-UR-144 were
at least as potent as THC because there were no in vitro studies in rodents that would permit him
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       In light of this testimony, we cannot say that the district court clearly erred

in relying on Trecki’s testimony to find that the synthetic cannabinoids at issue

were most similar to THC. 26 Because the district court’s factual findings were not

clearly erroneous, it follows that the district court did not err in applying the 1:167

marijuana equivalency ratio for THC, even though the conversion ratio has severe

results here, especially because much of the weight (more than 1,100 pounds of

synthetic cannabinoids) in this case comes from the plant material that was coated

with the drugs.

                                    IV.    CONCLUSION

       For the reasons set forth above, we affirm the judgment of the district court.

       AFFIRMED.




to draw conclusions about the potency of these substances. Because it was not practicable to
present evidence about the potency of these substances, the district court did not need to consider
this factor with respect to these two substances. See U.S.S.G. § 2D1.1, cmt. n.6; Chowdhury,
639 F.3d at 586.
       26
           This conclusion is consistent with the decisions of our sister circuits that have
addressed this issue. See United States v. Hurley, 842 F.3d 170, 173 (1st Cir. 2016) (concluding
that district court did not err in finding that most closely related substance in the Guidelines to
AB-Fubinaca and XLR-11 was THC); Novak, 841 F.3d at730 (concluding that district court did
not err in finding most closely related substance in the Guidelines to XLR-11, PB-22, and other
synthetic cannabinoids was THC); United States v. Malone, 828 F.3d 331, 337-38 (5th Cir.)
(concluding that district court did not err in finding that most closely related substance in the
Guidelines to a synthetic cannabinoid was THC), cert. denied sub nom. Green v. United States,
137 S. Ct. 526 (2016); United States v. Ramos, 814 F.3d 910, 919 (8th Cir.) (concluding that
district court did not err in finding that most closely related substance in the Guidelines to XLR-
11 and other synthetic cannabinoids was THC), cert. denied, 137 S. Ct. 177 (2016).

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