N,N-Dimethyltryptamine (DMT) is a psychedelic compound of the tryptamine family. This family of compounds also includes psilocybin and psilocin (both found in magic mushrooms), which are similar in molecular structure to DMT. DMT is also similar in molecular structure to the neurotransmitter serotonin. Indeed, this is precisely why these compounds can affect our minds in the way that they do. They are known as serotonergic substances because they produce effects via interactions with the serotonin system, either blocking or stimulating the release of serotonin between neurons in the brain.

The serotonin system has between 14 and 17 different subtypes of receptors. 5-HT2A is the stimulatory serotonin receptor, although it can have inhibitory (blocking) effects depending on its location. It mediates the effects of classic psychedelics – those belonging to the ergoline family (LSD), phenethylamine family (mescaline) and tryptamine family (psilocybin and DMT). There is a strong correlation between stimulation of these receptors and the hallucinogenic effects of these compounds. If you block this receptor, you block the hallucinogenic effects.

Orally Active DMT

DMT has a long history of use, in its oral form as ayahuasca. There is archaeological evidence of the ceremonial use of ayahuasca dating back to 500 BC in Ecuador, although anthropologists claim ayahuasca has been used by shamans for over 5,000 years (Narby, 1998, p. 154). This hallucinogenic brew involves the combination of two plants native to the Amazon rainforest: The Banisteriopsis caapi vine and the leaves of Psychotria viridis (in the indigenous Quehcua languages of South America it is called chacruna). The caapi vine contains monoamine oxidase inhibitors (MAOIs), which are chemicals that inhibit the activity of MAO. Chacruna contains DMT, but if it is consumed orally by itself, it won’t have any psychoactive effects. This is because the body’s widespread presence of MAO quickly breaks the down DMT. However, by combining DMT-containing plants with MAOIs, the DMT becomes orally active and intense psychedelic effects take place.

But it is a mystery how the indigenous peoples of South America figured out how to combine these two plant species together in order to make DMT orally active. To put this in perspective, there are around 80,000 plant species in the Amazon basin. But there is no evidence of how ayahuasca was ingeniously invented from the thousands of plant species available. Shamans believe that ‘plant spirits’ originally told rainforest tribes which plants to use. Of course, this explanation will not sit well with sceptics. To accept this supernatural explanation is to assume not only that plants have consciousness, but that they also have a non-material essence (spirit) that allows them to communicate with humans.

So did these ancient tribes just accidentally stumble upon this unlikely combination? Is pure chance the only other explanation? Well, a large degree of chance, of trial and error, may have been involved. But other factors could have been at play in its discovery. Humans may have learnt about the psychoactive properties of the caapi vine by observing jaguars consuming it and altering their consciousness. Tribespeople also believe that the jaguar consumes this vine in order to heighten its senses for hunting. Such tribes may have copied the consumption of caapi from jaguars so that they could improve their own hunting skills.

Many plants also have a history of being combined with caapi for medicinal purposes. An ancient tribe might have boiled caapi in water, with the new addition of a DMT-containing plant (such as chacruna), in the hope of discovering a new plant medicine to treat some illness or medical condition. Imagine their surprise when they unwittingly had an intense psychedelic experience as a result.

Chacruna is used by itself as a purgative and intestinal cleanser. This is what causes the ‘purge’ in ayahuasca – the uncontrollable vomiting and defecating. If caapi and chacruna were both being used medicinally at the same time their paths could have crossed at some point, resulting in the monumental invention of ayahuasca. Undoubtedly, there is an element of chance involved in this discovery, but once the event took place, it imprinted itself in history and created the unbroken tradition of ayahuasca use we see today. Ayahuasca was discovered against astronomical odds and probably due to a long process of trial and error, but as soon as that magic combination was found, knowledge about the brew may have spread very quickly among different tribes.

The Discovery of DMT

While DMT by itself is not orally active, it can be insufflated (snorted), vaporised or administered intramuscularly (IM), intravenously (IV) or rectally. This bypasses the MAO in the stomach. Using DMT in this way does not have a long history or cultural tradition like ayahuasca has. DMT was first synthesised in 1931 by Canadian chemist Richard Manske, but its psychoactive properties weren’t discovered until 1956 when Hungarian chemist Stephen Szara extracted DMT from the plant Mimosa hostilis and in daring experimental fashion injected the substance into his own body. He experienced hallucinations that were more intense and shorter lasting than other psychedelics. The DMT has been called the ‘businessman’s trip’, with the implication being that the trip can be had during a business lunch break. When vaporising freebase DMT, you’ll be back to baseline after an hour.

Oscar Janiger was one of the pioneering psychiatrists using LSD in the 50s and 60s. He introduced LSD to actor Cary Grant and writer Aldous Huxley. He is also the first recorded person in the US to have used DMT. Discovering the work of Szara, he had the local laboratory make him a batch. Then, one afternoon while he was alone in his office, he filled a syringe and shot it into his arm, describing it as “a dangerously stupid, idiotic thing to do.” In Storming Heaven: LSD and the American Dream (1987), author Jay Stevens reports:

Compared to DMT, LSD was like a lazy summer picnic. Janiger felt like he was inside a pin-ball machine, bombarded by flashing lights, clanging bells, infernal messages. There was no insight. He was lost, disconnected, and when he later regained consciousness (the DMT lasted only thirty minutes) he was convinced he had been “totally stark raving crazy”. Which was terrific! Perhaps he had found the elusive M [madness] factor.

…then he called up Alan Watts and bet him he had a drug that could finally shut him up. Watts took the bet and the DMT, and for thirty minutes he lay there staring at Janiger, who kept repeating “Alan, Alan, please say something. Talk to me. Your reputation is at stake.” But Watts never said a word…Everyone who took DMT agreed it was a hellish half hour, with absolutely no redeeming qualities.

William Burroughs, the author of Naked Lunch (1959), also became interested in psychedelics. In the 50s he was in search of a cure for his heroin addiction, which is described in semi-autobiographical fashion in his novel Junkie (1953). Burroughs travelled to the Amazon rainforest and became one of the first non-botanist/anthropologist Westerner to try yage (another name for ayahuasca). He described his experiences with the brew in a number of letters sent to Beat poet Allen Ginsberg; then later published as a small book entitled The Yage Letters (1963).

Then in 1961, while in London, UK, Burroughs obtained a supply of DMT to experiment with. But he then completely scared himself off the drug after believing he had nearly overdosed with a 100mg (IM) trip. He later called DMT a “terror drug”. In a letter to the ‘High Priest’ of LSD, Timothy Leary, he said his first impression of the drug was that it “closely resembled psilocybin in its effects”. Which makes sense, given its structural similarity. Indeed, many users of psychedelics note a similarity between a strong mushroom experience and the DMT experience. In any case, his 100mg trip shook him to his core, saying “…it was completely and horribly real and involved unendurable pain.”

The poet Allen Ginsberg offered Jack Kerouac, author of On the Road (1957), a chance to try the DMT he had brought back from Leary’s Millbrook estate (a mansion which played an important role in the psychedelic movement – it was where research and experimentation took place, and it was visited by figures such as author Ken Kesey, psychiatrist R.D. Laing, and philosopher Alan Watts). A photo shows Kerouac “grimacing” under the influence of DMT in Ginsberg’s apartment in 1964.

As we can see, DMT was not gaining an attractive reputation. But Leary, in true psychonautical fashion, decided that he had to try the drug himself. And during his first experience in 1966, he experienced anything but terror. As he recounts in High Priest (1968):

Suddenly I opened my eyes and sat up… the room was celestial, glowing with radiant illumination… light, light, light… the people present were transfigured… godlike creatures… we were all united as one organism. Beneath the radiant surface I could see the delicate, wondrous body machinery of each person, the network of muscle and vein and bone–exquisitely beautiful and all joined, all part of the same process.

Our group was sharing a paradisial experience – each one in turn was to be given the key to eternity – now it was my turn, I was experiencing this ecstasy for the group. Later the others would voyage. We were members of a transcendent collectivity.

Gradually, the brilliant illumination faded back to the three-d world and I sat up. Reborn. Renewed. Radiant with affection and reverence.

This experience took me to the highest point of LSD illumination – a jewel-like satori. It was less internal and more visual and social than my usual LSD experiences. There was never a second of fear or negative emotion. Some moments of benign paranoia – agent of the divine group, etc.

I am left with the conviction that DMT offers great promise as a transcendental trigger. The brevity of the reaction has many advantages – it provides a security in the knowledge that it will be over in a half hour and should make possible precise exploration of specific transcendental areas.

Set and Setting

Leary’s experience was clearly a lot more positive than Burroughs’s or Janiger’s. But it was more than just positive. His words reveal the mystical potential of DMT, referencing ‘satori’, which in the Zen Buddhist tradition means enlightenment. Perhaps, unlike Burroughs and Janiger, Leary had paid much closer and careful attention to set and setting – the mindset and environment in which one takes a psychedelic. Indeed, Leary pioneered this concept in the psychedelic scene in his works, and today it is still regarded as key advice when someone is considering embarking on a psychedelic journey.

Set includes the intentions one has when going into the experience, as well as one’s current mood, personality, personal history, so forth and so on. Setting includes not just the environment (i.e. indoors or outdoors) that the experience takes place in, but other external details that can make a big difference to the trip – including other people (how many people and what your relationship is with them), music, lighting, background noise, artwork, meaningful objects, and so on.

Some people question whether set and setting is so important for DMT, given how short-lasting it is, and how the trip doesn’t tend to involve an intense confrontation with one’s fears, weaknesses and insecurities like ayahuasca. Nevertheless, the stark difference between Leary’s trip and the nightmarish ones of Burroughs and Janiger suggest that feeling safe and comfortable in oneself and one’s environment can be the factor that decides if one travels to hellish or heavenly domains. In the words of psychiatrist Humphrey Osmond, who coined the term psychedelic (meaning ‘mind-manifesting’), “To fathom Hell or soar angelic, just take a pinch of psychedelic.” Humphrey’s research with LSD and mescaline demonstrated to him that the same psychedelic, at the same dose can offer either a positive or a negative experience – the outcome depends on how your mind manifests itself. And as we shall see, Dr Rick Strassman’s experiments with DMT shed light on the importance of setting as an influencing factor in the nature of the DMT experience.

Leary noted that the very nature of DMT made it an unpopular substance – it was short-acting, hard to be administered (this was before the discovery that freebase DMT could be smoked), and it was difficult to come by. Nonetheless, DMT gained a bit more popularity in the psychedelic scene in the 60s when Nick Sand became the first underground chemist to synthesise the substance. And he was the first to discover that the freebase version of the compound could be smoked, which made it much easier to use, compared to administration by injection. For Sand, DMT would always hold a unique mystery about it. As he says in an article titled Moving into the Sacred World of DMT, published in The Entheogen Review:

The world of DMT is incredibly vast. What DMT opens in us is so profound that it is impossible to truly express. I have been making, using, and initiating people into DMT use for around 40 years. I was the first one who discovered that free-base could be smoked. It has never ceased to amaze me, nor have I ever felt that one could fairly arrive at any hard or fast conclusions about what happens during a DMT trip.

Sand was a clandestine chemist working from 1966-1996 for the Brotherhood of Eternal Love, an organisation that produced and distributed drugs in the hope of starting a “psychedelic revolution” in the US. Sand was also the Chief Alchemist for the League for Spiritual Discovery, an organisation inspired by Timothy Leary and which pushed for the legal use of LSD. DMT didn’t become popular and intimately linked with the psychedelic culture of the 60s like LSD was. But some other notable individuals did experiment with it.

An Intense Experience

Robert Hunter, the lyricist for The Grateful Dead, began a series of email exchanges with ethnobotanist and DMT spokesperson Terence McKenna. Hunter considered himself a “serious DMT explorer between 1967-79”, having taken it “a thousand times”. But he eventually had to stop when the “Boss of that place” told him that he had seen all that’s to be seen, and not to return. He said “It [DMT] is, to LSD, as 198 proof rum is to hot milk with a few drops of brandy”, adding that:

Anyone who has been surprised by heavy surf, whirled helplessly and slammed on the sand, has a reasonable metaphor for the power of DMT.

Grace Slick, the lead singer of Jefferson Airplane, made this comparison between LSD and DMT before, famously saying that “LSD is like being sucked up by a straw, while DMT is like being shot out of a cannon.” DMT just isn’t the kind of thing that should be abused – in fact, the very nature of the experience gives it a very low potential for abuse. While there might be ‘acid-heads’ out there, ‘DMT-heads’ are not that common. As Hunter says in 1996: “I, who loved it, have only taken it twice in the last 20 years and that was too much.”

Hunter certainly shared McKenna’s self-avowed difficulty in summoning the “raw courage” to use DMT again. If psychonauts such as McKenna and Hunter (who had taken large quantities of LSD and smoked DMT – so he claims – a thousand times) can be so unnerved by DMT, then it must be an extremely potent substance. Indeed, it is often described as the most powerful psychedelic known to humankind. McKenna believed this to be so, and added that “if it gets stronger than that I don’t want to know about it.” So another reason that DMT didn’t share LSD’s popularity was that it was just way too dramatic an experience; too alien and overwhelming. This intensity factor is underlined out by the psychedelic chemist Alexander Shulgin, who in his book TiHKAL (Tryptamines I Have Known and Loved) – a follow up to PiHKAL (Phenethylamines I Have Known and Loved) – recounts his experience of smoking 100mg of DMT. Shulgin writes:

As I exhaled I became terribly afraid, my heart very rapid and strong, palms sweating. A terrible sense of dread and doom filled me — I knew what was happening, I knew I couldn’t stop it, but it was so devastating; I was being destroyed — all that was familiar, all reference points, all identity — all viciously shattered in a few seconds. I couldn’t even mourn the loss — there was no one left to do the mourning. Up, up, out, out, eyes closed, I am at the speed of light, expanding, expanding, expanding, faster and faster until I have become so large that I no longer exist — my speed is so great that everything has come to a stop — here I gaze upon the entire universe.

This experience is not for everyone. Without the right kind of footing entering the experience, or the tools to integrate such a mammoth experience when it’s over, it can no doubt leave an individual shaken up, confused and lost. It takes a certain sense of resolve and bravery to try any psychedelic, but perhaps only a certain kind of person can (or wants to) be flung so rapidly into an alien world, and to be shaken to one’s core. It’s an experience that may be best suited to the intrepid explorer.