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Registered: 08/08/03
Posts: 7,026
Loc: Vancouver, B.C.
Grey market troubles
    #2328567 - 02/12/04 11:10 PM (14 years, 2 months ago)


The Strange Case of Mark Niemoeller

By Travis Dunn, AlterNet

Mark Niemoeller, 46, of Columbus, Ind., decided to give up farming in 1987. With money loaned to him by a friend, Niemoeller set up a mail-order business that he ran from his family farm. The business, JLF Poisonous Non-Consumables, began with the sale of one product: amanita muscaria mushrooms. Niemoeller picked the red-capped mushrooms himself, dried them out in an old RV, then placed an ad in High Times magazine. Soon JLF Poisonous Non-Consumables was inundated with orders. By September 2001, JLF had become a multi-million-dollar business ? raking in $50,000 a month and branching out into the sale of hundreds of other plants, mushroom species and pure chemical compounds.

Why would a company that sells purportedly poisonous products advertise in High Times?

Perhaps because JLF's best-selling product, amanita muscaria, as well as dozens of other products now included in the catalogue, have powerful psychoactive properties ? when ingested.

Ingestion is the key here, since Niemoeller contends that the consumption of JLF's products is not an issue. The legal justification for his argument, he says, is right in the company's name ? JLF Poisonous Non-Consumables.

JLF requires that every customer recite a disclaimer in a recorded telephone conversation. The disclaimer states that the customer is over 18 years old and will not ingest products purchased from JLF.

In addition to the disclaimer, JLF's catalogue displays a lengthy warning, which makes it quite clear to the customer, Niemoeller says, that JLF products are not to be taken internally.

"Do not take orally (into your mouth) as a food, a beverage, a chew, a toothpick, a nutritional supplement, a medicine, a drug or an agent of suicide," reads a portion of the warning. "Do not eat, drink, inject, inhale, insert, absorb, snuff, snort, smoke, slam or ingest in any way. Do not stick, put, or throw into your or another person's mouth, nose, ear, eye, anus, urethra, vagina, or any other orifice or port-of-entry that may exist on your or another person's body."

For nearly 15 years no one called into question JLF and its unusual disclaimers.

In the late 1990s, however, several law enforcement agencies, including the Drug Enforcement Administration, the Food and Drug Administration and the Indiana State Police, began to take a keen interest in JLF.

On Sept. 7, 2001, police served Niemoeller with a search and seizure warrant. They confiscated about $250,000 in merchandise, $1 million in assets, bank books, financial records, business ledgers, lists of addresses and phone numbers, documentation of business expenditures, travel documentation, computers and Niemoeller's 1998 Dodge Ram utility van.

Niemoeller wrote out a check to Indianapolis attorney Andrew Matternowsky, who handles a lot of drug and civil liberties cases. Later that week, police froze about $750,000 in Niemoeller's bank accounts, and the check to Matternowsky bounced. (Matternowsky remains unpaid.)

For nearly five months nothing happened. Then on Jan. 28, police arrested Niemoeller and served him with a 13-count federal grand jury indictment. Niemoeller spent the night in the Marion County jail. On March 18, he will stand trial in a federal district court in Indianapolis.

JLF's Non-Consumables

Niemoeller, the grandson of hard-working German immigrants, built up his business atop a pile of red amanitas mushrooms.

While the ritual use of these mushrooms as hallucinogens dates back 8,000 years, back when Siberian shamans ate the mushrooms to induce visionary trances, the use of these mushrooms for such a purpose is not recognized by federal drug laws.

According to Erowid.org, an extensive on-line library of drug information, amanita muscaria is perfectly legal in every country in the world ? with the sole exception of Israel.

In the United States, possession or distribution of amanitas mushrooms cannot be prosecuted under federal drug analogue statutes. The psychoactive compounds contained in the mushroom, ibotenic acid and muscimol, bear no chemical relation to any other known drug.

As sale of these mushrooms brought in large profits, Niemoeller slowly began to add other products to JLF's catalogue.

Prior to the September raid, JLF Poisonous Non-Consumables offered dozens of products that had one thing in common with the amanitas mushrooms ? they were all psychoactive when consumed and not specifically covered by federal drug laws.

It is true, however, that a number of JLF's products are truly poisonous, such as the "destroying angel" mushroom, the leaves of the "deadly poison hemlock," and curare, the infamous dart-poison from the Amazon.

But many of JLF's products have psychoactive, and not poisonous, properties, and these are some of the very products that police have called into question.

Take, for example, 5-MeO-DMT. The chemical shares a certain similarity to dimethyltryptamine, or DMT, a powerful, short-acting hallucinogen, sometimes called "the businessman's trip," since its effects wear off entirely in an hour. According to federal law, DMT is a Schedule I substance.

5-MeO-DMT is another story. When LSD, DMT, PCP, psilocybin and mescaline became federally scheduled substances, 5-MeO-DMT did not.

But when even a few milligrams of the chemical are loaded into a pipe and smoked, the user is instantaneously overcome by psychoactive effects described as far more intense than those of any illegal drug.

Amanita muscaria mushrooms and pure powdered 5-MeO-DMT are not the only potentially psychoactive substances sold by JLF.

There's salvia divinorum, a plant from Oaxaca, Mexico, used by Mazatec Indian shamans to induce powerful visions. Or khat, an African plant, chewed for its amphetamine-like effects. Or yage, a vine used by South American sorcerers to contact the spirit world.

JLF also offers a smorgasbord of exotic chemicals that are unknown, and unpronounceable, to the average American.

JLF also sells products which the indictment claims are "misbranded" prescription drugs, like clenbuterol, L-Dopa, and Dopamine. (Clenbuterol is a sort of pseudo-steroid, which promotes muscle growth in both animals and humans; its only approved use is as a syrup given to horses. L-Dopa can be used, as prescription drug, to combat the symptoms of Parkinson's disease. Dopamine is injected by doctors into patients with dangerously low blood pressure.)

Jennifer Bragg, an FDA attorney, says these charges basically mean that Niemoeller was "dispensing prescription drugs without a prescription."

The indictment also alleges that JLF sells a products that can be used to manufacture illegal drugs. JLF sells sassafras oil, which contains a high concentration of safrole. Safrole can be used to make MDMA, or Ecstasy, and it is considered a Schedule I listed chemical, meaning that the DEA tracks and regulates its sale. JLF also sells 1,4 butanediol, another listed chemical, which can be used to manufacture GHB, a federal Schedule I drug (1,4 butanediol can also be ingested to produce effects similar to GHB).

The indictment also charges that JLF sells 2C-T-7, allegedly an analogue of 2C-B, the club drug known as Nexus.

The DEA and FDA have spent years going after Niemoeller, presumably on the assumption that Niemoeller is, in reality, operating a quasi-legal drug-dealing operation.

Whether the police are right, or whether Niemoeller is a legitimate businessman ? who has successfully carved out a lucrative niche market, carefully operating on the outskirts of federal drug laws ? has yet to be determined.

The FDA Investigation, Summer Rose Pray and Senator Daschle

According to discovery documents in the Niemoeller case, police were aware of JLF as early as 1990. A DEA report shows that agents came across packages of dried mushrooms (presumably amanita muscaria) in New York in 1990, as well as morning glory seeds, a San Pedro cactus and jimson weed in Detroit in 1994, all of which allegedly came from JLF.

There were reports from U.S. Customs, the U.S. Border Patrol and various informants about suspicious activity connected with JLF.

But police did not become especially interested in JLF until a series of overdose cases in the late 1990s that were allegedly caused by the consumption of JLF products.

Reports filed by Special Agent Vincent Perino of the FDA's Chicago Field Office show that the FDA first began investigating JLF in December 1998.

Perino writes that Detective Eric Hall of the Cincinnati Police Department informed him of the near-fatal overdose case of Michael Sims, who nearly died after ingesting 1,4 butanediol. Sims allegedly obtained the chemical from JLF.

Hall did some checking on JLF: he discovered that Jeff L. Frownfelter, 42, of Ellettsville, opened a P.O. Box for JLF in 1987. Mark N. Niemoeller added his name to the P.O. Box in 1991. Police guessed that the initials "JLF" most likely stood for Jeff L. Frownfelter.

Police also began to purchase JLF products for laboratory testing. Hall purchased a quantity of 5-MeO-DMT. Other agents were to follow, buying clenbuterol, sassafras oil, cohoba seeds, 2C-T-7 and several other products.

On March 3, 1999, Hall told Perino about the overdose death of a 20-year-old University of Minnesota sophomore named Summer Rose Pray. Pray committed suicide on Sept. 18, 1998, by taking a massive overdose of dextromethorphan hydrobromide, or DXM, which Pray allegedly obtained from JLF. Police have several receipts of the purchases Pray allegedly made from JLF.

DXM is the active ingredient in most over-the-counter cough syrups. In recommended doses, it acts as an expectorant; in large doses, it can cause hallucinations and out-of-body experiences ? "robotripping," as DXM enthusiasts call the unique state of consciousness produced by the drug.

Summer Pray's father, Ron Pray, was outraged by his daughter's death, and contacted Senator Tom Daschle's office.

Ron Pray sent a letter to Ace Gallagher, a Daschle staffer, on April 2, 2000, in which Pray chronicles his daughter's drug abuse (beginning with marijuana), her purported addiction to DXM, and her participation in various drug treatment programs. (A fax cover sheet, included in discovery documents, shows that Senator Edward M. Kennedy's Labor Police Office was also aware of Pray's letter.)

After Summer Pray finished an out-patient drug-treatment program and began "seeing a psychologist for depression," Ron Pray sent a letter to JLF in August, 2000, "asking that they not provide this substance [DXM] to her again."

According to a receipt obtained by police, however, Summer Pray did make another purchase of DXM from JLF shortly before she committed suicide.

"I investigated JLF and found that they readily sell dangerous drugs and mushrooms but have a disclaimer that it is not for consumption," Ron Pray wrote to Daschle's office. "They make the ridiculous claim that the materials they sell are for religious worship, research or for decorations. Reading between the lines it is obvious to me that they sell an assortment of drugs to individuals for the purpose of intoxication ...

"Summer's death was a result of the combination of depression and drug abuse ... I feel that we could have dealt with her depression successfully, had it not been for the strong addiction she developed to dextromethorphan ... Had this drug not been so readily available maybe Summer would be alive today.

"It does not seem reasonable that a company like JLF should be allowed to sell these dangerous and addictive substances. Basically, they are an internet drug dealer and apparently can operate within the laws. I would hope that somehow their activity could be stopped ... "

Ron Pray's letter, and the attention of Daschle's office, may have provided more momentum to the investigation of JLF. But distribution of DXM is not one of the charges that Niemoeller faces. In fact, DXM, while mentioned in the search warrant of Niemoeller's farm, is not listed in the federal grand jury indictment. That may be because DXM is perfectly legal and is specifically exempted from federal drug laws. And while Summer Pray may have overdosed on DXM purchased from Niemoeller, she could have accomplished the same outcome by drinking a few bottles of Robotussin.

But the case of Summer Pray may bolster the prosecution's argument that Niemoeller knows his customers are using his products for consumption.

Summer Pray isn't the only person to overdose on products that allegedly came from JLF.

At least one other death has been traced to a JLF product. Free-lance writer Mark Boal reports in the Jan. 31 issue of Rolling Stone that 17-year-old Joshua Robbins died on April 2, 2000, after snorting 35 mg of 2C-T-7 ("A Journey Into the Designer-Drug Underground"). Robbins obtained the drug from a friend, who allegedly purchased it from JLF.

(Boal also writes, more than half-way through the article, that Robbins also consumed a minithin ? 25 mg of ephedrine and 5 mg of guaifenisen ? immediately prior to snorting the whopping dose of 2C-T-7, and several hours after huffing nitrous oxide and swallowing a hit of Ecstasy, which typically can contain all sorts of adulterants.)

Boal's article also recounts the overdose death of 20-year-old Jacob Duroy, who died after snorting 35 mg of 2C-T-7, which again allegedly originated at JLF.

Discovery documents in the Niemoeller case also relate the nearly-fatal 2C-T-7 overdose of Christopher Little of Overland Park, Kan., on April 5, 2001.

Various reports from the DEA, FDA and ISP, included in discovery documents, mention at least a dozen other cases involving JLF products ? including poppy seeds intercepted in Buenes Aires, Argentina, 2C-T-7, DXM and DPT being sold at raves in Wisconsin, a bottle of sassafras oil with a JLF label found at a clandestine MDMA lab, and soldiers at Fort Campbell using 5-MeO-DIPT (or "Foxy Methoxy").

The Consumption of Non-Consumables

The big burden of proof for prosecutors will be to demonstrate that Niemoeller intentionally sold his products for consumption.

Niemoeller contends that JLF's exhaustive disclaimer is sufficient refutation of this argument.

However, Niemoeller will have to defend himself against recorded conversations he had with undercover agents regarding the consumption and illegal use of JLF products.

One of these conversations is likely to be a center piece of the case. On April 18, 2000, FDA Special Agent Vincent Perino went undercover, met with Niemoeller, bought several items, including clenbuterol, and had an extensive recorded conversation with Niemoeller.

Perino repeatedly attempts to draw Niemoeller into discussion about the illegal use of JLF's products by introducing the following topics: the pressing of Clenbuterol powder into pills, the use of Clenbuterol as a muscle-builder, the manufacture of MDMA from sassafras oil and the use of L-Tryptophan as a sleep aid.

But Perino is doing most of the talking on the tape, and much of Niemoeller's statements are somewhat ambiguous.

For example, after Perino and Niemoeller discuss the pressing of clenbuterol into pills, Niemoeller says, "Ah, I just heard this through the grapevine ... I haven't talked to any of them myself, this guy had the idea, I said, well yeah, it sounds like a pretty good idea ... "

In other portion of the conversation, Niemoeller makes these comments about "how to do business":

Niemoeller: On the other hand, you might have somebody look at my web site thinking, well that's not really the kind of web site I'm looking for, I'm looking for bodybuilding materials ...

Perino: Exactly, that's what I ?

Niemoeller: There's no bodybuilding anywhere ?

Perino: See that's what I'm thinking.

Niemoeller: On this site, they're thinking it's not gonna be there but it's really, it's all based on a lack of understanding of how ?

Perino: Right.

Niemoeller: How to do business.

Perino: Right, right, of course. I mean yeah that fucking disclaimer is the biggest ? that's hilarious.

Niemoeller: Nobody does business like us and nobody really knows how to go about thinking what we're doing.

'Nobody Really Knows'

Police and prosecutors obviously had a difficult time focusing the investigation ? particularly in figuring out how various substances were classified under federal laws and regulations.

Discovery documents, which include reports from the FDA, DEA, ISP and drug lab reports, show that police went through a whole gamut of JLF's products before deciding on the products mentioned in the indictment.

While many of these items are listed neither in the indictment nor in the search warrant, prosecutors did succeed in preventing Niemoeller from selling them, if only for a limited time.

In order to get out of the Marion County jail, Niemoeller says he made a deal with prosecutors, in which he agreed not to sell the items mentioned in the indictment, as well as those in the search warrant, as well as the following products: 2C-T-2, Brazilian sassafras oil, 5-MeO-DMT, 5-MeO-DIPT, the skins of bufo marinus toads, tramadol, benzylpiperazine, L-tryptophan and betel nuts.

Whether or not JLF can continue to sell these products will be determined in court.

Niemoeller has no idea why prosecutors chose the particular items they did, or why they did not chose other products in the JLF catalogue.

He suspects that prosecutors are "trying to throw their weight around" by undermining his business.

And his business certainly has been undermined: profits have dropped off 90 percent since Sept. 7, he says, and are likely to worsen now that he has signed an agreement to stop selling the abovementioned items.

But Niemoeller is particularly annoyed at how FDA officials have handled his case. First, Niemoeller questions why his business is being targeted for the sale of L-Dopa, dopamine and clenbuterol, when there are plenty of other companies that sell the same products ? for example, the chemical supply houses where he purchased these very items.

Second, Niemoeller wonders why the FDA did not send him a warning, as it habitually does to businesses found in violation of FDA regulations.

"They could have put those items in a warning letter, and we could have avoided all this," he says.

Instead Niemoeller says police chose to act in a manner that he describes as "domestic terrorism."

"Although on a much smaller and less violent scale, JLF suffered a similar attack at the hands of domestic terrorists whose activities, if unchallenged, will just as assuredly diminish and erode our freedoms as the any attack by religious zealots," reads an essay posted on (website edited)

The Legal Quagmire

The looming legal battle is likely to be long and strange, says Andrew Matternowsky, Niemoeller's attorney.

"There's virtuallly no precedent in this area," he says. "We're in an area where there's virtually no case law. If [the police] had gone in and found a pound of cocaine it would be different."

Some of the products they have in their possession are apt to cause all sorts of confusion.

Take, for example, cohoba seeds, a product offered by JLF, but one that was not mentioned either in the search warrant or in the indictment.

These South American seeds contain concentrations of 5-MeO-DMT, DMT and bufotenin. DMT and bufotenin are Schedule I chemicals. Because, however, the cohoba seeds contain DMT and bufotenin, Matternowsky argues, does not automatically imply that the seeds themselves are illegal to possess.

"Clearly those things [DMT and bufotenin] are illegal," he says, "but it's not so clear that the seeds ? a natural object containing them ? are illegal."

This confusion over the legal status of cohoba seeds may be the reason why prosecutors decided to leave them out of the indictment.

Another problem for prosecutors, Matternowsky says, is the legal status of sassafras oil.

While safrole may be on the DEA list of suspicious chemicals, there is no public information that specifically mentions sassafras oil.

Discovery documents, however, include a DEA teletype marked "sensitive" which dictates that the rule that applies to safrole also applies to sassafras oil. "This cable clarifies existing DEA policy," reads the October 1999 teletype.

But there is no way that Niemoeller could have had access to that document, or even had knowledge of the "clarification," which was apparently not made public.

Matternowsky also argues that the outcome of the case could be potentially "disastrous" for the civil liberties of all Americans.

"There are so many natural sources for controlled substances and chemicals that can be used to manufacture controlled substances ... that anybody could be at risk at any time," he says. He picks out the example of phalaris arundinacea, a common lawn grass that contains high concentrations of bufotenin and DMT.

"How do you know that the ornamental border grass around your flower garden doesn't contain DMT?" he says.

"It's very interesting. I'm really at a point where we don't know completely what to do because the whole thing is so obscure and vague," Matternowsky says. "I think, in a true-believer sense, these agents are convinced that what [Niemoeller] is doing is illegal. The problem is, there's not really a factual basis for them to say that."

Travis Dunn, a former police-beat reporter for The Star Democrat in Easton, Md., now works as a free-lance writer in Fort Myers, Fla. You can reach him at pressbuzzard@yahoo.com.

There's a thin line between sanity and insanity... and I just snorted it.

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Trip'n Time

Registered: 11/17/02
Posts: 2,207
Loc: Florida
Last seen: 12 years, 2 months
Re: Grey market troubles [Re: John]
    #2329606 - 02/13/04 07:39 AM (14 years, 2 months ago)

Thats fucked up. Well it looks like for now all he needs is a good lawyer and he's out. At most he's in the grey area of the law, hasn't broken anything...

Maybe he can sue them afterwards to recover court fees and lost profit.

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Registered: 05/25/02
Posts: 3,972
Re: Grey market troubles [Re: DailyPot]
    #2331935 - 02/13/04 08:27 PM (14 years, 2 months ago)

Damn, suicide by DXM??  :oogle:
That article is 2 years old

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Registered: 08/08/03
Posts: 7,026
Loc: Vancouver, B.C.
Re: Grey market troubles [Re: zeta]
    #2333819 - 02/14/04 11:24 AM (14 years, 2 months ago)

yeah old but still intersting, just a precaution to people. i had a rc site up for a while and operational for a week and read that and took everything down quick, i don't wanna have to deal with that shit especially since i post on here about consuming the stuff i sold.

There's a thin line between sanity and insanity... and I just snorted it.

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Registered: 09/07/02
Posts: 397
Last seen: 5 years, 25 days
Re: Grey market troubles [Re: John]
    #2335932 - 02/15/04 02:07 AM (14 years, 2 months ago)

Using LexisNexis, I was able to find the complete trial summary for the case. The motion to dismiss the case, brought on by Mark Niemoeller, was denied on January 24, 2003.



CAUSE NO. IP02-0009-CR-01-H/F


2003 U.S. Dist. LEXIS 4584

January 24, 2003, Decided


DISPOSITION: Defendant's motion to dismiss denied.

COUNSEL: For plaintiff: Bradley A Blackington, Office of the US Attorney, Indianapolis, IN.

For defendant: Jason-R Barclay, Mark D Stuaan, Barnes & Thornburg, Indianapolis, IN.

JUDGES: DAVID F. HAMILTON, JUDGE, United States District Court, Southern District of Indiana.



Defendant Mark Niemoeller has moved to dismiss Counts Nine, Eleven, and Twelve of the superseding indictment. Defendant argues that the Controlled Substance Analogue Enforcement Act of 1986, 21 U.S.C. ?? 813 and 802(32), is so vague that his conviction under the Act would deprive him of liberty without due process of law. The court held an evidentiary hearing on the motion on January 3, 2003, and the parties have submitted post-hearing briefs. For the reasons explained below, the motion to dismiss Counts Nine, Eleven, and Twelve is denied.

Counts Nine and Eleven charge that defendant violated 21 U.S.C. ? 841(a)(1) and ? 813 by knowingly distributing a substance known as 2-CT-7, which is [*2] a short name for 2,5-dimethoxy-4-(n)-propylthiophenethylamine. The indictment charges that 2-CT-7 is an unlawful analogue of the Schedule I controlled substance known as 2CB and "Nexus." Count Twelve charges that defendant violated 21 U.S.C. ? 841(a)(1) and ? 813 by knowingly distributing 1,4-butanediol, which the government charges is an analogue of the Schedule I controlled substance gamma hydroxybutyrate, also known as "GHB."

At the time of the alleged distributions, in April and June 2001, 2-CT-7 and 1,4-butanediol were not "scheduled" controlled substances under federal law. These charges in the superseding indictment are based on the Controlled Substance Analogue Enforcement Act ("the Act"). As amended, the Act provides: "A controlled substance analogue shall, to the extent intended for human consumption, be treated for the purposes of any Federal law as a controlled substance in schedule I." 21 U.S.C. ? 813. The Act includes a detailed definition of a "controlled substance analogue," which was added to the definition section of the Controlled Substance Act:
(32)(A) Except as provided in subparagraph (C), the term "controlled [*3] substance analogue" means a substance --

(i) the chemical structure of which is substantially similar to the chemical structure of a controlled substance in schedule I or II;

(ii) which has a stimulant, depressant, or hallucinogenic effect on the central nervous system that is substantially similar to or greater than the stimulant, depressant, or hallucinogenic effect on the central nervous system of a controlled substance in schedule I or II; or

(iii) with respect to a particular person, which such person represents or intends to have a stimulant, depressant, or hallucinogenic effect on the central nervous system that is substantially similar to or greater than the stimulant, depressant, or hallucinogenic effect on the central nervous system of a controlled substance in schedule I or II.

(B) The designation of gamma butyrolactone or any other chemical as a listed chemical pursuant to paragraph (34) or (35) does not preclude a finding pursuant to subparagraph (A) of this paragraph that the chemical is a controlled substance analogue.

(C) Such term does not include --

(i) a controlled substance;

(ii) any substance for which there is an approved new [*4] drug application;

(iii) with respect to a particular person any substance, if an exemption is in effect for investigational use, for that person, under section 355 of this title to the extent conduct with respect to such substance is pursuant to such exemption; or

(iv) any substance to the extent not intended for human consumption before such an exemption takes effect with respect to that substance.

21 U.S.C. ? 802(32). n1

- - - - - - - - - - - - - - Footnotes - - - - - - - - - - - - - - -

n1 The government has agreed with the defense in this case that the government must prove beyond a reasonable doubt both part (i) and either part (ii) or part (iii) of the definition of an analogue under ? 802(32)(A). Accord, United States v. Washam, 312 F.3d 926, 930 (8th Cir. 2002) (adopting same interpretation); United States v. Vickery, 199 F. Supp. 2d 1363, 1368 (N.D. Ga. 2002) (same); United States v. Forbes, 806 F. Supp. 232, 235-36 (D. Colo. 1992) (same); contra, United States v. Greig, 144 F. Supp. 2d 386, 389-94 (D.V.I. 2001) (requiring proof of only part (i) or part (ii) or part (iii)).

- - - - - - - - - - - - End Footnotes- - - - - - - - - - - - - - [*5]

Defendant Niemoeller contends that the Controlled Substance Analogue Enforcement Act is void as unconstitutionally vague, both on its face and as applied to the specific charges against him. Defendant has come forward with evidence from chemists and a physician asserting that the key concepts of "substantially similar" chemical structures and "substantially similar" stimulant, depressant, or hallucinogenic effects have no clear scientific meaning. Defendant contends these statutory terms fail to give fair notice of the conduct the criminal law forbids and punishes. The government has responded with evidence showing similarities of chemical structures and effects on the central nervous system, as well as some evidence regarding the circumstances of the charged distributions of these chemicals. The court considers first the "facial" challenge and then the challenge as applied to the two substances in question.

I. Facial Challenge to the Controlled Substance Analogue Enforcement Act

A criminal law "may be impermissibly vague because it fails to establish standards for the police and public that are sufficient to guard against the arbitrary deprivation of liberty interests. [*6] " Chicago v. Morales, 527 U.S. 41, 52, 144 L. Ed. 2d 67, 119 S. Ct. 1849 (1999) (plurality opinion of Stevens, J.), citing Kolender v. Lawson, 461 U.S. 352, 358, 75 L. Ed. 2d 903, 103 S. Ct. 1855 (1983). Such a law may raise two distinct problems: first, "it may fail to provide the kind of notice that will enable ordinary people to understand what conduct it prohibits; second, it may authorize and even encourage arbitrary and discriminatory enforcement." Chicago v. Morales, 527 U.S. at 56 (plurality opinion of Stevens, J.), citing Kolender, 461 U.S. at 357.

Defendant Niemoeller acknowledges that no federal circuit court of appeals has upheld a vagueness challenge to the Controlled Substance Analogue Enforcement Act. See United States v. Washam, 312 F.3d 926, 928 (8th Cir. 2002) (affirming conviction for distributing 1,4-butanediol as analogue of GHB); United States v. Fisher, 289 F.3d 1329 (11th Cir. 2002) (affirming conviction for distributing gamma-butyrolactone or GBL as analogue of GHB); United States v. Carlson, 87 F.3d 440, 443 (11th Cir. 1996) (affirming convictions [*7] for conspiracy to distribute MDMA as analogue of MDA); United States v. Hofstatter, 8 F.3d 316, 322 (6th Cir. 1993) (affirming convictions for distribution of listed precursor chemicals with intent to manufacture controlled substance analogues); United States v. Granberry, 916 F.2d 1008, 1010 (5th Cir. 1990) (affirming conviction for using telephone to distribute analogue of MDA); United States v. Desurra, 865 F.2d 651, 653 (5th Cir. 1989) (affirming convictions based on MDMA as analogue of MDA).

Defendant argues, however, that these cases failed to apply the proper standard to a facial challenge to the Act. The Eleventh Circuit in Carlson, the Sixth Circuit in Hofstatter, and the Fifth Circuit in Desurra indicated that the Act could not be challenged as facially invalid for vagueness because it does not threaten to chill protected First Amendment activity. All three courts cited United States v. Mazurie, 419 U.S. 544, 550, 42 L. Ed. 2d 706, 95 S. Ct. 710 (1975), to support their treatment of the issue, as did the Eighth Circuit in Washam and the Eleventh Circuit in Fisher.

In Mazurie, the [*8] Supreme Court affirmed convictions for introducing alcoholic beverages into "Indian country," despite some room for argument about the scope of a statutory exception for operating a tavern in a "non-Indian community." The Court wrote: "vagueness challenges to statutes which do not involve First Amendment freedoms must be examined in the light of the facts of the case at hand." 419 U.S. at 550. The Court evaluated the due process challenge only as applied to the actual facts of the case, rather than to hypothetical situations that might pose more difficulty in drawing the line between lawful and unlawful conduct. The Court explained that the term "non-Indian community" had "a meaning sufficiently precise for a man of average intelligence to 'reasonably understand that his contemplated conduct is proscribed.'" Id. at 553, quoting United States v. National Dairy Products Corp., 372 U.S. 29, 32-33, 9 L. Ed. 2d 561, 83 S. Ct. 594 (1963). Most important for present purposes, the Court based its decision on the facts of the specific case. After reviewing the evidence, the Court concluded: "Given the nature of the Blue Bull's location and surrounding [*9] population, the statute was sufficient to advise the Mazuries that their bar was not excepted from tribal regulation by virtue of being located in a non-Indian community." Id.

Defendant Niemoeller argues that Chicago v. Morales expressly authorizes facial void for vagueness challenges to statutes not involving the First Amendment, so that Mazurie, Carlson, Hofstatter, and Desurra should not longer be deemed reliable authority, and Washam and Fisher should not be followed.

The court is not persuaded by this argument, which is based on an unduly expansive reading of Morales. In Morales, a Chicago ordinance authorized police officers to order people to disperse if they reasonably believed the people to be gang members loitering in public places "with no apparent purpose," and to arrest a person who disobeyed the order. The Supreme Court majority found the ordinance invalid because it gave law enforcement officers no guidelines for enforcing it, especially in determining whether a person was loitering "with no apparent purpose." 527 U.S. at 60-64. In opinions concurring in part and concurring in the judgment, Justices O'Connor and Breyer emphasized [*10] this lack of guidance for law enforcement. They declined to join Justice Stevens' plurality opinion regarding the fair notice analysis, which is the portion defendant Niemoeller emphasizes in this case. See 527 U.S. at 65-67 (O'Connor, J.); 527 U.S. at 70-73 (Breyer, J.). The narrowest grounds for the Court's judgment are the controlling reasoning for the lower federal courts. See Marks v. United States, 430 U.S. 188, 193, 51 L. Ed. 2d 260, 97 S. Ct. 990 (1977).

Justice Breyer explained that the Chicago ordinance could not be applied constitutionally to anyone because it provided no standards for police officers in applying the "no apparent purpose" element:
The ordinance is unconstitutional, not because a policeman applied this discretion wisely or poorly in a particular case, but rather because the policeman enjoys too much discretion in every case. And if every application of the ordinance represents an exercise of unlimited discretion, then the ordinance is invalid in all its applications.

527 U.S. at 71 (Breyer, J., concurring) (emphasis in original). Justice O'Connor made a very similar point:
As [*11] it has been construed by the Illinois court, Chicago's gang loitering ordinance is unconstitutionally vague because it lacks sufficient minimal standards to guide law enforcement officers. In particular, it fails to provide police with any standard by which they can judge whether an individual has an "apparent purpose." Indeed, because any person standing on the street has a general "purpose" - even if it is simply to stand -- the ordinance permits police officers to choose which purposes are permissible.

Id. at 65-66 (O'Connor, J., concurring) (emphasis in original).

The Controlled Substance Analogue Enforcement Act poses challenges, to be sure, as discussed in more detail below regarding as applied challenges. The Act's challenges, however, are not comparable to the defect of the ordinance in Morales, and they do not support the sort of facial challenge that defendant has brought in this case. The Act provides substantial guidance, even though it may be difficult to apply in some cases. To convict someone for violating 21 U.S.C. ? 841(a)(1) and ? 813 by distributing a controlled substance analogue, the government must be prepared [*12] to prove knowing distribution of a substance intended for human consumption. The key concepts in the Controlled Substance Analogue Act -- substantial similarity of chemical structure and substantial similarity of stimulant, depressant, or hallucinogenic effects -- provide significant guidance for both law enforcement and citizens who seek to comply with the law. Those concepts may not provide absolute certainty in every case in which a person seeks to experiment in reaching the outermost boundaries of lawful conduct, but that is not the standard for due process. On its face, the statute gives fair notice to persons of average intelligence of the conduct proscribed. Whether that notice is sufficient must be determined in context, as applied to the facts of a specific case, including the details of the particular compounds in question, their actual, intended, or claimed effects, and the defendant's conduct regarding those compounds.

Defendant also points out that a person may need expert advice from a chemist and/or physician or psychologist to determine whether a compound is an analogue. The need for such additional information does not render the statute unconstitutionally vague. [*13] When dealing with legislation on complex or technical matters -- whether it concerns intricate corporate tax issues, the details of electronic securities transactions, or international trade in "dual use" technologies -- Congress can expect a person who wishes to engage in the activity to acquire the necessary specialized knowledge to conform the person's conduct to law. Similarly, when dealing with the distribution of organic chemical compounds for human consumption and with intended or hoped-for central nervous system effects, Congress could reasonably expect and require persons engaged in that activity to possess or obtain the specialized knowledge needed to conform their conduct to law. Also, it takes a chemist to understand many of the compounds on schedule I under the Controlled Substances Act. See 21 C.F.R. ? 1308.11. n2 Defendant Niemoeller's facial challenge to the Controlled Substance Analogue Enforcement Act is overruled.

- - - - - - - - - - - - - - Footnotes - - - - - - - - - - - - - - -

n2 Schedule I includes, among many compounds: Acetyl-alpha-methylfentanyl (N-[1-(1-methyl-2-phenethyl)-4-piperidinyl]-N-phenylacetamide); Alpha-methylfentanyl (N-[1-(alpha-methyl-beta-phenyl)ethyl-4-piperidyl] propionanilide; 1-(1-methyl-2-phenylethyl1)-4-(N-propanilido) piperidine); 4-Bromo-2, 5-dimethoxyphenethylamine; N, N-dimethylamphetamine (also known as N, N-alpha-trimethyl-benzeneethanamine; N, N-alpha-trimethylphenethylamine); and N-[1-(2-thienyl)methyl-4-piperidyl]-N-phenylpropanamide (thenylfentanyl), its optical isomers, salts and salts of isomers. Surely the "average" person on the street would need some help in interpreting and applying this law, but that need does not preclude the enforcement of the law. For another challenging provisions of federal law requiring expert guidance, see 26 U.S.C. ? 809 (tax provision designed to equalize tax burdens on mutual life insurance companies and stock life insurance companies); see generally 26 U.S.C. ? 1 et seq.

- - - - - - - - - - - - End Footnotes- - - - - - - - - - - - - -


II. Count Twelve: 1, 4-Butanediol as Analogue of GHB

As applied to Count Twelve, the alleged distributions of 1, 4-butanediol as an analogue of GHB, the Eighth Circuit's decision rejecting such a vagueness challenge in United States v. Washam is directly on point. 312 F.3d 926 (8th Cir. 2002). The case involved the same compounds and testimony from some of the same witnesses. Judge Sweet's decision to dismiss similar charges in United States v. Roberts, 2002 U.S. Dist. LEXIS 16778, 2002 WL 31014834 (S.D.N.Y. Sept. 9, 2002), is also on point and reached the opposite result regarding 1, 4-butanediol.

In Washam, the Eighth Circuit affirmed convictions in the face of a vagueness challenge presenting essentially the same arguments that defendant makes here: that the concepts of substantially similar chemical structure and substantially similar effects are too vague to give fair notice of the conduct proscribed, and that if courts and experts disagree on the meaning of the statute as applied to the case, a conviction must violate due process.

The Eighth Circuit relied on the "extraordinarily relevant" evidence to the effect that after a person ingests 1, 4-butanediol, [*15] the compound is metabolized by enzymes in two steps so as to become GHB. 312 F.3d at 932-33. The court also discussed the evidence that the effects on the central nervous system are substantially similar, though not necessarily identical. Id. The fact that not all available expert witnesses agreed that one substance is an analogue of the other did not mean the statute was unconstitutionally vague as applied. Washam, 312 F.3d at 931, citing United States v. McKinney, 79 F.3d 105, 108 (8th Cir. 1996), vacated on other grounds, 520 U.S. 1226, 137 L. Ed. 2d 1025, 117 S. Ct. 1816 (1997).

This is not to say that Washam determined as a matter of law that 1, 4-butanediol is an analogue of GHB. Rather, the Eighth Circuit affirmed a conviction by a jury that had heard conflicting evidence about the chemical structures and effects of the compounds, and that had been instructed on the statutory definition of a controlled substance analogue. 312 F.3d at 928-29. The government will still be required to prove the elements here beyond a reasonable doubt, if it can.

The court has also considered Judge Sweet's decision in Roberts, which the Eighth [*16] Circuit criticized in Washam. The court agrees with the Eighth Circuit's criticisms. The Roberts decision seems to conclude that similarity of chemical structure must be decided in the abstract, without consideration of other facts, such as the metabolism of the compound. See 2002 WL 31014835, *4 (minimizing significance of fact that body metabolizes 1, 4-butanediol into GHB, with similar pharmacological effects). But consideration of structural similarity does not or should not take place in a vacuum. The question must be refined -- similar in what ways and for what purposes? The answer is apparent from the provisions and purposes of the Controlled Substances Act and the Controlled Substances Analogue Act. The concern with analogues is with substances intended for human consumption. Such intent is an element of 21 U.S.C. ? 813. The government is also required to prove that the alleged analogue has stimulant, depressant, or hallucinogenic effects "substantially similar to or greater than" the effects of a controlled substance in schedule I or II (or that the defendant claimed it would have such effects). Such effects may be considered in [*17] evaluating structural similarity. Washam, 312 F.3d at 932-33 (court and jury may consider the effects on the human body when determining whether the chemical satisfies the structural similarity requirement). Consideration of such effects does not, in this court's view, conflate two distinct statutory requirements, but instead allows a pragmatic approach consistent with the Act's concerns about experiments with human consumption of organic compounds. But see Roberts, 2002 WL 31014834, *5 (criticizing government for conflating two elements of analogue definition).

The 1, 4-butanediol and GHB molecules are identical in structure along the central carbon chain and in the functional groups at one end of that chain. The two compounds have different functional groups at the other end of the chain. GHB contains a carboxylic acid functional group of one carbon atom bonded to two oxygen atoms, one of which also bonds with one hydrogen atom. 1, 4-Butanediol contains an alcohol functional group of one carbon atom bonded to one oxygen atom, bonded in turn to one hydrogen atom. It is possible to synthesize or discover many other organic compounds with the same [*18] common structure and different functional groups at the point where GHB and 1, 4-butanediol differ. In evaluating structural similarity, however, it is at least relevant that the body metabolizes 1, 4-butanediol in a matter of minutes to produce GHB. That combination of structural similarity and similar effects in the body could support a reasonable finding, as in Washam, that 1, 4-butanediol is an analogue of GHB. And that combination of structural similarity and similar effects can be sufficient to give fair notice to a person distributing 1, 4-butanediol for human consumption that the compound is an analogue of GHB. At least prior to trial, the court cannot say that a conviction here would violate due process. Defendant's motion to dismiss Count Twelve is hereby denied.

III. Counts Nine and Eleven: 2-CT-7 as Analogue of "Nexus"

A compound known as 2CB, also known as "Nexus," is a schedule I controlled substance. Its chemical name is 2,5-dimethoxy-4-bromo-phenethylamine. It has a phenyl ring, an amine side chain extending from the number one carbon atom on the ring, and oxygen-carbon chains extending from the number two and five carbon atoms on the ring. Attached to [*19] the number four carbon on the ring is a bromine atom.

Counts Nine and Eleven charge defendant Niemoeller with distributing 2-CT-7, also known as 2, 5-dimethoxy-4-(n)-propylthiophenethylamine. See Govt. Ex. 9. At the time of the alleged distributions in 2001 in this case, 2-CT-7 was not a controlled substance, but it has since been added to schedule I on a temporary and emergency basis. See 21 C.F.R. ? 1308.11(g)(5). The structure of 2-CT-7 is the same as that of 2CB except at the number four carbon on the phenyl ring. Instead of the bromine atom on 2CB, 2-CT-7 has a sulfur atom, from which extends a further chain of three carbon atoms with seven hydrogen atoms attached.

The evidence offered at the hearing concerning 2CB and 2-CT-7 was much more limited than that offered concerning 1,4-butanediol and GHB. Nevertheless, the government has come forward with some evidence tending to show substantial structural similarity and substantially similar hallucinogenic effects. Whether the government may ultimately meet its burden remains to be seen. The evidence offered concerning structure and effects is of the same general type that persuaded the Eighth Circuit [*20] in Washam and the Eleventh Circuit in Fisher to reject vagueness challenges to the analogue definition as applied to those cases. The court finds those decisions persuasive on this point, and defendant's motion to dismiss Counts Nine and Eleven is hereby denied.

So ordered.

Date: January 24, 2003


United States District Court

Southern District of Indiana

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