On August 4, 2006, the DEA published a Federal Register entry requesting information about the commercial, academic, and research uses for 53 named tryptamines, as well as a more general request for information about similar chemicals. On October 20, they published a parallel entry asking about a list of 165 phenethylamines.

The Federal Register entries indicate that these chemicals are not already scheduled. The information requests make direct reference to existing Schedule I substances and state that "some of these substances can be treated as controlled substance analogues if intended for human consumption". Although they do not directly identify their purpose, these requests seem to represent information gathering in preparation for adding some or all of these substances to Schedule I.

The Controlled Substances Act (CSA) gives the DEA the authority, as delegated by the Attorney General, to schedule a new drug after the Secretary of Health and Human Services (HHS) implements an eight-factor "scientific and medical evaluation" and recommends scheduling. The law requires the DEA and HHS to make an individualized determination for each substance, including such things as "actual or relative potential for abuse", "history and current pattern of abuse", "scope, duration, and significance of abuse", and "risk…to the public health". There has only been one instance where the DEA emergency scheduled a drug which then failed to be permanently added to Schedule I. In 2004, HHS rejected the inclusion of TFMPP in Schedule I after the FDA found there was little evidence of actual abuse.

The DEA's information requests, essentially, ask whether there are any commercial, academic, or research uses for any of the chemicals listed in the Shulgins' TIHKAL and PIHKAL.

Of the 53 tryptamines the DEA lists, 47 are described in TIHKAL, four are simple acetyl variants of TIHKAL chemicals, and the remaining two are allyl variants. Of the eleven TIHKAL chemicals that are not listed, seven are already scheduled, one is tryptamine itself, another is the widely-sold hormone melatonin, and the final two are harmine and harmaline.

Further evidence that the tryptamine list is simply copied from TIHKAL is that it includes what Alexander Shulgin calls 4-HO-DMT and the DEA calls "N,N-dimethyl-4-hydroxytryptamine", more commonly known as psilocin. This chemical has been explicitly listed in Schedule I since 1970, when the CSA was first passed. It seems that the DEA editors did not realize that this chemical is the already-scheduled psilocin. The DEA's phenethylamine list includes 165 chemicals. Although we did not examine the chemicals in this list exhaustively, it appears that all or nearly all are included among the 179 phenethylamines described in PIHKAL (14 of which are already scheduled).

Normally, to add new substances to Schedule I, the DEA must follow the statutory process described above. However, in May of this year, the DEA published a proposed redefinition of the technical term "positional isomer". If this new definition becomes the approved legal definition, it would add dozens of previously unlisted chemicals to Schedule I without having to go through the normal process.

Proposed Definition of Positional Isomer

...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).

The "hallucinogenic substances" subsection of Schedule I states that "optical, position, and geometric isomers" of listed chemicals are automatically considered to be Schedule I. The existing CSA provides no definition or explanation of "position isomer", but it has generally been assumed that it includes only ring-substitutional changes, such as moving a group or chain from the 4-position to the 5-position on the ring. Most chemists we spoke with assumed that, under the new definition, MIPT would qualify as a positional isomer of DET, for example. But we did not get a consensus on this issue, and other molecular comparisons would be even less clear.

The new definition would represent a change in the DEA's understanding of the term "positional isomer", since up to now they have treated PIHKAL and TIHKAL chemicals as controlled substance analogues and not as Schedule I isomers. The DEA states that the tryptamines and phenethylamines they list in their information request "are not subject to direct control in Schedule I". This strongly suggest that experts, even those who write and edit the DEA's technical Federal Register entries, would not consider those chemicals "positional isomers" of a Schedule I substance without a change in definition.

Because some labs must get DEA approval for each individual Schedule I substance they work with, this rule would significantly increase the burden on chemists who work with materials structurally similar to a scheduled chemical. Instead of just needing to track the list of controlled substances, they would need to determine if any of the intermediate or final chemicals they plan to work with would meet this definition and would then presumably need to apply for a license for each "positional isomer" they might encounter in their work.

In the November 2006 issue of Erowid Extracts, we published a short description of the Drug Enforcement Administration's proposed redefinition of "positional isomer". In that article, we stated that, "If this new definition becomes the approved legal definition, it would add dozens of previously unlisted chemicals to Schedule I without [the DEA] having to go through the normal process."

After reading this article, Alexander Shulgin commented that he believes the change would actually result in thousands of new scheduled chemicals, most of which have never before been synthesized.

This serves as a good reminder that the proposed definition would completely bypass the Schedule I requirements that a substance have "a high potential for abuse" and "no medical use", since we can't know whether those definitions apply to substances that have never been made.