Propionyl Chloride, 70610-70613 [2023-22570]
Download as PDF
<![CDATA[
ddrumheller on DSK120RN23PROD with PROPOSALS1
70610
Federal Register / Vol. 88, No. 196 / Thursday, October 12, 2023 / Proposed Rules
would then proceed to terminate the
Order.
This action would suspend the
Federal marketing order regulating dried
prunes produced in California though
July 31, 2030. Authority for this action
is provided in section 993.90(a) of the
Order.
Committee meetings are widely
publicized throughout the production
area. The California dried prune
industry and all interested persons are
invited to attend the meetings and
participate in Committee deliberations
on all issues. Similarly, the March 22,
2023, meeting was a public meeting and
all entities, both large and small, were
able to express views on this issue.
In accordance with the Paperwork
Reduction Act of 1995 (44 U.S.C.
Chapter 35), the Order’s information
collection requirements have been
previously approved by OMB and
assigned OMB No. 0581–0178,
Vegetable Crops. OMB’s three-year
approval of the forms in the Vegetable
Crops package expire March 31, 2024.
AMS’ submission of the renewal
package prior to its expiration will
retain prune forms but will drawdown
the information collection burden to
zero during the time when respondents
will not be completing and submitting
the forms during the seven-year
suspension. Should any changes
become necessary, they would be
submitted to OMB for approval.
This proposed rule would not impose
any additional reporting or
recordkeeping requirements on either
small or large California dried prune
handlers. As with all Federal marketing
order programs, reports and forms are
periodically reviewed to reduce
information requirements and
duplication by industry and public
sector agencies.
AMS is committed to complying with
the E-Government Act, to promote the
use of the internet and other
information technologies to provide
increased opportunities for citizen
access to Government information and
services, and for other purposes.
AMS has not identified any relevant
Federal rules that duplicate, overlap, or
conflict with this proposed rule.
A small business guide on complying
with fruit, vegetable, and specialty crop
marketing agreements and orders may
be viewed at: https://
www.ams.usda.gov/rules-regulations/
moa/small-businesses. Any questions
about the compliance guide should be
sent to Richard Lower at the previously
mentioned address in the FOR FURTHER
INFORMATION CONTACT section.
A 30-day comment period is provided
to allow interested persons to respond
VerDate Sep<11>2014
16:30 Oct 11, 2023
Jkt 262001
to this proposed rule. All written
comments timely received will be
considered before a final determination
is made on this rule.
List of Subjects in 7 CFR Part 993
Marketing agreements, Plum, Prunes,
Reporting and recordkeeping
requirements.
For the reasons set forth in the
preamble, the Agricultural Marketing
Service proposes to amend 7 CFR part
993 as follows:
PART 993—DRIED PRUNES
PRODUCED IN CALIFORNIA
1. The authority citation for 7 CFR
part 993 continues to read as follows:
■
Authority: 7 U.S.C. 601–674.
2. In Part 993, lift the suspension of
May 27, 2005, on §§ 993.21d, 993.41,
993.48, 993.49, 993.50, 993.51, 993.52,
993.53, 993.54, 993.55, 993.56, 993.57,
993.58, 993.59, 993.62, 993.65, 993.72,
993.73, 993.74, 993.75, 993.97, 993.104,
993.105, 993.106, 993.107, 993.108,
993.149, 993.150, 993.156, 993.157,
993.158, 993.159, 993.162, 993.165,
993.172, 993.173, 993.174, 993.400,
993.409, 993.501, 993.503, 993.504,
993.505, 993.506, 993.515, 993.516,
993.517, 993.518, 993.601, and 993.602.
■
PART 993—[STAYED]
3. Stay 7 CFR part 993 until July 31,
2030.
■
Erin Morris,
Associate Administrator, Agricultural
Marketing Service.
[FR Doc. 2023–22333 Filed 10–11–23; 8:45 am]
BILLING CODE P
DEPARTMENT OF JUSTICE
Drug Enforcement Administration
21 CFR Part 1310
[Docket No. DEA–1189]
Propionyl Chloride
Drug Enforcement
Administration, Department of Justice.
ACTION: Advanced notice of proposed
rulemaking.
AGENCY:
The Drug Enforcement
Administration finds that propionyl
chloride is used in the illicit
manufacture of the controlled substance
fentanyl, as well as fentanyl analogues,
and fentanyl-related substances and is
important to the manufacture of these
substances because it is often used in
synthetic pathways to illicitly
SUMMARY:
PO 00000
Frm 00003
Fmt 4702
Sfmt 4702
manufacture fentanyl, fentanyl
analogues, and fentanyl-related
substances. Prior to proposing to list
propionyl chloride as a list I chemical,
DEA is soliciting information on the
current uses of propionyl chloride
(other than for the synthesis of fentanyl)
in order to properly determine the effect
such a proposed action would have on
legitimate industry.
DATES: Comments must be submitted
electronically or postmarked on or
before November 13, 2023. Commenters
should be aware that the electronic
Federal Docket Management System
will not accept any comments after
11:59 p.m. Eastern Time on the last day
of the comment period.
ADDRESSES: To ensure proper handling
of comments, please reference ‘‘Docket
No. DEA–1189’’ on all electronic and
written correspondence, including any
attachments.
• Electronic comments: The Drug
Enforcement Administration (DEA)
encourages that all comments be
submitted electronically through the
Federal eRulemaking Portal which
provides the ability to type short
comments directly into the comment
field on the web page or attach a file for
lengthier comments. Please go to
https://www.regulations.gov and follow
the online instructions at that site for
submitting comments.Upon completion
of your submission, you will receive a
Comment Tracking Number for your
comment. Please be aware that
submitted comments are not
instantaneously available for public
view on Regulations.gov. If you have
received a Comment Tracking Number,
your comment has been successfully
submitted and there is no need to
resubmit the same comment.
• Paper comments: Paper comments
that duplicate electronic submissions
are not necessary. Should you wish to
mail a paper comment, in lieu of an
electronic comment, it should be sent
via regular or express mail to: Drug
Enforcement Administration, Attn: DEA
Federal Register Representative/DPW,
8701 Morrissette Drive, Springfield,
Virginia 22152.
FOR FURTHER INFORMATION CONTACT:
Terrence L. Boos, Drug and Chemical
Evaluation Section, Diversion Control
Division, Drug Enforcement
Administration; Telephone: (571) 362–
3249.
SUPPLEMENTARY INFORMATION:
Posting of Public Comments
Please note that all comments
received in response to this docket are
considered part of the public record.
They will, unless reasonable cause is
E:\FR\FM\12OCP1.SGM
12OCP1
Federal Register / Vol. 88, No. 196 / Thursday, October 12, 2023 / Proposed Rules
given, be made available by DEA for
public inspection online at https://
www.regulations.gov. Such information
includes personal identifying
information (such as your name,
address, etc.) voluntarily submitted by
the commenter. The Freedom of
Information Act applies to all comments
received. If you want to submit personal
identifying information (such as your
name, address, etc.) as part of your
comment, but do not want it to be made
publicly available, you must include the
phrase ‘‘PERSONAL IDENTIFYING
INFORMATION’’ in the first paragraph
of your comment. You must also place
all of the personal identifying
information you do not want made
publicly available in the first paragraph
of your comment and identify what
information you want redacted.
If you want to submit confidential
business information as part of your
comment, but do not want it to be made
publicly available, you must include the
phrase ‘‘CONFIDENTIAL BUSINESS
INFORMATION’’ in the first paragraph
of your comment. You must also
prominently identify the confidential
business information to be redacted
within the comment.
Comments containing personal
identifying information or confidential
business information identified as
directed above will be made publicly
available in redacted form. If a comment
has so much confidential business
information that it cannot be effectively
redacted, all or part of that comment
may not be made publicly available.
Comments posted to https://
www.regulations.gov may include any
personal identifying information (such
as name, address, and phone number)
included in the text of your electronic
submission that is not identified as
directed above as confidential.
An electronic copy of this advanced
proposed rule is available at https://
www.regulations.gov for easy reference.
ddrumheller on DSK120RN23PROD with PROPOSALS1
Legal Authority
The Controlled Substances Act (CSA)
gives the Attorney General the authority
to specify, by regulation, chemicals as
list I chemicals.1 A ‘‘list I chemical’’ is
a chemical that is used in
manufacturing a controlled substance in
1 21
U.S.C. 802(34).
2 Id.
3 21 U.S.C. 812(c) Schedule II(b)(6) and 21 CFR
1308.12(c).
4 United Nations Office on Drugs and Crime,
Global SMART Update Volume 17, March 2017.
https://www.unodc.org/documents/scientific/
Global_SMART_Update_17_web.pdf.
5 Centers for Disease Control and Prevention,
National Center for Health Statistics. National Vital
Statistics System, Provisional Mortality on CDC
WONDER Online Database. Data are from the final
VerDate Sep<11>2014
16:30 Oct 11, 2023
Jkt 262001
violation of the CSA and is important to
the manufacture of the controlled
substances.2 The current list of all listed
chemicals is published at 21 CFR
1310.02. Pursuant to 28 CFR 0.100(b),
the Attorney General has delegated his
authority to designate list I chemicals to
the Administrator of DEA
(Administrator). DEA regulations set
forth the process by which DEA may
add a chemical as a listed chemical. As
set forth in 21 CFR 1310.02(c), the
agency may do so by publishing a final
rule in the Federal Register following a
published notice of proposed
rulemaking with at least 30 days for
public comments.
70611
Background
The clandestine manufacture of
fentanyl, fentanyl analogues, and
fentanyl-related substances remains
extremely concerning as the distribution
of illicit fentanyl, fentanyl analogues,
and fentanyl-related substances
continues to drive drug-related overdose
deaths in the United States. Fentanyl is
a synthetic opioid and was first
synthesized in Belgium in the late
1950s. Fentanyl was introduced into
medical practice and is approved for
medical practitioners in the United
States to prescribe lawfully for
anesthesia and analgesia. Yet, due to its
pharmacological effects, fentanyl can be
used as a substitute for heroin,
oxycodone, and other opioids in opioid
dependent individuals. Therefore,
despite its accepted medical use in
treatment in the United States, DEA
controls fentanyl as a schedule II
controlled substance due to its high
potential for abuse and dependence.3
Moreover, there are a substantial
number of fentanyl analogues and
fentanyl-related substances that are
being distributed on the illicit drug
market despite DEA’s actions adding
them as schedule I controlled
substances. Illicit manufacturers attempt
to utilize unregulated precursor
chemicals to evade law enforcement
detection and precursor chemical
controls in order to manufacture
fentanyl, fentanyl analogues, and
fentanyl-related substances. This
strategy allows for the synthesis of a
variety of fentanyl analogues and
fentanyl-related substances by making
slight modifications to the core fentanyl
structure while maintaining the same
synthetic methodology used to
synthesize fentanyl, fentanyl analogues,
and fentanyl-related substances.
The unlawful trafficking of fentanyl,
fentanyl analogues, and fentanyl-related
substances in the United States
continues to pose an imminent hazard
to the public safety. Since 2012,
fentanyl has shown a dramatic increase
in the illicit drug supply as a single
substance, in mixtures with other illicit
drugs (i.e., heroin, cocaine, and
methamphetamine), and in forms that
mimic pharmaceutical preparations
including prescription opiates and
benzodiazepines.4
DEA has noted a significant increase
in overdoses and overdose fatalities
from fentanyl, fentanyl analogues, and
fentanyl-related substances in the
United States in recent years. According
to the Centers for Disease Control and
Prevention (CDC), opioids, mainly
synthetic opioids (which includes
fentanyl), are predominantly
responsible for drug overdose deaths in
recent years. According to CDC
WONDER,5 drug-induced overdose
deaths involving synthetic opioids
(excluding methadone) in the United
States increased from 36,359 in 2019 to
56,516 in 2020 to 70,601 in 2021. Based
on provisional data, the predicted
number of drug overdose deaths
involving synthetic opioids (excluding
methadone) in the United States for the
12 months ending October 2022 is
73,570 individuals, or approximately 68
percent of all drug-induced overdose
deaths for that time period.6 The
increase in overdose fatalities involving
synthetic opioids coincides with a
dramatic increase in law enforcement
encounters of fentanyl, fentanyl
analogues, and fentanyl-related
substances. According to the National
Forensic Laboratory Information System
(NFLIS-Drug),7 reports from forensic
laboratories of drug items containing
fentanyl, fentanyl analogues, and
fentanyl-related substances increased
dramatically since 2014, as shown in
Table 1.
Multiple Cause of Death Files, 2018–2021, and from
provisional data for years 2022–2023, as compiled
from data provided by the 57 vital statistics
jurisdictions through the Vital Statistics
Cooperative Program. Accessed at https://
wonder.cdc.gov/mcd-icd10-provisional.html on
March 16, 2023.
6 Ahmad FB, Cisewski JA, Rossen LM, Sutton P.
Provisional drug overdose death counts. National
Center for Health Statistics. 2023. Accessed at
https://www.cdc.gov/nchs/nvss/vsrr/drug-overdosedata.htm on March 15, 2023.
7 The National Forensic Laboratory Information
System (NFLIS-Drug) is a national forensic
laboratory reporting system that systematically
collects results from drug chemistry analyses
conducted by Federal, State and local forensic
laboratories in the United States. While NFLIS-Drug
data is not direct evidence of abuse, it can lead to
an inference that a drug has been diverted and
abused. See 76 FR 77330, 77332 (December 12,
2011). NFLIS-Drug data was queried on July 31,
2023.
PO 00000
Frm 00004
Fmt 4702
Sfmt 4702
E:\FR\FM\12OCP1.SGM
12OCP1
70612
Federal Register / Vol. 88, No. 196 / Thursday, October 12, 2023 / Proposed Rules
TABLE 1—ANNUAL REPORTS OF FENTANYL AND SELECT FENTANYL ANALOGUES AND FENTANYL-RELATED SUBSTANCES
IDENTIFIED IN DRUG ENCOUNTERS
Year
2014
ddrumheller on DSK120RN23PROD with PROPOSALS1
Annual Fentanyl Reports .............
Annual Reports of select fentanyl
analogues and fentanyl-related
substances ...............................
2015
2018
2019
2020
2021
2022
15,461
37,154
61,640
89,966
108,131
125,999
164,890
165,067
78
2,317
7,624
21,980
16,177
20,917
7,800
26,368
29,404
8 72
FR 20039 (April 23, 2007).
FR 20822 (May 15, 2020).
10 88 FR 21902 (May 12, 2023).
11 75 FR 37295 (August 30, 2010).
12 85 FR 21320 (May 18, 2020).
9 85
16:30 Oct 11, 2023
2017
5,554
Role of Propionyl Chloride in the
Synthesis of Fentanyl
Fentanyl, fentanyl analogues, and
fentanyl-related substances are not
naturally occurring substances. As such,
the manufacture of these substances
requires them to be produced through
synthetic organic chemistry. Synthetic
organic chemistry is the process in
which a new organic molecule is
created through a series of chemical
reactions, which involve precursor
chemicals. Through chemical reactions,
the chemical structures of precursor
chemicals are modified in a desired
fashion. These chemical reaction
sequences, also known as synthetic
pathways, are designed to create a
desired substance. Several synthetic
pathways to fentanyl, fentanyl
analogues, and fentanyl-related
substances have been identified in
clandestine laboratory settings; these
include the original ‘‘Janssen method,’’
the ‘‘Siegfried method,’’ and the ‘‘Gupta
method.’’ In response to the illicit
manufacture of fentanyl, fentanyl
analogues, and fentanyl-related
substances using these methods, DEA
controlled N-phenethyl-4-piperidone
(NPP),8 N-(1-benzylpiperidin-4-yl)-Nphenylpropionamide (benzylfentanyl),
N-phenylpiperidin-4-amine (4anilinopiperidine; including its amides
and carbamates),9 and 4-piperidone
(piperidin-4-one) 10 as list I chemicals
and 4-anilino-N-phenethylpiperidine
(ANPP) 11 and N-phenyl-N-(piperidin-4yl)propionamide (norfentanyl) 12 as
schedule II immediate precursors under
the CSA.
In 2017, the United Nations
Commission on Narcotic Drugs placed
NPP and ANPP in Table I of the
Convention Against Illicit Traffic in
Narcotic Drugs and Psychotropic
Substances of 1988 (1988 Convention)
in response to the international
reintroduction of fentanyl on the illicit
drug market. As such, member states of
the United Nations are required to
regulate these precursor chemicals at
VerDate Sep<11>2014
2016
Jkt 262001
the national level. Importantly, the
People’s Republic of China regulated
NPP and ANPP on February 1, 2018.13
Subsequently in 2022, the United
Nations Commission on Narcotic Drugs
placed norfentanyl, 1-boc-4anilinopiperidine, and 4anilinopiperidine in Table I of the 1988
Convention in response to the
international reintroduction of fentanyl
on the illicit drug market and the
introduction of new precursors used in
the illicit manufacture of fentanyl.
Propionyl Chloride
The original published synthetic
pathway to fentanyl, known as the
Janssen method, involves the list I
chemical benzylfentanyl and schedule II
immediate precursor norfentanyl. In this
synthetic pathway, benzylfentanyl, a list
I chemical under the CSA,14 is
synthesized by reacting propionyl
chloride with 4-anilino-1benzylpiperidine, which is then
converted to norfentanyl, the schedule II
immediate precursor in this synthetic
pathway.15 Norfentanyl is then
subjected to one simple chemical
reaction to complete the synthesis of
fentanyl. This synthetic pathway can
also be easily modified to produce
fentanyl analogues and fentanyl-related
substances.
Propionyl chloride also serves as a
precursor chemical in the Siegfried
method. In this synthetic pathway,
propionyl chloride is reacted with
ANPP,16 the schedule II immediate
precursor in the Siegfried method, to
complete the synthesis of fentanyl. This
synthetic pathway can also be easily
modified to produce fentanyl analogues
and fentanyl-related substances.
In addition to the Janssen and
Siegfried methods, clandestine
manufacturers are using other methods
to synthesize fentanyl, one of which is
known as the Gupta method. In this
synthetic pathway, 4-piperidone, a list I
chemical under the CSA, is used to
13 https://www.dea.gov/press-releases/2018/01/
05/china-announces-scheduling-controls-twofentanyl-precursor-chemicals. Accessed March 9,
2022.
14 85 FR 20822 (May 15, 2020).
15 85 FR 21320 (May 18, 2020).
16 75 FR 37295 (August 30, 2010).
PO 00000
Frm 00005
Fmt 4702
Sfmt 4702
synthesize 4-anilinopiperidine, another
list I chemical under the CSA,17 which
serves as an alternative precursor
chemical to NPP, a list I chemical, in the
synthesis of ANPP, a schedule II
immediate precursor albeit through a
different synthetic process. The
resulting ANPP is reacted with
propionyl chloride to manufacture the
schedule II controlled substance,
fentanyl. This synthetic pathway can
also be easily modified to produce
fentanyl analogues and fentanyl-related
substances.
Propionyl chloride is attractive to
illicit manufacturers because of the lack
of regulations on this chemical, it is
readily available from chemical
suppliers, and it can be easily used in
many known synthetic pathways used
in the illicit manufacture of fentanyl,
fentanyl analogues, and fentanyl-related
substances.
Solicitation for Information
With this advanced notice of
proposed rulemaking, DEA is soliciting
information on any possible legitimate
uses of propionyl chloride unrelated to
fentanyl production (including
industrial uses) in order to assess the
potential economic impact of
controlling propionyl chloride as a list
I chemical. DEA seeks to document any
unpublicized use(s) and other
proprietary use(s) of propionyl chloride
that are not in the public domain.
Therefore, DEA is soliciting comment
on the uses of propionyl chloride in the
legitimate marketplace.
DEA is soliciting input from all
potentially affected parties regarding: (1)
The types of legitimate industries using
propionyl chloride; (2) the legitimate
uses, legitimate needs and quantity
produced, used, and distributed of
propionyl chloride; (3) the size of the
domestic market for propionyl chloride;
(4) the number of manufacturers of
propionyl chloride; (5) the number of
distributors of propionyl chloride; (6)
the level of import and export of
propionyl chloride; (7) the potential
burden that controlling propionyl
chloride as a list I chemical may have
on any legitimate industry and trade; (8)
17 85
E:\FR\FM\12OCP1.SGM
FR 20822 (May 15, 2020).
12OCP1
Federal Register / Vol. 88, No. 196 / Thursday, October 12, 2023 / Proposed Rules
the potential number of individuals/
firms that may be adversely affected by
such regulatory controls (particularly
with respect to the impact on small
businesses); and (9) any other
information on the manner of
manufacturing, distribution,
consumption, storage, disposal, and
uses of propionyl chloride by industry
and others. DEA invites all interested
parties to provide any information on
any legitimate uses of propionyl
chloride in industry, commerce,
academia, research and development, or
other applications. DEA seeks both
quantitative and qualitative data.
Such information may be submitted
electronically to the address listed
above and is requested by November 13,
2023. This information will be used to
properly determine the effect that
proposed regulations to make propionyl
chloride a list 1 chemical under the CSA
would have on industry.
Handling of Confidential or Proprietary
Information
Confidential or proprietary
information may be submitted as part of
a comment regarding this advanced
notice of proposed rulemaking. Please
see the ‘‘POSTING OF PUBLIC
COMMENTS’’ section above for a
discussion of the identification and
redaction of confidential business
information and personally identifying
information.
ddrumheller on DSK120RN23PROD with PROPOSALS1
Regulatory Analyses
This ANPRM was developed in
accordance with the principles of
Executive Order (E.O.) 12866,
‘‘Regulatory Planning and Review’’ and
E.O. 13563, ‘‘Improving Regulation and
Regulatory Review.’’ Since this action is
an ANPRM, the requirement of E.O.
12866 to assess the costs and benefits of
this action does not apply.
Furthermore, the requirements of the
Regulatory Flexibility Act do not apply
to this action because, at this stage, it is
an ANPRM and not a ‘‘rule’’ as defined
in 5 U.S.C. 601. Following review of the
comments received in response to this
ANPRM, if DEA proceeds with a notice
of proposed rulemaking regarding this
matter, DEA will conduct all relevant
analyses as required by statute or E.O.
Signing Authority
This document of the Drug
Enforcement Administration was signed
on October 5, 2023, by Administrator
Anne Milgram. That document with the
original signature and date is
maintained by DEA. For administrative
purposes only, and in compliance with
requirements of the Office of the Federal
Register, the undersigned DEA Federal
VerDate Sep<11>2014
16:30 Oct 11, 2023
Jkt 262001
Register Liaison Officer has been
authorized to sign and submit the
document in electronic format for
publication, as an official document of
DEA. This administrative process in no
way alters the legal effect of this
document upon publication in the
Federal Register.
Heather Achbach,
Federal Register Liaison Officer, Drug
Enforcement Administration.
[FR Doc. 2023–22570 Filed 10–11–23; 8:45 am]
BILLING CODE 4410–09–P
DEPARTMENT OF HOMELAND
SECURITY
Coast Guard
33 CFR Part 165
[Docket Number USCG–2023–0795]
RIN 1–AA00
Safety Zone; Potomac River, Between
Charles County, MD and King George
County, VA
Coast Guard, DHS.
Notice of proposed rulemaking.
AGENCY:
ACTION:
The Coast Guard is proposing
to establish a temporary safety zone for
certain waters of the Potomac River.
This action is necessary to provide for
the safety of life on these navigable
waters at the old Governor Harry W.
Nice/Senator Thomas ‘‘Mac’’ Middleton
Memorial (US–301) Bridge, during
demolition operations from November
8, 2023 through January 30, 2024. This
proposed rulemaking would prohibit
persons and vessels from being in the
safety zone unless authorized by the
Captain of the Port, Sector MarylandNational Capital Region or a designated
representative. We invite your
comments on this proposed rulemaking.
DATES: Comments and related material
must be received by the Coast Guard on
or before October 27, 2023.
ADDRESSES: You may submit comments
identified by docket number USCG–
2023–0795 using the Federal DecisionMaking Portal at https://
www.regulations.gov. See the ‘‘Public
Participation and Request for
Comments’’ portion of the
SUPPLEMENTARY INFORMATION section for
further instructions on submitting
comments.
SUMMARY:
If
you have questions about this proposed
rulemaking, call or email LCDR Kate
Newkirk, Sector Maryland-NCR,
Waterways Management Division, U.S.
FOR FURTHER INFORMATION CONTACT:
PO 00000
Frm 00006
Fmt 4702
Sfmt 4702
70613
Coast Guard: telephone 410–576–2519,
email MDNCRWaterways@uscg.mil.
SUPPLEMENTARY INFORMATION:
I. Table of Abbreviations
CFR Code of Federal Regulations
COTP Captain of the Port
DHS Department of Homeland Security
FR Federal Register
NPRM Notice of proposed rulemaking
§ Section
U.S.C. United States Code
II. Background, Purpose, and Legal
Basis
Skanska-Corman-McLean, Joint
Venture notified the Coast Guard that it
will be conducting demolition of the old
Governor Harry W. Nice/Senator
Thomas ‘‘Mac’’ Middleton Memorial
(US–301) Bridge, which will occur from
12:01 a.m. on November 8, 2023, to
11:59 p.m. on January 30, 2024. The
bridge is located on the Potomac River,
at mile 43.3, between Charles County,
MD and King George County, VA. The
segment of the old bridge over waters
that include the bridge piers sections
between Piers 14 and the east riverbank
of the Potomac River requires the use of
explosives, and debris removal and
hydrographic surveying equipment.
Marine equipment, including barges,
positioned in the Potomac River will be
used to support the bridge demolition
and debris removal operation. This
operation also requires the use of a
temporary commercial mooring buoy in
the Potomac River south of the old
bridge where the explosives barge will
be kept. Hazards from the demolition
and debris removal work include
accidental discharge of explosives,
dangerous projectiles, hanging ropes or
cables, and falling objects or debris. The
Captain of the Port, Maryland-National
Capital Region (COTP) has determined
that potential hazards associated with
the demolition and removal of the old
Governor Harry W. Nice/Senator
Thomas ‘‘Mac’’ Middleton Memorial
(US–301) Bridge would be a safety
concern for anyone within or near
project area.
The purpose of this rulemaking is to
ensure the safety of vessels and the
navigable waters within or near the
Federal navigation channel at the old
Governor Harry W. Nice/Senator
Thomas ‘‘Mac’’ Middleton Memorial
(US–301) Bridge before, during, and
after the scheduled event. The Coast
Guard is proposing this rulemaking
under authority in 46 U.S.C. 70034.
III. Discussion of Proposed Rule
The COTP is proposing to establish a
safety zone from 12:01 a.m. on
November 8, 2023, to 11:59 p.m. on
E:\FR\FM\12OCP1.SGM
12OCP1
]]>Agencies
[Federal Register Volume 88, Number 196 (Thursday, October 12, 2023)]
[Proposed Rules]
[Pages 70610-70613]
From the Federal Register Online via the Government Publishing Office [www.gpo.gov]
[FR Doc No: 2023-22570]
=======================================================================
-----------------------------------------------------------------------
DEPARTMENT OF JUSTICE
Drug Enforcement Administration
21 CFR Part 1310
[Docket No. DEA-1189]
Propionyl Chloride
AGENCY: Drug Enforcement Administration, Department of Justice.
ACTION: Advanced notice of proposed rulemaking.
-----------------------------------------------------------------------
SUMMARY: The Drug Enforcement Administration finds that propionyl
chloride is used in the illicit manufacture of the controlled substance
fentanyl, as well as fentanyl analogues, and fentanyl-related
substances and is important to the manufacture of these substances
because it is often used in synthetic pathways to illicitly manufacture
fentanyl, fentanyl analogues, and fentanyl-related substances. Prior to
proposing to list propionyl chloride as a list I chemical, DEA is
soliciting information on the current uses of propionyl chloride (other
than for the synthesis of fentanyl) in order to properly determine the
effect such a proposed action would have on legitimate industry.
DATES: Comments must be submitted electronically or postmarked on or
before November 13, 2023. Commenters should be aware that the
electronic Federal Docket Management System will not accept any
comments after 11:59 p.m. Eastern Time on the last day of the comment
period.
ADDRESSES: To ensure proper handling of comments, please reference
``Docket No. DEA-1189'' on all electronic and written correspondence,
including any attachments.
Electronic comments: The Drug Enforcement Administration
(DEA) encourages that all comments be submitted electronically through
the Federal eRulemaking Portal which provides the ability to type short
comments directly into the comment field on the web page or attach a
file for lengthier comments. Please go to https://www.regulations.gov
and follow the online instructions at that site for submitting
comments.Upon completion of your submission, you will receive a Comment
Tracking Number for your comment. Please be aware that submitted
comments are not instantaneously available for public view on
Regulations.gov. If you have received a Comment Tracking Number, your
comment has been successfully submitted and there is no need to
resubmit the same comment.
Paper comments: Paper comments that duplicate electronic
submissions are not necessary. Should you wish to mail a paper comment,
in lieu of an electronic comment, it should be sent via regular or
express mail to: Drug Enforcement Administration, Attn: DEA Federal
Register Representative/DPW, 8701 Morrissette Drive, Springfield,
Virginia 22152.
FOR FURTHER INFORMATION CONTACT: Terrence L. Boos, Drug and Chemical
Evaluation Section, Diversion Control Division, Drug Enforcement
Administration; Telephone: (571) 362-3249.
SUPPLEMENTARY INFORMATION:
Posting of Public Comments
Please note that all comments received in response to this docket
are considered part of the public record. They will, unless reasonable
cause is
[[Page 70611]]
given, be made available by DEA for public inspection online at https://www.regulations.gov. Such information includes personal identifying
information (such as your name, address, etc.) voluntarily submitted by
the commenter. The Freedom of Information Act applies to all comments
received. If you want to submit personal identifying information (such
as your name, address, etc.) as part of your comment, but do not want
it to be made publicly available, you must include the phrase
``PERSONAL IDENTIFYING INFORMATION'' in the first paragraph of your
comment. You must also place all of the personal identifying
information you do not want made publicly available in the first
paragraph of your comment and identify what information you want
redacted.
If you want to submit confidential business information as part of
your comment, but do not want it to be made publicly available, you
must include the phrase ``CONFIDENTIAL BUSINESS INFORMATION'' in the
first paragraph of your comment. You must also prominently identify the
confidential business information to be redacted within the comment.
Comments containing personal identifying information or
confidential business information identified as directed above will be
made publicly available in redacted form. If a comment has so much
confidential business information that it cannot be effectively
redacted, all or part of that comment may not be made publicly
available. Comments posted to https://www.regulations.gov may include
any personal identifying information (such as name, address, and phone
number) included in the text of your electronic submission that is not
identified as directed above as confidential.
An electronic copy of this advanced proposed rule is available at
https://www.regulations.gov for easy reference.
Legal Authority
The Controlled Substances Act (CSA) gives the Attorney General the
authority to specify, by regulation, chemicals as list I chemicals.\1\
A ``list I chemical'' is a chemical that is used in manufacturing a
controlled substance in violation of the CSA and is important to the
manufacture of the controlled substances.\2\ The current list of all
listed chemicals is published at 21 CFR 1310.02. Pursuant to 28 CFR
0.100(b), the Attorney General has delegated his authority to designate
list I chemicals to the Administrator of DEA (Administrator). DEA
regulations set forth the process by which DEA may add a chemical as a
listed chemical. As set forth in 21 CFR 1310.02(c), the agency may do
so by publishing a final rule in the Federal Register following a
published notice of proposed rulemaking with at least 30 days for
public comments.
---------------------------------------------------------------------------
\1\ 21 U.S.C. 802(34).
\2\ Id.
---------------------------------------------------------------------------
Background
The clandestine manufacture of fentanyl, fentanyl analogues, and
fentanyl-related substances remains extremely concerning as the
distribution of illicit fentanyl, fentanyl analogues, and fentanyl-
related substances continues to drive drug-related overdose deaths in
the United States. Fentanyl is a synthetic opioid and was first
synthesized in Belgium in the late 1950s. Fentanyl was introduced into
medical practice and is approved for medical practitioners in the
United States to prescribe lawfully for anesthesia and analgesia. Yet,
due to its pharmacological effects, fentanyl can be used as a
substitute for heroin, oxycodone, and other opioids in opioid dependent
individuals. Therefore, despite its accepted medical use in treatment
in the United States, DEA controls fentanyl as a schedule II controlled
substance due to its high potential for abuse and dependence.\3\
Moreover, there are a substantial number of fentanyl analogues and
fentanyl-related substances that are being distributed on the illicit
drug market despite DEA's actions adding them as schedule I controlled
substances. Illicit manufacturers attempt to utilize unregulated
precursor chemicals to evade law enforcement detection and precursor
chemical controls in order to manufacture fentanyl, fentanyl analogues,
and fentanyl-related substances. This strategy allows for the synthesis
of a variety of fentanyl analogues and fentanyl-related substances by
making slight modifications to the core fentanyl structure while
maintaining the same synthetic methodology used to synthesize fentanyl,
fentanyl analogues, and fentanyl-related substances.
---------------------------------------------------------------------------
\3\ 21 U.S.C. 812(c) Schedule II(b)(6) and 21 CFR 1308.12(c).
---------------------------------------------------------------------------
The unlawful trafficking of fentanyl, fentanyl analogues, and
fentanyl-related substances in the United States continues to pose an
imminent hazard to the public safety. Since 2012, fentanyl has shown a
dramatic increase in the illicit drug supply as a single substance, in
mixtures with other illicit drugs (i.e., heroin, cocaine, and
methamphetamine), and in forms that mimic pharmaceutical preparations
including prescription opiates and benzodiazepines.\4\
---------------------------------------------------------------------------
\4\ United Nations Office on Drugs and Crime, Global SMART
Update Volume 17, March 2017. https://www.unodc.org/documents/scientific/Global_SMART_Update_17_web.pdf.
---------------------------------------------------------------------------
DEA has noted a significant increase in overdoses and overdose
fatalities from fentanyl, fentanyl analogues, and fentanyl-related
substances in the United States in recent years. According to the
Centers for Disease Control and Prevention (CDC), opioids, mainly
synthetic opioids (which includes fentanyl), are predominantly
responsible for drug overdose deaths in recent years. According to CDC
WONDER,\5\ drug-induced overdose deaths involving synthetic opioids
(excluding methadone) in the United States increased from 36,359 in
2019 to 56,516 in 2020 to 70,601 in 2021. Based on provisional data,
the predicted number of drug overdose deaths involving synthetic
opioids (excluding methadone) in the United States for the 12 months
ending October 2022 is 73,570 individuals, or approximately 68 percent
of all drug-induced overdose deaths for that time period.\6\ The
increase in overdose fatalities involving synthetic opioids coincides
with a dramatic increase in law enforcement encounters of fentanyl,
fentanyl analogues, and fentanyl-related substances. According to the
National Forensic Laboratory Information System (NFLIS-Drug),\7\
reports from forensic laboratories of drug items containing fentanyl,
fentanyl analogues, and fentanyl-related substances increased
dramatically since 2014, as shown in Table 1.
---------------------------------------------------------------------------
\5\ Centers for Disease Control and Prevention, National Center
for Health Statistics. National Vital Statistics System, Provisional
Mortality on CDC WONDER Online Database. Data are from the final
Multiple Cause of Death Files, 2018-2021, and from provisional data
for years 2022-2023, as compiled from data provided by the 57 vital
statistics jurisdictions through the Vital Statistics Cooperative
Program. Accessed at https://wonder.cdc.gov/mcd-icd10-provisional.html on March 16, 2023.
\6\ Ahmad FB, Cisewski JA, Rossen LM, Sutton P. Provisional drug
overdose death counts. National Center for Health Statistics. 2023.
Accessed at https://www.cdc.gov/nchs/nvss/vsrr/drug-overdose-data.htm on March 15, 2023.
\7\ The National Forensic Laboratory Information System (NFLIS-
Drug) is a national forensic laboratory reporting system that
systematically collects results from drug chemistry analyses
conducted by Federal, State and local forensic laboratories in the
United States. While NFLIS-Drug data is not direct evidence of
abuse, it can lead to an inference that a drug has been diverted and
abused. See 76 FR 77330, 77332 (December 12, 2011). NFLIS-Drug data
was queried on July 31, 2023.
[[Page 70612]]
Table 1--Annual Reports of Fentanyl and Select Fentanyl Analogues and Fentanyl-Related Substances Identified in Drug Encounters
--------------------------------------------------------------------------------------------------------------------------------------------------------
Year 2014 2015 2016 2017 2018 2019 2020 2021 2022
--------------------------------------------------------------------------------------------------------------------------------------------------------
Annual Fentanyl Reports.............................. 5,554 15,461 37,154 61,640 89,966 108,131 125,999 164,890 165,067
Annual Reports of select fentanyl analogues and 78 2,317 7,624 21,980 16,177 20,917 7,800 26,368 29,404
fentanyl-related substances.........................
--------------------------------------------------------------------------------------------------------------------------------------------------------
Role of Propionyl Chloride in the Synthesis of Fentanyl
Fentanyl, fentanyl analogues, and fentanyl-related substances are
not naturally occurring substances. As such, the manufacture of these
substances requires them to be produced through synthetic organic
chemistry. Synthetic organic chemistry is the process in which a new
organic molecule is created through a series of chemical reactions,
which involve precursor chemicals. Through chemical reactions, the
chemical structures of precursor chemicals are modified in a desired
fashion. These chemical reaction sequences, also known as synthetic
pathways, are designed to create a desired substance. Several synthetic
pathways to fentanyl, fentanyl analogues, and fentanyl-related
substances have been identified in clandestine laboratory settings;
these include the original ``Janssen method,'' the ``Siegfried
method,'' and the ``Gupta method.'' In response to the illicit
manufacture of fentanyl, fentanyl analogues, and fentanyl-related
substances using these methods, DEA controlled N-phenethyl-4-piperidone
(NPP),\8\ N-(1-benzylpiperidin-4-yl)-N-phenylpropionamide
(benzylfentanyl), N-phenylpiperidin-4-amine (4-anilinopiperidine;
including its amides and carbamates),\9\ and 4-piperidone (piperidin-4-
one) \10\ as list I chemicals and 4-anilino-N-phenethylpiperidine
(ANPP) \11\ and N-phenyl-N-(piperidin-4-yl)propionamide (norfentanyl)
\12\ as schedule II immediate precursors under the CSA.
---------------------------------------------------------------------------
\8\ 72 FR 20039 (April 23, 2007).
\9\ 85 FR 20822 (May 15, 2020).
\10\ 88 FR 21902 (May 12, 2023).
\11\ 75 FR 37295 (August 30, 2010).
\12\ 85 FR 21320 (May 18, 2020).
---------------------------------------------------------------------------
In 2017, the United Nations Commission on Narcotic Drugs placed NPP
and ANPP in Table I of the Convention Against Illicit Traffic in
Narcotic Drugs and Psychotropic Substances of 1988 (1988 Convention) in
response to the international reintroduction of fentanyl on the illicit
drug market. As such, member states of the United Nations are required
to regulate these precursor chemicals at the national level.
Importantly, the People's Republic of China regulated NPP and ANPP on
February 1, 2018.\13\ Subsequently in 2022, the United Nations
Commission on Narcotic Drugs placed norfentanyl, 1-boc-4-
anilinopiperidine, and 4-anilinopiperidine in Table I of the 1988
Convention in response to the international reintroduction of fentanyl
on the illicit drug market and the introduction of new precursors used
in the illicit manufacture of fentanyl.
---------------------------------------------------------------------------
\13\ https://www.dea.gov/press-releases/2018/01/05/china-announces-scheduling-controls-two-fentanyl-precursor-chemicals.
Accessed March 9, 2022.
---------------------------------------------------------------------------
Propionyl Chloride
The original published synthetic pathway to fentanyl, known as the
Janssen method, involves the list I chemical benzylfentanyl and
schedule II immediate precursor norfentanyl. In this synthetic pathway,
benzylfentanyl, a list I chemical under the CSA,\14\ is synthesized by
reacting propionyl chloride with 4-anilino-1-benzylpiperidine, which is
then converted to norfentanyl, the schedule II immediate precursor in
this synthetic pathway.\15\ Norfentanyl is then subjected to one simple
chemical reaction to complete the synthesis of fentanyl. This synthetic
pathway can also be easily modified to produce fentanyl analogues and
fentanyl-related substances.
---------------------------------------------------------------------------
\14\ 85 FR 20822 (May 15, 2020).
\15\ 85 FR 21320 (May 18, 2020).
---------------------------------------------------------------------------
Propionyl chloride also serves as a precursor chemical in the
Siegfried method. In this synthetic pathway, propionyl chloride is
reacted with ANPP,\16\ the schedule II immediate precursor in the
Siegfried method, to complete the synthesis of fentanyl. This synthetic
pathway can also be easily modified to produce fentanyl analogues and
fentanyl-related substances.
---------------------------------------------------------------------------
\16\ 75 FR 37295 (August 30, 2010).
---------------------------------------------------------------------------
In addition to the Janssen and Siegfried methods, clandestine
manufacturers are using other methods to synthesize fentanyl, one of
which is known as the Gupta method. In this synthetic pathway, 4-
piperidone, a list I chemical under the CSA, is used to synthesize 4-
anilinopiperidine, another list I chemical under the CSA,\17\ which
serves as an alternative precursor chemical to NPP, a list I chemical,
in the synthesis of ANPP, a schedule II immediate precursor albeit
through a different synthetic process. The resulting ANPP is reacted
with propionyl chloride to manufacture the schedule II controlled
substance, fentanyl. This synthetic pathway can also be easily modified
to produce fentanyl analogues and fentanyl-related substances.
---------------------------------------------------------------------------
\17\ 85 FR 20822 (May 15, 2020).
---------------------------------------------------------------------------
Propionyl chloride is attractive to illicit manufacturers because
of the lack of regulations on this chemical, it is readily available
from chemical suppliers, and it can be easily used in many known
synthetic pathways used in the illicit manufacture of fentanyl,
fentanyl analogues, and fentanyl-related substances.
Solicitation for Information
With this advanced notice of proposed rulemaking, DEA is soliciting
information on any possible legitimate uses of propionyl chloride
unrelated to fentanyl production (including industrial uses) in order
to assess the potential economic impact of controlling propionyl
chloride as a list I chemical. DEA seeks to document any unpublicized
use(s) and other proprietary use(s) of propionyl chloride that are not
in the public domain. Therefore, DEA is soliciting comment on the uses
of propionyl chloride in the legitimate marketplace.
DEA is soliciting input from all potentially affected parties
regarding: (1) The types of legitimate industries using propionyl
chloride; (2) the legitimate uses, legitimate needs and quantity
produced, used, and distributed of propionyl chloride; (3) the size of
the domestic market for propionyl chloride; (4) the number of
manufacturers of propionyl chloride; (5) the number of distributors of
propionyl chloride; (6) the level of import and export of propionyl
chloride; (7) the potential burden that controlling propionyl chloride
as a list I chemical may have on any legitimate industry and trade; (8)
[[Page 70613]]
the potential number of individuals/firms that may be adversely
affected by such regulatory controls (particularly with respect to the
impact on small businesses); and (9) any other information on the
manner of manufacturing, distribution, consumption, storage, disposal,
and uses of propionyl chloride by industry and others. DEA invites all
interested parties to provide any information on any legitimate uses of
propionyl chloride in industry, commerce, academia, research and
development, or other applications. DEA seeks both quantitative and
qualitative data.
Such information may be submitted electronically to the address
listed above and is requested by November 13, 2023. This information
will be used to properly determine the effect that proposed regulations
to make propionyl chloride a list 1 chemical under the CSA would have
on industry.
Handling of Confidential or Proprietary Information
Confidential or proprietary information may be submitted as part of
a comment regarding this advanced notice of proposed rulemaking. Please
see the ``POSTING OF PUBLIC COMMENTS'' section above for a discussion
of the identification and redaction of confidential business
information and personally identifying information.
Regulatory Analyses
This ANPRM was developed in accordance with the principles of
Executive Order (E.O.) 12866, ``Regulatory Planning and Review'' and
E.O. 13563, ``Improving Regulation and Regulatory Review.'' Since this
action is an ANPRM, the requirement of E.O. 12866 to assess the costs
and benefits of this action does not apply.
Furthermore, the requirements of the Regulatory Flexibility Act do
not apply to this action because, at this stage, it is an ANPRM and not
a ``rule'' as defined in 5 U.S.C. 601. Following review of the comments
received in response to this ANPRM, if DEA proceeds with a notice of
proposed rulemaking regarding this matter, DEA will conduct all
relevant analyses as required by statute or E.O.
Signing Authority
This document of the Drug Enforcement Administration was signed on
October 5, 2023, by Administrator Anne Milgram. That document with the
original signature and date is maintained by DEA. For administrative
purposes only, and in compliance with requirements of the Office of the
Federal Register, the undersigned DEA Federal Register Liaison Officer
has been authorized to sign and submit the document in electronic
format for publication, as an official document of DEA. This
administrative process in no way alters the legal effect of this
document upon publication in the Federal Register.
Heather Achbach,
Federal Register Liaison Officer, Drug Enforcement Administration.
[FR Doc. 2023-22570 Filed 10-11-23; 8:45 am]
BILLING CODE 4410-09-P
