Diprotic Acids – 4-Acetoxy-DMT Tartrate versus HCL Salt

A question came up yesterday about whether we need to add different dose information to our 4-Acetoxy-DMT Dose Page for different salts. Our team believes that the primary salt sold over the last fifteen years of 4-Acetoxy-DMT has been the fumarate salt (fumaric acid).

If one assumed that each fumarate molecule paired up with one 4-acetoxy-dmt molecule in the salt form, then there would be about a 25% difference in the potency between the fumarate and the hydrochloride (HCl) salt. Some vendors have reportedly sold the HCl salt instead of the fumarate, and so this could result in a difference of potency between different pure salts of 4-acetoxy-DMT of about 25%.

However, after consulting with some of our friends in the Erowid Expert Network who are senior analytical and synthetic chemists, they were able to confirm that the fumarate salt of 4-acetoxy-DMT is always diprotic, with some small technical caveats.

NC writes: “Although fumaric acid itself is diprotic, its salts may not necessarily incorporate two molecules of the base. AFAIK, it is not possible to predict the stoichiometry of such compounds a priori, it all depends on whether the mono- or di-substituted fumarate remains soluble in the solvent or precipitates out. NMR would tell the story.”

  • 4-AcO hemifumarate: 304.35 g/mol
  • 4-AcO HCl: 282.77 g/mol

So there’s only a few percent different in potency between the two.

In digging around in questions related to diprotic acids and how certain we can be that any given chemical salt has a given number of freebase target molecules, PD pointed out this obscure paper:

“USP Lysergic Acid Diethylamide Tartrate (LOT 1) Authentic Substance Recharacterized for Authentication of a House Supply of Lysergide (LSD) Tartrate”. .

The paper demonstrated, via extreme drug geekery, that the two samples of pure, high grade LSD they had were not identical.

In subjecting a commercial supply of lysergide (LSD) tartrate (Sandoz Lot 79001) to authentication for adoption as a "working standard", infrared (IR) proton nuclear magnetic resonance (1H-NMR) spectra of the working standard showed some dissimilar features to those obtained from the USP LSD Tartrate Authentic Substance (Lot I).

Although comparable mas spectral results were obtained from the two LSD samples, further investigation by 1-H- and 13C-NMR spectroscopy showed the USP material to contain appreciable excess tartaric acid. 

So, according to our experts, fumaric acid is almost always diprotic, but one cannot be certain without actually verifying that with a given ‘freebase’ molecule.

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.

Hawaii’s Paying for Drug Policy Research!

In a truly revolutionary step, the Hawaiian government is paying to review the effects of alternate drug policies.

They are specifically including Portugal and total decrim for personal possession. Amazing.

http://www.capitol.hawaii.gov/measure_indiv.aspx?billtype=HCR&billnumber=127&year=2016

Full Text:

http://www.capitol.hawaii.gov/session2016/bills/HCR127_HD1_.pdf

Ending section:

BE IT RESOLVED by the House of Representatives of the Twenty-eighth Legislature of the State of Hawaii, Regular Session of 2016, the Senate concurring, that the Legislative Reference Bureau is requested to conduct a study on the feasibility and advisability of decriminalizing the illegal possession of drugs for personal use in Hawaii; and

BE IT FURTHER RESOLVED that the study include:

(1) A survey of all existing criminal drug offenses in Hawaii that are a class C felony or lower and pertain to the illegal possession for personal use of a drug;

(2) A review of the current national drug policy of Portugal pertaining to the illegal possession of drugs for personal use, with a focus on the use of the policy as a potential model for the decriminalization of the offenses identified under paragraph (1); and

(3) The feasibility and advisability of decriminalizing the offenses identified under paragraph (1), such that the conduct constituting an offense would constitute an administrative or civil violation rather than a criminal offense; and

BE IT FURTHER RESOLVED that the Legislative Reference Bureau is requested to submit a written report of its findings and recommendations, including any proposed legislation, to the Legislature no later than twenty days prior to the convening of the Regular Session of 2017; and

BE IT FURTHER RESOLVED that the Judiciary and the Department of Public Safety are each requested to provide statistics and other information as may be requested by the Bureau to assist in the timely completion of the study; and

BE IT FURTHER RESOLVED that certified copies of this Concurrent Resolution be transmitted to the Director of the Legislative Reference Bureau, the Chief Justice, the Administrative Director of the Courts, and the Director of Public Safety.

EcstasyData: Looking Back at a 6-MAPB/6-APDB Sample – Now 5-APDB

In April 2015, we received a sample that was sold as 6-MAPB, but the lab tentatively identified as most likely to be 6-APDB. This week, the lab took another look at the sample with some new standards and using more updated Mass Spectrum databases.

After spending quite a bit of time on it, their new identification (not 100% match to a standard DDL has, but a close library match) has changed to 5-APDB, rather than the previous 6-APDB. Here’s what the lab wrote describing that process:


I reanalyzed 40900034. The best match is now to 5-APDB. It’s complicated, so here’s a little background.

There are four APDB compounds, the 4-APDB, 5-APDB, 6-APDB, and 7-APDB. They all elute very early according to Cayman spectras, but in this order, 5, 6, 7, and then 4 at a later time. So, it was determined that based on the ion ratios, 40900034 was CLOSEST and now BEST match to 5-APDB. The GCMS output spectras of 5,6,7 in comparison to the sample have been attached, just for curiosity.

[ Erowid: these are now attached to the ecstasydata entry: ID : 3276. ]

Also, it was interesting that the 6-APDB standard received from Cayman produced an extra minor peak, whereas only one peak is shown in Cayman’s database. Not sure there. Possible contamination of the standard we were sent? Or 6-APDB produces two peaks. ( I ran the standard three different times to confirm). GCMS output have also been attached.

I will be developing a new method to help separate and better identified compounds with functional groups at a different carbons for APDB and the many other new drugs.

EcstasyData: Confirmed 5-MAPDB

We received a sample this month that was sold as 6-APB but the lab identified by library match to be 5-MAPDB. A “library match” is not 100% guaranteed to be a positive identification because it means that the mass spectrum was consistent with a published mass spectrum from an established library. What library matches are missing is exactly the gas chromotagraphic timing and the exact minor details around the edges of the spectrum that are unique to each type of analytic equipment.

To confirm the identification, we ordered analytical standards from Cayman for 5-MAPDB. The lab ran the standard and then compared them against the submitted sample (ID:3688) and found they matched exactly, confirming their library match that the sample is 5-MAPDB.

New Upgraded SSL Certificates on Erowid and EcstasyData

This last week we installed upgraded security certificates on Erowid and EcstasyData.

Over the last couple years there have been lots of new exploits and problems discovered with SSL. Although we have kept up with all the security updates as soon as they were announced (thanks to JL and Brian!), we had not upgraded our web security certificates that allow for substantially more secure connections for browsers that request it.

The new certs support SHA-2. SHA-1 is now considered “dangerously weak” and some groups have declared that they will no longer support it by the end of 2015. https://www.symantec.com/page.jsp?id=sha2-transition

As of today, SSLLabs.com gives Erowid.org an “A” :

SSL Labs Gives Erowid A
SSL Labs Gives Erowid A

Morphine from BioSludge: Not Yet, But Soon

As drug geeks have already seen, in May and June 2015, a bunch of news came out of a publication of, perhaps, the final genetic puzzle piece to be able to engineer custom organisms (such as yeasts, slimes, goops, and other things that grow well in petri dishes and buckets) that could produce morphine.

The puzzle pieces have not all been assembled yet to prove that the puzzle has been solved, but it appears close enough that we added a Bioengineering section to our Poppy Vault as a place to keep track of the progress.

The global pharmaceutical industry has been designing organisms, altering DNA and RNA, to act as microbial factories to perform steps of synthetic chemistry since around 1980 (see Goeddel D, et al. 1978). So the technologies necessary to insert genes into microbes and use them to generate, synthesize, or convert one chemical to another are becoming fairly mature.

As Robert Service, an author at ScienceMag writes:

With the last piece of the puzzle now in hand, Dueber says the challenge will be to express the genes for the full synthetic pathway into yeast. That’s a “considerable” hurdle, Dueber says, but likely doable within a few years. Even when that’s done, the microbes will still likely only make vanishingly small quantities of the final medicines. So then the task will be to increase the efficiency of each of the steps. That, too, is likely not an insurmountable challenge. (http://news.sciencemag.org/biology/2015/06/final-step-sugar-morphine-conversion-deciphered)

The two primary law enforcement implications of this technology are the future simplification of disallowing natural poppy growing and the problem of having morphine as a possible home brew drug. If in vitro morphine production is successful, the giant, legal poppy fields used to generate the source material for some of the most popular pharmaceuticals in the world could be eliminated. That would allow global drug enforcement agencies to outlaw all poppy fields, making them easier to police and destroy.

But the other edge of that technology is that it makes it possible and even likely that there will be dark and gray market availability of engineered organisms that generate morphine or related compounds. Currently, the global heroin and oxycodone markets depend on massive grow operations in remote locations. 20-40 years from now, it could nearly all be switched over to vat and bucket sourced molecules.

MSM Trace in MDMA Sample?

A visitor asked about result 3669. This result was determined by DDL via GC/MS to contain primarily MDMA but also a trace amount of Methylsulfonylmethane (MSM). MSM has some practical applications in the final crystallization of some recreational stimulants (notably methamphetamine) but could also be used as a bulking agent to boost retail profits.

The visitor wanted to know how sure we are that the MSM was only a trace and not a more major component of the sample. Here’s an answer from our lab trying to address the issue:


There are numerous complications when asking how certain the ‘trace’ finding is for MSM in the testing process.

First, DDL has never done a quantitative analysis of MSM using our testing process. So our methods for analyzing MSM have not been validated by our team.

It could be that it might take a little more MSM to show up compare to say meth or MDMA, since MSM is a much smaller compound. We don’t know this for certain and would need to spend time verifying it if this is important to the project.

Second, MSM is easily detected and seen. We know it shows up we have detected it in many samples over the years.

Third, although we do not know for certain how a known quantity of MSM mixed uniformly with a known quantity of MDMA would show up in our GC/MS, it is hard to imagine the trace we saw with this sample representing more than a tiny amount in the actual sample analyzed.

Fourth, process issues it is possible that the sample submitted contained more MSM proportionally than we reported due to process issues. It could be that the sample might not be homogenized. If a baggie or capsule is filled with MSM and Meth, but wasn’t thoroughly mixed when filled, and when we open the capsule a pour a good representative amount to use, maybe there’s more MSM powder at the end of the capsule. Or perhaps MSM is not homogenized on a sample tablet when a good portion is scraped off or a portion broken off and crushed for analysis.

If we were primarily concerned about homogenization, we would dissolve the entire sample in a solvent, but we don’t do this for several reasons. We don’t want to use up the whole sample on the first attempt because a sample may not dissolve perfectly in the first solvent we choose or we may need to re-evaluate the analytical process from scratch and we would not want to add a solvent to all of the powder if we can avoid it. There are more reasons to keep the original solid sample than there are to homogenize the whole thing.

Fifth, one thing is certain, we can’t be certain. The way each drug appears using each analytical technique different. Because of this, quantitative analysis of drugs in forensic toxicology typically involves very technical development of validated processes using the drugs in their deuterated forms as internal standards.

So, there are numerous variables that may explain it only being trace relative to other drugs. Most likely, the sample only contained a tiny amount of MSM, but without further analysis this point, there’s no way to be certain.