                                                              FILED
                                                  United States Court of Appeals
                   UNITED STATES COURT OF APPEALS         Tenth Circuit

                         FOR THE TENTH CIRCUIT                   November 27, 2019
                         _________________________________
                                                                 Elisabeth A. Shumaker
                                                                     Clerk of Court
    UNITED STATES OF AMERICA,

          Plaintiff - Appellee,
                                                        No. 18-2121
    v.                                        (D.C. No. 1:15-CR-03394-WJ-1)
                                                         (D.N.M.)
    FIDAL ABDELJAWAD,

          Defendant - Appellant.
                        _________________________________

                          ORDER AND JUDGMENT *
                          _________________________________

Before BACHARACH, McHUGH, and SEYMOUR, Circuit Judges.
                 _________________________________

         This appeal involves sentencing for drug crimes. When deciding on

the sentence, district courts ordinarily consider the potency and weight of

the drugs. To aid courts in considering potency and weight, the U.S.

Sentencing Commission has created guidelines. But new drugs frequently

enter the market, 1 creating gaps in the Sentencing Commission’s



*
      This order and judgment does not constitute binding precedent except
under the doctrines of law of the case, res judicata, and collateral estoppel.
But the order and judgment may be cited for its persuasive value if
otherwise appropriate. Fed. R. App. P. 32.1(a); 10th Cir. R. 32.1(A).

1     See United States v. Ono, 997 F.2d 647, 649 (9th Cir. 1993) (noting
that “[t]he illicit drug industry is constantly changing and experimenting to
create new ‘designer drugs,’” preventing the Sentencing Commission from
handiwork. An example is the emergence of synthetic marijuana, which

was involved in Mr. Abdeljawad’s crimes. Synthetic marijuana is the

combination of synthetic cannabinoid, which is a controlled substance, and

inert plant material.

      At the time of Mr. Abdeljawad’s sentencing, the guidelines did not

specify how to consider mixtures containing synthetic cannabinoid. So the

district court had to decide how to handle this gap in the guidelines. The

district court decided to handle this gap by excluding the inert plant

material and considering only the synthetic cannabinoid. Mr. Abdeljawad

argues that the district court should have included the inert plant material.

We disagree.

1.    When gaps exist, the district court must find an equivalent drug
      from a list of controlled substances.

      To decide on the sentence, the district court must determine the

guideline range for the applicable year. (Here, the applicable year is

2017.) 2 To determine this range, the court considers the drug weight. See

U.S. Sentencing Guidelines Manual § 2D1.1 cmt. n.5 (U.S. Sentencing

Comm’n 2016).


“list[ing] or predict[ing] every potential chemical composition that yields a
new drug”).
2
     In 2017, however, the U.S. Sentencing Commission did not publish a
new set of the guidelines. The Commission instead continued to use the
2016 version throughout 2017.

                                         2
      But different drugs may weigh the same yet differ dramatically in

potency. Given these variations in potency, the Sentencing Commission

provides two lists that guide consideration of relatively common drugs:

(1) a drug-quantity table and (2) a drug-equivalency table. Id. § 2D1.1(c)

(drug-quantity table), cmt. n.8(D) (drug-equivalency table). The drug-

quantity table lists the base-offense level, which is triggered by the type

and weight of the controlled substance; and the drug-equivalency table

provides a list to convert the weights for various drugs into a uniform

system of measurement. But many drugs are omitted from both lists.

      When the defendant’s drug is omitted, it must be compared to one of

the drugs on the Sentencing Commission’s lists. 3 For this comparison, the

Sentencing Commission specifies that both the actual drug and the listed

drug must be “controlled substance[s].” Id. § 2D1.1 cmt. n.6. The actual


3
      The application note requires comparison to “the most closely related
controlled substance referenced in this guideline.” U.S. Sentencing
Guidelines Manual § 2D1.1 cmt. n.6 (U.S. Sentencing Comm’n 2016)
(emphasis added). Some circuits treat the italicized phrase (“in this
guideline”) as a reference to the drug-equivalency table. United States v.
Ramos, 814 F.3d 910, 918 (8th Cir. 2016). Other circuits treat this phrase
as a reference to either of the two lists (either the drug-quantity table or
the drug-equivalency table). United States v. Moreno, 870 F.3d 643, 645–
46 (7th Cir. 2017); United States v. Giggey, 867 F.3d 236, 239 (1st Cir.
2017).

       This difference would not affect our analysis. Both sides agree that
the court had to compare Mr. Abdeljawad’s drug with THC (as well as
marijuana). THC appears in the list for the drug-equivalency table but not
the list for the drug-quantity table.

                                         3
drug is described as “a controlled substance that is not specifically

referenced in this guideline.” Id. (emphasis added). The court must

compare this “controlled substance” to another “controlled substance” that

is “referenced in this guideline.” Id.

2.    The district court considered only the synthetic cannabinoid
      (without the plant material) to make the comparison.

      This case requires the Court to decide how to conduct this

comparison when the case involves synthetic marijuana. Until recently,

marijuana consisted of plant material that naturally contains THC. Now,

however, marijuana can also be synthetic. Synthetic marijuana is a mixture

of synthetic cannabinoid (a synthetic substance that binds to the same brain

cell receptors as THC) and inert plant material. The inert plant material

serves as a carrier medium for someone to use the synthetic cannabinoid.

      Prior to 2018, natural marijuana and THC appeared in the Sentencing

Commission’s lists, but synthetic cannabinoid was omitted. U.S.

Sentencing Guidelines Manual § 2D1.1(c) (drug-quantity table), cmt.

n.8(D) (drug-equivalency table) (U.S. Sentencing Comm’n 2016).

Notwithstanding this omission, the district court had to calculate the

converted drug weight of Mr. Abdeljawad’s drug in order to use the drug-

quantity table.

      To calculate the converted drug weight, the court had to determine

which listed controlled substance on the drug-equivalency table most


                                         4
closely resembled Mr. Abdeljawad’s drug. Among the possibilities, Mr.

Abdeljawad picked marijuana and the government picked THC.

3.    The inert plant material was properly excluded from the phrase
      “controlled substance that is not specifically referenced.”

      Before these drugs could be compared, the district court had to apply

Application Note 6, which instructs courts on how to calculate the weight

of drugs omitted from the Sentencing Commission’s lists. The application

note refers to a drug omitted from these lists as “a controlled substance

that is not specifically referenced in this guideline.” U.S. Sentencing

Guidelines Manual § 2D1.1 cmt. n.6 (U.S. Sentencing Comm’n 2016).

      The district court had to interpret this phrase in the context of Mr.

Abdeljawad’s case. Does this phrase refer to

           just the synthetic cannabinoid or

           the mixture of the synthetic cannabinoid and the inert plant
            material?

The district court decided to consider just the synthetic cannabinoid

(without the inert plant material).

      A.    Ordinary Meaning

      In considering this decision, we must interpret the guidelines.

Because interpreting the guidelines involves a legal question, we engage in




                                         5
de novo review. United States v. Archuleta, 865 F.3d 1280, 1285 (10th Cir.

2017).

      Conducting this review requires us to determine the Sentencing

Commission’s intent. United States v. Rivera-Oros, 590 F.3d 1123, 1129

(10th Cir. 2009). To do so, we use “accepted rules of statutory

construction.” United States v. Marrufo, 661 F.3d 1204, 1207 (10th Cir.

2011) (quoting United States v. Nacchio, 573 F.3d 1062, 1066 (10th Cir.

2009)). These rules generally involve consideration of a guideline term’s

ordinary meaning. United States v. Thomas, 939 F.3d 1121, 1123 (10th Cir.

2019).

      We must interpret the term “controlled substance that is not

specifically referenced in this guideline.” This phrase can be broken down

into a noun (“controlled substance”) and a restrictive modifier (“that is not

specifically referenced in this guideline”). The noun itself (“controlled

substance”) is undefined in the guidelines. And “[w]hile the word

‘controlled’ may have a plain and ordinary meaning, whether a substance is

‘controlled’ must, of necessity, be tethered to some state, federal, or local

law.” United States v. Leal-Vega, 680 F.3d 1160, 1167 (9th Cir. 2012)

(footnote omitted). We thus interpret the term “controlled substance” based

on its legal definition.




                                         6
      The legal definition of “controlled substance” comes from the

Controlled Substances Act. 21 U.S.C. § 802(6); 4 see Leal-Vega, 680 F.3d at

1167 (holding “that the term ‘controlled substance,’ as used in the ‘drug

trafficking offense’ definition in U.S.S.G. § 2L1.2, means those substances

listed in the [Controlled Substances Act]”). This statute defines a

“controlled substance” as “a drug or other substance . . . included in

schedule I, II, III, IV, or V of [the Act].” 21 U.S.C. § 802(6). Schedule I

includes synthetic cannabinoid (without the inert plant material). Id. § 812

sched. I(d). But none of the schedules include the mixture of synthetic

cannabinoid and inert plant material.

      Given the absence of the mixture in any of the Act’s schedules, the

mixture can’t constitute a “controlled substance.” And if the mixture isn’t

a “controlled substance,” it can’t fall into an even narrower class of

controlled substances that are “not specifically referenced in this

guideline.” 5


4     The Sentencing Commission showed its intent to use the Controlled
Substances Act’s definition by using the Act to create a “drug-quantity
table,” which standardizes the courts’ consideration of common drugs. See
U.S. Sentencing Guidelines Manual § 2D1.1 cmt. n.8(A) (U.S. Sentencing
Comm’n 2016) (explaining that the Sentencing Commission used the
Controlled Substances Act to create the drug-quantity table).
5
      Mr. Abdeljawad points out that Application Note 6 also requires
consideration of “[w]hether 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

                                         7
     B.    Comparison of Chemical Structures of the Actual and Listed
           Drugs

     The meaning of the term “controlled substance” comes not only from

the Controlled Substances Act but also from the context of the criteria in

Application Note 6. These criteria include a comparison of the chemical

structures for the actual drug and the listed drug. U.S. Sentencing

Guidelines Manual § 2D1.1 cmt. n.6(A) (U.S. Sentencing Comm’n 2016) .

     Suppose that we adopt Mr. Abdeljawad’s interpretation, including the

inert plant material in the comparisons to THC and marijuana. If we were

to do so, we’d consider the chemical structure of the inert plant material.

But this material serves only as the carrier medium for the synthetic

cannabinoid. Why would the carrier medium’s chemical structure be

pertinent? If the chemical structure of THC or marijuana matched the

chemical structure of the synthetic cannabinoid, that match should be

enough. Comparing the chemical structure of the carrier medium to

marijuana or THC would serve no conceivable purpose.



substance referenced in this guideline.” U.S. Sentencing Guidelines
Manual § 2D1.1 cmt. n.6(c) (U.S. Sentencing Comm’n 2016) . According to
Mr. Abdeljawad, this criterion “does not permit the sentencing judge to
disregard controlled substances that are, by their very nature, mixtures.”
Appellant’s Opening Br. at 17 (quoting United States v. Ramos, 814 F.3d
910, 922 (8th Cir. 2016) (Bright, J., concurring in part and dissenting in
part) (emphasis added)). But synthetic marijuana is not a “controlled
substance.” Synthetic marijuana thus can’t constitute a “controlled
substance that is not specifically referenced in this guideline.”

                                         8
        Given the context of Application Note 6’s criteria, it would make

little sense to consider the inert plant material as part of Mr. Abdeljawad’s

drug.

        C.   The Sentencing Commission’s Alleged Intent to Increase
             Punishment Based on the Concentration of THC

        Considering only the synthetic cannabinoid as the “controlled

substance that is not specifically referenced in this guideline,” the district

court compared the synthetic cannabinoid to marijuana and THC. The

district court found that between the two controlled substances, synthetic

cannabinoid more closely resembled THC.

        Selecting THC catapulted the guideline range, making every gram of

synthetic cannabinoid the equivalent of 167 grams of marijuana. Mr.

Abdeljawad argues that this astronomic increase in weight undermines the

Sentencing Commission’s intent to punish based on the concentration of

THC. According to Mr. Abdeljawad, the Sentencing Commission intended

to mete out the most severe punishment for THC, followed by hashish oil

(which is more diluted than THC), then by hashish (which is more diluted

than hashish oil). U.S. Sentencing Guidelines Manual § 2D1.1 cmt. n.8(D)

(U.S. Sentencing Comm’n 2016) .

        But later events show that a multiplier of 167 is consistent with the

Sentencing Commission’s intent. After Mr. Abdeljawad was sentenced, the

Commission amended the drug-equivalency table to include synthetic


                                           9
cannabinoid. In this amendment, the Commission assigned each gram of

synthetic cannabinoid the marijuana equivalent of 167 grams—precisely

the same result as if the court were to consider THC as the most

comparable controlled substance. U.S. Sentencing Guidelines Manual

§ 2D1.1 cmt. n.8(D) (U.S. Sentencing Comm’n 2018) ; see United States v.

Koss, 812 F.3d 460, 471 (5th Cir. 2016) (“[T]he plain language of the

Guidelines states that mixtures or substances containing a detectable

amount of THC are properly calculated using the 1:167 gram ratio.”).

Given this change in the guidelines, we view the district court’s exclusion

of the inert plant material as consistent with the Sentencing Commission’s

intent.

      D.   Absurdity of Ruling Out Other Possible Candidates for
           Comparison

      Mr. Abdeljawad also argues that our interpretation leads to an

absurdity because it would prevent consideration of marijuana as the

equivalent of any mixture of a THC-based substance and inert plant

material. We reject this argument.

      The issue before the district court was simply how to define Mr.

Abdeljawad’s drug: Was it just the synthetic cannabinoid or did it include

the inert plant material? Mr. Abdeljawad suggests that excluding the inert

plant material would prevent any court from considering marijuana as the

equivalent of a mixture of inert plant material and synthetic cannabinoid.


                                        10
If this suggestion is right, however, including the inert plant material

would presumably prevent a court from considering THC as the equivalent.

So regardless of whether the Court considers inert plant material as part of

the controlled substance, the decision could affect all future cases

involving consideration of synthetic marijuana. 6

      E.    Dilution of the THC

      Mr. Abdeljawad also argues that (1) our interpretation leads to unjust

results because his synthetic cannabinoid was diluted by inert plant

material and (2) the dilution should soften his base-offense level. But our

interpretation accords with “the language and design of the [guidelines] as

a whole.” K Mart Corp. v. Cartier, Inc., 486 U.S. 281, 291 (1988).

      Even if Mr. Abdeljawad were correct that the inert plant material

diluted his synthetic cannabinoid, the guidelines generally treat controlled

substances identically regardless of their dilution. For example, a

defendant bearing responsibility for 10 kilograms of marijuana with 1%

THC would be assigned the same base-offense level as a defendant



6
      Mr. Abdeljawad also argues that the district court’s approach would
never permit selection of hashish or hashish oil as the equivalent of
synthetic marijuana. In district court, however, Mr. Abdeljawad picked
marijuana and the government picked THC. See Part 2, above. So the
district court had no reason to compare Mr. Abdeljawad’s controlled
substance to hashish or hashish oil. We thus express no opinion on whether
hashish or hashish oil would resemble Mr. Abdeljawad’s controlled
substance more closely than THC.

                                         11
responsible for 10 kilograms of marijuana with 99% THC (even though the

marijuana in the first case was far more diluted). See Chapman v. United

States, 500 U.S. 453, 461 (1991) (“Congress adopted a ‘market-oriented’

approach to punishing drug trafficking, under which the total quantity of

what is distributed, rather than the amount of pure drug involved, is used

to determine the length of the sentence.”). The guidelines thus do not

generally account for dilution in connection with the base-offense level.

See United States v. Upthegrove, 974 F.2d 55, 56 (7th Cir. 1992) (“The

Sentencing Commission made an explicit decision to focus on the weight

and not the purity of the drugs in determining the offense level.”); United

States v. Skelton, 901 F.2d 1204, 1205 (4th Cir. 1990) (stating that “the

purity of the drug is not usually a consideration for purposes of

determining the base offense level”). 7

      F.    The Rule of Lenity

      Mr. Abdeljawad also argues that if the guidelines are unclear, the

rule of lenity should give him the benefit of any doubt. But the guidelines

are clear. They specify that the actual drug must be a “controlled

substance,” which can refer only to the synthetic cannabinoid (not the



7
      The guidelines instead account for purity through departures. See
U.S. Sentencing Guidelines Manual § 2D1.1 cmt. n.27 (U.S. Sentencing
Comm’n 2016). For example, the guidelines permit an upward departure if
the defendant possesses unusually pure drugs. Id. § 2D1.1 cmt. n.27(C).

                                          12
mixture of the synthetic cannabinoid and inert plant material). Given the

clarity of this language, we have no reason to apply the rule of lenity. See

United States v. Randall, 472 F.3d 763, 766–67 (10th Cir. 2006)

(concluding that the rule of lenity did not apply because the guideline

provision was unambiguous).

                                     * * *

      The phrase “controlled substance that is not specifically referenced

in this guideline” refers to synthetic cannabinoid, not the mixture of

synthetic cannabinoid and inert plant material. Because the mixture isn’t a

controlled substance, the mixture can’t constitute a “controlled substance

that is not specifically referenced in this guideline.” The district court thus

did not err in using only the synthetic cannabinoid to decide the equivalent

controlled substance level.

      Affirmed.
                                       Entered for the Court



                                       Robert E. Bacharach
                                       Circuit Judge




                                         13
