Tryptamines are one of the most popular and prominent classes of psychedelics. Tryptamines include compounds like DMT, psilocybin, and all of the substituted tryptamines such as 4-ACO-DMT. Even lysergamides (like LSD) are considered ‘complex tryptamines,’ so when you really think about the sheer number of tryptamines it can seem overwhelming.
Furthermore, most of the tryptamines that are discussed online are fairly established. There are lots of other mysterious tryptamines that no one is talking about. If you’ve heard of Alexander Shulgin’s book, TiHKAL (Tryptamines I Have Known and Loved), you might be interested to know that it contains over 900 pages. Half of these pages contain Shulgin’s information on the synthesis of various tryptamines.
Shulgin himself synthesized more than 200 drugs in his lifetime. That’s more than any other chemist in the history of mankind. So, unless you’re up to Shulgin’s level, chances are you haven’t had much of a chance to learn about these rare tryptamines. Many of these are sold online as Designer Drugs and research chemicals.
What Are Tryptamines?
Tryptamines are drugs that produce psychedelic and hallucinogenic effects. They work by influencing the serotonin system, especially a specific receptor called the 5-HT2A receptor.
Even though individual tryptamines can vary quite a bit in terms of their effects, most of them operate in a similar manner. They vary in their duration, their potency, and the specific types of effects that they cause.
The most commonly-associated symptoms of tryptamine usage are hallucinogenic and psychological in nature. Hallucinations can be visual or audio-based.
Tryptamine
Tryptamine is the base compound found in the various tryptamine derivatives, which are themselves known as substituted tryptamines. All of the compounds that we discuss in this article are considered substituted tryptamines, but they contain the tryptamine base.
Tryptamine itself is a monoamine alkaloid. It occurs naturally in people, animals, plants, and fungi. Because they contain the structure of a compound that the body naturally produces, substituted tryptamines tend to have powerful and profound effects because they bind neatly to the receptor sites.
The tryptamine molecule is quite similar to tryptophan, an amino acid that is aso naturally occurring. Tryptamine’s name is actually derived from tryptophan.
The compound contains an indole ring attached to a monoamine chain. Substituted tryptamines are based on the tryptamine core but produced by substituting one or more of the hydrogen atoms.
Rare Tryptamines
Here are a few very interesting, rare tryptamines that don’t get a lot of attention.
MPT
Methylpropyltryptamine, or MPT, is a powerful synthetic tryptamine. It’s very similar to DMT (dimethyltryptamine) in terms of structure. Its effects are fairly similar as well, although there are marked differences between the two compounds.
MPT is one of the oldest synthetic tryptamines. It was first produced in 1931 by Manske. However, despite its age, the compound has been the subject of very little research. Between 1931 and 2005, there was no mention of MPT in any scientific literature until it was described in a tryptamine synthesis report by Brandt, et al.
That doesn’t mean that nobody was talking about it, though. MPT is included in Shulgin’s legendary book, TiHKAL. However, he touches on it only briefly while he describes the synthesis of another rare tryptamine, MiPT.
In the last few years, MPT has begun to circulate more widely on the internet. It’s still nowhere near as popular as many of the other research chemicals, but there is a growing interest. So much so that professional researchers Chadeayne, et. al, solved the crystal structure of MPT (as well as 4-AcO DMT) so that it can be studied in different ways.
That said, there is still very little pharmacological data available regarding the use of MPT. It’s speculated that it exerts its effects in a similar manner as other tryptamines, through agonism of the 5-HT2a receptor. However, its unique properties make it appealing and interesting to medical and therapeutic researchers.
Compared to DMT, a compound containing two methyl groups, MPT swaps out one of these methyl groups for a propyl carbon chain.
4-HO-DET
4-HO-DET, also known as ethocin or, chemically, 4-hydroxy-N,N-diethyltryptamine, is another rare tryptamine. It is structurally very similar to psilocin, the main active component found in magic mushrooms.
It is similar in terms of its effects and capabilities as well. Psilocin (4-HO-DMT) is nearly identical in structure to ethocin (4-HO-DET), the main difference being that the methyl component of 4-HO-DMT is exchanged for an ethyl.
4-HO-DET was first discovered by Albert Hofmann in the 1950s. After discovering LSD and its powerful therapeutic benefits, Hofmann dedicated a lot of his time to exploring natural psychedelics and synthesizing analogs and alternatives.
His first experiments with the substance were done alongside its phosphoryloxy analog, 4-PO-DET. These psychoactive substances were used in clinical trials during the 60s in Germany.
Aside from these trials, however, there hasn’t been a lot of research done on 4-HO-DET and the compound remains obscure and unpopular. There is virtually no history of 4-HO-DET being sold at street level; even online research chemical distributors rarely stock the compound.
Nobody is certain why this is. Like other tryptamines, 4-HO-DET produces its effects by working as a partial agonist at the 5-HT2a receptor. The results of research are invariably similar to other psychedelics, which leave us with a mystery. Why is 4-HO-DET so rare and uncommon when it shares so many similarities with other psychedelics?
Shulgin made some interesting comments regarding 4-HO-DET in TiHKAL. He mentioned that he is often asked whether or not it’s true that psilocybin is immediately converted by the body into psilocin, in effect making the two compounds identical in terms of effects.
Shulgin acknowledged that there was no evidence, at the time, to prove this. But he believed that due to the ‘ubiquitous esterases in the body,’ that tryptamine esters ‘would all be easily split to the archetypal indole,’ or psilocin. In essence, he’s saying that all of these different analogs of psilocin basically turn back into psilocin by the time they reach the brain which is why they all have such similar effects.
He also comments on one of the most mysterious and subjective debates in the history of drug culture. He quotes a study that was done by German scientists who fed psychedelic compounds to a certain type of fungi. It was determined that any tryptamine fed to the mushrooms would be hydroxylated.
When the mushrooms were fed DMT, they turned it into 4-HO-DMT. When they were fed DET — a completely man-made chemical that is not known to be found anywhere in nature — they quickly converted it to 4-HO-DET.
At the time, 4-HO-DET was also unknown to mankind and still has not been discovered in nature — except when produced by these mushrooms, as the result of being fed a man-made chemical. So, Shulgin asks, does this make 4-HO-DET, produced naturally by a mushroom fed a man-made chemical, natural or not?
MiPT
Methylisopropyltryptamine, or MiPT, is a tryptamine that shares a similar structure as DMT, DiPT, and miprocin. Despite its similarities to these substances, MiPT is known for having a fairly different result in terms of research. Studies done by chemists report that it is a fairly mild compound.
Like most of the world’s tryptamines, MiPT was first synthesized by Shulgin and TiHKAL remains one of the densest sources of information on the compound. Here, Shulgin reports that the compound is highly distinct from other N,N,-disubstituted tryptamines sheerly due to its lack of effects.
Despite this, it remains available as a research chemical, although it remains obvious why it might be less popular than other compounds. Many psychedelic researchers are interested in potent compounds that produce powerful results when studied. That said, MiPT might be a great option for casual researchers or for those who are unfamiliar with the space.
Shulgin describes the compound as having more of an emphasis on ‘psychedelic effects rather than hallucinogenic,’ suggesting that this compound can be studied without significantly interfering with daily activities.
The crystal structure of MiPT was solved around the same time, and by the same people, as MPT in 2019. Chadeayne et al. discovered the fumarate salt of MiPT. MiPT seems to be more resistant to natural degradation than other tryptamines which are particularly susceptible to oxidizing when they come into contact with oxygen.
Conclusion
If you’re interested in trying out some of the tryptamines that we’ve described in this list for your lab, check out the Rare Tryptamines sample pack. You’ll be able to take advantage of all of the compounds described today, as well as several others. The rare tryptamines list is fairly extensive and includes a number of obscure compounds.
