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!

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

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 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 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, has been blocked in China for even longer, starting sometime in the mid 2000s.

“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:


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.

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 :]

The Church of Sleep – Sleepists & Dreamists

Fire had a dream last night where she went to a religious retreat that was oriented around “Sleep as Prayer”. Participants were required to sleep more than 12 hours, but could not stay in bed more than 16 “because it would attract the wrong sort”.

In the dream, “Somnambulation” was the term that stuck in her head. Beds lined up like military cots. Fire and Earth were coming in late and had to pull a bed out lengthwise, we had to pull it out in order to get into our spot because there was no walking path without rearranging the beds.

In what-seems-not-to-be-dream life, there is no question that we are believers in the Church of Sleep. Sleep cures physical and spiritual ailments of all sorts and scientifically brings us closer to the Atman / Buddha Mind.

And, of course, the curious, dubious, yet telling world of dreams.

Get back to work!

3-Methylmethcathinone? Nope, 4-MMC

We’ve been getting samples sold as 4-methylmethcathinone (Mephedrone, 4-MMC), but there has been discussion online and some submitters have suggested that much of what is sold as 4-MMC is, in fact, 3-MMC. The argument is that the positional isomer, with the methyl on the 3 position, has similar effects, but is not strictly controlled in some jurisdictions where 4-MMC is specified, but positional isomers are not covered under some countries’ laws.

We obtained a 3-MMC standard from Cayman this week and DDL ran it through their equipment and re-ran a recent sample that a submitter said might be 3-MMC. The standard for 3-MMC had a distinct retention time in the GC (Gas Chromatograph), meaning that it is easy to differentiate as a different chemical from 4-MMC. While the Mass Spectrum fingerprints of 3-MMC and 4-MMC are nearly identical, the different retention times cause the two chemicals to show up as two separate “peaks” in the GC output.

See EcstasyData 4178.