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5-MEO-DMT Chemistry
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trypt-amine / ‘trip-ta-, men / n. [tryptophan fr. Tryptic, fr. Trypsin, fr. Gk. Tryein, to wear down (from its occurrence in pancreatic juice as a proteolytic enzyme) + amine fr. NL ammonia} 1: A naturally occurring compound found in both the animal and plant kingdoms. It is an endogenous component of the human brain. 2: Any of a series of compounds containing the tryptamine skeleton, and modified by chemical constituents at appropriate positions in the molecule.

 

~ Alexander and Ann Shulgin, TIHKAL (Tryptamines I have known and loved): The Continuation, (1997).

 

5-MEO-DMT5-Methoxy- Dimethyltryptamine (5-MeO-DMT) is a member of the tryptamine family of compounds that include biologically active compounds that include both neurotransmitters such as serotonin (5-hydroxytryptamine) and the primary pineal hormone, melatonin, and entheogens, includingpsilocybin (O-phosophoryl-4-HO-DMT), DMT (dimethyltryptamine), bufotenine (5-HO-DMT), and 5-MeO-DMT (5-methoxy-dimethyltryptamine). These compounds all share a basic indole ring structure (see Fig 1). This same indole backbone can also be identified as part of the structure of more complex entheogens such as LSD and ibogaine.

 

Figure 1. The basic indole ring

 

The basic indole ring

 

While LSD and psilocybin (magic mushrooms) are the psychedelic tryptamines best known to our society due to their prominent role in the 1960’s youth rebellion and the subsequent psychedelic cultures that they have spawned, the tryptamines that should be of particular interest to humanity – and that are the main subject of this website - are the super-powerful entheogens DMT and 5-MeO-DMT.

 

Figure 2. DMT

 

DMTWhy should these two entheogenic tryptamines be of such vital interest to us? Because these two entheogens – arguably the most powerful (in effect) know to Man - need not be manufactured in a laboratory, nor extracted from a plant or the venom of a toad, but are actually produced somewhere within the human body. They are, quite simply put, as much a part of us as are our bones, our teeth, or our hair.

 

 

 

Figure 3. 5-MeO-DMT

 

5-MEO-DMTBecause these entheogens posses the same basic structure as neurotransmitters, they are able to cross the human blood-brain-barrier, allowing them to have a dramatic effect upon human consciousness. Unlike other known entheogens, however, 5-MeO-DMT, DMT, and bufotenine have all proved to be endogenous to the human body, which is to say they are produced naturally within us. Thus they can be defined not only as organic entheogens, but also (depending on your viewpoint) as “endogenous psychotoxins” or “natural neurotransmitters”…. DMT has also been described as a “brain hormone”.

~ James Oroc, Tryptamine Palace (2009).

 

 

Figure 4. Serotonin

 

SerotoninEndogenous means that a compound that is made in the body; endo, “within,” and genous, “generated” or formed. DMT and 5-MeO-DMT are thus not only two of the most powerful entheogens we know (i.e. compounds that can effect both our consciousness and our perception of spirituality) but they are also the only two* that we know are produced naturally within our own bodies. The human body is also known to produce other ‘drugs’ that we are all now familiar with – for example, the production of endogenous morphine-like compounds called endorphins.

 

 

Figure 5. Melatonin

 

MelatoninThe discovery of endorphins in our bodies was considered a major scientific break-through – and its discoverers were awarded the Nobel Prize for their efforts. One would think that the discovery of naturally occurring entheogens would have been regarded as of equal importance. However, due to the draconian measures that were brought against all known psychedelics in the United States in the late 1960’s, the study of entheogens – endogenous or not – has been virtually prohibited since that time, and little notice was made of the discovery of DMT within the human body at that time. Fortunately this ridiculous scientific prohibition seems to now be lifting, and American Universities are again beginning to look at compounds like psilocybin and LSD in search of therapeutic uses. The only DEA approved clinical-research into the properties of DMT were carried out by Dr. Rick Strassman at the University of New Mexico between 1990 and 1995. Since this time – and in many respects thanks to the interest generated by the publication of Dr Strassman’s book – DMT has increasingly re-entered the public consciousness, and we can only hope that further research will be carried out on the unique properties of both DMT and 5-MeO-DMT.

 

“DMT is the simplest of the tryptamine psychedelics. Compared to other molecules, DMT is rather small. Its weight is 188 “molecular units”, meaning it is not significantly larger than glucose, the simplest sugar in our bodies, which weighs 180, and only 10 times heavier than a water molecule, which weighs 18. By comparison consider the weight of LSD at 323, or of mescaline at 211.


DMT is closely related to serotonin, the neurotransmitter that psychedelics affect so widely. The pharmacology of DMT is similar to that of other well-known psychedelics. It affects the receptor sites for serotonin in much the same way that LSD, psilocybin, and mescaline do. These serotonin receptors are widespread throughout the body and can be found in blood vessels, muscle, gland, and skin.


However, the brain is where DMT exerts its most interesting effects. There, sites rich in these DMT-sensitive serotonin receptors are involved in mood, perception, and thought. Although the brain denies access to most drugs and chemicals, it takes a particular and remarkable fancy to DMT. It is not stretching the truth to suggest that the brain “hungers” for it.


The brain is a highly sensitive organ, especially susceptible to toxins and metabolic imbalances. A nearly impenetrable shield, the blood-brain-barrier, prevents unwelcome agents from leaving the blood and crossing the capillary walls into the brain tissue. This defense extends to even keeping out the complex carbohydrates and fats that other tissues use for energy. The brain burns instead only the purest form of fuel: simple sugar or glucose.
However a few essential molecules undergo “active transport” across the blood-brain barrier. Little specialized carrier molecules ferry them into the brain, a process that requires a significant amount of precious energy. In most cases, it is obvious why the brain actively transports particular compounds into its hallowed ground; amino acids required for maintaining brain protein, for example, are allowed in.

 

Twenty-five years ago Japanese scientists discovered that the brain actively transports DMT across the blood-brain-barrier into its tissues. I know of no other psychedelic drug** that the brain treats with such eagerness.”

 

~ Dr. Rick Strassman, DMT: The Spirit Molecule.
A Doctor's revolutionary research into the biology of Near-Death and Mystical Experiences.
(2001)

 

* While bufotenine is also endogenous, its entheogenic or even psychoactive properties are still a matter of debate.

** The information in this excerpt is equally relevant to 5-MeO-DMT

 

Why is 5-MEO-DMT more potent then DMT?

A lunch time conversation with Sasha Shulgin

 

Anne and Sasha ShulginOne of the many puzzles I have tried to understand about 5-MeO-DMT is why is it more potent (in terms of size of dosage and speed of onset) then DMT, since the compound itself is the DMT molecule with a Methoxy molecule added in the fourth position. Logic would seem to dictate that a larger molecule would take longer to pass thru the Blood Brain Barrier (BBB) but with 5-MeO-DMT this is not the case, since it generally takes only one toke and often hits you before you have even had a chance to put down the pipe. When I asked my friends with an organic chemistry background about this, I was told that this was a common effect – that a molecule in the fourth position increases potency in many compounds – but no one could explain why. So I thought I would take the question to the best authority there is, and I asked for elucidation from Alexander ‘Sasha’ Shulgin, the great chemist and co-author of T.I.H.K.A.L. himself, while we sat at a lunch-break at the 2010 MAPS conference.

 

Sasha reiterated the fact that when a molecule is placed in the fourth position on either the tryptamine or the phenethylamine ring increased the potency of the compound. When I asked him why, he said no one was really sure, but he suspected it had something to do with the tension of the molecule – and with that explanation I could visualize the 5-MeO-DMT molecule as a potent dart that penetrated the BBB at will, while the less potent molecules ‘bounced’ off.

Sasha then looked at me with a rascally grin and said:

 

“But what if we put a molecule in the fifth postion? Well, this would create a super-potent tryptamine, even more powerful than 5-MeO-DMT!”

 

I said that that sounded like a frightening proposition, and we both had a good chuckle at that. But then the light twinkled again in those 85 year old eyes, and Sasha started back in on the possibilities of the fifth position, with just the faintest hint of a smile.

 

“No one has tried this as far as I know,” Sasha said, “And it really is a fascinating possibility for a whole new range of compounds. My suggestion is that you learn some simple organic chemistry, and then have a go yourself!”

 

I only wish that Sasha and Anne were my grandparents! Not only are they indisputably two of the most interesting people in the world, they also seem to be two of the nicest.  

 

Next Topic > History and Discovery of 5-MEO-DMT

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