Erowid Crew Blog – Page 4 – Random, Irregular Posts

Technical Oddity: Dutch Testing Service (DIMS) Defines Pure MDMA Crystal as 84% Pure

Executive Summary: Different labs use different standards for reporting percentage purity assessments and also for mass when doing quantitative measurements for psychoactive drugs like MDMA. One lab’s 84% might be another lab’s 100%. This also means one lab’s 84 mg might be another lab’s 100 mg.

Long Version:

Erowid friend and Internet drug geek, Borax, pointed out a paper that analyzed some of the Dutch Trimbos Institute’s DIMS data. The peer-reviewed article was published in the journal Addiction: “Purity, adulteration and price of drugs bought online versus offline in the Netherlands” (2016). We love the Dutch DIMS testing service and have written about it before.

The publication of this article did not reveal a lot that we didn’t already know, but has brought into focus a heated argument that has been ongoing in public and private discussion forums about analytical methodologies for on-site and lab drug analysis.

What does it mean when a lab reports that a powder is 100% pure MDMA? What does it mean when a lab reports that a tablet contains 100 mg of MDMA?

The reason for writing about this is that there are no simple answers to those questions, though it seems like there should be.

Some online vendors of research chemicals have stated that various labs’ purity results in the 75-85% range mean that the sample was really “100% pure”, because of different ways of handling the mass of the sort-of-attached non-psychoactive salt anion. An anion is a negatively charged counter-ion that balances the positively charged, nitrogen-bearing drug molecule. When freebases are turned into salts, an anion is added.

The main case and the one that’s relatively easy to talk about is MDMA. MDMA is normally produced and distributed as MDMA hydrochloride (HCl), which is MDMA in a solution that has been converted to a crystalline form—-a “salt”-—by bubbling hydrochloric acid gas through the liquid. This causes the MDMA to turn insoluble in the solvent, precipitating out as MDMA HCl crystals. There are other possible salt forms of MDMA, but this is the “table salt” (most common salt form) of ecstasy/molly.

In fact, normal table salt or culinary salt is usually considered Sodium Chloride, or NaCl. We’re virtually swimming in tiny amounts of acids and salts in our normal environments. Remember your protective eyewear!

In addition to chloride salts like HCl, there are numerous anion salts possible, such as sulfide, fluoride, and bromide. For some psychoactive chemicals, the specific salt form can make a big difference in determining a dose. Mescaline has been distributed historically as Mescaline hydrochloride, Mescaline sulfate, Mescaline citrate, and Mescaline acetate. All of these have slightly different mass ratios between the base mescaline molecule and the portion that is the partially-bound anion. One could theoretically get 25% more or less mescaline, from a consistently weighed amount, depending on which salt form is involved.

This can be super complicated and technical and I doubt anyone is reading this who doesn’t get the basic premise. But there are technical issues like having some salt anions that bind two-to-one or one-to-two in crystalline forms. See What is the molecular weight of LSD tartrate? and many, many other discussions for crazy-making levels of detail.

As lab testing using GC/MS, HPLC, and FTIR has become more available and more projects are publishing their data and providing harm reduction information to individuals on the basis of their findings, it becomes increasingly important for more people to understand basic elements of some of the technical issues involved.

When this question of MDMA mass came up again this week, we asked the authors of the paper and the folks who work at Trimbos the following:

It has been suggested that DIMS might be using MDMA Freebase as the basis for mass and purity calculations, rather than salt masses, such as MDMA HCl. It is not described in any of your papers that I can find, but perhaps these questions will simplify the issue:

1) If DIMS received a powder sample of material that contained only MDMA HCl and nothing else, what would the reported purity be? 100%?

2) If DIMS received a tablet sample that contained 100 mg of MDMA HCl and 200 mg of lactose and inactive binders, what would the reported amount of MDMA be in that tablet? 100 mg? or would that qualify under your reporting rules as 84 mg of MDMA (freebase)?

And we got a very clear answer from the excellent Dr. Tibor Brunt:

“Indeed we use freebase as analysis standard. That actually means that if we report 100 mg MDMA in a pill, it is 119 mg in MDMA HCl. Our lab has always left out the salt component of psychoactive substances, since this component is not psychoactive. And if we’d receive a powder with 100% MDMA HCl this would be 84% maximum purity like you said.”

The reason they would define pure MDMA HCl crystal as only 84% pure is a little technical, but suffice to say it is not the only way to report an analytical result.

The reason that an expert group like Trimbos would decide to report masses this way is to normalize all their information across all salt forms of MDMA. I imagine, though I don’t know, it could be related to different types of quantitative methodologies that they have been working with for a long time.

So, dear drug geek reader, the question is not whether this issue is real, but, exactly what methodology and reporting measures are used by the analytical group you’re working with.

Update Jan 17, 2017: #

Energy Control of Spain, on the other hand, answered that they use MDMA HCl as their mass standard. They answered the questions clearly:

1) Our results directly provide the result of the salt of the substance, as
we’re using a salt as a reference standard. This means that the purity of a
sample with only MDMA HCl could be 100%.

2) Therefore, a tablet with 100mg of MDMA. HCl would be reported as 100mg
of MDMA.

Update Jan 18, 2017: Safer Party #

SaferParty and the cluster of groups in Switzerland that do work around that brand are very clear in all of their caution and warning publications that they are using MDMA HCl as their basis. For instance, “120 mg MDMA * HCl können zu viel sein”.

On Jan 30, 2017, they followed up with a long detailed answer to our questions.

Dear Earth,

Here the answer from our lab, i hope this clears things up:

As a reference standards-producing laboratory we’ve got most of our standards as solids in our hands, e.g. (water-free) salts. This is in contrast from what you get most times when buying solutions of reference standards from other companies (e.g. Cerilliant etc.). They usually sell the free base as a solution. Due to that, we are using mostly salts for calibrations. The second reason for that is, most of the time we are obtaining samples in salt forms for analysis (e.g. cocaine, heroine, MDMA, amphetamine, methamphetamine and other phenethylamines etc.); though we do not determine what kind of salt the sample consists of (e.g. hydrochloride, sulfate, acetate etc.).

We have had quite good experiences with this so far, as the sum of e.g. mixtures of amphetamine-coffeine-containing samples, when otherwise pure, reach 100% in sum when calculated with amphetamine hydrochloride. When exceeded 100% one may assume it contains a certain amount or all as free base. When the results are displayed as free base one can calculate any possible salt form. We think, according to the black market products here in Switzerland, it makes sense to give the results calculated for the hydrochloride salts, but for comparison with other labs/other countries the use of free base content would be the only value to make sense. Nevertheless, our results can easily be recalculated to the free base content, at least when knowing the type of compound we applied for calibrations/calculations.

We see it from the way that most dosage recommendations for a psychoactive compound to be taken orally or by snorting are given in the salt form (if possible), so this substantiates the indication as salt. With DMT as an example, we indicate the free base as content.

A short question the relatives the senses of indicating “purity” or “content”:

When having a chemically pure amphetamine sulfate (e.g. 100% Amphetamine sulfate”), its content of amphetamine free base is 73.4%. When having chemically pure amphetamine hydrochloride (e.g. 100% amphetamine hydrochloride), its content of amphetamine free base is 78.8%. When only seeing these numbers, which would you judge to be more pure? The lay would say it to be the second, but chemically both salt forms are chemically absolutely pure (100%).

A problem that comes in is, when having, e.g., a chemically impure amphetamine hydrochloride and reaching a displayed content of 73% amphetamine free base, one may imagine this to be a nearly chemically pure sulfate (close to the maximum content of 73.4%), but in fact it is a rather impure hydrochloride (73% out of a maximum content of 78.8%). As long as one does not determine the counterion (salt) this remains problematic.

When calibrating and calculating with salts, a measured sample consisting of free base would yield a result above 100%.

Each calibration/calculation has its own advantages, be it the use of free base, hydrochlorides, or hydrochlorides monohydrate, etc.

Let’s go to your questions:

“1) If SaferParty received a powder sample of material that contained only MDMA HCl and nothing else, what would the reported purity be? 100% ?”
As we used waterfree MDMA*HCl for calibration, we would report 100% content. As most of the samples measured here are on hand as the monohydrate (MDMA*HCl*H2O), the measured content mostly lies around a maximum of 93%.

“2) If SaferParty received a tablet sample that contained 100mg of MDMA HCl and 200mg of lactose and inactive binders, what would the reported amount of MDMA be in that tablet? 100mg ? or would that qualify under your reporting rules as 84mg of MDMA (freebase)?”
Our reported content would be 100mg MDMA*HCl.

Best regards,

For saferparty.ch
CK

Update Jan 19, 2017: The Loop #

The Loop offers analysis at music events in the UK to improve safety for partygoers and facilitate care by medical staff. When they report quantitative results for MDMA, they answered our questions as follows:

1. 100% purity
2. 100mg of MDMA (since the HCl salt is ubiquitous and service users
simply call MDMA.HCl “MDMA” we do not complicate the information they are
already getting with a description of why we are calling it something
different).

http://wearetheloop.co.uk/

Update Jan 19, 2017: CheckIt! Austria #

CheckIt! Austria very generously took their question to their technical staff and verified their answer before getting back to us:

Our chief chemist just got back to regarding your question.

We use MDMA.HCl to prepare our standards for quantitative measurements. So if we would receive sample solely consisting of MDMA.HCl, the result would be 100%. Quantitative MDMA results in tablets are also reported as HCl. So if a tablet contains 100mg MDMA.HCl and let’s say 100 mg alpha-Lactose monohydrate we would report 100mg MDMA content.

Xiao Ren Ren : The “Little People” of Yunnan

This is a very fun paper.

Xiao Ren Ren : The “Little People” of Yunnan by David Arora in 2008. It’s about his visit to Yunnan, China where he encountered edible boletes (mushrooms with spore pores instead of gills) that stained blue and reportedly caused people to see “little people”.

Also on ResearchGate.

“And if I don’t stir-fry [the mushrooms] for ten minutes?”

“Ahhh,” the man said, his eyes bright and mischievous and his wide grin punctuated by a massive, gleaming metal molar. “Well, then of course ‘ni kan xiao ren ren’ (you will see the little people).”

I don’t understand why Arora wouldn’t have collected dry and wet samples of each, sent parts to a lab, and saved parts for later confirmation. Even tiny parts of biomaterial can have the DNA sequenced relatively cheaply these days.

But, regardless, there are many fungal mysteries still to be worked out in the world.

Successful September Drive – Thanks

Thanks to all who helped by donating, spreading the word, or working on the site! Erowid got 1,240 donations in September, the most ever in a single month. We’re still finalizing some of the donations, there are always some that get reversed and have to be removed, but we probably have a few mailed-in checks that haven’t gotten into the number either.

Median donation size was, once again, $10. 316 donations on the last day of the drive and 779 donations in the last five days.

Additional Backing Drive Funding

A couple more folks have stepped up and added to our matching drive. Today we got an additional $2,500 in matching funds. Right now, at midnight west coast time, we have $17,002 in matching funds and have used about $7,000. We’re hoping maybe to get another couple thousand in backing over the next few days, but it will be a stretch.

But, a longer stretch is to keep building momentum with next Friday as our end date.

Another Revision of Bitcoin Transaction Importer

Most bitcoin donations to Erowid come in very small amounts and not super often. But, ever September, I need to have a daily tracking of incoming bitcoin donations to keep our daily September Drive numbers accurate.

Otherwise, there’s no reason to do day-to-day tracking of bitcoin donations. But, each year it seems each system I use to do server-side pull and parse of bitcoin donations into our contribution tracker change format or meaning. And again this year.

After some very generous folks contributed 45 bitcoin donations yesterday, it became clear that I needed to stop entering them manually into our contribution list and had to update the importer. So, this year, I’m using the JSON output from :

http://webbtc.com/address/

It took me a few hours of figuring out the differences between the different formats I’d been reading.

So, that makes 65 bitcoin donations so far in September. Hurray!

Sept Drive

Overdose Awareness Day

International Overdose Awareness Day (IOAD) is today. I became aware of this event when browsing the Harm Reduction Coalition site. Clicking through to overdoseday.com, I learned that IOAD was founded over a decade ago in Australia.*

Also over a decade ago, I lost my dear friend Carla to a drug-related accidental death that one might call an “overdose”, except that no single drug found in her system would, alone, have precipitated her falling asleep and not waking up. I’ve since come to call this type of death a death by “medi-mix”, a mixing and matching of drugs and alcohol to tackle unwanted symptoms, thoughts and feelings like pain, sadness, sleeplessness, tension or anxiety.

I’ve also found myself using her first name as a verb, as in “I don’t want to get a call and learn he Carla’d out!” or, sadly, more recently, “she Carla’d out”. Maybe dark humor helps me deal with the feelings of grief and helplessness. Details of how Carla died came to light because she died in a county where autopsy reports are a matter of public record. Ordering one cost less than $30. That was the price of learning details on how this healthy woman of 42 “died in her sleep”.

That the risky mixing and matching of sleep aids, anxiolytics, opioids, stimulants, and alcohol even has a name in my lexicon (“medi-mix”) is disturbing. It’s not that it happens often, it’s that it follows a recognizable pattern. Since Carla’s death, several friends and acquaintances have exhibited concerning patterns with various depressants, usually during times of great stress, but not always. Most have survived without dying, so far.

The Overdose Awareness Day site promotes wearing a silver ribbon pin; I’ve worn one this month to remember Carla and anyone else in my acquaintance, any public figure, and any other person who has died or suffered from a non-lethal overdose, whether it’s a result of taking too much of a single drug or a drug combination accident.

Please talk with family and friends about this topic, even if it feels awkward. It might make make a difference in someone’s life!

*IOAD is now managed by Penington Institute, a nonprofit group that “advances health and community safety by connecting substance use research to practical action”. Actions dedicated to overdose awareness on August 31 are organized outside Australia, too.

Research Shows Having Illegal Drugs in the Home Makes it More Likely People Will Use Them

Huh?

Researchers and the drearily uncreative folks at ScienceDirect tell us that those teens who have access to illegal drugs in the home from their parents are more likely to have tried them before those young people who do not get the drugs from their parents’ stash.

Odds ratio for using Cannabis or “Other Drugs” was about 2, meaning that people who reported having “illegal drugs easily available” in the home were twice as likely to have tried cannabis or illegal drugs compared to those who said that illegal drugs were not “easily available” in their homes as teenagers.

Overall, I was expecting to hate the article but think it’s pretty decent. But it’s incessantly annoying to read summaries of research findings, like Science Direct’s, that do not describe the magnitude of the effects nor how well known the finding is. What every summary of this should say is “the following is what everyone knew ahead of time and this is the first step in trying to sort out exactly how all the variables are associated in the populations we study.”

One thing that the summary didn’t highlight is that just being male had about the same effect size: around twice.

If that seems interesting to you, then you might want to read this crap:

https://www.sciencedaily.com/releases/2016/07/160729110923.htm

Or the abstract and paid article in this low end journal “Journal of Child & Adolescent Substance Abuse”. The journal isn’t even index by PubMed. 🙁 At least their publisher can afford a DOI subscription.

Erowid Ref 9080 or http://www.tandfonline.com/doi/abs/10.1080/1067828X.2015.1103346

They keep having to move domains, but the full article is available via Sci-Hub.

Experience Vault Micro Update: Published Date Added

Summary: Added a new field “Date Published” to Experience Reports and moved all code over to use that instead of “Date Reviewed”. If anyone sees errors in the Experience Vault lists or What’s New, please let me know.

tl;dr

Changes to the Experience Vaults are hard because I wrote the code for almost all of it back in 2000 and then a major update in 2004. All written in ancient Perl that’s extremely fragile and a pain to set up as a development environment. On the plus side, it mostly works.

As a preliminary step towards a couple of other new features for crew and public, yesterday I added the very obvious “date published” field. We’d been skating by using Reviewed Date (the date that the first reviewer edited the report and marked it ready to be live) as the date published. But there are lots of reasons why one doesn’t want to have a single value for editing history and publication date. So, editing history is now properly just editing history and we don’t have to jury-rig and falsify the editing date in order to have the date of publication be correct. woo. :]

Date published is now the primary sort.

It’s a tiny update, but because of the complexity and fragility of the old code, the perl library I chose to use was failing in weird ways and it took five hours to debug to the point where I realized I could solve the problem by moving the logic out into a separate library (namespace) and it all magically just started working.

Stupidly Misused Neo-Terminology: E-Psychonaut

In reading a recent paper by Schifano F, Orsolini L, Papanti D, Corkery J, we ran across their ridiculous term “e-psychonauts” from this and a previous paper.

It’s always sad to see people writing new articles, especially medical or anthropology papers that pretend that the use of electronic communication is somehow noteworthy or aberrant. It is not.

Vulnerable subjects, including both children/adolescents and
psychiatric patients, may be exposed to a plethora of pro drug web pages, from which unpublished/anecdotal levels of knowledge related to the NPS are typically provided by the ‘e-psychonauts’ (e.g. drug fora/blog communities’ members; [124]).

That refers back to a a paper from 2015 by the same authors.

The authors define the term in their abstract:

Within online drug fora communities, there are some educated and informed users who can somehow provide reliable information on psychoactive compounds and combinations. These users, also called e-psychonauts, may possess levels of technical knowledge relating to a range of novel psychoactive substances (NPS).

And then go on to tout how excitingly new the idea of “e-psychonauts” is, despite the idea of online drug geeks being not remotely new by any reasonable standard. Not new to published articles, not new to published medical articles, not new to agencies funding massive “web surveillance”, not new to the mega mainstream media scare machinery, not new to anyone.

To the best of the authors’ knowledge, this paper represents the first systematic study aimed at providing a description of e-psychonauts, which may be of some use in prevention activities.

Demographics of online drug geeks? Not new. Perhaps it’s just a simple indictment of the “authors’s knowledge” and the knowledge of the article’s unnamed reviewers and editors.

The term “e-psychonaut” seems like it could be useful to mean psychonauts who are using new electronic psychoactives, such as electroceuticals, mind machines, transcranial magnetic stimulation, direct neural stimulation, or the like.

But, no, these authors and the terrible editors who helped them foist the term into the medical literature, seem to have missed that very approximately 100% of the adult populations under 60 years old in advanced countries now use “computers” or “electronic devices”. [To be clear, I know that it’s not actually 100%, it’s more like 90% of adults in the US under 60 years old, but virtually everyone /has used/ the internet.]

Perhaps in the 1990s it might have been helpful to distinguish between “psychonauts” who used electronic communication and those who did not. But in 2016? Not so much.

We appreciate that the authors and the low-end journals they publish in are willing to use Google to learn about “novel drugs” like 2C-B. But it really seems depressingly quaint in 2016.

As one indication of how well edited their papers are, in reading through them, I noticed this excellent reference in the opening paragraph of their 2015 paper “Ectasy.org [sic]”, cited to “Ectasy.org. www.ectasy.org (accessed Jan. 22, 2014).”

Oops. Don’t they use spell check? Regardless of spell check, getting through publication with a sad typo in the opening paragraph indicates bad things about the publication’s editorial process and overall quality. In case it’s not clear, that’s a typo for Ecstasy.org. Ectasy.org is a long-squatted typo domain with no content.

Woohoo! New SSL Cert (4096 key)

Since all of our HTTPD traffic is forced SSL, valid credentials are required to prevent visitors to Erowid.org and EcstasyData.org from seeing a very nasty error message when trying to access the sites. With an expiration date looming, it was time to renew Erowid.org’s low-end SSL certificate. Why low end? Because we consider the browser certificate authority to be an illegal global racket.

First, the good news. Check out our “A” rating from Qualys SSL Labs:

SSL Labs A Rating of Erowid HTTPD Server Security

We mostly achieved this a couple of years ago when our sysadmin team worked to eliminate all of the basic problems, like removing support for dangerously weak encryption ciphers and forcing more secure handshake methods. But, if you look at the Qualys report, you’ll see that our server doesn’t allow the known-broken encryption algorithms.

And, as of today, we’re trying out a 4096 bit key. Many of the sites I looked at suggested that the CPU load cost of doing the key negotiation wasn’t worth the extra security, but JL, our main sysadmin, said we should give it a try. We’ll watch the server load over the next week or two, but right now it seems fine.

As far as the rant about the global criminal conspiracy that is the certificate authority, well, I will leave that to others. To be clear, I think it’s all a money scam, facilitated by the browser folks.

We choose to buy a cheap chained certificate because of the usurious pricing of the better, greener, happier certificates. They punish us by making the URL bar not as pretty and also making the certificate viewing experience worse. Despite the CSR having all the right info, the $50-100 per year wildcard-SSL certs don’t display our organization name or location properly. Pay $200-1000 per year and, with no additional security, we would get a happy-looking green bar and Erowid displayed in the browser URL bars.

Snake oil forever.

As I was searching for an example of an expensive green bar, I discovered that trying to view the front page of CNN via SSL resulted in terrifyingly bad browser behavior. It looks like a hijack (MTM) or just fails.

I'm Glad I'm Not a CNN Sysadmin — I’m Glad I’m Not a CNN Sysadmin

In early 2015, Erowid joined EFF’s HTTPS Everywhere campaign, because we believe that, today, virtually no communications should occur online in clear text. It is a sad statement about humanity that most of us, including institutions handling sensitive data about us, still use unencoded plaintext email that requires no warrant and is, essentially, a public broadcast.

P.S. In an insanely conspiratorial way, I believe that the NSA and other anti-public-crypto agencies have worked to torpedo efforts over the last twenty years to get email more secure. In the United States, a fig leaf of privacy is enough to trigger Fourth Amendment protections.