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'Born Illegal' -- Exploring the Powerful Advanced Psychedelics Invented by the Father of Ecstasy

Surveying Alexander Shulgin's pioneering work with phenethylamine compounds, the ‘alchemy of medicinal chemistry,’ and the threat posed by the Federal Analogue Act.
 
 
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By all accounts Anthony Reed was what you would have called a model citizen. In a very traditional sense, he was a hardworking young man looking at a very bright future. He attended an exclusive boarding school for gifted students, and after posting a near-perfect score on the ACT and a 3.7 GPA at Louisiana Tech University, he found himself wooed by graduate programs across the country. Rather than go straight to grad school, though, Reed felt it was his obligation to volunteer a portion of his most able-bodied years to what he called “the betterment of society.” He applied for an Americorps post and was quickly accepted and dispatched to the Berkshires in Massachusetts to begin work on a conservation project that helped maintain federally protected land.

In mid-April of this year, the 22-year old Reed took a well-deserved break and drove to the Wanee Music Festival in Live Oak, Florida. He brought with him gallons of homemade gumbo that he and a friend planned to give away, and three small doses of an obscure psychedelic compound known as “2C-I.” Each 10 mg dose was just enough for a stimulant effect, according to Reed, to keep him awake and dancing all night to Government Mule, Widespread Panic, and the Allman Brothers Band.

Reed was introduced to psychedelics sometime in his sophomore year of college, where he was very active on campus and maintained a high GPA, all the while choosing to smoke marijuana instead of doing “the typical college drinking thing.” He already knew marijuana was not the “evil, dangerous drug people portrayed it to be.”

“My experimentation with psychedelics came as a result of the same understanding I went through with marijuana... if I had been lied to my whole life about that, I figured I'd find out what else I was lied to about.”

Reed was interested in exploring psychedelics and researched a number of them on Erowid, the free and extensive internet archive of psychoactive substances that contains thousands of anonymous reports of the effects of various substances. After some basic experimentation with LSD,  Reed came to many profound realizations that fundamentally changed his life and worldview.

“I feel like I got a boost of motivation a nd developed my own understanding of how I relate to the rest of the universe and what part I play in this world.”

He shared his experiences anonymously on Erowid, and soon began exploring more compounds, where he learned about the 2C drugs. He was looking for something that had the potential “to give me other perspectives I had not otherwise experienced on LSD.”

Reed first heard of 2C-I by reading the experience reports on Erowid, and the book PIHKAL, an archive of psychedelic compounds created by Dr. Alexander “Sasha” Shulgin , a former research chemist for Dow Chemical who is best known for introducing MDMA to psychedelic culture, and who was also the inventor of 2C-I. Reed felt he made an informed decision that 2C-I was safe to try. No deaths had ever been reported on the substance.

“It also had the benefit, so I thought, of keeping me out of trouble.”

Reed believed it was not against the law to possess 2C-I since it is an “unscheduled” compound, meaning it does not appear on the federal schedule (or ranking system) of Controlled Substances, nor is it explicitly made illegal in any known law. This makes it technically “not-illegal.” This distinction was critical to Reed, because he had worked too hard to jeopardize everything he had going for him to risk getting busted for possession of illegal drugs.

That measure of security would prove to be chimeric.  

Expecting only 10,000 people, the festival was overwhelmed when three times that number flowed through the gates. In response, like flies to a bloated carcass, it also appears that a commensurate number of undercover police officers joined in. Word quickly began to circulate about the sheer number of cops among them, and the equally audacious number of people getting busted for what seemed like ultra-petty offenses like smoking pot.

Pot busts are extremely rare at major music festivals like this one, where smoking in the open is de rigeur.   The conventional wisdom has been that these festivals provide safe containers for minor drug use, and the logistics of hauling out petty offenders to face misdemeanor busts was too cumbersome for zealous enforcement. Not so at Wanee, where it seemed like the police were out for blood (or at the very least, bank).

After the Allman Brothers set, Reed and two friends left the main stage and were hanging out together in a darker, quieter area of the festival grounds when a young man approached them and struck up a conversation. At gatherings like these, this is not at all out of character.

“We started talking about music we like, and he mentioned Phish and STS9. He started naming individual shows, like the Rothbury (Michigan) STS9 show in 2008, which we both agreed was amazing. We connected immediately.”

Appearing as if he might be fishing (or Phishing, as the case may be) for a hook-up, about a half hour later the stranger says, "It just sucks. I got some bunk tabs earlier. I wish I could find something here that wasn't fucking bunk. You guys know where to get any molly (MDMA)?"  This too is not an unfamiliar practice at festivals, which, the police would argue, is why their presence is justified.

“I told him that I didn't have any molly, but I had this one 2C-I pill left. He seemed curious so I explained to him what it was. He begged me to let him buy it, so I let him have it. He offered me ten dollars for it. I shrugged and took it. As soon as that happened, BAM! He grabbed my arm, and told me that I had sold to an undercover.”

Reed maintained a level head though, did not struggle, and pleaded his innocence while remaining calm and avoiding the stupid kinds of self incrimination most fall into once confronted by police.  He informed the undercover and his Sergeant  that the substance they took from him was not illegal. They were having none of it. They charged him with “sale of MDMA” and “possession of MDMA with intent to distribute.” In other words, they not only set him up, and got the charge wrong, but they called him a drug dealer too.

“I told the undercover the charges wouldn’t stick,” Reed said.

He also claims the Sergeant told the undercover that he could let Reed go, and that the only way Reed might have broken the law is if he sold the 2C-I in “lieu of MDMA”  as if he tried to pass it off as MDMA.”

“That’s exactly what he did,” the undercover told his superior.

Reed was incensed, and protested, but they laughed him off. It was only the beginning. He must have felt like he was in an alternate universe when the police later informed him that his 2C-I “field tested positive for MDMA.”

Whether this was true, or whether it was simply a charge that would stick, the net result was that Reed, the ostensibly well-read, law-abiding, volunteer civil servant, was now facing a felony bust, and the end of that promising future.

2C, or not 2C...that is the question

How is it that a purportedly legal substance (or at the very least, one that is not explicitly illegal) garners a felony bust? Perhaps we should begin by taking a look at the mysterious compound that caused all the trouble.

2C-I (or 2,5-dimethoxy-4-iodophenethylamine) belongs to a family of twenty-nine “2C” compounds which include the more notable 2C-B, 2C-E, and 2C-T-7 that are designated Schedule 1 or “dangerous with a high abuse potential and no known or accepted medicinal applications.” All of these compounds were invented (“synthesized” is how the chemists put it) by Shulgin.

Of course, that’s just the government talking, so you know where to rank their opinion. They say the same thing about marijuana, LSD, peyote, psilocybin, and DMT, none of which are addictive in the strict sense of the word, even though arguably marijuana can and does produce some “psychological dependency.” As to whether any of these substances are dangerous, well, that’s really all in how you define “dangerous.”  

Psychedelics are certainly considered dangerous by the powers that be, but not because of any imminent physical harm; it’s their perceived power to up-end the social order that is the real threat. But forty years after that particular breed of hysteria swept the nation, the scientific establishment is quickly reversing their opinions on much of this fear-mongering.  Let us remember that most these substances have been used as traditional medicines for thousands of years, and too much of anything is no good. Even ancient tribes had their rules and regulations, and the Shamans usually lived on the fringes of society.

The 2C drugs are psychedelic compounds that some classify as “entheogenic,” or substances that facilitate spiritual experiences.  Sasha, as a scientist, prefers the term “psychedelic,” derived from the Greek word for for “mind-manifesting.”   These substances are mostly found in the self-described “psychonaut” or consciousness-expanding culture, but regularly pop-up in rave culture as well, particularly 2C-B, which is as common as MDMA in many rave circles.

For anyone who thinks the “entheogen” moniker is a ruse that lacks virtue, 2C-B is used as a healing sacrament by some indigenous South African tribes. 2C-B is the active ingredient of a semi-synthetic “herbal” compound called “Ubulawu Nomathotholo” or the “Medicine of the Singing Ancestors.”  What makes this unique is that in this case shamanic healers chose this semi-synthetic over their traditional healing plants.

The 2C compounds produce a wide range of effects. Some are highly visual, while some are deeply introspective. Others enhance cognition or have primarily emotional effects. Many have few overt psychedelic effects at all. They are generally less potent and shorter acting than other more well known psychedelics.

2C-B is known as a sensual, tactile drug, often referred to as an “aphrodisiac.” 2C-T-7 is called “7th-Heaven” because it tends to produce states of enlightenment. 2C-E is known as “the teacher” because it promotes optimism, thoughtfulness and creativity. 2C-I is a more traditional, overtly LSD-like psychedelic, tending to be more visual and intellectual.

“The story of the 2C compounds,” says chemist Paul Daley, co-author with Sasha Shulgin and Tania Manning of The Shulgin Index: Psychedelic Phenethylamines & Related Compounds, “really starts with the first attempts to modify known naturally occurring psychedelics, to change their activity. This began in 1949 with the creation of the first synthetic analog of mescaline.”  

Mescaline, the principle active agent in peyote, was the first known psychedelic. Its use goes back over 7,000 years. It belongs to a family of compounds known as “phenethylamines,” which include the 2C family and more well-known drugs like MDMA, MDA, amphetamine, anti-depressants like Wellbutrin and Effexor, and essential amino acids like L-tyrosine. Phenethylamines are structurally close to dopamine, which is naturally occurring in the brain, and is involved with the sensing of pleasure and ‘reward.’ Phenethylamines are thought to be involved in the drive to repeat dosing with drugs such as cocaine and amphetamines, that stimulate dopamine receptors in the brain.

Until the 20th century, mescaline and cannabis were the only known drugs that were considered “psychedelic” (cannabis has mostly freed itself of this misclassification, although many assert that in the context of “mind-manifesting” it is a classic “psychedelic”). As of the passage of the Controlled Substances Act, there were another 150 known psychedelics, 11 of which including those mentioned above ended up on the federal drug schedule. This had the single largest impact on drug policy, because it took down the titans of psychedelia and began the 40-year dark age where legal scientific exploration of these compounds nearly ground to a halt.

As we enter the second decade of the new millennium, The Shulgin Index identifies some 1350 known compounds, of which roughly a third have been tested on humans and proven as psychoactive. Shulgin is credited with many of their discoveries as well.

Each of these enumerate phenethylamine compounds, sometimes referred to as “Sasha’s children,” are catalogued in PIHKAL, which stands for Phenethylamines I Have Known And Loved.”  This remarkable work of science and psychology by Shulgin and his wife Ann is a book for the ages. It also brought them no end of grief, or adulation, for daring to publish the results of their lifelong “relationship” with their “children.”

Paul Daley is part of a core group of people referred to as Team Shulgin by their friends, who help Ann and Sasha to carry on the legacy of their work. Team Shulgin includes Ann’s daughter Wendy Tucker, who edited PIHKAL and the sequel, TIHKAL (Tryptamines I Have Known And Loved) , and is the head of Transform Press, the publisher of Shulgin books; and Greg and Tania Manning, the Shulgin researchers/writers/archivists/personal assistants who live, work and travel with them. An honorable mention goes to Earth and Fire Erowid, co-founders of their eponymously named website, who the Shulgins call “trusted family.” Erowid is the largest drug info library in the world, and they have posted large sections of both Shulgin books, PIHKAL and TIHKAL (which I affectionately refer to as “Pickle-Tickle”).

Atop Shulgin Hill

Ann and Sasha’s hilltop home east of the San Francisco Bay bears all the traits of a hidden sanctuary. It’s located off a tiny road named “Shulgin Lane” along a winding highway that straddles the hills around Mount Diablo. The modest ranch-style house is tucked in the fold of a hill, shrouded beneath an ancient grove of trees. Beside the house lies a short path that leads to Sasha’s laboratory, the most well-known, and revered, part of the property. This 10x20 foot wood and corrugated metal shack is to many around the world a holy site, a place where divine spiritual energy was distilled from the ether, concentrated into molecules, and given unto humanity through the work of a chemical prophet.

Hyperbole aside, calling the Shulgins prophets is not that big a stretch of the imagination. Their books have touched millions of lives through their naked and fearless exploration of the human psyche, and their most intimate life moments. More than that, the canon of compounds Sasha created has been at the core of a psychedelic revolution many years in the making that is just now re-emerging with force. This time, however, the revolution comes with bona fides , slowly walking hand in hand with policy and medicine. Timothy Leary may have been the mad prophet of modern psychonaut culture, as much as Albert Hofmann was their Werner Von Braun. But Sasha and Ann are Adam & Eve; for it was they, in a manner of speaking, who first dared to taste of the molecular tree of knowledge.

“Being an organic, medicinal chemist is a bit like chemistry bifurcated from alchemy,” offers Paul Daley.

Still, for all the chemical wizardry, there is more doctor in their efforts than alchemist. In the traditional practice of making medicines, the chemist would first extract a compound from  natural sources, like plants or fungi. Once the molecular structure of that compound was determined, the chemist would make modifications (consisting of moving certain atoms around the core rings of the structure) based upon certain hypotheses: We can make this drug work faster by making it more fat-soluble, by having it cross the blood-brain barrier faster, etc.

This was the precise approach Sasha took in all his work, which became known as The Shulgin Method. It is to make hypotheses about a group of closely related chemical structures, and then make the actual compounds, and then test them to evaluate their action. Sasha tested through self-experimentation. He would start with tiny doses, then wait a few days, double the dose, then wait a few days, repeat, repeat. He and Ann would measure every aspect of the experience, the medical and physiological effects, the psychological and social effects, slowly and systematically increasing the dose until he reached the point where “the true nature of the compound revealed itself.”

Anthony Reed has great respect for Sasha Shulgin. It fits, both are legitimate overachievers defined by open minds and compassionate hearts, and both got into trouble when they wandered into the legal gray zone of “designer drugs.” Of course, it was Shulgin himself who was the original “designer,” and no one knew it was a gray zone until he pioneered his way in there and opened Pandora’s Box, or discovered the Philosopher's Stone, depending on your point of view.

In response to Sasha’s “crimes” – which amount to indulging in the spirit of scientific discovery with a DEA license, and having a Promethean need to disseminate the results – his lab has been raided three times, twice by the DEA, and once by local authorities. This all but forced Sasha to give up his license to study illicit substances (although it wasn’t revoked as many believe, but rather it was a “voluntary relinquishment”).

The raids, and his designation as the “Godfather of Psychedelics,” brought negative media attention and the kinds of itinerant pleasure seekers who thought Sasha’s lab would be the new Millbrook with wild experimentation in every corner. The Shulgins prefer to stay out of the limelight. After a lifetime devoted to scientific exploration and the betterment of humanity, which they downloaded into their books, they recently appeared in Dirty Pictures , an exceptional  documentary by Etienne Sauret about “Ann and Sasha's lifelong quest to unlock the complexities of the human mind.”

Ann and Sasha are now in their twilight years, and Sasha’s health is precarious. Because of this, they value their privacy, and precious time with their family.  This is why, with few exceptions they no longer grant interviews. When they do, its usually because they have something important to say, and because they trust the messenger.

Prohibition is one of those topics on which they have much to say. The unfortunate side effect of drug prohibition is that the legitimate, objective evaluation of all of “Sasha’s children” for the betterment of humanity has, at the very least, been derided and discredited, and in some cases, been made impossible. This means that the 2C compounds, and so many of the other phenethylamines, have never been properly evaluated, for either their positive or negative properties.

“Some of them might have amazing potential for medicinal, psychological or spiritual growth and healing,” Paul Daley muses, then shrugs. “Under prohibition, certainly as it exists today, we’ll never know.”

A quick look around the circle reveals unanimous confirmation. There is so much these people could accomplish if set free to explore again. It is tragic to think of the sheer brainpower that is going to waste, but that’s a minor sacrifice when judged against those who have lost their freedom fighting for their cognitive liberty. In this context, Sasha and the rest of Team Shulgin understand his historical role quite differently. Not only are they deeply hurt by the lost knowledge caused by the 40-year dark age, they are devastated by the lost lives.  Because of the War on Drugs, the compounds Sasha discovered in pursuit of beneficent human evolution have instead led paradoxically to the arrest, incarceration, and often immiseration, of so many promising souls.

Sasha is painfully conscious of this, even though he knows it’s not his fault. Still, you have to believe that in some indirect way, they must feel at least partially responsible. These are compassionate, loving people; they have existed on this planet to heal others. Prison and criminality are the very antitheses of what they represent.   

What may be worse is that, as a direct consequence of Sasha’s work, drug laws were greatly expanded in 1986 under the Federal Analogue Act. This sweeping piece of legislation was enacted after a legal explosion in MDMA production during the mid-1980s. MDMA wasn’t explicitly illegal before 1986, so once it took hold in the culture it proliferated with the swiftness of the gods, scaring the bejeezus out of conservative America...as all of these spiritual, loving, hyper-perceptive compounds tend to do when they first roll into town.

Seeing What They Want 2C  - The Controlled Substance Analogue Enforcement Act of 1986

2C-I is not explicitly illegal, but that doesn’t mean it is legal either. Confusing? Of course it is, it’s American drug policy.

The Controlled Substance Analogue Enforcement Act was kind of like the Patriot Act for drugs. It made sure that any chemical compound even marginally similar to any scheduled compound was itself illegal, even if it hadn’t yet been synthesized and in effect existed only in theory.

According to Erowid, the Analogue Act (sometimes referred to as the “Designer Drug Law”) was explicitly enacted to allow the DEA to arrest and prosecute underground chemists who make minor changes to an existing illegal and/or scheduled substance, resulting in a new substance that can be sold as a recreational drug with the same or similar effects, but which is not specifically listed as illegal. Shulgin does not qualify here, since everything he did was legal and licensed, and as Paul Daley points out, “Sasha’s motivation was scientific and medical; quite different from a clandestine chemist seeking to make a buck.”  The broadness and vagueness of the law makes it “one of the most oppressive laws ever written, making the very creation of a new, unknown and untested chemical, illegal.” Even if the substance isn’t psychoactive, it’s still born illegal.

“Its the same with nuclear weapons technology,” Daley continues. “Any as yet uninvented piece of nuclear technology immediately becomes classified the second it is created. It’s born classified.”

This is not widely known, and so it often leads to situations, like with Anthony Reed, in which people believe they are engaging in lawful, or at least “not-illegal” behavior, when in fact they are breaking the law and putting themselves and others at risk.

“I didn’t think 2C-I was legal, per se, but I knew it existed in a gray area,” Reed admits.

He knew more than that. This is a careful kid, and he had good reason to be. This was not the first time he was involved in an egregious abuse of authority and miscarriage of justice.

When Reed was 16 he underwent major gall bladder surgery and during his recovery used marijuana, with his doctor’s knowledge, to help him eat. By his late teens he had become an advocate for marijuana reform. On Mar 26, 2009 he became something of a household name amongst the marijuana reform community when he published “Lets have an honest talk about marijuana” on the liberal website Daily Kos, and it rocketed into mega-traffic status, garnering over 1100 comments.

Less than a month later Reed’s Louisiana home was raided by twelve squad cars full of heavily armed drug interdiction cops from the Lincoln Parish Narcotics Enforcement Team. Reed and his ex-wife were home at the time. It turns out Reed’s marijuana supplier, who had prior convictions, got pinched and gave up the names of all his clients, including Reed, in an attempt to stay out of prison. With such a high-profile article about marijuana in circulation, many speculated that the police thought Reed was some kind of weed kingpin and used it as justification for the severity of the raid.

In spite of the firepower, all the police found was a small discarded ziploc bag with a few stems and seeds. Nonetheless, Reed was charged with “misdemeanor possession of marijuana.” He appealed to the Daily Kos community for help and was able to raise enough funds to hire a lawyer, who was provided by Keith Stroup, the erstwhile founder of NORML.

From that moment forward, Reed made it his business to know every legal angle when it came to drugs. In choosing to travel across state lines to attend Wanee, he made sure that Florida did not have an Analogue Act. Even if it did, he assumed it was unlikely he would be prosecuted, especially for a possession-level offenses. Only a handful of successful prosecutions had ever emerged from the Federal Analogue Act, “and those were for major suppliers,” Reed explained.

The most successful prosecution under the Analogue Act was probably Operation Web Tryp, which went down on July 21, 2004. Five websites involved in the widespread sale of “grey market” drugs – unregulated tryptamines and phenethylamines (“Sasha’s children”) – were shut down and ten people were charged. Following this bust, 2C-T-7 and a few other compounds were explicitly made Schedule 1.

The charges stuck in Operation Web Tryp because the websites explicitly stated the chemicals they sold were for human consumption, a stipulation of the Analogue Act that was reinforced after USA v. Damon S. Forbes et al., the 1992 case that challenged the legality of the Analogue Act. In the ruling handed down by the US District Court of Colorado, the government’s definition of "analogue" provided “neither fair warning nor effective safeguards against arbitrary enforcement” and so the law was voided for its “vagueness.”  The ruling made clear that the burden of proof was on the government to show that the chemicals in question were specifically intended for human consumption if any prosecution under the Federal Analog Act was to occur.

Of course, not knowing all this history or policy can be excused in young people experimenting with their own consciousness, but there is less room for error in those who actually have the knowledge and wherewithal to synthesize analog compounds, or who are advocating their use to others. At an Evolver Regional event in Long Beach last March where I was a speaker a young man held up a copy of PIHKAL and said something to the effect of, “Sasha has left us his cookbook, and all we need do is learn how to make his recipes. These substances are 100% legal!”

He had never heard of the Analogue Act. He obviously had also not read the book, because right in the opening pages you will find the following:

 
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