[Federal Register Volume 69, Number 188 (Wednesday, September 29, 2004)]
[Rules and Regulations]
[Pages 58050-58053]
From the Federal Register Online via the Government Publishing Office [www.gpo.gov]
[FR Doc No: 04-21755]


=======================================================================
-----------------------------------------------------------------------

DEPARTMENT OF JUSTICE

Drug Enforcement Administration

21 CFR Part 1308

[Docket No. DEA-252F]


Schedules of Controlled Substances: Placement of Alpha-
Methyltryptamine and 5-Methoxy-N,N-Diisopropyltryptamine Into Schedule 
I of the Controlled Substances Act

AGENCY: Drug Enforcement Administration (DEA), Department of Justice.

ACTION: Final rule.

-----------------------------------------------------------------------

SUMMARY: This final rulemaking is issued by the Deputy Administrator of 
the Drug Enforcement Administration (DEA) to place alpha-
methyltryptamine (AMT) and 5-methoxy-N,N-diisopropyltryptamine (5-MeO-
DIPT) into Schedule I of the Controlled Substances Act (CSA). This 
action by the DEA Deputy Administrator is based on a scheduling 
recommendation by the Department of Health and Human Services (DHHS) 
and a DEA review indicating that AMT and 5-MeO-DIPT meet the criteria 
for placement in Schedule I of the CSA. This final rule will continue 
to impose the regulatory controls and criminal sanctions of Schedule I 
substances on the manufacture, distribution, and possession of AMT and 
5-MeO-DIPT.

EFFECTIVE DATE: September 29, 2004.

FOR FURTHER INFORMATION CONTACT: Christine Sannerud, PhD, Chief, Drug 
and Chemical Evaluation Section, Office of Diversion Control, Drug 
Enforcement Administration, Washington, DC 20537, Telephone (202) 307-
7183.

SUPPLEMENTARY INFORMATION: On April 4, 2003, the Deputy Administrator 
of the DEA published a final rule in the Federal Register (68 FR 16427) 
amending Sec.  1308.11(g) of Title 21 of the Code of Federal 
Regulations to temporarily place AMT and 5-MeO-DIPT into Schedule I of 
the CSA pursuant to the temporary scheduling provisions of 21 U.S.C. 
811(h). This final rule, which became effective on the date of 
publication, was based on findings by the Deputy Administrator that the 
temporary scheduling of AMT and 5-MeO-DIPT was necessary to avoid an 
imminent hazard to the public safety. Section 201(h)(2) of the CSA (21 
U.S.C. 811(h)(2)) requires that the temporary scheduling of a substance 
expires at the end of one year from the effective date of the order. 
However, if proceedings to schedule a substance pursuant to 21 U.S.C. 
811(a)(1) have been initiated and are pending, the temporary scheduling 
of a substance may be extended for up to six months. On March 31, 2004, 
the Acting Deputy Administrator published a notice of proposed 
rulemaking in the Federal Register (69 FR 16838) to place AMT and 5-
MeO-DIPT into Schedule I of the CSA on a permanent basis. The temporary 
scheduling of AMT and 5-MeO-DIPT, which would have expired April 3, 
2004, was extended to October 3, 2004 (69 FR 17034, April 1, 2004). One 
comment was received regarding the proposed placement of these 
substances into Schedule I of the CSA.
    The DEA has gathered and reviewed the available information 
regarding the pharmacology, chemistry, trafficking, actual abuse, 
pattern of abuse, and the relative potential for abuse for AMT and 5-
MeO-DIPT. The Acting Deputy Administrator submitted these data to the 
Acting Assistant Secretary for Health, Department of Health and Human 
Services (DHHS). In accordance with 21 U.S.C. 811(b), the Acting Deputy 
Administrator also requested a scientific and medical evaluation and a

[[Page 58051]]

scheduling recommendation for AMT and 5-MeO-DIPT from the Acting 
Assistant Secretary of DHHS. On September 17, 2004, the Acting 
Assistant Secretary for Health recommended that AMT and 5-MeO-DIPT be 
permanently controlled in Schedule I of the CSA.
    Alpha-methyltryptamine (AMT) and 5-methoxy-N,N-
diisopropyltryptamine (5-MeO-DIPT) are tryptamine (indoleethylamine) 
derivatives and share several similarities with the Schedule I 
tryptamine hallucinogens such as alpha-ethyltryptamine (AET) and N,N-
dimethyltryptamine (DMT). Several other tryptamines also produce 
hallucinogenic/stimulant effects and are controlled as Schedule I 
substances under the CSA (bufotenine, diethyltryptamine, psilocybin and 
psilocyn). Although tryptamine itself appears to lack consistent 
hallucinogenic/stimulant effects, substitutions on the indole ring and 
the ethylamine side-chain of this molecule result in pharmacologically 
active substances (McKenna and Towers, J. Psychoactive Drugs, 16: 347-
358, 1984). The chemical structures of AMT and 5-MeO-DIPT possess the 
critical features necessary for hallucinogenic/stimulant activity. In 
drug discrimination studies, both AMT and 5-MeO-DIPT substitute for 1-
(2,5-dimethoxy-4-methylphenyl)-aminopropane (DOM), a phenethylamine-
based hallucinogen in Schedule I of the CSA. The potencies of DOM-like 
discriminative stimulus effects of these and several other similar 
tryptamine derivatives correlate well with their hallucinogenic 
potencies in humans (Glennon et al., Eur. J. Pharmacol. 86: 453-459, 
1983).
    AMT, besides its full generalization to DOM, also partially mimics 
amphetamine and 3,4-methylenedioxymethamphetamine (MDMA) in drug 
discrimination tests in experimental animals. AMT increases systolic 
and diastolic arterial blood pressures, dilates pupils and produces 
strong motor stimulant effects. The behavioral effects of orally 
administered AMT (20 mg) in humans are slow in onset, occurring after 3 
to 4 hours, and gradually subsiding after 12 to 24 hours, but may last 
up to 2 days in some subjects. The majority of the subjects report 
euphoria, stimulation, muscle tension, muscle ache, nervous tension, 
irritability, restlessness, dizziness, impaired motor coordination, 
unsettled feeling in stomach, inability to relax and sleep, and visual 
effects such as blurry vision, apparent movement of objects, sharper 
outlines, brighter colors, longer after images, and visual 
hallucinations. The majority of the subjects equate the effects of a 20 
mg dose of AMT to those of 50 micrograms of lysergic acid diethylamide 
(LSD). AMT also produces dextroamphetamine-like mood elevating effects 
in humans (Hollister et al., J. Nervous Ment. Dis., 131: 428-434, 1960; 
Murphree et al., Clin. Pharmacol. Ther. 2: 722-726, 1961).
    Similar to other classical hallucinogens, AMT binds to serotonin 
receptors. It also inhibits 5-HT uptake, induces catecholamine release 
and inhibits monoamine oxidase activity. The available experimental 
evidence suggests that both serotonergic and dopaminergic systems 
mediate behavioral effects of AMT.
    5-MeO-DIPT produces pharmacological effects similar to those of 
several Schedule I hallucinogens. The synthesis and preliminary human 
psychopharmacology study on 5-MeO-DIPT was first published in 1981 
(Shulgin and Carter, Comm. Psychopharmacol. 4: 363-369, 1981). 
According to this report, subjective effects of 5-MeO-DIPT are 
substantially similar to those of MDMA, 3,4-methylenedioxyamphetamine 
(MDA) and 4-Bromo-2,5-dimethoxyphenethylamine (2C-B). 5-MeO-DIPT is an 
orally active hallucinogen. Following oral administration of 6-10 mg, 
5-MeO-DIPT produces subjective effects with an onset of about 20-30 
minutes, a peak at about 1-1.5 hours and duration of about 3-6 hours. 
Subjects who have been administered 5-MeO-DIPT are talkative and 
disinhibited. 5-MeO-DIPT dilates pupils. High doses of 5-MeO-DIPT 
produce nausea, jaw clenching, muscle tension and overt hallucinations 
with both auditory and visual distortions. As mentioned above, 5-MeO-
DIPT fully mimics the discriminative stimulus effects of DOM, a 
Schedule I hallucinogen. According to the discriminative stimulus 
studies conducted by the Drug Evaluation Committee of the College on 
Problems of Drug Dependence, 5-MeO-DIPT dose-dependently (0.1-3 mg/kg, 
IP) generalizes to LSD with a maximal response of about 70% at doses (3 
mg/kg) that severely disrupted responding.
    The abuse of stimulant/hallucinogenic substances in popular all 
night dance parties (``raves'') and in other venues has been a major 
problem in Europe since the 1990s. In the past several years, this 
activity has spread to the United States. The Schedule I controlled 
substance MDMA and its analogues, collectively known as Ecstasy, are 
the most popular drugs abused at these raves. Their abuse has been 
associated with both acute and long-term public health and safety 
problems. These raves have also become venues for the trafficking and 
abuse of other substances in place of or in addition to ``Ecstasy.'' 
AMT and 5-MeO-DIPT belong to such a group of substances.
    The abuse of AMT and 5-MeO-DIPT began to spread in 1999. Since that 
time, these tryptamines have been encountered by law enforcement 
agencies in several states. These substances have been commonly 
encountered in tablet, capsule or powder forms. The tablet form often 
bears imprints commonly seen on MDMA tablets such as spider, alien head 
and ``?'' logos. These tablets also vary in colors such as pink, 
purple, red, and orange. The powder in capsule was also found to vary 
in colors such as white, off-white, gray, and burnt orange. Data from 
law enforcement officials indicate that 5-MeO-DIPT is often sold as 
``Foxy'' or ``Foxy Methoxy'', while AMT has been sold as ``Spirals'' at 
least in one case. Data gathered from published studies indicate that 
these are administered orally at doses ranging from 15-40 mg for AMT 
and 6-20 mg for 5-MeO-DIPT.
    According to the Florida Department of Law Enforcement (FDLE) 
report issued in 2002, the abuse by teens and young adults of AMT and 
5-MeO-DIPT is an emerging problem. There have been reports of abuse of 
AMT and 5-MeO-DIPT at clubs and raves in Arizona, California, Florida 
and New York. Many tryptamine-based substances are illicitly available 
from United States and foreign chemical companies and from individuals 
through the Internet. There is also evidence of attempted clandestine 
production of AMT and 5-MeO-DIPT in Nevada, Virginia and Washington, 
DC.
    According to data from the System to Retrieve Information on Drug 
Evidence (STRIDE), since 1999 Federal law enforcement authorities 
seized 34 drug exhibits and filed 14 cases pertaining to the 
trafficking, distribution and abuse of AMT during 1999 to 2003. The 
corresponding STRIDE data for 5-MeO-DIPT included 63 drug exhibits 
pertaining to 32 cases. AMT drug seizures included 21 capsules and 
1,011.8 grams of powder, while 5-MeO-DIPT drug seizures included 12,070 
tablets, 560 capsules, and 6,532.3 grams of powder. Since 2001, the 
National Forensic Laboratory Information System (NFLIS) registered 10 
and 12 cases of AMT and 5-MeO-DIPT, respectively. AMT drug exhibits 
included 17 dosage units and 7.53 grams of powder, while 5-MeO-DIPT 
drug exhibits included 24 capsules, 3 tablets and 14.42 grams of 
powder.

[[Page 58052]]

    AMT and 5-MeO-DIPT share substantial chemical and pharmacological 
similarities with other Schedule I tryptamine-based hallucinogens in 
Schedule I of the CSA. AMT shares pharmacological effects of 
amphetamine, a stimulant, and DOM and LSD, the Schedule I 
hallucinogens. AMT acts as a stimulant, produces euphoria and increases 
heart rate and blood pressure. The evidence suggests that 5-MeO-DIPT 
mimics pharmacological effects of MDMA, MDA, and 2C-B, the Schedule I 
hallucinogens. It also partially mimics amphetamine effects. The risks 
to the public health associated with the above mentioned controlled 
substances are well known and documented. AMT and 5-MeO-DIPT, similar 
to other tryptamine-or phenethylamine-based hallucinogens, through the 
alteration of sensory perception and judgment can pose serious health 
risks to the user and the general public. Tryptamine, the parent 
molecule of AMT and 5-MeO-DIPT, is known to produce convulsions and 
death in animals (Tedeschi et al., J. Pharmacol. Exp. Ther. 126: 223-
232, 1959). Following extensive studies on AMT as a possible 
antidepressant drug in 1960s, The Upjohn Company concluded that AMT is 
a highly toxic substance and discontinued the clinical studies on this 
substance. In fact, there were two recent published case reports 
describing the instances of emergency department admissions resulting 
from abuse of AMT and 5-MeO-DIPT in 2003 (Long et al., Vet. Human 
Toxicol., 45: 149, 2003; Meatherall and Sharma, J. Anal. Toxicol., 27: 
313-317, 2003). There has been at least one confirmed death caused by 
the abuse of AMT in Florida in 2003. The above data show that the 
continued, uncontrolled tablet or capsule production, distribution and 
abuse of AMT and 5-MeO-DIPT pose hazards to the public health and 
safety. There are no recognized therapeutic uses of these substances in 
the United States.
    The DEA received one comment from an organization in response to 
the proposed placement of AMT and 5-MeO-DIPT into Schedule I of the 
CSA. This organization did not support the proposed placement of these 
drugs into Schedule I on the following basis: (1) They believed 
insufficient data exists to support placement into Schedule I as the 
mere use of these substances was not abuse and (2) Prohibiting the 
possession of these substances is a substantial infringement of the 
fundamental right of adults to freedom of thought. Both the DEA and the 
DHHS have found that sufficient scientific, trafficking and abuse data, 
as summarized herein, does exist to place AMT and 5-MeO-DIPT in 
Schedule I of the CSA on a permanent basis. As these substances have no 
legitimate medical use in the United States, the trafficking in, and 
use by individuals for the psychoactive effects they produce, is 
considered abuse. In addition, the control of these substances in 
Schedule I of the CSA does not violate any legally protected right.
    Based on all the available information gathered and reviewed by the 
DEA and in consideration of the scientific and medical evaluation and 
scheduling recommendation by the Assistant Secretary of the DHHS, the 
Deputy Administrator has determined that sufficient data exist to 
support the placement of AMT and 5-MeO-DIPT into Schedule I of the CSA 
pursuant to 21 U.S.C. 811(a). The Deputy Administrator finds:
    (1) AMT and 5-MeO-DIPT have a high potential for abuse.
    (2) AMT and 5-MeO-DIPT have no currently accepted medical use in 
treatment in the United States.
    (3) AMT and 5-MeO-DIPT lack accepted medical safety for use under 
medical supervision.
    In accordance with 21 U.S.C. 811(h)(5), the Deputy Administrator 
hereby vacates the order temporarily placing AMT and 5-MeO-DIPT into 
Schedule I of the CSA published in the Federal Register on April 4, 
2003.

Regulatory Requirements

    With the issuance of this final order, AMT and 5-MeO-DIPT continue 
to be subject to regulatory controls and administrative, civil and 
criminal sanctions applicable to the manufacture, distribution, 
dispensing, importing and exporting of a Schedule I controlled 
substance, including the following:
    1. Registration. Any person who manufactures, distributes, 
dispenses, imports or exports AMT and 5-MeO-DIPT or who engages in 
research or conducts instructional activities with respect to AMT and 
5-MeO-DIPT or who proposes to engage in such activities must submit an 
application for Schedule I registration in accordance with part 1301 of 
Title 21 of the Code of Federal Regulations.
    2. Security. AMT and 5-MeO-DIPT are subject to Schedule I security 
requirements and must be manufactured, distributed and stored in 
accordance with Sec. Sec.  1301.71, 1301.72(a), (c), and (d), 1301.73, 
1301.74, 1301.75 (a) and (c) and 1301.76 of Title 21 of the Code of 
Federal Regulations.
    3. Labeling and Packaging. All labels and labeling for commercial 
containers of AMT and 5-MeO-DIPT which are distributed on or after 
October 29, 2004 shall comply with requirements of Sec. Sec.  1302.03 -
1302.07 of Title 21 of the Code of Federal Regulations.
    4. Quotas. Quotas for AMT and 5-MeO-DIPT are established pursuant 
to Part 1303 of Title 21 of the Code of Federal Regulations.
    5. Inventory. Every registrant required to keep records and who 
possesses any quantity of AMT and 5-MeO-DIPT is required to keep an 
inventory of all stocks of the substances on hand pursuant to 
Sec. Sec.  1304.03, 1304.04 and 1304.11 of Title 21 of the Code of 
Federal Regulations. Every registrant who desires registration in 
Schedule I for AMT and 5-MeO-DIPT shall conduct an inventory of all 
stocks of AMT and 5-MeO-DIPT.
    6. Records. All registrants are required to keep records pursuant 
to Sec. Sec.  1304.03, 1304.04 and Sec. Sec.  1304.21-1304.23 of Title 
21 of the Code of Federal Regulations.
    7. Reports. All registrants required to submit reports in 
accordance with Sec.  1304.33 of Title 21 of the Code of Federal 
Regulations shall do so regarding AMT and 5-MeO-DIPT.
    8. Order Forms. All registrants involved in the distribution of AMT 
and 5-MeO-DIPT must comply with the order form requirements of part 
1305 of Title 21 of the Code of Federal Regulations.
    9. Importation and Exportation. All importation and exportation of 
AMT and 5-MeO-DIPT must be in compliance with part 1312 of Title 21 of 
the Code of Federal Regulations.
    10. Criminal Liability. Any activity with AMT and 5-MeO-DIPT not 
authorized by, or in violation of, the Controlled Substances Act or the 
Controlled Substances Import and Export Act occurring on or after 
September 29, 2004 will continue to be unlawful.

Regulatory Certifications

Regulatory Flexibility Act

    The Deputy Administrator of the DEA hereby certifies that the 
placement of AMT and 5-MeO-DIPT into Schedule I of the CSA will not 
have a significant economic impact upon entities whose interests must 
be considered under the Regulatory Flexibility Act, 5 U.S.C. 601 et 
seq. This action involves the control of two substances with no 
currently accepted medical use in the United States.

Executive Order 12866

    This final rule is not a significant regulatory action for the 
purposes of Executive Order 12866. Drug

[[Page 58053]]

Scheduling matters are not subject to review by the Office of 
Management and Budget pursuant to provisions of Executive Order 12866, 
section 3(d)(1).

Executive Order 12988

    This regulation meets the applicable standards set forth in 
sections 3(a) and 3(b)(2) of Executive Order 12988 Civil Justice 
Reform.

Executive Order 13132

    This final rule does not have substantial direct effects on the 
States, on the relationship between the national government and the 
States, or on the distribution of power and responsibilities among the 
various levels of government. Therefore, in accordance with Executive 
Order 13132, it is determined that this rule will not have sufficient 
federalism implications to warrant the preparation of a federalism 
assessment.

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 
$114,000,000 or more in any one year, and it will not significantly or 
uniquely affect small governments. Therefore, no actions were deemed 
necessary under 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 $100,000,000 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 1308

    Administrative practice and procedure, Drug traffic control, 
Reporting and recordkeeping requirements.

    Under the authority vested in the Attorney General by Section 
201(a) of the CSA (21 U.S.C. 811(a)), and delegated to the 
Administrator of the DEA by the Department of Justice regulations (28 
CFR 0.100) and re-delegated to the Deputy Administrator pursuant to 28 
CFR 0.104, the Deputy Administrator amends 21 CFR Part 1308 as follows:

PART 1308--SCHEDULES OF CONTROLLED SUBSTANCES

    1. The authority citation for Part 1308 continues to read as 
follows:

    Authority: 21 U.S.C. 811, 812, 871(b) unless otherwise noted.

    2. Section 1308.11 is amended by:
    A. Redesignating existing paragraphs (d)(15) through (d)(32) as 
paragraphs (d)(16) through (d)(33),
    B. Adding a new paragraph (d)(15),
    C. Further redesignating paragraphs (d)(19) through (d)(33) as 
paragraphs (d)(20) through (d)(34),
    D. Adding a new paragraph (d)(19),
    E. Removing paragraphs (g)(3) and (g)(4) to read as follows:


Sec.  1308.11  Schedule I.

* * * * *
    (d) * * *
    (15) Alpha-methyltryptamine (other name: AMT)--7432.
* * * * *
    (19) 5-methoxy-N,N-diisopropyltryptamine (other name: 5-MeO-DIPT) 
--7439.
* * * * *

    Dated: September 23, 2004.
Michele M. Leonhart,
Deputy Administrator.
[FR Doc. 04-21755 Filed 9-28-04; 8:45 am]
BILLING CODE 4410-09-P