Court Opinion

ID: 4215979
Source: CourtListenerOpinion
Date Created: 2017-10-30 17:01:45.223075+00
Date Added: 2024-06-11T14:42:01.308033
License: Public Domain

FOR PUBLICATION

  UNITED STATES COURT OF APPEALS
       FOR THE NINTH CIRCUIT

UNITED STATES OF AMERICA,                No. 16-10460
                 Plaintiff-Appellee,
                                            D.C. No.
                 v.                      2:15-cr-00041-
                                          GMN-NJK-1
MICAH JOEL AHKEEM IVERSON
KELLY, AKA Iverson Kelly Micah
Johel Ahkeem,                              OPINION
              Defendant-Appellant.

     Appeal from the United States District Court
              for the District of Nevada
   Gloria M. Navarro, Chief District Judge, Presiding

      Argued and Submitted September 15, 2017
              San Francisco, California

                Filed October 30, 2017

    Before: Ronald M. Gould, Richard C. Tallman,
         and Paul J. Watford, Circuit Judges.

              Opinion by Judge Tallman
2                   UNITED STATES V. KELLY

                          SUMMARY *

                          Criminal Law

   The panel affirmed a conviction for selling and
possessing with the intent to sell over 446 grams of ethylone,
and dismissed the defendant’s challenge to his sentence.

    The panel rejected the defendant’s contention that the
Drug Enforcement Administration violated the non-
delegation doctrine by temporarily adding ethylone as a
Schedule I controlled substance. The panel explained that
the plain language of the Controlled Substances Act, as
codified at 21 U.S.C. §§ 811(h) and 812(b), permits the DEA
to make findings for a parent substance as a basis to
temporarily schedule that substance and its isomers.

    The panel rejected the defendant’s contention that the
DEA violated due process by failing to provide adequate
notice that ethylone was a controlled substance. The panel
explained that the defendant received fair notice when the
DEA filed the Notice and Order in the Federal Register.

    The panel held that the rule of lenity does not apply
because the text, history, and purpose of the Controlled
Substances Act make unambiguous that Congress intended
to empower the DEA to temporarily schedule isomers.

    The panel held that because the intent of Congress is
clear that the DEA has authority to temporarily schedule a

    *
      This summary constitutes no part of the opinion of the court. It
has been prepared by court staff for the convenience of the reader.
                 UNITED STATES V. KELLY                     3

parent substance and its isomers, the district court properly
accorded Chevron deference to the agency interpretation.

    The panel held that the defendant’s challenge to the
district court’s criminal history calculation and resulting
sentence is waived.

                        COUNSEL

Erica J. Choi (argued), Assistant Federal Public Defender;
Rene L. Vallardes, Federal Public Defender; Office of the
Federal Public Defender, Las Vegas, Nevada; for
Defendant-Appellant.

Nancy M. Olson (argued), Assistant United States Attorney;
Elizabeth O. White, Appellate Chief; Steven W. Myhre,
Acting United States Attorney; United States Attorney’s
Office, Las Vegas, Nevada; for Plaintiff-Appellee.

                         OPINION

TALLMAN, Circuit Judge:

    Defendant-Appellant Micah Joel Ahkeem Iverson Kelly
(“Kelly”) challenges the district court’s denial of his motion
to dismiss the indictment charging him with distributing so-
called “designer drugs.” Kelly entered a conditional plea of
guilty to selling and possessing with the intent to sell over
446 grams of ethylone under the street name “Ecstasy.” On
appeal, Kelly argues he preserved the following issues:
(1) the Drug Enforcement Administration (“DEA”) violated
the non-delegation doctrine by failing to comply with the
Controlled Substances Act, as codified at 21 U.S.C.
4                    UNITED STATES V. KELLY

§§ 811(h) and 812(b) in temporarily scheduling ethylone;
(2) DEA violated due process by failing to provide adequate
notice that ethylone was a controlled substance; (3) the rule
of lenity applies because § 811(h) is ambiguous as to
whether DEA may temporarily schedule unnamed isomers;
(4) DEA’s temporary scheduling of ethylone is not entitled
to deference under Chevron, U.S.A., Inc. v. Natural
Resources Defense Council, Inc., 467 U.S. 837 (1984); and
(5) the district court erred in finding that his criminal history
category was V, instead of IV, in violation of the Sentencing
Guidelines. We have jurisdiction under 28 U.S.C. § 1291
and we affirm as to the first four issues and dismiss as to the
last, which we find barred by his partial appellate waiver.

                                    I

    Congress enacted the Controlled Substances Act
(“CSA”) as part of the Comprehensive Drug Abuse
Prevention and Control Act of 1970 to restrict the illegal
trafficking of various substances found to pose a danger to
the health and general welfare of the nation. Pub. L. No. 91-
513, § 101(2), 84 Stat. 1242 (codified at 21 U.S.C.
§ 801(2)). 1 The CSA makes it unlawful to knowingly
manufacture, distribute, or possess any controlled substance
except in a manner authorized by the CSA. §§ 841(a)(1),
844(a). The CSA categorizes all controlled substances into
five schedules. § 812. 2 The initial schedules established by

    1
      All further statutory and regulatory citations are to Title 21 of the
United States Code and Title 21 of the Code of Federal Regulations,
unless otherwise noted.

    2
       A controlled substance is “a drug or other substance” that is
included in Schedule I, II, III, IV, or V. § 802(6). “Control” is a term of
art in the CSA, meaning “to add a drug or other substance . . . to a
schedule.” § 802(5).
                 UNITED STATES V. KELLY                    5

Congress are found at 21 U.S.C. § 812(c), and the current
schedules are published in 21 C.F.R. Part 1308. “Violations
involving schedule I substances carry the most severe
penalties, as these substances are believed to pose the most
serious threat to public safety.” Touby v. United States,
500 U.S. 160, 162 (1991).

    The CSA authorizes the Attorney General to add,
remove, or transfer substances to, from, or between
schedules. § 811. The Attorney General has delegated this
authority to the Administrator of the DEA, who in turn has
delegated it to the Deputy Administrator. 28 C.F.R.
§ 0.100(b). “When adding a substance to a schedule, the
[DEA] must follow specified procedures.” Touby, 500 U.S.
at 162. The DEA may add a drug to a schedule in one of two
ways: permanently or temporarily.

                             A

    To permanently schedule a drug, the DEA first must
obtain a scientific and medical evaluation of the drug and a
recommendation as to whether it should be controlled from
the Secretary of Health and Human Services (“HHS”).
§ 811(b). The DEA may not schedule the drug if the
Secretary recommends against it. Id. Second, the DEA must
consider eight statutory factors, including the drug’s actual
or relative potential for abuse, scientific evidence of its
pharmacological effect, the state of current scientific
knowledge regarding the drug, the drug’s psychic or
physiological dependence liability, and whether it is an
immediate precursor of a drug that is already controlled.
§ 811(c).

   If the DEA wants to place the drug into Schedule I, it
must also find that the drug has a high potential for abuse,
no currently accepted medical use in treatment, and no
6                   UNITED STATES V. KELLY

accepted safe use under medical supervision. § 812(b)(1). 3
The DEA must then comply with the formal rulemaking
provisions of the Administrative Procedure Act (“APA”),
5 U.S.C. §§ 556–57. § 811(a). Lastly, it must issue a final
rule adding the drug to 21 C.F.R. § 1308.11, which contains
the current list of Schedule I substances. Id. This final rule,
which concludes the permanent scheduling process, is
subject to judicial review. § 877.

    Because of these procedural requirements, it often takes
six to twelve months for the DEA to permanently schedule a
new drug after the DEA identifies it. Touby, 500 U.S. at 163.
This delay produced predictable results. “Drug traffickers
were able to take advantage of this time gap by designing
drugs that were similar in pharmacological effect to
scheduled substances but differed slightly in chemical
composition, so that existing schedules did not apply to
them.” Id. “These ‘designer drugs’ were developed and
widely marketed long before the Government was able to
schedule them and initiate prosecutions.” Id.

                                  B

    To combat the designer drug problem and reduce the
inherent regulatory delay, Congress amended the CSA in
1984 to create an expedited procedure by which the DEA
can temporarily schedule a new drug 30 days after
identifying it if doing so is “necessary to avoid an imminent
hazard to the public safety.” § 811(h)(1); see Touby,
500 U.S. at 163. A temporarily scheduled drug may only be

    3
      These three factors, in varying gradations, are used to categorize
drugs into the other four schedules. For example, Schedule II drugs have
a high potential for abuse, but they have a currently accepted medical
use. § 812(b)(2).
                  UNITED STATES V. KELLY                     7

placed into Schedule I, and only if the Secretary has not
approved it for sale or exempted it for research under the
Food, Drug, and Cosmetic Act (“FDCA”), 21 U.S.C. § 355.
Id. Temporary scheduling under § 811(h) allows the DEA
“to bypass, for a limited time, several of the requirements for
permanent scheduling.” Touby, 500 U.S. at 163.

    To find that a drug poses an imminent hazard to public
safety justifying temporary scheduling, the DEA must
consider only three of the eight factors required for
permanent scheduling: (1) the drug’s history and current
pattern of abuse; (2) the scope, duration, and significance of
the abuse; and (3) what, if any, risk it poses to the public
health. § 811(c)(4)–(6), (h)(3). In considering these factors,
the DEA must consider the drug’s “actual abuse, diversion
from legitimate channels, and clandestine importation,
manufacture, or distribution.” § 811(h)(3). In addition, the
DEA must find that it has a high potential for abuse, no
currently accepted medical use in treatment, and no accepted
safe use under medical supervision. § 812(b)(1).

    Rather than comply with the APA formal rulemaking
provisions attending permanent scheduling, the DEA must
provide only 30-days’ notice of the proposed temporary
scheduling in the Federal Register. § 811(h)(1)(A). The
DEA must also transmit to the Secretary a 30-days’ notice of
its intent to temporarily schedule the drug, and it must
consider any comments the Secretary submits in response.
§ 811(h)(1)(B), (h)(4).      However, unlike permanent
scheduling, the Secretary’s prior approval of the temporary
scheduling is not required. Touby, 500 U.S. at 163. Lastly,
the DEA must issue a final order adding the drug to
21 C.F.R. § 1308.11(h). § 811(h)(1). The temporary
scheduling order remains valid for two years, during which
time the DEA presumably will initiate permanent scheduling
8                    UNITED STATES V. KELLY

proceedings, in which case the order may be extended for an
additional year. § 811(h)(2). A temporary scheduling order
is not subject to judicial review, except (as here) when
challenged by a criminal defendant in defense to
prosecution. § 811(h)(6); Touby, 500 U.S. at 168.

    If the drug is later permanently scheduled, it is removed
from § 1308.11(h) and added to § 1308.11(b)–(g),
depending on whether it is designated as an opiate, opium
derivative, hallucinogenic substance, depressant, stimulant,
or cannabimimetic agent. See § 811(h)(5).

                                    C

    On November 7, 2013, the DEA notified the Secretary
by letter of its intent to temporarily schedule ten synthetic
cathinones, including butylone, because doing so was
necessary to avoid an imminent hazard to the public safety.
Synthetic cathinones are recreational drugs popular with
some youth and young adults in the United States. They
produce pharmacological effects substantially similar to
MDMA, cathinone, methcathinone, amphetamine, and
methamphetamine. Synthetic cathinones are commonly
marketed on the street as “Ecstasy” or “bath salts,” sold in
the form of tablets and powders, and ingested by swallowing
or snorting.

    The DEA’s letter to the Secretary did not mention the ten
synthetic cathinones’ isomers 4 or salts. On December 4,
2013, the Secretary advised the DEA that there were no
investigational or approved new drug applications for the ten
    4
      An isomer is “any of two or more chemical compounds having the
same constituent elements in the same proportion by weight but differing
in physical or chemical properties because of differences in the structures
of their molecules.” Isomer, Webster’s New College Dictionary (2009).
                    UNITED STATES V. KELLY                            9

synthetic cathinones and that HHS had no objection to their
temporary placement in Schedule I. On January 28, 2014,
the DEA published in the Federal Register a Notice of its
intent to temporarily schedule the ten synthetic cathinones,
along with their “optical, positional, and geometric isomers,
salts and salts of isomers.” On March 7, 2014, the DEA
issued a final Order temporarily adding the ten synthetic
cathinones to Schedule I at § 1308.11(h)(19)–(28). As
relevant here, the Order temporarily added “[b]utylone, its
optical, positional, and geometric isomers, salts and salts of
isomers” to Schedule I at § 1308.11(h)(22). 5

                                  II

                                  A

    In January 2015, a Nevada drug task force learned that
Kelly was selling large quantities of MDMA 6, or “Ecstasy,”
in the Las Vegas area. An undercover officer arranged to
purchase the MDMA from Kelly, and Kelly sold
approximately 140 grams of powder to the officer in two
separate transactions. During the third transaction, Kelly
was arrested possessing another 306 grams. Forensic
analysis later revealed that the powder was ethylone, not

    5
      Three years later, after the events in this case, the DEA issued a
final Rule permanently scheduling the ten synthetic cathinones. See
82 Fed. Reg. 12171 (Mar. 1, 2017) (codified at 21 C.F.R.
§ 1308.11(d)(59)–(68)). Currently, butylone and its optical, positional,
and geometric isomers, salts, and salts of isomers are designated as
Schedule I(c) hallucinogenic substances listed in the regulations at
§ 1308.11(d)(62).

    6
      “3, 4-methylenedioxy-methamphetamine (MDMA) is a synthetic
drug that alters mood and perception.” National Institute on Drug Abuse,
What is MDMA?, https://www.drugabuse.gov/publications/drugfacts/m
dma-ecstasymolly (last visited Oct. 6, 2017).
10                UNITED STATES V. KELLY

MDMA. A grand jury indicted Kelly on three counts of
distributing and possessing with intent to distribute
“Ethylone, a Schedule I controlled substance,” in violation
of 21 U.S.C. § 841(a)(1) and (b)(1)(C).

    It is undisputed here that ethylone is a positional isomer
of butylone. An isomer is a molecule with the same
chemical formula as another molecule, but its atoms are
arranged in a different sequence. For example, butylone and
ethylone share the chemical formula C12H15NO3, but they
differ in the location of a functional group:

    Based on how the atoms are arranged, isomers can be
classified as chain, functional, positional, conformational,
optical, or geometric. See A Brief Guide to Types of
Isomerism in Organic Chemistry, http://www.compound
chem.com/2014/05/22/typesofisomerism/ (last visited July
24, 2017). Not all isomers of a scheduled drug are illegal,
however. Thus, Schedule I categorically controls all
permanently scheduled drugs’ optical isomers only. An
exception exists if the permanently scheduled drug is a
hallucinogenic substance listed in § 1308.11(d), in which
case Schedule I categorically controls its optical, positional,
and geometric isomers. See §§ 802(14), 812(c)(I); 21 C.F.R.
§ 1300.01(b).     Permanently scheduled hallucinogenic
substances are called “Schedule I(c)” drugs, which refers to
                 UNITED STATES V. KELLY                    11

the initial statutory schedule in which they are placed.
§ 812(c)(I)(C).

                              B

    On the morning that his trial was set to begin, Kelly
moved to dismiss the indictment on the ground that ethylone
was not a Schedule I controlled substance. He did not
contest for purposes of his motion, and does not contest on
appeal, that ethylone is a positional isomer of butylone. He
argued, however, that ethylone was not properly scheduled
because (1) the DEA failed to comply with §§ 811(h) and
812(b)’s procedural requirements; (2) the DEA did not
provide adequate notice that ethylone was a controlled
substance; (3) § 811(h) was ambiguous as to whether the
DEA was authorized to temporarily schedule unnamed
isomers without identifying or making the requisite findings
for them, and the rule of lenity required the court to resolve
that ambiguity in Kelly’s favor; and (4) the DEA’s
temporary scheduling of ethylone was arbitrary and
capricious.

    A magistrate judge issued a report and recommendation
denying Kelly’s motion, which the district court adopted in
full. The district court found that § 811(h) unambiguously
authorized the DEA to schedule unnamed isomers. It
declined to apply the rule of lenity because the DEA’s Order
was not a criminal statute, but rather an administrative
regulation that was entitled to Chevron deference. Applying
Chevron, the court upheld the DEA’s Order because
(1) § 811(h) was unambiguous that the DEA could schedule
ethylone as an unnamed positional isomer of butylone; and
(2) the DEA’s action was not arbitrary or capricious. Lastly,
the court found that Kelly had adequate notice that ethylone
was a controlled substance because the DEA’s Notice and
12                   UNITED STATES V. KELLY

Order expressly included butylone’s “optical, positional, and
geometric isomers.” 7

                                   C

    After his motion to dismiss was denied, Kelly pleaded
guilty to all three counts in the indictment under a
conditional plea agreement that reserved his right to bring
this appeal of the district court’s denial of his motion to
dismiss. In support of his guilty plea, Kelly admitted to
selling and possessing with the intent to sell over 446 grams
of ethylone. He also agreed that the district court would
determine his criminal history category under the Sentencing
Guidelines. He stipulated to a recommended sentence of
57 months “so long as the Criminal History Category [was]
IV or less.” If the “Criminal History Category [was] V or
greater,” he stipulated that his recommended sentence would
be at the “low-end of the Sentencing Guidelines range
determined by the Court.” In addition, Kelly expressly
waived his “right to appeal any sentence imposed within or
below the applicable Sentencing Guideline range as
determined by the Court,” as well as “the manner in which
the Court determined that sentence.”

    At sentencing, the district court adopted the Presentence
Report, found a criminal history category of V, and
sentenced Kelly to 70 months’ imprisonment at the low end
of his applicable Guidelines range. After judgment was

     7
       The district court also denied Kelly’s request for an evidentiary
hearing to present expert testimony that “a substance’s isomer does not
necessarily have the same effects and properties as the substance itself.”
The court held that such a hearing was not necessary because it was
sufficient, for purposes of the motion to dismiss, that Kelly agreed
ethylone was a positional isomer of butylone.
                 UNITED STATES V. KELLY                    13

entered, Kelly timely appealed the denial of his motion to
dismiss the indictment and his sentence.

                             III

    We have jurisdiction under 28 U.S.C. § 1291. “We
review the sufficiency of an indictment de novo.” United
States v. Kaplan, 836 F.3d 1199, 1216 (9th Cir. 2016). “We
review de novo a district court’s decision whether to dismiss
a charge in an indictment based on its interpretation of a
federal statute.” United States v. Olander, 572 F.3d 764, 766
(9th Cir. 2009). We review de novo both an “agency’s
interpretation or application of a statute,” Snoqualmie Indian
Tribe v. FERC, 545 F.3d 1207, 1212 (9th Cir. 2008), and the
constitutionality of an agency’s regulation, see Gonzalez v.
Metro. Transp. Auth., 174 F.3d 1016, 1018 (9th Cir. 1999).
And we review de novo whether a defendant has waived his
appeal rights pursuant to a plea agreement. United States v.
Lightfoot, 626 F.3d 1092, 1094 (9th Cir. 2010).

                             IV

    Federal Rule of Criminal Procedure 12(b) allows a
defendant to file a pretrial motion to dismiss an indictment
for failure to state an offense if the motion “can be
determined without a trial on the merits.” Fed. R. Crim. P.
12(b)(3)(B)(v). “A motion to dismiss is generally capable of
determination before trial if it involves questions of law
rather than fact.” United States v. Nukida, 8 F.3d 665, 669
(9th Cir. 1993) (quotations omitted). Because Kelly’s
challenges to the indictment are based on legal issues and he
does not dispute that ethylone is a positional isomer of
butylone, we may resolve the issues here without intruding
upon the “province of the ultimate finder of fact.” Id.
(quotation omitted); see United States v. Covington,
395 U.S. 57, 60 (1969). In determining whether an
14                UNITED STATES V. KELLY

indictment charges a cognizable offense, we are bound by
the four corners of the indictment, must accept the truth of
the allegations in the indictment, and cannot consider
evidence that does not appear on the face of the indictment.
United States v. Lyle, 742 F.3d 434, 436 (9th Cir. 2014);
United States v. Jensen, 93 F.3d 667, 669 (9th Cir. 1996).

                              A

    Kelly argues that the DEA did not place ethylone into
Schedule I as a matter of law because §§ 811(h) and 812(b)
require that the DEA name and make findings for each
individual isomer it intends to temporarily schedule. He
contends that the DEA’s failure to do so violated the
Constitution’s non-delegation doctrine. Kelly’s argument is
a misreading of the CSA. The plain language of the statute
permits the DEA to make findings for a parent substance as
a basis to temporarily schedule that substance and its
isomers. The DEA properly made findings for butylone and
provided notice covering butylone and its isomers as
required by §§ 811(h) and 812(b). In following the
congressional mandate, we hold the DEA did not violate the
non-delegation doctrine.

    The Constitution states that “[a]ll legislative Powers
herein granted shall be vested in a Congress of the United
States.” U.S. Const., art. I, § 1. The non-delegation doctrine
provides that “Congress may not constitutionally delegate its
legislative power to another branch of Government.” Touby,
500 U.S. at 165. “It is clear that in [§ 811(h)] and [§ 812(b)]
Congress has placed multiple specific restrictions on the
[DEA]’s discretion to define criminal conduct.” Id. at 167.
“These restrictions satisfy the constitutional requirements of
the nondelegation doctrine.” Id.
                  UNITED STATES V. KELLY                    15

    Section 812(b) prohibits any substance from being
placed into Schedule I unless the DEA finds that it has (1) a
high potential for abuse, (2) no currently accepted medical
use in treatment, and (3) no accepted safe use under medical
supervision. § 812(b)(1). Section 811(h) requires that, to
temporarily schedule a drug, the DEA must consider (4) the
history and current pattern of the drug’s abuse, (5) the scope,
duration, and significance of the abuse, and (6) what risk, if
any, the drug poses to the public health. § 811(c)(4)–(6),
(h)(3). In doing so, the DEA “shall be required to consider”
the drug’s “actual abuse, diversion from legitimate channels,
and clandestine importation, manufacture, or distribution.”
§ 811(h)(3).

    The DEA must consider these factors “with respect to
each drug or other substance proposed to be controlled.”
§ 811(c). The effect of scheduling a substance in Schedule
I(c) includes:

       Unless specifically excepted or unless listed
       in another schedule, any material, compound,
       mixture, or preparation, which contains any
       quantity of the [parent] hallucinogenic
       substances, or which contains any of their
       salts, isomers, and salts of isomers whenever
       the existence of such salts, isomers, and salts
       of isomers is possible within the specific
       chemical designation[.]

21 U.S.C. § 812, Schedule I(c). Under this section, if the
required findings are made for a parent hallucinogenic
substance, then the scheduling also includes its isomers.
21 U.S.C. § 812, Schedule I(c); 21 C.F.R. § 1308.11(d).
Substances are temporarily scheduled under Schedule I.
§ 811(h)(1). As it did for butylone, if the DEA makes
16               UNITED STATES V. KELLY

findings for the parent hallucinogenic substance, that
substance’s isomers may be included in the emergency
scheduling. Once the findings have been made, the DEA
may not issue an order temporarily scheduling a drug
without publishing in the Federal Register a 30-day notice of
its intent “to issue such [an] order and the grounds upon
which such order is to be issued.” § 811(h)(1)(A) (emphasis
added).

    The DEA did not violate the non-delegation doctrine
when it temporarily scheduled ethylone. The agency made
specific findings as to the parent drug, butylone. For
example, the Notice and Order found that the ten synthetic
cathinones “can cause acute health problems leading to
emergency department admissions, violent behaviors
causing harm to self or others, or death.” The DEA also
found that “the possibility of death for individuals abusing
[the ten synthetic cathinones] indicates that these substances
are serious public health threats,” and it provided examples
of two individuals who died after ingesting butylone or a
mixture containing butylone and another controlled
substance. Although Kelly contends otherwise, the DEA
was not required to make specific findings for every isomer
of butylone. The findings for butylone are sufficient to
satisfy the requirements for temporary listing under § 811(h)
because under Schedule I findings regarding the parent
substance are sufficient to justify the scheduling of its
isomers.

    Thus, by complying with §§ 811(h) and 812(b)’s
“specific restrictions on [its] discretion to define criminal
conduct,” the DEA’s temporary scheduling of ethylone did
not amount to an exercise of legislative power in violation of
the non-delegation doctrine. Touby, 500 U.S. at 167; see
also Gonzales v. Oregon, 546 U.S. 243, 259–60 (2006)
                   UNITED STATES V. KELLY                       17

(recognizing that the CSA gives the DEA “limited powers,
to be exercised in specific ways,” that “[t]o exercise [its]
scheduling power, the [DEA] must follow a detailed set of
procedures,” and that the CSA is “specific as to the manner
in which the [DEA] must exercise this authority”); Chrysler
Corp. v. Brown, 441 U.S. 281, 303 (1979) (“[A]gency
discretion is limited not only by substantive, statutory grants
of authority, but also by the procedural requirements which
assure fairness and mature consideration of rules of general
application.” (quotation omitted)). The DEA properly
exercised its limited powers as defined by Congress to
temporarily list butylone and its isomers, including ethylone.

                                B

    When the DEA filed the Notice and Order in the Federal
Register, Kelly received fair notice that ethylone was a
controlled substance. The Fifth Amendment provides that
“[n]o person shall . . . be deprived of life, liberty, or property,
without due process of law.” U.S. Const. amend. V. “It is a
basic principle of due process” that the law must provide a
“person of ordinary intelligence a reasonable opportunity to
know what is prohibited, so that he may act accordingly.”
Grayned v. City of Rockford, 408 U.S. 104, 108 (1972). Due
process “mandate[s] that no individual be forced to
speculate, at peril of indictment, whether his conduct is
prohibited.” Dunn v. United States, 442 U.S. 100, 112
(1979); see also Lanzetta v. State of New Jersey, 306 U.S.
451, 453 (1939) (“All are entitled to be informed as to what
the State commands or forbids.”). To that end, “the terms of
a penal statute creating a new offense must be sufficiently
explicit to inform those who are subject to it what conduct
on their part will render them liable to its penalties.”
Lanzetta, 306 U.S. at 453 (quotation omitted). “Congress
has provided that proper publication in the Federal Register
18                UNITED STATES V. KELLY

shall act as constructive notice to all of those affected by the
regulation in question.” United States v. Wilhoit, 920 F.2d
9, 10 (9th Cir. 1990) (citing 44 U.S.C. § 1507).

     Kelly had notice through the DEA’s temporary
scheduling of butylone and its isomers that his drug-selling
conduct was forbidden. The agency fully complied with its
statutory authority granted by Congress to address this
emergency prompted by synthetic compounds like Ecstasy,
which endanger the public. Here, the DEA’s Order stated
that “[a]s a result of this order, the . . . criminal sanctions
applicable to schedule I controlled substances will be
imposed on persons who handle (manufacture, distribute,
import, export, engage in research, conduct instructional
activities, and possess) . . . [the ten] synthetic cathinones.”
Further, under the heading “Criminal Liability,” it warned
that “[a]ny activity involving [the ten synthetic cathinones]
not authorized by, or in violation of the CSA, occurring as
of March 7, 2014, is unlawful, and may subject the person to
. . . criminal sanctions.” More specifically, the Order
advised that “[b]utylone, its optical, positional, and
geometric isomers, salts and salts of isomers,” were
temporarily scheduled under Schedule I. The DEA’s Notice
contained substantially similar language.

    Through the Federal Register, Kelly had public notice
that distributing Ecstasy in the form of ethylone could result
in criminal sanctions. See Wilhoit, 920 F.2d at 10.

                               C

    The rule of lenity does not apply to Kelly’s case. “The
rule of lenity requires ambiguous criminal laws to be
interpreted in favor of the defendants subjected to them.”
United States v. Santos, 553 U.S. 507, 514 (2008) (plurality
opinion). It derives from the fundamental principle that “no
                  UNITED STATES V. KELLY                     19

man shall be held criminally responsible for conduct which
he could not reasonably understand to be proscribed.”
United States v. Harriss, 347 U.S. 612, 617 (1954).

    The rule of lenity “only applies if, after considering text,
structure, history, and purpose, there remains a grievous
ambiguity or uncertainty in the statute such that the Court
must simply guess as to what Congress intended.” Barber v.
Thomas, 560 U.S. 474, 488 (2010) (citation and quotations
omitted). “In these circumstances—where text, structure,
and history fail to establish that the Government’s position
is unambiguously correct—we apply the rule of lenity and
resolve the ambiguity in [the defendant’s] favor.” United
States v. Granderson, 511 U.S. 39, 54 (1994); People v.
Materne, 72 F.3d 103, 106 (9th Cir. 1995) (“Only where the
defendant’s interpretation is unreasonable does the rule of
lenity not apply.”).

    The text, history and purpose of the CSA paint a clear
picture that Congress intended to empower the DEA to
temporarily schedule isomers. The plain language of §§ 811
and 812 discusses isomers and their scheduling in
conjunction with the parent substances. The CSA defines an
isomer for Schedule I(c) under § 802(14). The regulations
further clarify what an isomer is under 21 C.F.R.
§ 1300.01(b). These definitions refer to Schedule I generally
and do not purport to limit isomers to the DEA’s permanent
scheduling authority. In addition, when the DEA schedules
a parent substance under Schedule I(c), unless otherwise
prohibited, that scheduling also includes its isomers. § 812
Schedule I(c). The plain language of the CSA clearly
contemplates the scheduling of isomers under both the
temporary and permanent scheduling authority.

   History also demonstrates that isomers can be
temporarily listed. In 2000 Congress ordered the DEA to
20               UNITED STATES V. KELLY

temporarily list the performance enhancing drug “GHB”
“together with its . . . isomers” in the same way that the DEA
always does under § 811(h), confirming its approval of the
DEA’s actions. See Pub. L. No. 106-172, § 3(a), 114 Stat.
7, 8 (Feb. 18, 2000). Dozens of drugs have been temporarily
listed with their isomers since 1984, and 16 are listed now.
21 C.F.R. § 1308.11(h).

    Finally, the purpose of the DEA’s temporary scheduling
power is to stop dangerous designer drugs as they are
developed. The 1984 amendments giving the DEA the
temporary scheduling power clarified the definition of
“isomer” to avoid the “isomer defense”—when clever drug
designers switch an isomer in an effort to avoid prosecution.
S. Rep. No. 98-225, at 263 (1983). Congress sought to avoid
“clandestine manufacturers [attempting] to circumvent the
law by manufacturing positional and geometric isomers of
hallucinogens in schedule I.” Id. Congress unambiguously
granted the temporary scheduling authority to prohibit
conduct, like Kelly’s, of distributing dangerous substances
that have yet to be permanently listed. If the DEA could not
temporarily schedule isomers of parent substances, the entire
emergency scheduling scheme would collapse. The DEA
would be in a never-ending inquiry to temporarily schedule
every single isomer and make findings on every chemical
variation of a dangerous drug. It is highly unlikely the
agency could keep up with the pace of clandestine drug
manufacturers.

   The plain language, history, and purpose of temporary
scheduling authority make congressional intent clear. The
                    UNITED STATES V. KELLY                           21

rule of lenity only applies to “ambiguous criminal laws.”
Santos, 553 U.S. at 514. There is no ambiguity here. 8

                                   D

    The DEA’s decision to temporarily schedule ethylone
was authorized pursuant to its temporary scheduling power
and a clear directive from Congress. The district court
properly found the DEA’s temporary scheduling authorized
at Chevron step one.

    Chevron sets forth a two-step test for reviewing an
agency’s interpretation of a federal statute. Chevron, U.S.A.,
Inc. v. Natural Resources Defense Council, Inc., 467 U.S.
837, 842–44 (1984). Under Chevron step one, the court
must determine “whether Congress has directly spoken to
the precise question at issue.” Id. at 842. “If the intent of
Congress is clear, that is the end of the matter,” and the court
“must give effect to the unambiguously expressed intent of
Congress.” Id. at 842–43. However, “if the statute is silent
or ambiguous with respect to the specific issue,” the court
must proceed to the second Chevron step. Id. at 843. Under
Chevron step two, the court must uphold the agency’s
interpretation unless it is “arbitrary, capricious, or manifestly
contrary to the statute.” Id. at 844.

    The plain language of the CSA evinces Congress’ intent
to permit the DEA to temporarily schedule a parent
substance and its isomers, such as butylone and ethylone.
First, under the permanent scheduling authority, if the drug

    8
      Kelly argues the rule of lenity trumps the deference we give to the
agency under Chevron. Mujahid v. Daniels, 413 F.3d 991, 999 (9th Cir.
2005) (the Supreme Court has not “address[ed] when the rule of lenity
takes priority over Chevron deference.”). As we find that the rule of
lenity does not apply, we do not address this argument.
22               UNITED STATES V. KELLY

is in a subcategory of Schedule I (a through c) then the DEA
is only required to make findings regarding the “parent”
substance and then permits the scheduling of the isomers of
that parent. § 812 Schedule I(c). In conjunction with this
authority, the statute defines isomers: “[a]s used in schedule
I(c), the term ‘isomer’ means any optical, positional, or
geometric isomer.” 21 U.S.C. § 802(14). In defining and
discussing isomers the CSA does not confine them to
permanent scheduling, rather this applies to the DEA’s
overall scheduling authority, permanent and temporary.
Congress was contemplating the scheduling of isomers
throughout the CSA, not only in their permanent scheduling.

    The temporary scheduling authority is broader and more
efficient than permanent scheduling.        The temporary
authority is intended to permit the DEA to react quickly to
new drugs on the market that present a threat to human
health. S. Rep. No. 98-225, at 263–64 (1983). In order to
properly address this threat, Congress gave the DEA the
power to schedule threatening substances more efficiently,
but only for a two-year period. § 811(h)(2). The agency
need only make three findings in order to temporarily
schedule a substance, which makes it less burdensome to
quickly schedule dangerous substances.         § 811(h)(3).
Congress granted this broad authority to schedule drugs and
their isomers to expedite the scheduling process to avoid
limiting law enforcement actions against traffickers and
creating a “serious health problem.” S. Rep. No. 98-225, at
264 (1983).

    The intent of Congress is clear that the DEA has
authority to temporarily schedule a parent substance and its
isomers. Our inquiry ends at the first step of Chevron.
467 U.S. at 842. The district court properly accorded
Chevron deference to the agency interpretation.
                     UNITED STATES V. KELLY                            23

                                    E

    Kelly’s plea agreement clearly and unambiguously
waived his right to appeal the very sentencing issue he raises
here. Kelly does not contend that his waiver of this right was
unknowing or involuntary. See United States v. Speelman,
431 F.3d 1226, 1229 (9th Cir. 2005); see also United States
v. Arzate-Nunez, 18 F.3d 730, 737 (9th Cir. 1994) (“A
defendant who enters a conditional guilty plea . . . must state
in writing any issues he wishes to reserve for appeal and may
lose the right to appeal issues not so expressly reserved.”). 9
As Kelly fails to argue that his unambiguous waiver of his
right to appeal was involuntary, the plea agreement controls
on this issue and we hold his sentencing challenge was
waived.

                                    V

    We affirm the district court’s denial of Kelly’s motion to
dismiss the indictment; affirm Kelly’s conviction; and
dismiss Kelly’s challenge to the district court’s criminal
history category calculation and resulting 70-month
sentence.

    AFFIRMED in part, DISMISSED in part.

    9
      Kelly also argues, for the first time in his reply brief, that he is
released from his appeal waiver because the Government breached the
plea agreement. We decline to consider this argument because Kelly
waived it by failing to raise it in his opening brief. See United States v.
Alcan Elec. & Eng’g, Inc., 197 F.3d 1014, 1020 (9th Cir. 1999).