United States v. Ronen Nahmani , 696 F. App'x 457 ( 2017 )

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[DO NOT PUBLISH]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
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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.
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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.
20
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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
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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
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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
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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).
42