DEA Stopping Civil Forfeiture Against Cannabis Vendors?

In very exciting news, it appears that the DEA may be backing off from their quasi-legal use of civil asset forfeiture for fighting against state and local differences in drug laws.

Read about the news California Cannabis- Civil forfeiture proceedings against the nation’s largest medical marijuana dispensary halted – that Harborside, a major medical cannabis dispensary business in the Oakland, California area, has been fighting for years against forfeiture.

Harborside is one of the few dispensaries Fire and I have toured the operations of and it has remained an important medical cannabis dispensary of the last decade.

Civil asset forfeiture is a tragedy as it has been allowed to evolve in the United States. If you don’t know about it, very simply it’s the use of civil proceedings that do not require the “beyond a reasonable doubt” standards required for criminal prosecutions. The government (usually the police, DEA, FBI, etc) seizes assets with an accusation (not a conviction) that the assets were involved in criminal activity. It makes taking away people’s private property very easy compared to convicting someone of breaking a law.

For years, the Drug Enforcement Administration has been using civil asset forfeiture and threats of forfeiture proceedings to try to keep local areas from changing drug laws. And to punish high profile individuals and businesses in state level cannabis policy change. In the main cases, property owners who rent their buildings to medical cannabis dispensaries in California or property owners who themselves are dispensaries have the DEA come in and try to have the ownership of the real estate or building taken away without any criminal court proceeding.

It’s been a big deal, because most owners of buildings are not willing to spend millions of dollars on legal fees fighting the DEA to protect a medical cannabis operation. So this is one of the many quasi-legal bludgeons the federal drug police have been wielding against those who are complying with state, but not federal cannabis laws.

Excerpt from AP story:

OAKLAND, Calif. (AP) — Federal prosecutors have agreed to drop a nearly four-year effort to seize the property of a California medical marijuana dispensary billed as the nation’s largest, the dispensary’s attorney said Tuesday.

[…]

The federal government’s decision to end the case against Harborside would be the second time in recent months it has backed off a California medical marijuana dispensary. Prosecutors dropped their appeal of a judge’s October ruling in a similar case against the Marin Alliance for Medical Marijuana.

[…]

“We are beginning to see the beginning of the end of federal prohibition,” Harborside’s executive director, Steve DeAngelo, said.

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

Marquis and LSD: Is color change visible?

Short Summary: Marquis, Mecke, Mandelin, and Simons are not reliable tools for confirming or disproving the presence of LSD in blotter, liquid, gel, or tablet forms.

Figure 1 Confirmed LSD blotter produces little or no reaction to Marquis, Mecke, and Mendelin when tested on white porcelain.
Figure 1 Confirmed LSD blotter produces little or no reaction to Marquis, Mecke, and Mendelin when tested on white porcelain.

Long Version: We get asked a lot about how specific drugs react to the various drug-detection field tests like Marquis, Mecke, Mandelin, Simons, Robadope, Ehrlich’s, etc. In most cases, it’s a matter of getting some of the pure target compound, a fresh set of reagents, and doing a little testing, photographing, and documentation..

However, with drugs active below 1mg, such as LSD, this may not be so simple. Because the amount of target compound is often very small, the reactions can be altered, slowed, or blocked by tiny amounts of other substances present. In the case of LSD blotter paper, where the amount of LSD on a 1/4″ square (6mmx6mm) is usually at or below 100 micrograms, the paper and the ink on the paper are far more likely to be the cause of a color change than the LSD itself. With liquid LSD, the alcohol carrier can dilute the response enough that no color change is visible. Thus, a color change or the lack of color change can be due to the form in which the substance is being tested.

LSD is said to create an olive green or black reaction with a Marquis reagent test. Organizations that sell reagent tests such as Dancesafe and Bunk Police report that LSD has an olive-black reaction with a Marquis test. This may be based upon sources such as this Department of Justice article stating that LSD causes an “Olive black” result. [ Fatah A. “Color Test Reagents/Kits for Preliminary Identification of Drugs of Abuse” (2000) ].

Figure 2 LSD sample confirmed by GC/MS produces no response to Marquis, Mecke, or Mandelin reagents. Black squares shown to illustrate blotter location do not indicate a “black” color reaction to these tests.
Figure 2 LSD sample confirmed by GC/MS produces no response to Marquis, Mecke, or Mandelin reagents. Black squares shown to illustrate blotter location do not indicate a “black” color reaction to these tests.

However, the results of our own lab’s field tests on samples confirmed to contain LSD using GC/MS show varying responses to Marquis and other field tests. When tested with a Marquis reagent, most of these samples showed no reaction or only a very slight reaction and none produced an olive green or black reaction. For examples of these test results see Figure 1 and Figure 2. Furthermore, the blotter paper itself—not the LSD—may be causing these slight reactions.

You can see a list of numerous LSD samples on EcstasyData along with their field test color changes here:

http://www.ecstasydata.org/results.php?start=0&search_field=substance&s=lsd&detail=true

Despite claims that LSD produces an olive green or black reaction to Marquis, evidence collected and published through EcstasyData does not support this. Furthermore, a 1979 paper by by Johns et al is consistent with these EcstasyData results. The researchers tested a wide variety of drugs from that era with nine different reagent tests, including Marquis and Ehrlich (Table 1). This paper reports that LSD only reacts with Ehrlich and not with any of the other reagents. Interestingly, the researchers used dry LSD from Sandoz Laboratories. Other publications claiming that LSD produces olive green or black reactions to Marquis do not report the source or form (i.e. liquid, crystal, or blotter) of the LSD tested. The results of the Johns et al., study suggests that confirmed pure crystal LSD has no reaction with a Marquis test. Below is a summary of the results:

Compound Reagent test Color reaction Testing surface
LSD Marquis no reaction Porcelain
LSD Mecke no reaction Porcelain
LSD Madelin no reaction Porcelain
LSD Cobalt thiocyanate no reaction Porcelain
LSD Dille-Koppanyi no reaction Porcelain
LSD Ehrlich purple Porcelain
LSD Froehde no reaction Porcelain
LSD Sulfuric acid no reaction Porcelain
LSD Nitric acid no reaction Porcelain

Although other sources say that LSD causes an olive-black reaction with a Marquis reagent test, this study, along with the EcstasyData results, suggests that LSD may not cause an olive-black reaction with a Marquis test—at least not on blotter paper in the amounts it is commonly sold. Based on this evidence, the Marquis is not a reliable for test for LSD. On the other hand, the Ehrlich may be an alternative test for this purpose based on the findings published by Johns et al. The Ehrlich reagent produces a color change when LSD or another indole is present. However, like all reagent tests, an Ehrlich is not a confirming test, it is just another in a wide array of rule in / rule out tests that can help confirm or deny the presence of LSD in a given sample.

Thanks to W and Shaolin at the DMT Nexus for their work on this issue.