[Federal Register: May 25, 2006 (Volume 71, Number 101)]
[Proposed Rules]
[Page 30097-30100]
From the Federal Register Online via GPO Access [wais.access.gpo.gov]
[DOCID:fr25my06-22]
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DEPARTMENT OF JUSTICE
Drug Enforcement Administration
21 CFR Part 1300
[Docket No. DEA-260P]
RIN 1117-AA94
Definition of ``Positional Isomer'' as It Pertains to the Control
of Schedule I Controlled Substances
AGENCY: Drug Enforcement Administration (DEA), U.S. Department of
Justice.
ACTION: Notice of proposed rulemaking.
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SUMMARY: The Controlled Substances Act (CSA) and its implementing
regulations specify which hallucinogenic substances are considered
Schedule I controlled substances. The CSA states that all salts,
isomers and salts of isomers of these substances are also Schedule I
controlled substances. In non-technical terms, an isomer of a substance
is a different compound, but a compound which has the same number and
kind of atoms. The terms ``optical isomer'' and ``geometric isomer''
are specific scientific terms and it is easy to determine whether one
substance is an optical or geometric isomer of another. The term
``positional isomer,'' however, is subject to scientific
interpretation.
This Notice of Proposed Rulemaking proposes the addition of a
specific definition for the term ``positional isomer'' to allow for the
systematic determination of which isomers of Schedule I substances
would be considered to be ``positional'' and, therefore subject to
Schedule I control.
The addition of a definition for the term ``positional isomer''
will assist legitimate research and industry in determining the control
status of materials that are ``positional isomers'' of Schedule I
hallucinogens. While the DEA will remain the authority for ultimately
determining the control status of a given material, providing a
specific definition for ``positional isomer'' will ensure consistent
criteria are utilized in making these determinations.
This rule is relevant only to specialized forensic or research
chemists. Most of these individuals are existing DEA registrants who
are authorized by the DEA to handle Schedule I hallucinogenic
substances.
DATES: Written comments must be postmarked, and electronic comments
must be sent, on or before July 24, 2006.
ADDRESSES: To ensure proper handling of comments, please reference
``Docket No. DEA-260P'' on all written and electronic correspondence.
Written comments being sent via regular mail should be sent to the
Deputy Administrator, Drug Enforcement Administration, Washington, DC
20537, Attention: DEA Federal Register Representative/ODL. Written
comments sent via express mail should be sent to the DEA Headquarters,
Attention: DEA Federal Register Representative/ODL, 2401 Jefferson-
Davis Highway, Alexandria, VA 22301. Comments may be directly sent to
the DEA electronically by sending an electronic message to
dea.diversion.policy@usdoj.gov. An electronic copy of this document is
also available at the http://www.regulations.gov Web site. The DEA will
accept attachments to electronic comments in Microsoft Word,
WordPerfect, Adobe PDF, or Excel file formats only. The DEA will not
accept any file format other than those specifically listed here.
FOR FURTHER INFORMATION CONTACT: Christine A. Sannerud, Ph.D., Chief,
Drug and Chemical Evaluation Section, Office of Diversion Control, Drug
Enforcement Administration,
[[Page 30098]]
Washington, DC 20537 at (202) 307-7183.
SUPPLEMENTARY INFORMATION:
Background
In many instances, the control of a substance under the CSA often
includes the specific substance listed under the CSA, as well as the
substance's salts, isomers and/or salts of isomers. In most instances,
the term isomer includes only optical isomers. In other instances,
however, the term isomer includes positional and/or geometric isomers.
In non-technical terms, isomers are different compounds that have
the same molecular formula (the same number and types of atoms). The
terms ``optical isomer'' and ``geometric isomer'' are specifically
defined and well understood scientific terms, and it is easy to
determine whether one substance is an optical or geometric isomer of
another. The term ``positional isomer,'' however, is not universally
defined and, therefore, is subject to scientific interpretation. In
order to ensure that consistent criteria are utilized in determining
whether one substance is considered a ``positional isomer'' of another,
the DEA is proposing that a specific definition for ``positional
isomer'' be added to 21 CFR 1300.01(b)(21).
Existing CSA and CFR References to ``Positional Isomers''
The CSA and its implementing regulations (21 CFR 1308.11(d))
specify which hallucinogenic substances are considered Schedule I
controlled substances. Under the CSA and its implementing regulations,
there are only three references to the term ``positional isomer'':
(1) Pursuant to 21 U.S.C. 802(14), ``the term `isomer' means the
optical isomer, except as used in Schedule I(c) and Schedule II(a)(4).
As used in Schedule I(c), the term ``isomer'' means any optical,
positional, or geometric isomer. As used in Schedule II(a)(4), the term
``isomer'' means any optical or geometric isomer.''
(2) Under 21 CFR 1300.01(b)(21), ``The term ``isomer'' means the
optical isomer, except as used in Sec. Sec. 1308.11(d) and
1308.12(b)(4) of this chapter. As used in Sec. 1308.11(d) of this
chapter, the term ``isomer'' means the optical, positional, or
geometric isomer. As used in Sec. 1308.12(b)(4) of this chapter, the
term ``isomer'' means the optical or geometric isomer.''
(3) 21 CFR 1308.11(d) states, ``Hallucinogenic substances. Unless
specifically excepted or unless listed in another schedule, any
material, compound, mixture, or preparation, which contains any
quantity of the following hallucinogenic substances, or which contains
any of its salts, isomers, and salts of isomers whenever the existence
of such salts, isomers and salts of isomers is possible within the
specific chemical designation (for purposes of this paragraph only, the
term ``isomer'' includes the optical, positional and geometric
isomers).''
Why Proposed Definition Is Needed
The CSA (21 U.S.C. 802(14) and 21 U.S.C. 812(c)(I)(c)) and its
implementing regulations (21 CFR 1308.11(d)) specify which
hallucinogenic substances are considered Schedule I controlled
substances. The CSA further states that all salts, isomers and salts of
isomers of these substances are also Schedule I controlled substances.
Under the definition of ``isomer'' found in 21 CFR 1300.01(b)(21),
``The term ``isomer'' means the optical isomer, except as used in
Sec. Sec. 1308.11(d) and 1308.12(b)(4) of this chapter. As used in
Sec. 1308.11(d) of this chapter, the term ``isomer'' means the
optical, positional, or geometric isomer. As used in Sec.
1308.12(b)(4) of this chapter, the term ``isomer'' means the optical or
geometric isomer.''
Therefore, according to this definition as it specifically applies
to hallucinogens, the term ``isomer'' includes all optical, positional,
or geometric isomers. As such, all salts, isomers (including optical,
positional, or geometric isomers) and salts of isomers (including
optical, positional, or geometric isomers) of the hallucinogenic
substances listed in 21 U.S.C. 812(c)(I)(c) and 21 CFR 1308.11(d) are
considered Schedule I controlled substances.
Because the determination as to whether a substance is considered a
``positional isomer'' can be subject to scientific interpretation, the
DEA believes it is necessary to specifically define the term
``positional isomer''. This definition will only pertain to those
substances that are ``positional isomers'' of Schedule I controlled
substances pursuant to 21 U.S.C. 812(c)(I)(c) and 21 CFR 1308.11(d).
The DEA is not proposing the addition of definitions for either
optical or geometric isomers. The DEA believes that these terms are
highly specific and are not subject to differing scientific
interpretation.
Proposed Criteria That Will Apply to Positional Isomers
Pursuant to 21 U.S.C. 802(14), 21 U.S.C. 812(c)(I)(c) and 21 CFR
1308.11(d) positional isomers of Schedule I hallucinogens are any and
all substances which:
(1) Are not already controlled in a different Schedule I category,
or are listed in another Schedule, or are specifically exempted from
control by law; and
(2) Have the same molecular formula and core structure as a
Schedule I hallucinogen; and
(3) Have the same functional group(s) and/or substituent(s) as
those found in the respective Schedule I hallucinogen, attached at any
position(s) on the core structure, but in such manner that no new
chemical functionalities are created and no existing chemical
functionalities are destroyed relative to the respective Schedule I
hallucinogen; except that
(4) Rearrangements of alkyl moieties within or between functional
group(s) or substituent(s), or divisions or combinations of alkyl
moieties, that do not create new chemical functionalities or destroy
existing chemical functionalities, would be within the definition of
positional isomer (and therefore be controlled).
As clarification, note that the ``core structure'' is the parent
molecule that is the common basis for the class; for example,
tryptamine, phenethylamine, or ergoline. The following are examples of
rearrangements resulting in creation and/or destruction of chemical
functionalities. These rearrangements result in compounds which are not
positional isomers: ethoxy to alpha-hydroxyethyl, hydroxy and methyl to
methoxy, or the repositioning of a phenolic or alcoholic hydroxy group
to create a hydroxyamine. Examples of rearrangements resulting in
compounds which would be positional isomers include, but are not
limited to: tert-butyl to sec-butyl, methoxy and ethyl to isopropoxy,
N,N-diethyl to N-methyl-N-propyl, or alpha-methylamino to N-
methylamino.
Impact of Rule Limited to Specialized Forensic or Research Chemists
The addition of a definition for the term ``positional isomer'' as
it applies to 21 CFR 1308.11(d) will assist legitimate research and
industry in determining the control status of substances that are
isomers of Schedule I hallucinogens. While the DEA will remain the
authority on ultimately determining the control status of a given
substance, providing a specific definition for ``positional isomer''
will greatly reduce any potential confusion or inconsistencies in
making these determinations.
This definition will enable researchers and industry to determine
definitively whether a substance is a
[[Page 30099]]
``positional isomer'' of a Schedule I hallucinogen. As such, they will
be able to know the control status of a particular substance when
considering new research.
This rule is relevant only to specialized forensic or research
chemists. Most of these individuals are existing DEA registrants who
are authorized by the DEA to handle Schedule I hallucinogenic
substances.
Specific Changes and Proposed Definition
As currently defined in 21 CFR 1300.01(b)(21), the term ``isomer''
means the optical isomer, except as used in Sec. 1308.11(d) and Sec.
1308.12(b)(4) of this chapter. As used in Sec. 1308.11(d) of this
chapter, the term ``isomer'' means any optical, positional, or
geometric isomer. As used in Sec. 1308.12(b)(4) of this chapter, the
term ``isomer'' means any optical or geometric isomer.
Title 21 CFR 1300.01(b)(21) is proposed to be revised to include a
specific definition for the term ``positional isomer''. The proposed
modification will specify that, as used in Sec. 1308.11(d), the term
``positional isomer'' means any substance possessing the same molecular
formula and core structure and has the same functional group(s) and/or
substituent(s) as those found in the respective Schedule I
hallucinogen, attached at any position(s) on the core structure, but in
such manner that no new chemical functionalities are created and no
existing chemical functionalities are destroyed relative to the
respective Schedule I hallucinogen. Rearrangements of alkyl moieties
within or between functional group(s) or substituent(s), or divisions
or combinations of alkyl moieties, that do not create new chemical
functionalities or destroy existing chemical functionalities, would be
within the definition of positional isomer. For purposes of this
definition, the ``core structure'' is the parent molecule that is the
common basis for the class. Some examples would include tryptamine,
phenethylamine, or ergoline. Examples of non-permissible rearrangements
resulting in creation and/or destruction of chemical functionalities
(and therefore would not be considered positional isomers) include, but
are not limited to: ethoxy to alpha-hydroxyethyl, hydroxy and methyl to
methoxy, or the repositioning of a phenolic or alcoholic hydroxy group
to create a hydroxyamine. Examples of permissible rearrangements (that
are within the definition of positional isomers) include: tert-butyl to
sec-butyl, methoxy and ethyl to isopropoxy, N,N-diethyl to N-methyl-N-
propyl, or alpha-methylamino to N-methylamino.
Scientific/Technical Nature of Proposed Definition
The DEA understands that the proposed definition is highly
technical and laden with scientific terms. However, the DEA believes
that such a highly technical definition is necessary to ensure that
consistent criteria are utilized in determining whether one substance
is a ``positional isomer'' of another.
Request for Comments
The proposed definition of ``positional isomer'' will be used in
the determination of the control status of substances as Schedule I
controlled substances pursuant to 21 CFR 1308.11(d). This definition is
highly technical in nature and the DEA has sought to provide specific
criteria for determination as to whether a substance is a ``positional
isomer'' of Schedule I hallucinogens. The DEA welcomes input from all
interested parties regarding the proposed definition of ``positional
isomer.'' Prior to publication of a Final Rule, the DEA will consider
all comments received. Comments must be submitted on or before July 24,
2006.
Regulatory Certifications
Regulatory Flexibility Act
The Deputy Administrator hereby certifies that this rulemaking has
been drafted in accordance with the Regulatory Flexibility Act (5
U.S.C. 605(b)), has reviewed this regulation, and by approving it
certifies that this regulation will not have a significant economic
impact on a substantial number of small entities. The inclusion of the
definition of positional isomer set forth herein is unlikely to subject
any new substances to CSA control. Also, this rule does not require the
obtaining of new DEA registrations. Most persons affected by this rule
are already DEA registrants (or would have to become registrants even
absent this rule in order to handle Schedule I hallucinogens.) Further,
this rule does not impose any additional regulatory burden on the
regulated community. The proposed change simply will ensure that
consistent criteria are utilized in making scheduling determinations.
Executive Order 12866
The Deputy Administrator further certifies that this rulemaking has
been drafted in accordance with the principles in Executive Order 12866
section 1(b). The DEA has determined that this is not a significant
regulatory action. Therefore, this action has not been reviewed by the
Office of Management and Budget.
Executive Order 12988
This regulation meets the applicable standards set forth in
Sec. Sec. 3(a) and 3(b)(2) of Executive Order 12988 Civil Justice
Reform.
Executive Order 13132
This rulemaking does not preempt or modify any provision of state
law; nor does it impose enforcement responsibilities on any state; nor
does it diminish the power of any state to enforce its own laws.
Accordingly, this rulemaking does not have federalism implications
warranting the application of Executive Order 13132.
Unfunded Mandates Reform Act of 1995
This rule will not result in the expenditure by state, local, and
tribal governments, in the aggregate, or by the private sector, of
$117,000,000 or more in any one year, and will not significantly or
uniquely affect small governments. Therefore, no actions were deemed
necessary under the provisions of the Unfunded Mandates Reform Act of
1995.
Small Business Regulatory Enforcement Fairness Act of 1996
This rule is not a major rule as defined by section 804 of the
Small Business Regulatory Enforcement Fairness Act of 1996. This rule
will not result in an annual effect on the economy of $114,000,000 or
more; a major increase in costs or prices; or significant adverse
effects on competition, employment, investment, productivity,
innovation, or on the ability of United States-based companies to
compete with foreign-based companies in domestic and export markets.
List of Subjects in 21 CFR Part 1300
Controlled substances, Definitions, Drug traffic control.
For the reasons set out above, 21 CFR part 1300 is proposed to be
amended as follows:
PART 1300--DEFINITIONS [AMENDED]
1. The authority citation for part 1300 continues to read as
follows:
Authority: 21 U.S.C. 802, 871(b), 951, 958(f).
2. Sec. 1300.01 is proposed to be amended by revising paragraph
(b)(21) to read as follows:
[[Page 30100]]
Sec. 1300.01 Definitions relating to controlled substances.
* * * * *
(b) * * *
(21)(i) The term isomer means the optical isomer, except as used in
Sec. 1308.11(d) and Sec. 1308.12(b)(4) of this chapter. As used in
Sec. 1308.11(d) of this chapter, the term ``isomer'' means any
optical, positional, or geometric isomer. As used in Sec.
1308.12(b)(4) of this chapter, the term ``isomer'' means any optical or
geometric isomer.
(ii) As used in Sec. 1308.11(d) of this chapter, the term
``positional isomer'' means any substance possessing the same molecular
formula and core structure and having the same functional group(s) and/
or substituent(s) as those found in the respective Schedule I
hallucinogen, attached at any position(s) on the core structure, but in
such manner that no new chemical functionalities are created and no
existing chemical functionalities are destroyed relative to the
respective Schedule I hallucinogen. Rearrangements of alkyl moieties
within or between functional group(s) or substituent(s), or divisions
or combinations of alkyl moieties, that do not create new chemical
functionalities or destroy existing chemical functionalities, are
allowed i.e., result in compounds which are positional isomers. For
purposes of this definition, the ``core structure'' is the parent
molecule that is the common basis for the class; for example,
tryptamine, phenethylamine, or ergoline. Examples of rearrangements
resulting in creation and/or destruction of chemical functionalities
(and therefore resulting in compounds which are not positional isomers)
include, but are not limited to: ethoxy to alpha-hydroxyethyl, hydroxy
and methyl to methoxy, or the repositioning of a phenolic or alcoholic
hydroxy group to create a hydroxyamine. Examples of rearrangements
resulting in compounds which would be positional isomers include: tert-
butyl to sec-butyl, methoxy and ethyl to isopropoxy, N,N-diethyl to N-
methyl-N-propyl, or alpha-methylamino to N-methylamino.
* * * * *
Dated: May 17, 2006.
Michele M. Leonhart,
Deputy Administrator.
[FR Doc. E6-7979 Filed 5-24-06; 8:45 am]
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