“Intractable Byproduct” in 5-MeO-DMT Samples

Erowid’s DrugsData project recently tested two samples of 5-MeO-DMT that both contained an unidentified chemical. The first was dd10559, published Jun 08, 2021 and the second was dd10808, published July 19, 2021. Both samples were sold as 5-MeO-DMT and were reportedly sourced from the Netherlands to California. The unidentified chemical in the two samples appeared to be the same substance.

In June, one of our EEN experts (Eddee) proposed a possible identification for the chemical in the first sample, and we began consulting others in our network. Once we received the second sample, with apparently the same unidentified chemical, an outside expert weighed in with a slightly different proposed identification. We examined these more closely and with Eddee’s help, we think we’ve finalized our current opinion on the identity of the chemical dd10559-unid1 and dd10808-unid1:

6-methoxy-2-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

This chemical is likely an unwanted byproduct resulting from imperfect synthesis of 5-MeO-DMT. Borax, one of Erowid’s main chemistry experts, proposed the name “N-methyl-Pinoline”, and Eddee proposed “N-methyl-5-Methoxytryptoline”.

Another expert pointed out that PubChem’s synonym list for this chemical includes 2-Methyl-6-methoxy-1,2,3,4-tetrahydro-beta-carboline (CAS# 6582-80-5), and cites the Japan Chemical Substance Dictionary for the CAS#. Isomer Design, a longtime supporter of the DrugsData project, refers to it as 6-MeO-2-Me-THβC.

We do not believe it has any common trivial name, and are currently settling on the name “N-methyl-Pinoline”. Its structure:

There were no published GC/MS graphs for this chemical. The identification is based on analysis of the fragmentation pattern, and on a 2020 paper, Synthesis and Characterization of 5‑MeO-DMT Succinate for Clinical Use, by Sherwood et al. Because of this paper, we originally considered calling this chemical “5-MeO-DMT Synthesis Byproduct A”, to parallel names given to unwanted synthesis products in other drugs.

The other proposed identification was the very similar compound 2,3,4,5-Tetrahydro-8-methoxy-2-methyl-1H-pyrido[4,3-b]indole (CAS# 41505-84-4).

The two proposed identified chemical structures have the same number of elements and chemical formula: C13 H16 N2 O ( C13H16N2O ). The only difference is which order the carbons are coming off the indole ring relative to the amine nitrogen.

This very technical image shows a comparison of the two chemicals, with our proposed ID in the upper panel and CAS 41505-84-4 in the bottom:

Now look again at the drawing of our identification and note the red line showing the bond between the indole ring and the methyl (carbon) coming off the nitrogen.

Finally, take a look at the structure of 5-MeO-DMT:

Imagine that the red line in the structure of N-methyl-Pinoline was broken where it connects to main rings. That substance, with that connection free, is 5-MeO-DMT. 5-MeO-DMT just happens to also have the same chemical formula: C13H18N2O.

Quoting from the Sherwood et al. 2020 paper: “Several small-scale attempts were initially evaluated with reaction monitoring by liquid chromatography-mass spectrometry (LCMS). Though product formation was evident, the reaction was plagued by challenges that would likely multiply at larger scales. The Pictet−Spengler reaction to the corresponding tryptoline (8) was difficult to suppress and removal of this structurally similar and possibly biologically active byproduct was challenging. Further optimization to Route 1 may be possible, but ultimately, the reaction was not recommended for further development.”

Their Scheme 1 Graphic shows what they label the “intractable byproduct”, which is the chemical we are proposing as the identification of the impurity in these two 5-MeO-DMT samples.

Thanks to everyone who participated in this: the submitter of the samples, Eddee, our anonymous experts, Borax, Sylvia, and the authors Sherwood AM, Claveau R, Lancelotta R, Kaylo KW, and Lenoch K for their excellent 2020 paper, which nailed down the reason for this unwanted contaminant in these synthetic 5-MeO-DMT samples.

Name Change from Levamisole to Tetramisole/Levamisole

Erowid’s DrugsData lab has recently changed from reporting simply “levamisole” to instead reporting “tetramisole/levamisole”. Tetramisole is the “real” primary name for this substance, a chemical that has two stereoisomers/enantiomers. For those unfamiliar, left (“lev”) and right (“dex”) isomers are only different in the same way that left- and right-handed gloves are different. They are also referred to as the “S-enantiomer” (lev) and the “R-enantiomer” (dex) of tetramisole. (Tetramisole refers to the “racemic” or mix of the S-enantiomer and R-enantiomer of the chemical.)

Many (though certainly not all) chemicals have this type of physical isomerism. An update in 2020 to the SWGDrug library that our lab uses as one of its sources changed the way it reports the name of the substance upon match. Neither the chief chemist at our lab nor any of our team remembers ever seeing the name “tetramisole” before December 2020. The technical distinction and update merits some further explanation.

The technical language can be pretty confusing. In some cases, the FDA allows commercial pharmaceuticals to use a shorthand, where they prepend “es” or “ar” (or “lev” and “dex”) to the front of a pharmaceutical name to denote an enantiomer-specific product. Examples include “armodafinil”, “eszopiclone”, and “escitalopram”.

Erowid’s DrugsData lab, using GC/MS testing, has no ability to isolate, separate, or identify which enantiomer is present, yet we’ve previously reported “levamisole” (the left or S-enantiomer) since first identifying this substance in cocaine samples in 2009 (see DrugsData Levamisole Results). Our lab’s techniques can’t distinguish the stereoisomer composition of any substance we analyze, e.g. a specific chemical identified in a single sample could be a 50/50 mix of R-enantiomer & S-enantiomer; 100% R-enantiomer and 0% S-enantiomer; 0% R-enantiomer and 100% S-enantiomer; or any ratio combination of the different physical isomers. This would be true for any lab using GC/MS for its testing process.

While DrugsData has been reporting “levamisole” since 2009, the question of enantiomers had not come up before. However, the “lev-” syllable should have been a giveaway. Sorry we didn’t identify this issue earlier!
In the last few years, research appears to indicate that most of the “levamisole” mixed with cocaine is actually the racemic tetramisole. In 2019, Madry et al. seemed to nail this issue down through analysis of hair samples from 627 cocaine users. The authors write: “Samples mainly contained racemic tetramisole (87.5%), only one sample contained levamisole only and two samples contained non-racemic [tetramisole].”

All of that, combined with our inability to test which spatial isomer we have in the samples we analyze, means that we’re going to switch to using “tetramisole” as the primary name for this substance, with “levamisole” being included so as to help avoid confusion due to the switch.

Reference:
Madry MM, Kraemer T, Baumgartner MR. “Cocaine adulteration with the anthelminthic tetramisole (levamisole/dexamisole): Long-term monitoring of its intake by chiral LC-MS/MS analysis of cocaine-positive hair samples”. Drug Test Anal. 2019 Mar;11(3):472-478. doi: 10.1002/dta.2505. Epub 2018 Oct 17. PMID: 30239147. Erowid Ref9448

You’ve Won! Or have you? Is RaffleWinner#33 Performance Art, Prank, or Fraud?

There’s a puzzling fraud that’s been going on using the Erowid name. Beginning in 2018 and continuing through 2020, several people have emailed Erowid trying to claim a prize they ‘won’ through an alleged Erowid raffle ticket. Yet Erowid hasn’t participated in nor offered a raffle of any sort in more than a decade. These raffle tickets were not issued by Erowid Center and there is no prize to be claimed.


Inside of the fake Erowid raffle ticket card.

So far, we have limited details. What we know…

  • The so-called ‘tickets’ appear to be a collage based on a photocopy of an old (actual) Erowid raffle from the Mind States 2008 conference with the addition of a 2009-era Erowid logo.
  • A couple of people have specified that they received it by (snail)mail. One person said it was left “in a card at their door”. (eek!)
  • In at least one case it was pasted inside a greeting card style card with a cover that had “gefeliciteerd” (Dutch for ‘congratulations’) on it.
Cover of one of the fake Erowid
winning raffle tickets.
  • The cards bear a ‘WinnersCode’, referred to as ‘RaffleWinner#33’.
  • One person claims they won “because of a donation”, and the card itself says “thank you for your generous donation to Erowid”

    • These tickets are not related in any way to bona fide donations made to Erowid Center. It has been suggested that it might be a research chemical vendor that is sending them out with purchases, but we haven’t been able to verify that (or which vendor). Erowid definitely isn’t involved in whatever transactions happened prior to the arrival of these cards.

    We’d love any help in tracking down what’s going on so we can try to reduce confusion!

    Comments:

    Swan Nov 2, 2020: I don’t know if you already know this info, but NamasteLSD is sending these with whatever you buy from him, im sure its just a prank.

    RobbyRob : Nov 13, 2020 : Hi Guys, maybe it is a bit late or not interessing anymore, but i got one of you “Winner tickets” also and i can verify that (at least partially) a vendor is using them. Best Greetings

    Evolving the Approach to Reagents and LSD Gel Tabs

    Drug checking is a complex and evolving area of research. In EcstasyData’s effort to show accurate findings to the public, we’re working with the unique conditions of each sample. Most recently, the lab has innovated in its handling of LSD gel tabs.

    There’s LSD, and then there’s gel tab LSD

    Since 2014, the year EcstasyData’s lab developed its procedure for a practical and time-efficient way to identify LSD using GC/MS, gel tabs have been infrequently submitted for analysis. The majority of LSD samples submitted to our lab use blotter paper as the carrier (the lab requires that all samples be dry, no liquid samples are accepted without prior arrangement), though it is Erowid Center’s opinion that most of the LSD currently in distribution is in liquid/solution form.

    Prior to 2017, the rare gel tab sample would get refused by the lab’s main chemist, who at the time did not feel confident that these samples could be adequately analyzed for the presence of LSD.

    Besides analyzing each sample using GC/MS, which is the analytical method EcstasyData uses to detect the presence of chemicals, the lab also tests samples with reagents. Reagent testing adds descriptive data that adds to the collective knowledge base for drug checking. (Reagent testing can’t positively identify chemicals.)

    It turns out that gelatin as a medium makes reagent testing more complicated; the pH conditions required to dissolve the gel affect the reagent even when dried. For this reason, gel tabs do not react normally to field reagents such as Marquis or Ehrlich.

    De-weirding reagent colors

    Between 2017 and November 2018, five gel tab samples were analyzed by EcstasyData, with GC/MS showing that four of them were LSD. The Ehrlich reagent reactions for these four samples were atypical. LSD normally reacts to Ehrlich reagent by turning purple, but when Ehrlich was applied directly to the dry (or even wet) gelatin in these cases, the results were mixed, turning brown or brown-purple, or other atypical reactions.

    The lab began working with the special needs of these samples, and in November 2018, they developed a sample-preparation procedure that allows Ehrlich reagent to show a typical positive (rule-in) response to LSD in gel tabs.

    New process for gelatin

    We are publishing Erowid Center / DDL’s new procedure that is being used to process dry-gelatin-tab dose units, for the historical record, and so that others can duplicate it and critique it.

    The following is the procedure that was used to produce the photo shown for Sample 6813, the first sample treated in this way:

    1. Gel medium placed in small amount of water.
    2. Basify gel-water mixture with NaOH.
    3. Gel medium fully dissolves.
    4. Solvent (ethyl acetate) added to gel-water mixture.
    5. Solvent separated off and dropped onto ceramic well plate.
    6. Unheated evaporation of solvent until dry.
    7. Drop field reagents into wells, photograph.

    This is the process that the lab will use to prep future gel tab samples for reagents. It will be interesting to see how other samples respond to it, and whether further tinkering with the process will be required.

    Shulgin Archiving: Absurd Item: Kids Shooting Peanut Butter (1969)

    An absurd news piece that Sasha collected and studiously filed in the wall of filing cabinets behind his desk. Scanned and pointed out as ludicrous by Trout:

    Kids Shooting Peanut Butter News Headline

    Authored by the Associated Press and published in the San Francisco Chronicle in 1969, the “Kids Shooting Peanut Butter” article claims that IV use of peanut butter and mayonnaise is a new trend. It reports that there are “several documented cases” of deaths, though no documentation is provided.

    Similar articles were published in other newspapers and the story has been repeated for decades in books and online. Although we were able to find the transcribed text of this article on various websites, we did not find any scans or other direct documentation of the fact that something this stupidly wrong was published as factual news by major publications. Amusingly, the meme is repeated in Richard Nixon’s public papers in October 1969: “In certain regions, they [kids] are so crazy and insane as to inject into their bloodstream peanut butter, because somebody said that peanut butter gives you a high, and they die from that. Mayonnaise they are inserting into their bodies”. [Public Papers of the Presidents of the United States: Richard M. Nixon, 1969, pg 851.]

    The short AP article makes several errors indicating that the authors and editors had little or no expertise in the area they wrote about. It cites the information to Ernest A. Carabillo Jr. from the Federal Bureau of Narcotics. Unfortunately, it is not uncommon for members of law enforcement agencies to be as confused as the news people who repeat the errors they make. Or perhaps the unnamed reporter misunderstood Mr. Carabillo. Who knows!

    We’ve been unable to find any scientific papers or real documentation that this was a trend, or led to any deaths, or was in fact ever tried by anyone. There are zero references in PubMed about this topic between 1960 and 1975. One guess as to the source of this rumor is that “peanut butter” and “mayonnaise” might have been used as slang terms for other drugs. We speculate that ‘peanut butter’ might have been used as slang somewhere to mean tar-type heroin. An Erowid team member says he personally heard “peanut butter” being used to refer to brown colored methamphetamine in the early 1980s. Some drug slang dictionaries list “mayo” as a slang term for heroin or cocaine. An Erowid

    The story is a good example of false and essentially baseless Drug War hysteria. Sadly, this type of egregious error continues to plague drug news, for example the well-loved Face-Eating Zombie Drug meme from 2012-2018.

    Shulgin Geek Note: The news article was clipped, then taped to paper either by Sasha or Nina to make it more stable when filing. In the upper corner of the paper, “Newspaper – drugs” is written in long-hand pen in Sasha’s handwriting.

    Kids Shooting Peanut Butter

    A Federal drug expert says youngsters in some parts of the country have taken to injecting peanut butter and mayonnaise into their veins as a substitute for narcotics.

    In several documented cases the result has been death, Ernest A. Carabillo Jr., a lawyer-pharmacist in the Federal Bureau of Narcotics, told newsmen Monday.

    Carabillo said the information that peanut butter and mayonnaise would send users “on a little trip” was contained in an underground recipe book purporting to outline “culinary escapes from reality.”

    Other recent fads, he said, include the use of paragoric (sic) cleaning fluid, the local anesthetic ethyl chloride and freon, the pressurized propellant gas in aerosols.

    Carabillo said users of narcotic substances confused the bizarre and toxic reactions with the so-called “high” provided by such drugs as heroin or marijuana. He cited the smoking of dried banana skins, a fad of a couple of years ago, as an example.

    Frank Gulich, a narcotics bureau official stationed in Chicago, said the underground “cook books” usually sell for about $1 and often give the formulas for preparing drugs such as LSD.

    Drug users, Gulich said, are “always looking for new drugs that won’t be a violation of the law.”

    [Associated Press]

    Revision History:
    1.0 Published Sep 28, 2018
    1.1 Added note that Erowid staff member personally knew people who used term ‘peanut butter’ to refer to brown methamphetamine: He wrote “I’ve never heard heroin called peanut butter but it has been fairly commonly used as slang for crude impure meth that has not yet been recrystallized — or at least I’ve heard that name being used by tweakers since sometime in the early 1980s. Even the people who commented on using it believed it was bad to be using. Go figure.”

    Shulgin Archiving: 1967 Nature Editors Confused and Fearful on LSD Synthesis

    Background: In late 2017, Erowid Center again began sponsoring the Shulgin Archiving project. We’ve made a lot of progress in the last twelve months. Keeper Trout has been doing most of the scanning and indexing work. The materials in the archive are primarily focused on research and data collection about the chemistry, pharmacology, and use of psychoactive plants and chemicals.

    But Sasha had a penchant for collecting absurd, silly, disturbing, and bizarre published materials, including Drug War nonsense, weird drug-related advertisements, and other oddities.

    One such item that was recently uncovered is an editorial from the October 21, 1967 issue of the highly-respected peer-reviewed “scientific” journal, Nature. The editorial is titled “Hallucinations to Order”.



    The unnamed author, which implicitly makes this authored by the editorial staff of the journal, is responding to an article published a few months earlier, “Some New Behaviour-disrupting Amphetamines and their Significance” by Smythies et al, which explores the topic of substituted amphetamines and their relative hallucinogenic potential.

    The editorial opens with a frightened, inaccurate, anachronistic, and telling rant:

    One of the most alarming features of the drug LSD is that it can be made in the laboratory. In other words, there is no natural physical limitation of the scale on which, in suitably bizarre circumstances, it could be supplied to the public. It follows that those who are concerned to see that the use of drugs is controlled by legislation are at least a little nonplussed by the appearance of synthetic processes for manufacturing drugs which were originally derived from natural sources and, more especially, by the application of synthetic processes to the design of new drugs. Although it will be a long time before the flower children and their like would be able to synthesize their own psychomimetic agents, it is entirely proper that there should now be considerable anxiety about problems of control.

    This bizarre little hysterical opinion piece includes the strange gem: “Although it will be a long time before the flower children and their like would be able to synthesize their own psychomimetic agents […]”. As of the date of publication of this issue of Nature (October 1967), the so-called “flower children” were not only “synthesizing their own psychotomimetic agents”, but were doing so at a scale and efficiency that could be described as “awe-inspiring”.

    By October 1967, Nick Sand, Tim Scully, Owsley Stanley, and others had already set up, broken down, and moved their high-volume LSD production labs several times. This is documented not only in biographies and books, but also in contemporaneous testimony from law enforcement agents in criminal investigations and prosecutions. The complex issues related to the potency of LSD and its control were not only widely discussed, but were part of the reasoning for criminalizing these “dangerous drugs” in 1967.

    It is worth pointing out that the journal Nature was at the time (and for many years after) a key part of the machinery generating anti-drug hysteria and “scientific” public fears, such as the completely false claim that LSD caused chromosome damage.

    As the Shulgin Archiving project continues to progress, we will be providing access to an indexed collection, but will also point out individual curiosities with commentary. We hope that reminding people of the absurd history of the Drug War and the persistent presence of confused stories supporting it and presented as “scientific” or “news” might help society limit its repetition of the worst type of errors.

    Milestone: Most Experience Reports Ever Published In a Year

    We’re excited to announce that as of Saturday, September 9, the Erowid crew has reached a new high for the number of experience reports published in a single calendar year. We’ve not seen such an active year of reviewing since 2007, when by year’s end, 4,461 reports had been published.

    As of September 26, with three months left in 2018, we’ve published 4,671 reports, exceeding the decade-old record.

    Late last year in November, as we began working on issue #30 of Erowid Extracts, focused on the Experience Vaults, we realized that it might be possible to beat 2007’s record number if we set the goal early. Crew members Spoon and SellieG together took on this herculean task and immediately started ramping up their reviewing of triaged submissions, publishing hundreds of reports in the final two months of 2017.

    But to beat 2007, they and other reviewers would need to shoot for publishing 400 reports per month in 2018. And they did it, publishing 519 reports each month for the first nine months of 2018!

    Erowid Extracts #30 goes into retrospective detail about the type of information that is found in experience reports, the perspectives of volunteers (in their own words), and reflections on how the collection has developed since its inception.

    Erowid relies on the help of dedicated volunteers to read, filter, flag, grade, categorize, and edit submitted reports. It takes around ten hours to go through the training program and then a few hours a week to be a part of the team. If you’re interested in joining the Erowid Crew, please apply at https://erowid.org/volunteer. We’d love your help!

    The newest issue of Erowid Extracts, dedicated to information about experience reports and our process of editing and reviewing, is available to current members. Erowid Center is a non-profit run solely on donations of members and supporters. Though much of the work publishing experience reports is done by volunteers, it requires staff and technology to keep the project growing and improving. The full-issue PDF and individual articles will be released publicly in the next six to nine months. (All back issues are available at erowid.org/newsletter.)

    Sturgill Simpson’s Turtles All the Way Down Appreciation

    Fuck yeah, I should be able to do these lyrics by memory. Maybe a friend learns to play the song on a guitar so we can sing it. I would have to do a light rewrite of the first stanza, since I have not, myself, seen what I would say fits my understanding of liturgical, mythological, and historical “Jesus” play with flames. But, I do hear tell. Y’all are loved.

    If you try the song and don’t like it immediately, give it another minute or two, actually listen to it and you might be impressed where it goes.

    https://www.youtube.com/watch?v=LWx6csgGkg4

    I’ve seen Jesus play with flames
    In a lake of fire that I was standing in
    Met the devil in Seattle
    And spent 9 months inside the lions den
    Met Buddha yet another time
    And he showed me a glowing light within
    But I swear that God is there
    Every time I glare in the eyes of my best friend

    Says my son, “It’s all been done
    And someday you’re gonna wake up old and gray
    So go and try to have some fun
    Showing warmth to everyone
    You meet and greet and cheat along the way”

    There’s a gateway in our minds
    That leads somewhere out there, far beyond this plane
    Where reptile aliens made of light
    Cut you open and pull out all your pain
    Tell me how you make illegal
    Something that we all make in our brain
    Some say you might go crazy
    But then again it might make you go sane

    Every time I take a look
    Inside that old and fabled book
    I’m blinded and reminded of
    The pain caused by some old man in the sky
    Marijuana, LSD
    Psilocybin, and DMT
    They all changed the way I see
    But love’s the only thing that ever saved my life

    So don’t waste your mind on nursery rhymes
    Or fairy tales of blood and wine
    It’s turtles all the way down the line
    So to each their own ’til we go home
    To other realms our souls must roam
    To and through the myth that we all call space and time

    Highest Number of Current Members Ever

    We’re still 7 hours away from the end of this donation drive and the close of March 10 2018 at the International Date Line (GMT-12). Fire is still working on merging in the 386 donation records from all the various payment methods in the last three days.

    But, as of March 9th, we are now at the highest number of “current members” we’ve ever had, around 1750.

    The definitions are pretty complicated, since some donors do not like to be called members and other people move and it takes a while to figure out if they are the same person.

    About 3000 individuals have donated each year over the last few years, but only around half donate $30 or more as “members”.

    It’s a fabulous service to the world by these 3,000 people.

    PS: Fire wants me to make sure to say that these numbers are approximate :]