In recent years, a number of the more interesting and rewarding derivatives of DMT have become available on the research chemical market. Some, such as DPT and DiPT, have been available for decades, while others, such as MET, EPT and MiPT, have become commercially available only in more recent years.

I had the good fortune to study many of these compounds before Australia adopted far-reaching analogue laws. Recently, I became aware of many new anecdotal reports for some of the compounds on the research chemical market, but for certain compounds (like DsBT or di-sec butyl tryptamine), there are no first-hand accounts, or indeed experimental data of any kind. Given this shortage of information, a presentation of the effects of these compounds seems a useful contribution.  

The DMT family, as I define it here, includes all higher analogues of tryptamine substituted on the terminal nitrogen only. For the purposes of our current discussion, it excludes the 5-substituted group (5-MeO-DMT; 5-MeO-MiPT; 5-HO-DMT; 5-Br-DMT, et cetera). These I would call the 5-MeO-DMT family. It also excludes the 4-substituted group (psilocybin; 4-Acetoxy DMT; 4-HO-MET, et cetera). These I would call the psilocin family. These families richly deserve their own separate articles, but are not part of the current topic. 

The group thus defined includes DMT itself, as well as DET, both of which have been prohibited drugs since the 1970s, plus MET, EPT, DPT, DiPT, and MiPT: all of which have been staples of the research chemical market. In addition to these, a number of others are only occasionally available: MPT; MALT; DALT; EiPT; PiPT and DsBT.

All these tryptamines may be smoked or vaporized, and this is the most convenient and economical way to enjoy them. They may also be insufflated (snorted), and apart from DMT itself, they are orally active at sufficiently high dosages. As each route of administration produces somewhat different effects, I will focus on the effects of each compound via the smoked route, as the oral route of administration would require an entire article to itself. 

When approaching a novel substance of any kind, it is essential to assess the risks involved and to ascertain the appropriate dose range for a given substance. In some cases, the substance may be so novel that there is no published information on the dosage, duration and effects. In such cases, it is essential to be very prudent. A new substance may have unexpected potency and unknown properties. For example, DiPT had an unexpected and very dramatic effect on auditory perception that could not have been predicted, and which makes it unique among this series of tryptamines. 

Generally, though, one can reason by analogy to make educated guesses about the properties of new substances. For example, we know that most freebase tryptamines are active when smoked in the vicinity of 15-25 mg. We also observe that the potency decreases slightly as the alkyl groups on the nitrogen get bigger: we know that DBT with two four-carbon butyls is not as potent as DMT with two one-carbon methyls. So when I came to investigate DBT’s isomer DsBT, I made the prediction that it would be satisfactorily active as a smoked freebase at around 20 mg, without being overly intense. Consequently, I chose to start conservatively at 5 mg, which gave a mild effect, and subsequently go to 20-25 mg, which did, in fact, present an optimum level. Although I made an informed guess about the dosage and it worked out very well, I did indeed take a risk in doing so. As such, I took that risk myself, as the solitary test subject, while under close supervision. As described below, DsBT turned out to be an enjoyable, rich, well-rounded psychedelic and very much a typical tryptamine, like EPT or MiPT, with similar dosage range, effects and duration. 

When exploring this series, I tried to create a relaxed, somewhat neutral setting in which to experience them. Generally, I liked to smoke these tryptamines in the early afternoon, indoors with a comfortable bed to lay back on, usually on a lazy weekend. Many people are taken by surprise by the intensity of tryptamines, and it is important to have a quiet, safe, peaceful setting to enjoy them without obligations or distractions. Now, without further ado, here are the most interesting base tryptamines, starting with the simplest (DMT) and progressing with the addition of carbons through to the more complex members of the series.

 

DMT (N,N-dimethyltryptamine)

 

DMT is by far the best studied and most widely used of the base tryptamines. It occurs in nature in many plant species. It is also a controlled substance and illegal to possess in most parts of the world. Smoking DMT can be a life-changing experience. It can rapidly produce an overwhelming expansion of sensory and mental activity. It routinely produces a full range of psychedelic visual effects, especially brightly coloured, fast moving geometric patterns and is quite capable of producing “break through” experiences of an alternate dimension inhabited by autonomous entities. The big question for me personally, when propelled into these encounters, is often “what business is it of mine to be here?” Perhaps the most immediate benefit of making the journey is that it often feels like the energy or sensation in my body is more aligned and harmonious afterwards, mood and motivation are greatly improved, and the body and mind are much more relaxed subsequently. An experience of wonder is also an excellent balance to the reductionistic and materialistic mindset encouraged by capitalism and technocracy. Nonetheless, it is potentially a seriously altered state of consciousness to be approached with due preparation. Smoked dosages (as freebase) range from about 10 mg (threshold) to 60+ mg (heavy). A reasonable mid-range is 20-40 mg.

 

MET (N-methyl-N-ethyltryptamine)

 

MET is similar to DMT in terms of its visual geometry, but much gentler and lighter in character. Psychologically, it is very comfortable and very comforting, at least that is my own experience and that of many who have tried it. It is soothing physically, and like DMT, it leaves my body feeling relaxed and rebalanced. The visuals for me include geometric mandalas with eyes opened and closed. They resemble the patterns I see as I come out of a 5-MeO-DMT experience, with a similar afterglow, but again much milder and gentler than 5-MeO-DMT, and without anything resembling a near-death experience. It seems like a good choice for a novice psychonaut, a kind of DMT-with-training-wheels. This is not to understate its beauty, grace and the pervading sense of well being it can produce. It has an emotionally grounding and motivation-enhancing effect that can last for days afterwards. This is a more approachable psychedelic with a lot of psychological benefits and fewer psychological risks, and would seem well suited to the world of psychedelic therapies. A dose of 20 mg of the freebase absorbed onto dry mint and smoked felt intermediate between DMT and 5-MeO-DMT, with rainbow coloured geometry of the former and the expansive, time dilating properties of the latter. An amplifier of sensation, it feels extremely friendly.

 

DET (N,N-diethyltryptamine)

DET is extremely rare. It has been explicitly illegal (along with DMT) since 1971. Its effects are said to mostly closely resemble those of MET.

 

MPT (N-methyl-N-propyltryptamine)

MPT is a very rare compound with subjective similarities to DMT and EPT. Where it has been available as a research chemical, it has been well-received. Dosage has been given as around 30 mg of freebase smoked.

 

EPT (N-ethyl-N-propyltryptamine)

EPT is active by all routes, with 20 mg to 50 mg suggested for the freebase, smoked. I have smoked the freebase (infused on peppermint) at 30 mg. Strong, deep and completely effective at this range. Reminded me a little of psilocin, with visual geometry, tingling, euphoria, yawning and crying a little. I became hyper-talkative after the initial rush, at about the ten-minute mark. Outstanding material. About an hour of major effects. Similar to DPT, in some ways, though not as heavy psychologically. Analysis and insight are definitely present. Complex geometry is also present, but not completely overwhelming. A colleague was surprised to find her quilt transformed into a writhing mass of geometric patterns, again a bit like psilocin.

 

DPT (N,N-dipropyltryptamine)

DPT is generally regarded as the most intense and visionary of the tryptamines, an assessment I agree with. The freebase, smoked at 10-15 mg, was for me physically euphoric, with visions of extraterrestrial and technological spaces and spiritual beings. 30 mg smoked resulted in a full ++++  “break-through” experience. I am reluctant to discuss this experience, but I believe DPT to be among the most intense, profound, and other-worldly of all entheogenic substances. Rudolf Otto, the German Lutheran theologian and scholar of comparative religion, characterised religion by its special feeling tone, which Otto called the mysterium tremendum et fascinans. This is the feeling of being repelled by fear in the presence of supernatural power, and yet simultaneously so enraptured by the beauty and majesty of the experience that one is compelled to abide. This for me, is very much a characteristic of high-dose DPT. 

 

MiPT (N-methyl-N-isopropyltryptamine)

MiPT is orally active from about 10 mg through to 80 mg and 5-30 mg smoked. We tried this initially at 25 mg of the freebase infused onto dried mint and smoked, and found it very heady. Extremely swirly, warm, intoxicating, stimulating and physically and mentally woozy and “rushy”. Somewhat reoriented at the half hour mark, able to walk and do basic activities, but still quite inebriated for another couple of hours. Colour enhancement with eyes open and subtle closed eye visuals, no distortion of pitches, but music a little overwhelming. Similarities to DMT, 5-MeO-DMT, aMT, 5-MeO-MiPT and MET, but also unique to itself and set a little apart from all of these. Only resembling DiPT in that it was stimulating and ego-dissolving. We revisited MiPT at 20 mg smoked, and found it just as intense, relaxing and ego-dissolving. I would say 20 mg is the better dosage as it allows for more engagement, retention and integration of the experience.

 

EiPT (N-ethyl-N-isopropyltryptamine)

EiPT is a very rare tryptamine apparently first synthesised by Alexander Shulgin. Shulgin studied the effects of this substance at 25-40 mg, orally, finding some similarities to DET and MiPT, but overshadowed by nausea and dysphoria. There were no visuals or auditory distortions at this dosage, and Shulgin discontinued his experimentation on account of the unacceptable body load. A strangely unsatisfactory substance. Beyond Shulgin’s description in TiHKAL, I could find no other reports of the effects of EiPT and no accounts at all of the effects of smoking it. This represents a gap in our knowledge because the effects of smoked tryptamines can be substantially different from the same drug taken orally.

 

PiPT (N-propyl-N-isopropyltryptamine)

Dosages given online as around 100 mg orally and 25-30 mg smoked. This is a very rare tryptamine, for which there are a handful of anecdotal reports scattered throughout Reddit and Bluelight forums. It has been reported especially in British Columbia, Canada, from around 2021. Despite its structural relationship to DiPT and DPT, it is said to be subtle and indistinct compared to those quite remarkable compounds. It has been described as a milder version of MiPT. 

 

DiPT (N,N-dipropyltryptamine)

DiPT is orally active in the range of 25 mg to 125 mg, with higher doses producing bizarre distortions of sound that are unique to DiPT and 2-Me-DET.  Anecdotally, dosages range from 10 mg to 50 mg of the freebase, smoked. Previously, we had tried high dose DiPT orally and had not enjoyed the pitch distortions and total loss of harmony in music that this substance produces. It was nonetheless a valuable ear-opening experience. For us, 25 mg of the freebase smoked produced only mild auditory distortion and harmony remained intact. The perceived timbre of musical instruments was subtly altered in a way that made recorded music sound fresh and new, but oddly dulled, like the notes were hollowed out and the edges of sound made fuzzy. The body load of DiPT is unusual. I commented to my partner that it felt like a chocolate pudding: dense and dark, velvety and rich and sticky. He had the same perception and said it was like a ripe black sapote, dense and sweet. With my eyes closed, I had flashes of what might have been past lives. To me, there is something haunted and uncanny about smoked DiPT. For my partner, it was more of a woozy sensation, like drinking beer too quickly. Onset takes a few minutes, the rush and peak are about 30 to 50 minutes, with residual trippiness for a few hours after that.

 

MALT (N-methyl-N-allyltryptamine)

Anecdotally, dosages range from 25 mg to 50 mg of the freebase, smoked. The experience is reported to be powerful, with visuals a little less immersive than DMT, more immersive than MET and MiPT, and similar in style to MPT and psilocin. Most reports I’ve read suggest that 50 mg is often a little more MALT than people had bargained for. MALT is rare, but has been well received by many who have had the opportunity to try it. The higher analogues appear not to have yet been synthesized or explored, with the exception of DALT (N,N-diallyltryptamine), which was synthesized and tested by Dr. Stephen Szara and reported by Faillace et al in 1967. It was found to be active, although no dosage was published. Shulgin later explored it up to 42 mg orally, but was unimpressed. 

 

DsBT (N,N-disecbutyltryptamine) 

This was new territory, with no published information at all. I cautiously smoked 5 mg of the freebase deposited on dried peppermint leaves. This is a threshold dose. My notes from the time: “From this small first trial, I can affirm the following: It is definitely active. It is initially physically very relaxing and mentally both relaxing and stimulating. Laying down, the closed eye sensory dance typical of many smoked tryptamines is present, consisting of subtle, flowing, dancing energy behind the eyelids. It feels very benign and enjoyable. I am not certain I could distinguish this compound from low dose EPT or MiPT in a blind trial. Subsequent to the initial rush, I felt rather stimulated and enjoyed physical exercise and being outdoors in nature. This reminded me especially of MiPT. Yet it did feel a little different too, somehow sharper and clearer; more connected and flowing and less excited. No distortion of sound was noticeable at this dosage, although acuity of hearing and emotional responsiveness to music were enhanced. The taste and smell of this material is distinctly reminiscent of DMT and other tryptamines. It also produced the sharp, pleasurable tingling of the mouth, lips and face that is characteristic of many smoked tryptamines. Overall, the experience was enjoyable, sensory and embodied with very few negatives. The short duration was similar to other smoked tryptamines: Onset within 30 seconds, main effects for about fifteen minutes, afterglow an hour or two, gradually tapering off into a thoughtful integration phase. As long as no worrying symptoms present themselves presently, I look forward to proceeding to higher smoked dosages. Update: 20-25 mg is a satisfactory level for this material, producing the same full range of relaxing, sensory-enhancing and mental effects with greater intensity and duration of about an hour”.

 

Concluding remarks

Taking a retrospective overview of this series of closely related compounds, I am primarily struck by their similarities on the one hand, and their diversity and distinctiveness on the other. While DPT, DMT, MPT, EPT, DsBT and MET tend to be narratively and visually rich, MiPT is physically relaxing and mentally stimulating with few visuals, and DiPT stands in a strange class of its own. At 25 mg smoked, the sound distortions that DiPT is famous for are very minor, but the intoxication is still strong and very hard to put into words. It has a velvety, sticky, sweet quality to the body high, without being particularly euphoric. It is relaxing, and yet there is this underlying feeling of uncanniness, of having taken a ‘wrong turn’ in consciousness, possibly due to subtle alterations in auditory sensory processing.

 

An important point to keep in mind when assessing anecdotal reports like those I have presented is the extent to which they are subjective and specific to the individual. For example, I tend to have a certain amount of eyes-closed visual content, whereas my partner generally has more somatic and cognitive content, more emphasis on embodied knowing. People are neurologically diverse and this leads to a lot of variation in psychedelic experiences. We are also differently sensitive to different materials.

 

While this group of compounds demonstrates how small structural changes can lead to big alterations in effects, there are certain things they all have in common. The most obvious similarity has to do with the loss of a coherent sense of self during the onset. Most of us are used to automatically maintaining a sense of an ego ‘center’. This is something we as humans have evolved to have, part of our social survival program. The sense of self arises from a set of mental processes such as having memories of who we have been, day-dreaming about what we intend to do in the future, ideas about how people around us think and feel, judgements about social interactions. When these different mental processes are synchronised, we are maintaining a background day-dream or internal narrative we may refer to as the ‘self’ or ‘ego’. These mental processes that constitute the ‘self’ seem to depend on brain anatomical regions known collectively as the Default Mode Network (DMN), which DMT-like psychedelics appear to disrupt. Specifically, neuroscientists have observed that psilocybin reduces blood flow to these regions, leading to a decrease in their activity, and that LSD causes desynchronisation of the different regions of the DMN (Gattuso, 2022; Soares, 2023). This may explain why, during the onset after smoking these tryptamines, I realise that I cannot ‘hold to the center’. I have to ‘let go’ of my sense of self. I have to loosen my mental grip on past events. I have to forget about tomorrow and my plans, and just let go of it all and experience raw sensation and perception and just be for a while. It’s like a reprieve from the ego, and an opportunity to be objective, compassionate and critical about the ‘self’. This is, perhaps, the essence of the psychedelic experience and something the N,N-dialkyl tryptamines excel at facilitating.

This article was printed in “Entheogenesis Australis Journal 6”, commemorating 21 years of Australian ethnobotanical research and community. The journal is available from the EGA website: www.entheogenesis.org/shop

References

PsychonautWiki. DMT [accessed 2024 Dec 4]. https://psychonautwiki.org/wiki/DMT

Faillace LA. 1967. Clinical evaluation of some hallucinogenic tryptamine derivatives. Journal of Nervous and Mental Disease. 145(4):306-313.

James, Gattuso J. 2023. Default Mode Network Modulation by Psychedelics: A Systematic Review. International Journal of Neuropsychopharmacology. 26(3):155-188.

Otto, Rudolf. 1968. The Idea of the Holy: An Inquiry Into the Non-rational Factor in the Idea of the Divine and Its Relation to the Rational. 2nd ed. Oxford University Press.

Shulgin, Alexander, Shulgin A. 1997. TiHKAL: The Continuation. Transform Press.

Soares, Carla. 2023 Sep. The relationship between the default mode network and the theory of mind network as revealed by psychedelics – A meta-analysis. Neuroscience & Biobehavioral Reviews. 152.

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