Shulgin Archiving: What’s the Metadata?

— By The Erowid Crew

We have made tons of progress on the Shulgin Archiving project.

We are very close to being done with the digitizing process. Practically speaking, all paper documents have been scanned: over 250,000 unique documents. The final count will be complete once we finish “the Metadata Process”, since some of the scan PDFs contain multiple documents and there will be some duplicates to remove.

The Metadata Process involves indexing and categorizing all the documents. The first pass requires trusted members of the Erowid Crew to review each scanned file and record the document type, date, author, title, keywords, and a brief description. But the most important part of this first pass is reviewing each document for privacy concerns.

The Shulgin Archive includes a complex mix of document types, including private communications that describe illegal activity, medical records, checking account ledgers, and receipts. Many items have no privacy concerns, some will require redaction before sharing, others need to be embargoed for a period of time, and some should never be part of any archive. As of September 2023, the Erowid Crew has created first-pass metadata entries for 50,000 PDFs.

As of September 2023, the Erowid Crew has created first-pass metadata entries for 50,000 PDFs.

One of the last sets of materials left to be digitized is the Shulgins’ collection of approximately 40,000 photographs. This has been held up due to the the cost of professional scanning, but we’re hoping our 2023 September Drive will raise enough financial support that we can begin high-resolution photo scanning in October or November 2023. In the meantime, the photos are being stored in a temperature-controlled, secure location. For more about the Shulgin Archiving Project and its funding needs see our September 2023 Update PDF

Despite not yet being able to share the full collection publicly, we’ve picked out a few documents to spotlight. The first example is an untitled page of writing by Alexander Shulgin, circa 2007. It was scanned out of Sasha’s office’s main filing cabinets, from Cabinet 6, Drawer 2, in a hanging folder labeled “Papers in Press / Being Written / Thought About”: Untitled “Many, many years ago… “

There are lots of interesting pieces. A draft Sasha wrote in December 2001, obviously intended for what Ann & Sasha called “Book Three”— meaning the third book in their PiHKAL, TiHKAL, and ?iHKAL trilogy—muses about mortality and death, with some highly personal elements, a signature feature of their P/TiHKAL writing style. It contains some beautifully relevant thoughts on what will happen to Sasha’s “strange collection” of stuff: “Mortality” (draft 2001-Dec-28) .

The third example is a gem that we can thank Keeper Trout and Tania Manning for finding. Rather than organizing all of his correspondence in his filing cabinets or in his various “basements”, Sasha saved some written communications tucked in the pages of books they were related to. After realizing this, Trout conducted an exhaustive search through the pages of all the books shelved in Sasha’s office. A letter from Richard Evans Schultes was found in a copy of Schultes’s Where the Gods Reign: Plants and Peoples of the Colombian Amazon (1988). The content is curious, not super important, but a hidden treasure nonetheless: Letter from R.E. Schultes to A.T. Shulgin (1991-Nov-13) .

We are looking for more people to help with the Shulgin Archive, though we promised Ann & Sasha personally and contractually that the first-pass privacy review would only be conducted by people with whom we have an established relationship of trust or who were close to the Shulgins. We will soon be looking for people to help with the second pass of the Metadata Process. Let us know if you’re interested in helping get the collection in shape for public display.

And please consider contributing to Erowid’s 2023 September Drive so that we can get the photos scanned!

What is Ketamine Precursor A?

It’s been noticeable that most (nine out of ten) ketamine samples analyzed by DrugsData since March 2019 have contained 1-[(2-Chlorophenyl)(methylimino)methyl]cyclopentanol (CAS #6740-87-0), or “Ketamine Precursor A”. Synonyms of this substance in the literature include “Ketamine Related Compound A” and “Ketamine Impurity A”.

Since 2019, only 37 ketamine samples have been analyzed by DrugsData that contain only ketamine (zero in 2022). An additional 297 sample contained Ketamine + Ketamine Precursor A, and 19% of these 297 samples also contained MSM.

Ketamine Precursor A has been notably present in black market ketamine, but should not be present in commercial, pharmaceutical ketamine inside the United States or Europe.

Ketamine Precursor A is not considered harmful, just a waste of mass and chemical. We do not know of any good research on its toxicity, but unfortunately, most drug research that shows “no effect” doesn’t get published. If it were super toxic, we’d probably know about it.

A subreddit has covered this topic: https://www.reddit.com/r/AskDrugNerds/comments/e6iz5r/any_info_on_ketamine_impurity_a_and_whether_or/

We don’t know anyone who has tried it on its own, but it’s unlikely to be active within 10x the dose of ketamine. Just a boring contaminant.

If you have any insights to contribute about Ketamine Precursor A, please let us know, info(at)drugsdata(dot)org.

Shulgin Archiving: A Requiem For Marty

The Erowid Crew has been making a lot of progress on the Shulgin Collection archiving project. There is still scanning and digitizing happening, but the majority of Erowid person time right now is on the preliminary “metadata” step, where each item is quickly looked at and assigned a document type, name, date, and evaluated for privacy/redaction. More about this soon.

While metadataing, Trout came across a series of news clippings Sasha saved in 1974. Trout felt compelled to write the following requiem. It’s interesting both for the weird story told in the “news” series, to show Sasha’s meticulous collection of articles about psychoactives he found interesting, and to document the way the San Francisco Chronicle and Los Angeles Times covered it. Enjoy :]

A Requiem for Marty
by Keeper Trout, August 2022

Marty never had a chance. He had the might of the San Jose police department out to get him. Ideally alive but it was not required. They had tried everything. Even going so far as to use sex to lure him into a trap. Nothing had been working to catch the elusive rodent. Few mice can say that they’ve eluded the police for months and have also found themselves discussed in multiple news articles.
Marty’s crime was portrayed as being a drug addict but we never were able to learn Marty’s true relationship to drugs. Calling him Marty the Marijuana Mouse, suggests a preference for cannabis. Clearly he liked weed and had apparently sampled cocaine and PCP. At one point it was suggested that he was going to move on to heroin but we would have heard about it if he had done so.
Eventually Marty was caught. Not with the hare-brained idea of introducing a female mouse variously said to be named “Mata Hairy” or “Mona” but by removing the drugs from the evidence room and baiting a live animal trap with weed seeds.
Once trapped, Marty found his behavior ascribed to his imagined drug-deprived mania. It was said he needed to be placed into a glass box containing nothing at all to prevent him from harming himself by frantically trying to escape. One officer suggested they may need to give him a little cannabis to get him through detox.
For the crimes commonly associated with being a mouse, death is a common punishment. Instead, Marty got life imprisonment, following rehabilitation. His detox and rehab were said to be provided by a local college professor but the details of how that was to be done were not made clear.
He was said to be the “narcotic squad’s mascot”; “Marty M. Mouse”. Their very own imprisoned drug-deprived former drug user, serving a life sentence after being booked for “possession of marijuana, use of narcotics and destruction of evidence”.
A snap-trap somehow sounds kinder.
True story.

San Francisco Chronicle, Thursday, 12 Dec., 1974. Mouse on Hard Stuff.
San Francisco Chronicle, Thursday, 19 Dec., 1974. Cops Desperate — A Turn-On for Junkie Mouse.
San Francisco Chronicle, Tuesday, 24 Dec., 1974. Mouse Caught in the Grass.
Los Angeles Times, Tuesday, 24 Dec., 1974. p. 1: Intensive Hunt Ends With Mouse Going to Seed, p.3: Marty M. Mouse Has Monkey on His Back When Caught.
See also https://www.weirduniverse.net/blog/comments/marty_marijuana_mouse/

DrugsData | Meth and the N-Isopropylbenzylamine “N-Iso” Boogeyman

For over forty years, methamphetamine-using communities have been speculating why some batches of meth seem qualitatively different than others. When we started working in this field in the 1990s, the claim was that l-meth, solvents, and synthesis impurities were the culprits.

Since around 2010, the DEA’s policies have resulted in most methamphetamine inside the United States coming from large manufacturers outside the US. In the ensuing years, some have claimed that the unpleasant effects of street meth in the US are a result of meth containing N-Isopropylbenzylamine (isopropylbenzylamine; N-IPBA; “N-iso”) [PubChem]. It is a common enough claim that many skeptics have called N-iso the new meth boogeyman.

The most common claims about isopropylbenzylamine are that it is present in combination with meth, and causes more paranoia, psychotic ideation, and worse hangovers. It’s also blamed for effects atyptical for stimulants, such as lethargy and “brain fog”, 1-3 days into a meth-using session.

We’ve been asked about N-iso many times between 2019 and 2022. We purchased the certified reference lab standard for isopropylbenzylamine twice in the last two years in order to run experiments to check our methods. We have repeatedly confirmed that zero (0) meth samples analyzed by DrugsData to date have contained it:

https://drugsdata.org/results.php?substance1=94&substance2=2036

Erowid’s DrugsData reported those findings to the people submitting the samples in question, and on the corresponding entries on DrugsData.org. Up until now, we haven’t specifically pointed out publicly that multiple submitters have claimed that isopropylbenzylamine could be present in their methamphetamine and that our findings have not substantiated their claims.

Our results caused others to ask us more and more pointed questions about how sure we were that N-iso wasn’t in the meth we tested. So we dug deeper. After re-analyzing and examining the GC/MS data for more than a dozen samples submitted to DrugsData for which the submitter was certain their meth sample contained isopropylbenzylamine, we’ve still seen no results where this is the case.

Out of 271 samples containing methamphetamine analyzed between January 2019 and July 2022, none contained isopropylbenzylamine:

https://drugsdata.org/results.php?s=methamphetamine&search_field=substance&y1=2019&y2=2022

Re-examining Our Findings

In late 2020, we ran several samples of alleged meth + N-iso and they came back meth only. We bought the reference standard and tried slightly-modified procedures using this standard. It seemed to us that meth + isopropylbenzylamine resolved easily via GC/MS. That is to say, meth and N-iso were easily differentiated in our lab. They are close, but we deal with much harder problems all the time.

In May 2022, D.M. contacted us to point out a paper that said it is possible that mixed samples containing both meth and isopropylbenzylamine could cause analysis to fail to see one or the other. Essentially, they claimed our previous findings might be wrong because one of the two could hide inside the GC curve of the other and then elute (come out) at such a similar time into the Mass Spectrometer that our software would report only one of the two chemicals.

That paper is Luo Y, et al. (2021) “Simultaneous Determination of Methamphetamine and Its Isomer N-Isopropylbenzylamine in Forensic Samples by Using a Modified LC-ESI-MS/MS Method”. (ResearchGate Link) The authors write:

“However, the two compounds [methamphetamine (MA) N-isopropylbenzylamine ([N-IPBA]) ] were hard to be effectively discriminated by GC/MS when there was a large concentration difference between them. Because the retention times for MA and [N-IPBA] chromatographic separation were very close due to their high similar chemical structure, the compound with high concentration would interfere with another one with low concentration as the two compounds yield similar ion fragments for detection [25].”

Note the relevant claim in their paper is actually cited to someone else and is not something these authors themselves demonstrate in their article. The original citation (Xuan J et al 2015) is a paper in a Chinese journal that we’ve been unable to locate.

Given this new, reasonably specific claim from a 2021 paper, despite having done it before, we purchased a new isopropylbenzylamine reference standard, this time from a different chemical supplier. Unsurprisingly, it matched exactly the previous standard and also matched the GC/MS data in the main public/research/commercial/forensic libraries.

A Series of Experiments

We mixed pure d-meth with N-IPBA at 1:1, 1:10, 1:100, 10:1, and 100:1 ratios. In all of the conditions, our setup showed isopropylbenzylamine as clearly distinct from methamphetamine. They would not be mistaken for one another or lost, even way below 1:100. Our standard procedure involves methanol run through an Agilent GC/MS 5973 MSD with the GC column being an HP-5ms Ultra inert (5%-phenyl)-methylpolysiloxane. Unless you’re a lab tech, that won’t mean anything to you, but it’s a fairly normal setup for doing drug work like this and it’s well suited to analyzing chemicals of this type.

GC of N-Iso and Meth (1:100)

The GC output pictured above is from N-IPBA (“N-iso”) (1 part) mixed with meth (100 parts). The other main peak (9.972) is a calibration chemical. The slightly messy baseline to the right of the meth peak is related to the way that the salt versions (Meth HCl, for instance) of the two drugs differ in their elution times in the GC column. This example graph is after several tests in a row using different ratios of meth and isopropylbenzylamine. It is common when running methamphetamine salts to end up with a little right-side, baseline noise after the sharp freebase meth peak.

Methamphetamine and isopropylbenzylamine do elute at similar times, but using our procedure, they are clearly distinct. Note in the GC image the sharp valley between the N-iso and meth peaks: N-iso at 3.4777 minutes and meth at 3.687 minutes in this run.

And they always have clearly distinct Mass Spectra (MS), so they simply don’t get confused at our lab. If a lab were running a different column and procedure that isn’t targeted for doing work on methamphetamine and related drugs, it’s easy to imagine other procedures and rigs where an analytical chemist could confuse one with the other.

As of August 2022, DrugsData’s lab has found isopropylbenzylamine in eight samples total, ever, and two DEA-tested samples are republished in our database:

https://www.drugsdata.org/results.php?search_field=substance&s=Isopropylbenzylamine

It is Erowid’s view that most negative effects from meth use are a result of lack of sleep combined with irregular water and food consumption. People mistakenly attribute differences in experience from time to time to differences in impurities in the drugs, instead of other factors such as diet, mood, context, electrolyte levels, and physical rest.

It’s certainly possible that a sample analyzed in DrugsData’s lab in the future could contain both methamphetamine and isopropylbenzylamine. We feel certain that for such a sample, lab results would clearly show this to be the case.

—earth, Sylvia, Fire, Roi

DrugsData | Identifying the Unidentifieds: Ethyl-Despropionyl-Fentanyl (Ethyl-4-ANPP)

This is a description of how we identified the unidentified substance in a fentanyl sample (#12495) analyzed in March 2022.

The unidentified substance has mass spectrum major ions at 96; 217.1; 174.1 with an elute time at around 10.7 in our main setup.

This small sample of white powder in a blue bindle was submitted to DrugsData via research partners we’re working with to do lab confirmatory testing. Besides Fentanyl and 4-ANPP, it contained a third chemical we were initially unable to identify.

We publish the Mass Spectrum (MS) images for substances we need help identifying. A colleague at UNC’s drug checking project examined this substance’s image and reached out with some clues, which put us on the path of figuring out what its structure is.

One of our top volunteer analytical chemistry experts, Eddee, found a close match in Wiley’s 2020 “Designer Drugs” library, a library that our DrugsData lab doesn’t have. The close (though not perfect) match is for ethyl-despropionyl-fentanyl (ethyl-4-ANPP). Our experts (thanks, Koby!) guess that this is likely to be much less potent than fentanyl and might not be very active, similar to despropionyl-fentanyl (4-ANPP).

There’s a PubChem page for it, but no CAS number yet:

https://pubchem.ncbi.nlm.nih.gov/compound/156346345

Eddee speculated that the difference between our sample and the Wiley library match might not be meaningful. In the following image, which is pretty complex to look at, the top chemical is our DrugsData sample’s unidentified substance. The lower chemical is the Mass Spectrum for the presumptive ethyl-despropionyl-fentanyl. The middle part of this image is a comparison of the two, with our sample on the top (lines going up) and the proposed match on the bottom (lines going down). You’ll need to open it in a new tab to see the detail, it’s dense stuff.

What you’re looking at are the relative heights of the largest peaks (vertical lines), aka the “ions”. Mass spectrometry (MS) relies on breaking up a chemical with a high energy stream of electrons; Erowid’s DrugsData lab uses an “electron spray” method. The resulting bits are highly charged ions that get spun through a magnetic whirlwind inside a specialized detector. The heights of the lines indicate how many of each ion was detected for this chemical using specific equipment and methods. Perfect matches usually require using the exact same equipment at the same settings, but there’s a lot of similarity when using equivalent machines.

Looking at the middle graph, where the two are compared against each other, you can see there’s a short line on our sample at 199 that doesn’t exist in the lower sample. And the relative heights of some of the key ions are different between the two. That doesn’t mean it’s not a match, but it isn’t a perfect match.

So Eddee checked and his lab did have a tiny bit of despropionyl-Fentanyl (aka 4-ANPP) left in their Fentanyl Analog Screening Kit (FAS Kit, sometimes referred to as a Traceable Opioid Material Kit, or TOM Kit).

There wasn’t much left, but he decided to try wet chemistry “derivitization” (a simple synthesis) using iodoethane, and was able to get a tiny amount of product he believes to be ethyl-despropionyl-fentanyl. He then ran that new product through a GC/MS and got the following output.

As above, in this image our unidentified substance is on the top; Eddee’s new ethyl-despropionyl-fentanyl is on the bottom.

Again, if one looks closely, there are some important differences between our sample (in blue on the top of the middle graph) and the newly synthesized chemical. There are several complexities we can’t completely account for. First, Eddee had only a teeny tiny amount of his synthesized chemical and sometimes “very low signal” amounts of a drug can have different Mass Spectrum profiles. Usually this doesn’t make a difference in which ions show up (except at the shortest peaks), but it can cause the relative ratios to be slightly different. Second, Eddee isn’t using the exact same GC/MS brand, model, and components as we have.

We might be able to change our GC coil and run parameters to better match this, but it’s so close, we’re going to consider this matter closed.

If you’re interested, you can check out the unidentified substances detected by DrugsData in 2021-2022 that haven’t been solved yet. This list changes as we make identification breakthroughs, thanks to tips from the Erowid Expert Network and others.

In an amusing postscript, one day after Eddee finalized this identification (Apr 4, 2022), DEA Special Testing and Research Laboratory (SFL1) wrote that they had come to the same identification of the so-called “308-G impurity”.

Supporting Free and Accurate Information in Ukraine

The February 2022 Russian invasion of Ukraine and the Kremlin’s attacks on Ukrainian, Russian, and global information has reminded us at Erowid how fundamental free and accurate information is to our mission.

In late 2012, Putin’s Russian Federation formally created an internet ban list. Erowid was in the first list of sites Russia ordered to be completely blocked by all ISPs and information systems in Russia. It took a year for all the ISPs in Russia to comply with the ban and Erowid.org has not been available inside Russia since.

Erowid Center just donated ~$2,000 USD to a group supporting Ukrainian independent media/news. See GoFundMe: Keep Ukraine’s Media Going
. We chose this relief fund based on recommendations from Timothy Snyder and mentions in media sources such as The Guardian, and others.

Erowid Supports Free & Accurate Press

The text mirrors one of the early Ukrainian responses to the Russian invasion and attempt to decapitate the Ukrainian government (Russian warship, go fuck yourself). We’ve sent out this image via social media to mention our support of the free press in Ukraine.

Erowid Center is planning further financial support of Ukrainian free press and accurate information (as well as harm reduction and drug checking in Russia and the Ukraine, although those seem less possible in this moment). We invite suggestions for other Ukrainian or Russian organizations to support.

The GoFundMe we contributed to was set up by Jakub Parusinski, a senior executive at The Kyiv Independent, and is “aimed at helping media relocate, set-up back offices, and continue their operations from neighboring countries”.

From the GoFundMe: “This campaign is run by a consortium of The Fix, Are We Europe, Jnomics, and Media Development Foundation, as well as multiple media partners from across Europe. We are working with a growing list of Ukrainian media, including Ukrainska Pravda, Zaborona, Detector Media and others. Support is allocated based on urgency of needs in the first place, then distributed proportionally.”

Below is a screenshot from Feb 2013 of a search showing Erowid.org listed among websites censored in Russia.

russian censorship website image

There were hundreds of other domains in the initial banned-domain list, which has grown substantially since then. We don’t have the complete records, but we saw the list more than double over the next few years. We are no longer able to access their full list, which we believe is now mostly secret.

To combat the censorship, we set up a couple of simple proxies inside Russia in 2013 which we maintained until late 2021. It was cheap and easy to rent virtual machines inside the Russian Federation and operate forwarding proxies that allowed non-Erowid domains to serve our content inside Russia uncensored. As each proxy domain got noticed and blocked, we bought another random domain name and seeded Russian search engines.

As a side note, Erowid.org has been blocked in China for even longer, starting sometime in the mid 2000s.

A Noble Slog through the Wonderful World of the Stolaroffs and Shulgins

by Flamingo Jones

Introduction & Overview, by earth

The Erowid Crew had a good pace going in 2018 and 2019 with the archiving of Alexander and Ann Shulgin’s collection of documents, but efforts slowed to a near stop as the global pandemic took hold in early 2020. More than 150,000 documents have been scanned (mostly scanned by K Trout). This number is expected to climb to well over 250,000 before we’re done.

The step we’re working on currently is recording first-pass metadata for scanned documents. It’s a privacy-sensitive process; each PDF is examined and coded for things like document type (published paper, personal letter, chemistry analysis, etc.), author name, date, and title.

Many articles from Sasha’s filing cabinets have previously been published elsewhere need to be tagged so they can be fast-tracked to the next step. While others have privacy issues that make them inappropriate for public view as they are now, either because they need redaction of names or email addresses, or because they contain other types of private information that shouldn’t be published at this time.

Three people currently work on Erowid archiving projects, made possible by the move towards remote work during the pandemic. Flamingo Jones is an Erowid intern whose primary responsibilities have involved the Stolaroff and Shulgin collections. We asked Flamingo to share some thoughts about the archiving process.

Now into my second archiving project at Erowid, I began work on archiving about a year ago (October 2020), starting with writing summary abstracts for documents in the Stolaroff Collection. I’m now creating metadata for the literal barn-full of documents in the Shulgin Collection.

I’ve really enjoyed working with these collections. It has been fascinating to say the least. One of the more interesting things for me is the interconnectedness of the world of psychedelic research: I get to observe the changes as I travel through the decades of records that have been collected.

From the months I spent on the Stolaroff Collection, I felt like I got a sense of the people and communities that Myron and Jean immersed themselves in. In writing abstracts I collected keywords, the names, places, events, and materials used, and wrote a summary for what was in each document that I reviewed. These included letters, stories, reports, articles, and news about the world they lived in. From professional work to business ventures, from otherworldly psychedelic reports and stories to friendships forged, the collection provides an unexpectedly strong sense of the way Myron saw and paid attention to the world around him.

The archiving work has ups and downs; one day it’s tax forms and dull details about the road next to the Stolaroffs’ Lone Pine property, another day, I’m reading a brilliant psychedelic experience report or a meaningful letter. Content varies greatly through the decades, following the focus of what was on the minds of researchers and those who collected and generated these records. The friendship between the Stolaroffs and the Shulgins highlights how the two archiving projects complement each other, each bringing the other more alive than it would be alone.

My work on the Shulgin archiving project so far has been quite different, as I’m covering a different step in the process. I’m creating first-pass metadata, which is much less intimate. I don’t read every article or letter fully, but instead try to quickly identify what each one is, and what level of privacy it requires. I’ve gone through around 10,000 files as of September 2021. The amount of research materials that Sasha collected is truly immense and his work has touched so many: I find myself smiling when I come across an article reprint sent to Sasha, with a note of gratitude from the authors for the work that Sasha has done.

The size of the project (likely over 250K unique documents) is vast, and there are ways that the work can be a slog, but there are some gems and treasures throughout. It is truly a wonder what I will stumble across on any day. Making this work accessible to others and digitizing this library is noble work, and I am happy to be a small part of it.

Tryptamine Turns Purple with Ehrlich Reagent

— by: earth, Sylvia, Fire, Jurek, and anonymous experts

Here’s a peek into how Erowid works with a network of drug-checking experts around the world work. Just another day at DrugsData. :]

On June 30, we published the test results for a sample of 1P-LSD blotter (dd10683), confirming the presence of 1P-LSD.

On July 12, Jurek from protestkit.eu, a Polish harm reduction and field reagent specialist, inquired about this sample, noting that the Ehrlich reagent photo showed an unexpected purple reaction. Jurek pointed out that 1P-LSD isn’t known to result in a purple color in the presence of Ehrlich reagent, helping to differentiate it from LSD-25, which does cause a purple color change with Ehrlich reagent.

We discussed this with our lab and learned that there was a small GC peak they had not initially reported in the results: inactive salts and inks on blotter do not always get reported due to DEA-imposed limitations.

Given the unexpected Ehrlich reaction, we published the spectrum for the unidentified chemical and added it to the results as a second chemical present in the sample.

A chemist in the Erowid Expert Network identified the unknown chemical as tryptamine, so we ordered a lab standard for tryptamine and found that it was a perfect match via GC/MS.

Further, DrugsData’s lab did side-by-side comparison in a ceramic well plate of lab standards for 1B-LSD, 1P-LSD, and LSD-25. The third of four wells is the ‘blank’ labeled MeCN (acetonitrile) which was the solvent used to dissolve each of the ergoloid standards (1B-LSD, 1P-LSD, LSD-25). Ehrlich reagent was applied to each, demonstrating that neither 1B-LSD nor 1P-LSD turn purple with Ehrlich, where LSD-25 does.

So the mystery of the the unexpected Ehlrich reaction for this 1P-LSD blotter is resolved, but the reason why someone added tryptamine to 1P-LSD blotter is still open. We all guess the goal was to be able to sell the 1P-LSD blotter as LSD-25, and that adding tryptamine to the 1P-LSD will result in reagent reactions consistent with LSD-25.

This is the first time Erowid has seen this type of adulteration of non-LSD ergoloids with the chemical tryptamine.

The image below is a link to a video of the reagent test:

Then, a photo of lab-grade tryptamine reacted with Ehrlich. A strong purple color:

“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