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All 'Smiles': the history of the 2C designer drug class

All 'Smiles': the history of the 2C designer drug class


The drugs' creator thought he'd made something beautiful; others want more evidence

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Alexsey Kashtelyan

The first time I tried 2C-B, I was at a punk rock show; I threw back the pills as we walked to the venue. 2C-B was both mild and intense, depending on the moment. "The lights dimmed and brightened, forcing a woman’s leopard-print coat to feather and contract with the shadows," I later wrote of the night. "An image decorating the wall of a woman with her hands pushed forward seemed to reach out and grab at the crowd." I experienced light psychedelic visuals, moments of paranoia, euphoria, and at one point anger, when an idiot playing pool kept getting in the way of the concertgoers. My body felt warm, electric, and sensitive to the touch, and the objects and people I looked at seemed to expand and contract in a moment.

The 2C family of drugs has a complex and sometimes controversial pastI first heard of the 2C family of drugs when a friend came to visit me while I was living in Portland, Oregon. He was a veteran in the psychedelic drug world, and he told me 2C drugs are closely related to substances like MDMA; I’d get a similar effect to MDMA but with increased psychedelic visuals and feelings. There are many versions of 2C drugs, from 2C-I to 2C-B to the infamous 2C-P, which allegedly keeps you high for as long as 24 hours. Each one has its own unique chemical properties and particular effects.

The 2C family of drugs has a complex and sometimes controversial past. They are synthetic psychedelics in the phenylethylamine class. They were first synthesized by the late Alexander Shulgin around 1974, who is known for popularizing MDMA. Like MDMA, 2C drugs were first utilized for therapeutic purposes among Shulgin and his colleagues and later became known as club drugs. No official clinical trials were done, but there was some experimentation. Rumor has it that a German company distributed 2C-B in the 1980s for use as an aphrodisiac called "Eros." If this is true, there are no records of it.

The increased interest in MDMA may revive research on 2C drugsShulgin and others have long speculated 2Cs could be used for therapeutic purposes, but a lack of basic research creates a catch-22: without any information, there’s no reason to conduct a study, says David Nichols, founding president of the Heffter Research Institute, which studies psychedelic drugs. 2Cs are known to have certain effects and dangers, but the kinds of trials a scientist would do to get a better understanding of those elements are missing. Because clinical trials are expensive, it’s hard to provide enough justification to study this family of drugs in any serious way. That means we don’t even know what dosages are dangerous. But an increased level of research interest in MDMA, the 2Cs’ older cousin, may revive interest in the drugs.

psychedelic visual

(Lukas Kästner)

When MDMA was banned in the US in 1985, 2C drugs became a quick replacement in the club scene. As was the case for many synthetic drugs, 2C drugs’ existence wasn’t well-known among government officials — which meant they weren’t illegal for some time. The main 2C varieties were eventually named as Schedule 1 drugs and became illegal around 1994. Also, like many synthetic drugs, renegade chemists began creating slightly different versions of the drugs so they could claim to sell a legal version.

When MDMA was banned in the US, 2C drugs became a quick replacement

Since the 1990s, a lot of other illegal drugs — MDMA, marijuana, LSD, and psilocybin — have been more widely studied by the medical research community. The 2C family has been an exception, though. At least in part because of a lack of knowledge around the family, some compounds have caused overdoses that can end in death. Some experts claim the deaths associated with the original 2C varieties should actually be attributed to tainted versions of the drugs, as investigators may have misidentified what kind of 2C it was — but problems can happen when too much of any 2C is taken. Altered versions of the original 2C types can also be significantly more potent, and one known physiological effect is a dangerously elevated heart rate. Problems can also occur when 2C drugs are taken with other substances.

Overdoses related to the derivative 2C-I-NBOMe have been widely publicized; users apparently often thought they were taking LSD. Some experts told The Verge it’s easier to overdose on drugs like 2C-I than it is drugs like MDMA, since it’s more potent. But with the correct dosage, 2C-I is typically regarded as being as safe as MDMA among Erowid users — a group with an interest in psychoactive chemicals.

"Smiles" is a term the media uses for 2C-I, though I've never heard anyone from the psychedelic community use that nameMost people know the family through lurid headlines like this one: "Johnny Lewis, ‘Smiles,’ and the Latest Designer Drug Panic," a story from Grantland when a Sons of Anarchy actor died in 2012. "Smiles" is a term the media has used for 2C-I, though I’ve never heard anyone in the psychedelic community refer to the compound that way.

Around 2000, three deaths were recorded related to the 2C-T–7 derivative. Shulgin, who was still alive at the time, expressed his frustration over what amateur chemists were doing to his promising creation. "I’m disturbed by the fact that you get someone who wants to make a pile of money and doesn’t give a damn about the safety or the purity," he told The Guardian at the time. "It’s a motivation that I’m uncomfortable with. People using psychedelics, I’m not uncomfortable with. I consider it a very personal exploration. But I’m very disturbed by the overpowering of curiosity with greed." Shulgin’s creation, which he believed had serious therapeutic potential, became the synthetic killer of its time.


(Erich Ferdinand)

MDMA-assisted psychotherapy has shown promise as a treatment for disorders like PTSD and anxiety in clinical studies. Shulgin always believed 2C drugs could provide similar benefits. "[2C-B] is, in my opinion, one of the most graceful, erotic, sensual, introspective compounds I have ever invented," he said during an interview with the Center for Cognitive Liberty & Ethics in 2003. "For most people, it is a short-lived and comfortable psychedelic, with neither toxic side effects nor next-day hangover. Its effects are felt very much in the body, as well as in the mind, and thus it has found clinical use as a follow-up to MDMA." MDMA could be used to help people identify their problems during therapy — then 2C-B could be administered to help them open up the "emotional, intuitive, and archetypal" areas of the brain to help them solve those problems, Shulgin said.

Studying clinical uses would require toxicity studies — which likely will cost $200,000The main issue with the 2C family of drugs continues to be the void of information on their effects and dangers. Much more research has been done on MDMA than any 2C compound. "To study any possible clinical uses would require first carrying out toxicity studies, likely at a cost of around $200,000," Nichols says. "To justify that cost to a private investor, one would have to have a good idea that the compound to be studied actually would prove to have beneficial medical effects." The evidence isn’t there yet.

That’s because when 2Cs were born, no one did any major investigations regarding medical uses of the class — or even toxicity. Even though MDMA and other compounds are relatively under-studied, enough information existed to suggest they might benefit some people. But because no similar studies have been conducted on 2Cs, there’s no hint the drugs may have therapeutic benefits.

It's possible things could change, and once again, MDMA may lead the way Right now, the information void makes for polarized rhetoric — think of the chasm between the deaths from overdose and Shulgin’s hopes. But it’s possible to imagine that could change, and once again, MDMA may lead the way. If MDMA-assisted psychotherapy gains acceptance, doctors may consider ways to alter or heighten that therapy with other compounds, says Brad Burge, director of communications and marketing at the Multidisciplinary Association for Psychedelic Studies. And given Shulgin’s thoughts on the class, the 2Cs seem like a natural choice for combination therapy. "That’s the future of psychedelic therapy research," Burge told The Verge. "Once MDMA-assisted psychotherapy is legal and approved, therapists and patients will want to know how to maximize these tools." Now that MDMA is starting to break free of government restrictions, perhaps Shulgin’s dream of using 2C drugs as medicine will be realized.