[Federal Register: March 31, 2004 (Volume 69, Number 62)]
[Proposed Rules]               
[Page 16838-16841]
From the Federal Register Online via GPO Access [wais.access.gpo.gov]
[DOCID:fr31mr04-31]                         

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DEPARTMENT OF JUSTICE

Drug Enforcement Administration

21 CFR Part 1308

[Docket No. DEA-252P]

 
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: Notice of proposed rulemaking.

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SUMMARY: The Acting Deputy Administrator of the Drug Enforcement 
Administration (DEA) is issuing this notice of proposed rulemaking to 
place alpha-methyltryptamine (AMT) and 5-methoxy-N,N-
diisopropyltryptamine (5-MeO-DIPT) into Schedule I of the Controlled 
Substances Act (CSA). This proposed action is based on data gathered 
and reviewed by the DEA. If finalized, this proposed action would 
continue to impose the criminal sanctions and regulatory controls of 
Schedule I substances under the CSA on the manufacture, distribution, 
and possession of AMT and 5-MeO-DIPT.

DATES: Written comments must be postmarked, and electronic comments 
must be sent, on or before April 30, 2004.

ADDRESSES: To ensure proper handling of comments, please reference 
``Docket No. DEA-252'' on all written and electronic correspondence. 
Written comments being sent via regular mail should be sent to the 
Acting Deputy Administrator, Office of Diversion Control, Drug 
Enforcement Administration, Washington, DC 20537, Attention: DEA 
Federal Register Representative/CCD. Written comments sent via express 
mail should be sent to DEA Headquarters, Attention: DEA Federal 
Register Representative/CCD, 2401 Jefferson-Davis Highway, Alexandria, 
VA 22301. Comments may be directly sent to DEA electronically by 
sending an electronic message to dea.diversion.policy@usdoj.gov. 
Comments may also be sent electronically through http://www.regulations.gov
 using the electronic comment form provided on that 

site. An electronic copy of this document is also available at the 
http://www.regulations.gov Web site. DEA will accept electronic 

comments containing MS word, WordPerfect, Adobe PDF, or Excel files 
only. DEA will not accept any file format other than those specifically 
listed here.

FOR FURTHER INFORMATION CONTACT: Christine Sannerud, Ph.D., Chief, Drug 
and Chemical Evaluation Section, Drug Enforcement Administration, 
Washington, DC 20537, (202) 307-7183.

SUPPLEMENTARY INFORMATION: On April 4, 2003, the Deputy Administrator 
of the DEA published a final rule in the Federal Register amending 
Sec.  1308.11(g) of title 21 of the Code of Federal Regulations to 
temporarily place AMT and 5-MeO-DIPT (68 FR 16427) 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. The CSA (21 U.S.C. 811(h)(2)) 
requires that the temporary scheduling of a substance expire at the end 
of one year from the date of issuance of the order. However, if 
proceedings to schedule a substance pursuant to 21 U.S.C. 811(a)(1) are 
pending, the temporary scheduling of a substance may be extended for up 
to six months. Under this provision, the temporary scheduling of AMT 
and 5-MeO-DIPT, which would expire on April 3, 2004, may be extended to 
October 3, 2004. This extension is being ordered by the

[[Page 16839]]

DEA Acting Deputy Administrator in a separate action.
    In accordance with 21 U.S.C. 811(b) of the CSA, DEA has gathered 
and reviewed the available information regarding the pharmacology, 
chemistry, trafficking, actual abuse, pattern of abuse, and the 
relative potential for abuse of AMT and 5-MeO-DIPT. The Acting Deputy 
Administrator has submitted these data to the Acting Assistant 
Secretary for Health, Department of Health and Human Services. In 
accordance with 21 U.S.C. 811(b), the Acting Deputy Administrator also 
requested a scientific and medical evaluation and a scheduling 
recommendation for AMT and 5-MeO-DIPT from the Acting Assistant 
Secretary for Health. The Food and Drug Administration (FDA) has 
notified the DEA that there are no exemptions or approvals in effect 
under 21 U.S.C. 355 of the Food, Drug and Cosmetic Act for AMT and 5-
MeO-DIPT. A search of the scientific and medical literature revealed no 
indications of current medical use of AMT and 5-MeO-DIPT in the United 
States.

Explanation of Alpha-methyltryptamine and 5-methoxy-N, N-
diisopropyltryptamine

    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.

Control of AMT and 5-MeO-DIPT

    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), 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

[[Page 16840]]

evidence of attempted clandestine production of AMT and 5-MeO-DIPT in 
Nevada, Virginia, and Washington, DC.
    According to the data from System to Retrieve Information on Drug 
Evidence (STRIDE), Federal law enforcement authorities seized 31 drug 
exhibits and filed 13 cases pertaining to the trafficking, distribution 
and abuse of AMT during 1999 to 2003. The corresponding STRIDE data for 
5-MeO-DIPT included 59 drug exhibits pertaining to 28 cases. AMT drug 
seizures included 21 capsules and 1,006 grams of powder, while 5-MeO-
DIPT drug seizures included 11,373 tablets, 560 capsules, and 6,531.6 
grams of powder. From 2001 to 2003, 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. In addition, there have been several 
local cases involving trafficking and abuse of AMT and 5-MeO-DIPT.
    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 Acting Deputy Administrator, based on the information gathered 
and reviewed by her staff and after consideration of the factors in 21 
U.S.C. 811(c), believes 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 specific findings required pursuant to 21 U.S.C. 
811 and 812 for a substance to be placed into Schedule I are as 
follows:
    (1) The drug or other substance has a high potential for abuse.
    (2) The drug or other substance has no currently accepted medical 
use in treatment in the United States.
    (3) There is a lack of accepted safety for use of the drug or other 
substance under medical supervision.
    Before issuing a final rule in this matter, the DEA Acting Deputy 
Administrator will take into consideration the scientific and medical 
evaluation and scheduling recommendation of the Department of Health 
and Human Services in accordance with 21 U.S.C. 811(b). The Acting 
Deputy Administrator will also consider relevant comments from other 
concerned parties.
    Interested persons are invited to submit their comments, 
objections, or requests for a hearing in writing, with regard to this 
proposal. Requests for a hearing should state with particularity the 
issues concerning which the person desires to be heard. All 
correspondence regarding this matter should be sent to the Drug 
Enforcement Administration according to the instructions found in the 
Addresses section of this proposed rule. In the event that comments, 
objections or requests for a hearing raise one or more questions that 
the Acting Deputy Administrator finds warrants a hearing, the Acting 
Deputy Administrator shall publish a hearing notice in the Federal 
Register summarizing the issues to be heard and setting the time for 
the hearing.

Regulatory Certifications

Regulatory Flexibility Act

    The Acting Deputy Administrator hereby certifies that this proposed 
rule 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. This proposed rule, 
if promulgated, would permanently place AMT and 5-MeO-DIPT into 
Schedule I of the Controlled Substances Act.

Executive Order 12866

    This proposed rule is not a significant regulatory action for the 
purposes of Executive Order (E.O.) 12866 of September 30, 1993. Drug 
scheduling matters are not subject to review by the Office of 
Management and Budget (OMB) pursuant to provisions of E.O. 12866, Sec.  
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 Federalism

    This proposed rulemaking will 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 proposed rulemaking 
will not have sufficient federalism implications to warrant the 
preparation of a federalism assessment.

Unfunded Mandates Reform Act

    This proposed rulemaking will not result in the expenditure by 
State, local and tribal governments, in the aggregate, or by the 
private sector, of $100,000,000 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 proposed rulemaking is not a major rule as defined by Sec.  
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.

[[Page 16841]]

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 Acting Deputy Administrator proposes to amend 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: March 25, 2004.
Michele M. Leonhart,
Acting Deputy Administrator.
[FR Doc. 04-7218 Filed 3-30-04; 8:45 am]

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