*WARNING* The substances mentioned in this series have little to no record of human use, and thus the effects they have on humans are either poorly understood or entirely unknown. Much of what this information is simply hypotheses based on animal trials or very small human sample sizes. Very little information exists about their acute or long-term toxicity. Under no circumstances should any of these substances be ingested by a human outside of a clinical setting where psychological and physiological effects can be closely monitored and extremely precise doses can be prepared and TITRATED. DO NOT seek any of these out if you do not have access to those resources.
As I said in the last part, I am well aware of Shulgin's assessment that "Butyl is futile" as a dismissal of Butyl compounds as simply being so high dosing and lacking in interesting effects that they perhaps are not worth pursuing. While I certainly trust his judgment on that, I decided to still write about them at length because they are still an interesting variation on the theme of tryptamine substitution, lend some interesting observations with respect to structure-activity relations, and prevent a vast field of possibilities for various combinations of substitutions, many of which have never been attempted and may yield unexpected interesting effects.
NBT
Meet N-Butyltryptamine, or NBT. This was first synthesized in 1964 for Brimblecome et al's study into tryptamine derivatives4. The paper only mentions in passing that NBT has psychotomimetic properties similar to that of NET and DBT, which are both extremely obscure so this is fairly meaningless4. The effects of NET in humans are unknown. N-methyltryptamine is demonstrated to be an odd non-visual psychedelic so NET and this chemical may be similar in that regard (and as mentioned earlier, Shulgin noted odd non-visual and perhaps empathogenic activity in other N-butyl variations). A similar behavioral response in an open field test (where behavior in an empty space is closely observed) was also observed between NBT, NET, DBT, and DiPT4.
The later 1972 study by Leonard and Shallice noted that no behavioral effects were observed at a dose of 10 mg/kg5. It was also observed that NBT decreased the amount of serotonin in the brain5.
These perhaps indicate a substance that is active only at higher doses but may not be entirely fun or enjoyable. The results of the few studies done on it don't paint a definitive picture so its hard to say with certainty either way what the effects of this drug may be in people.
4-HO-DiBT & 4-HO-DsBT
Now we get into some of the variations on the straight chain butyl-tryptamine theme. Both of these compounds are the 4-HO analogues (see last entry on last post for what the 4-HO denotes). Shulgin hypothesizes on the base structures seen here- DiBT he presumes may not be active because of the dense tangle of interfering carbons in the Di-isobutyl structure. He sees more promise in the cleaner and more stable looking DsBT. He notes that 4-HO-DsBT comes in liquid form at room temperature- an oil that didn't crystallize2.
Only one study in history has produced and observed the effects of these compounds other than Shulgin. This was a pharmacological assay done by Mckenna et al. in 1990. This was a simple receptor affinity study done with a number of tryptamines, some familiar some very obscure. In its lineup of obscure analogues was 4-HO-DiBT and 4-HO-DsBT.
This study determined the inhibition constant (IC50) for the compounds on the 5-HT1A, 5-HT2A, and 5-HT2B receptors, 3 of the receptors whose activation is responsible for the constellation of effects in the psychedelic experience. Most important of these for contributing to the psychedelic state is the 5-HT2A receptor. The IC50 is a value that denotes the concentration of a compound required to activate a receptor- the higher the value is, the less potent a substance is likely to be (though this isn't always a direct correlation, there are all sorts of complicating factors). The two compounds of interest, 4-HO-DiBT and 4-HO-DsBT showed an IC50 of 260±60 and 39±10 respectively (on the 5-HT2A receptor). What does this mean? Well when we look at the IC50 of other compounds in this study that are known to be psychedelic, we can paint a larger picture: Psilocin (6.0±.5), 4-HO-MiPT (13±4), 5-MeO-DMT (5±1), and DMT (75±16).
So this tells us that 4-HO-DiBT and 4-HO-DsBT both activate the receptor necessary for a psychedelic experience to a meaningful degree. This tells us that both compounds are much less potent than most other familiar psychedelics and likely require a much higher dose than others. This tells us that Shulgin's prediction based purely on structure- that 4-HO-DiBT would be significantly less potent than 4-HO-DsBT, is correct.
This does NOT tell us with certainty whether these are actually psychedelic when ingested by humans, what the quality of the experience is actually like, what the possible toxicity is, or what the exact dosage or duration may be. Those are simply things that can only be found out with further in-vivo study. The effects in a test tube can only tell us so much.
Vast Possibilities
4 carbons man.... 4 carbons can be arranged in so many different ways the amount of possible iterations is dizzying. Let's take a look at what all is possible. I have drawn most of the possible variations for base tryptamines utilizing the -butyl group in some way. This is just purely based on what substitutions have already been invented and created for tryptamines. There is a near-infinite amount of possibilities.
Now look at all of these 50 compounds and multiply by 3 for the 3 major substitutions possible on the base structure (4-HO, 4-AcO- and 5-MeO), and we get 200 possible compounds. Yikes.
ow.
That's a lot to think about and a lot to speculate on. Too much in my opinion.
Some of these definitely show more promise than others, some can be presumed inactive or even physically impossible to produce. It serves to warn that the next section is purely SPECULATION based on the tidbits of information known about butyl tryptamine and patterns observed with respect to chemical structure and psychoactive effects in other similar familiar compounds. The real effects these will have on people can be roughly predicted, but are impossible to know with certainty until they have been tried (through titration!) by people. There are always surprises and new patterns.
The dibutylated variations are a good place to start.
The Dibutylated structures serve as a good basis to work from due to ease of production. DBT has been demonstrated to very likely be active (albeit at a high dose), and the 4-HO analogue shows promise. What about the others? As mentioned before, Shulgin speculates on the possible activity of these in his entry for 4-HO-DBT. He saw the most promise in DsBT, as that had the least "tangled" mess of carbons on the nitrogen in the middle. He speculated that the di-isobutyl groups in DiBT would clash together, making it less active, and lastly that DtBT had so much crowding around the nitrogen that it might literally be impossible to make as the atoms would all be bonking into one another. The 4-HO analogues of DiBT and DsBT have been demonstrated to be active (though not very potent) in vitro, though their activity in humans is yet to be seen. A dicyclo- substituted tryptamine in any form has never been attempted, and I am doubtful if such a thing is physically possible from the two tense constrained ringed structures. There can be no conjecture on what effects such a drug would even have as there are absolutely zero existing analogous examples. Thus, DBT, DiBT, and DsBT all show promise as base structures.
The big limiting factor we run into when speculating on compounds is crowding- too many carbons stuffed too close to that active nitrogen renders the compound inactive or simply physically impossible. Most of the -tBT variations are thus, probably unlikely. I am going to arbitrarily guess that the crowding becomes too much for the molecule or the body to handle past having an ethyl group next door. There exists zero information on effects a cyclobutyl group would have in a tryptamine, and it is for now impossible to predict as there are no structural-activity relationships recorded that would even offer hints as to how those might behave- but more likely such molecules would be unstable or exceedingly difficult to produce. If the effects of a cyclobutyl group are to be studied, it should be done with a much simpler substitution on the nitrogen, so I am tossing anything past an ethyl group into the reject pile for now too. Furthermore, it seems that the longer the chains are and the more carbons are involved in the overall formula, the less active and less potent the chemical will be. So the shorter we keep it, the more promising everything is. With this in mind, it's likely that we cannot expect much from the following compounds:
BiBT, BtBT, DiBT, iBiPT, iBsBT, iBtBT, sBiPT, tBsBT, PtBT, DtBT, tBiPT, tBALT, PcBT, BcBT, DcBT, cBiPT, cBiBT, sBcBT, tBcBT, cBALT, and cBcPT.
I'm not saying that these should all be dismissed as inactive or impossible, but they are more likely than not going to be subpar experiences that require extremely high doses and may have a litany of uncomfortable side effects. And some may indeed be physically impossible to make.
Despite the fact that the rule seems to be the less carbons, the more promising the effects, the N-x tryptamines with the lowest amount of carbons out of this series are also fairly lackluster in effects. NBT is questionably active, NsBT may perhaps be interesting as an empathogen, and NtBT was barely active. The activity of NiBT is still unknown. Whether these substances yield interesting substituted analogues is unknown, as substituted N-x-tryptamines have never been made, even with simpler variations like NMT, NET, or NPT (with the exception of 5-MeO-NMT, whose effects in people are still undocumented). Nonetheless, substitutions of N-x-tryptamines should be explored in ones with something simpler than weird butyl groups first.
NsBT or some substituted analogue may be interesting however.
So the next step up from there is likely the most promising, the Methyl-Butylated tryptamines.
Shulgin had already demonstrated that MBT was active, albeit in very high doses. To gauge the effects of the other variations, we can look to the tryptamines a step down- the propyl tryptamines. Dipropyltryptamine, DPT, with two straight chains the least potent of the base tryptamines commonly available, dosing into the 100s of mgs. Diisopropyltryptamine, DiPT, meanwhile, has the same amount of carbons but in a much tighter arrangement, and is considerably more potent (with extremely unique auditory effects). So perhaps having a long straight chain involved does something to the potency. Perhaps MiBT, MsBT, and MtBT may be more potent than MBT due to the this effect, but this is just raw speculation and I don't know for sure. But in general, many base tryptamines are less recreational, potent, or interesting than their 4-HO and 4-AcO counterparts, and in the world of butylated tryptamines, I think these substitutions are where they would shine the most. Ethyl substitutions may also prove fruitful. The one standing example of mixing an ethyl group with a higher order of carbon chain is EPT, which has two very interesting and useful analogues in 4-HO-EPT and 4-AcO-EPT. Ethylisopropyltryptamine (EiPT) has also been attempted, and though little information exists on it, the few reports show promise. As mentioned before, the effect of a cyclobutyl group is completely unknown and nearly impossible to predict, so that's a big question mark for now. However, there exists one 4-HO substituted tryptamine that has a cyclopropyl group in its base structure 4-HO-McPT, which is a fairly lackluster and higher dosing psychedelic. I wonder if the extremely tense cyclopropyl group would be hydrolized into an isopropyl, serving as prodrug to 4-HO-MiPT, in which case a cyclobutyl would be hydrolyzed into a sec-butyl group. For now I am leaving McBT and EcBT out of consideration, until any information on such compounds at all is attained.
Nevertheless, based on that, out of all the butylated tryptamines that are possible, I believe the following compounds may prove the most interesting psychedelics of the bunch:
4-HO-MBT, 4-AcO-MBT, 4-HO-MiBT, 4-AcO-MiBT, 4-HO-MsBT, and 4-AcO-MsBT
and with the ethyl variants,
4-HO-EBT, 4-AcO-EBT, 4-HO-EsBT, and 4-AcO-EsBT.
or if you want to see it illustrated:
I didn't include 4-HO or 4-AcO analogues of MtBT or EtBT, because the stability and activity of the tert-butyl groups in tryptamines in any context is still almost entirely unknown. The only one to ever have been manufactured and tested was NtBT (which doesn't have another carbon stuck to the nitrogen to worry about) (and which was also found to be brief and lackluster). All of the others have never been manufactured in human history, and of course have never been tested under any circumstance, and the one that was made and tested did not show much promise.
EiBT analogues were also not included for the sake of being thoroughly crowded around the nitrogen.
Also seen as possible substitutions are the various butyl groups combined with an Allyl group and a cyclopropyl group. For both Allyl Tryptamines and Cyclopropyltryptamines, no examples exist of other substitutions beyond a methyl group (namely in the MALT series and the McPT series), so it is entirely unknown what effect paring them with even longer and more complex chains may have. For both examples, the products are considered fairly mild and lackluster, so it follows that building them up with even longer and more complex chains may further reduce interesting effects. But of course it cannot be known or predicted until it is tried.
Of course, the base structures for most of these have never been manufactured in human history or been tested, so their baseline activity is simply not known for now. Some unforseen structural anomaly in one of these benign seeming compounds could end up rendering it and all of its analogues completely inactive. Once again, we don't know until we make it and try.
As the various carbon chains get longer, it can be expected that activity and potency will further decrease, though not to the point where they are rendered totally inactive. They might just prove to not be particularly fun or interesting.
Now looking at the effects of known Butyl tryptamines, one might think "They dose so high and they don't sound particularly exciting. Why bother?" Well, a lot of the compounds explored in this entry are speculation based on structure or animal trials, we really don't know what truly unique effects in humans will arise from these chemicals until we try them. Who could've predicted the unique auditory effects of DiPT just by looking at the molecule? All sorts of idiosyncratic effects could be hiding in this infinite variety, just waiting to be discovered. Furthermore, the low potency seems a curse, but it could perhaps be a blessing- in a world of irresponsible researchers who don't use scales or misuse scales, perhaps it could prove helpful to have high-dosing failsafe psychedelics that have a broad margin of error, where a 20-30 mg discrepancy in dose won't really be noticeable.
It's unlikely that we will ever encounter these however- from a market perspective, there really isn't much payoff. Large amounts of product are needed for the desired effects, meaning it will likely be more expensive for the end user. Production of some, especially the sterically fussy ones that crowd around the nitrogen may be very difficult and complicated, and the products may be fairly unstable or difficult to work with (indeed 4-HO-DsBT is an oily liquid at room temperature)2. And furthermore, the effects may be so lackluster that they don't really have much broad appeal to market beyond their novelty for intrepid psychonauts. I would personally love to see and sample some of these, but perhaps that is just a pipe dream.
I set out to write about the butyl tryptamines, and it ended up making for an extremely long article, so I split it in two. You can read part 1 here. The first entry explores in depth some of the substances mentioned in the writings of Alexander Shulgin. As I mention there, I'm wary to just pick and choose obscure chemicals only mentioned in his seminal works PiHKAL and TiHKAL, as there is nothing I can say about them that he hasn't already said better. His work on butyl tryptamines as a coherent group however, I found worth noting and expanding upon.
Now we will look at ones mentioned in other literature, before I go on a wild ride of speculating other potential compounds- as it turns out there are many many variations on how you can assemble 4 carbons with all sorts of other tryptamine substitutions. The specific compounds looked at here are NBT, 4-HO-DiBT, and 4-HO-DsBT. These ones have 0 history of human use and all information on them is purely speculative and extrapolated from animal studies. The effects they have in humans simply will never be known for sure until they are tried.
In the last section I also speculate on which potential compounds show the most promise as interesting psychedelics.
In the last section I also speculate on which potential compounds show the most promise as interesting psychedelics.
As I said in the last part, I am well aware of Shulgin's assessment that "Butyl is futile" as a dismissal of Butyl compounds as simply being so high dosing and lacking in interesting effects that they perhaps are not worth pursuing. While I certainly trust his judgment on that, I decided to still write about them at length because they are still an interesting variation on the theme of tryptamine substitution, lend some interesting observations with respect to structure-activity relations, and prevent a vast field of possibilities for various combinations of substitutions, many of which have never been attempted and may yield unexpected interesting effects.
NBT
 |
| NBT |
The later 1972 study by Leonard and Shallice noted that no behavioral effects were observed at a dose of 10 mg/kg5. It was also observed that NBT decreased the amount of serotonin in the brain5.
These perhaps indicate a substance that is active only at higher doses but may not be entirely fun or enjoyable. The results of the few studies done on it don't paint a definitive picture so its hard to say with certainty either way what the effects of this drug may be in people.
4-HO-DiBT & 4-HO-DsBT
 |
| 4-HO-DiBT (left) and 4-HO-DsBT (right) |
Only one study in history has produced and observed the effects of these compounds other than Shulgin. This was a pharmacological assay done by Mckenna et al. in 1990. This was a simple receptor affinity study done with a number of tryptamines, some familiar some very obscure. In its lineup of obscure analogues was 4-HO-DiBT and 4-HO-DsBT.
This study determined the inhibition constant (IC50) for the compounds on the 5-HT1A, 5-HT2A, and 5-HT2B receptors, 3 of the receptors whose activation is responsible for the constellation of effects in the psychedelic experience. Most important of these for contributing to the psychedelic state is the 5-HT2A receptor. The IC50 is a value that denotes the concentration of a compound required to activate a receptor- the higher the value is, the less potent a substance is likely to be (though this isn't always a direct correlation, there are all sorts of complicating factors). The two compounds of interest, 4-HO-DiBT and 4-HO-DsBT showed an IC50 of 260±60 and 39±10 respectively (on the 5-HT2A receptor). What does this mean? Well when we look at the IC50 of other compounds in this study that are known to be psychedelic, we can paint a larger picture: Psilocin (6.0±.5), 4-HO-MiPT (13±4), 5-MeO-DMT (5±1), and DMT (75±16).
So this tells us that 4-HO-DiBT and 4-HO-DsBT both activate the receptor necessary for a psychedelic experience to a meaningful degree. This tells us that both compounds are much less potent than most other familiar psychedelics and likely require a much higher dose than others. This tells us that Shulgin's prediction based purely on structure- that 4-HO-DiBT would be significantly less potent than 4-HO-DsBT, is correct.
This does NOT tell us with certainty whether these are actually psychedelic when ingested by humans, what the quality of the experience is actually like, what the possible toxicity is, or what the exact dosage or duration may be. Those are simply things that can only be found out with further in-vivo study. The effects in a test tube can only tell us so much.
Vast Possibilities
4 carbons man.... 4 carbons can be arranged in so many different ways the amount of possible iterations is dizzying. Let's take a look at what all is possible. I have drawn most of the possible variations for base tryptamines utilizing the -butyl group in some way. This is just purely based on what substitutions have already been invented and created for tryptamines. There is a near-infinite amount of possibilities.
ow.
That's a lot to think about and a lot to speculate on. Too much in my opinion.
Some of these definitely show more promise than others, some can be presumed inactive or even physically impossible to produce. It serves to warn that the next section is purely SPECULATION based on the tidbits of information known about butyl tryptamine and patterns observed with respect to chemical structure and psychoactive effects in other similar familiar compounds. The real effects these will have on people can be roughly predicted, but are impossible to know with certainty until they have been tried (through titration!) by people. There are always surprises and new patterns.
The dibutylated variations are a good place to start.
 |
| Dibutylated Tryptamines- the way to go? |
The Dibutylated structures serve as a good basis to work from due to ease of production. DBT has been demonstrated to very likely be active (albeit at a high dose), and the 4-HO analogue shows promise. What about the others? As mentioned before, Shulgin speculates on the possible activity of these in his entry for 4-HO-DBT. He saw the most promise in DsBT, as that had the least "tangled" mess of carbons on the nitrogen in the middle. He speculated that the di-isobutyl groups in DiBT would clash together, making it less active, and lastly that DtBT had so much crowding around the nitrogen that it might literally be impossible to make as the atoms would all be bonking into one another. The 4-HO analogues of DiBT and DsBT have been demonstrated to be active (though not very potent) in vitro, though their activity in humans is yet to be seen. A dicyclo- substituted tryptamine in any form has never been attempted, and I am doubtful if such a thing is physically possible from the two tense constrained ringed structures. There can be no conjecture on what effects such a drug would even have as there are absolutely zero existing analogous examples. Thus, DBT, DiBT, and DsBT all show promise as base structures.
The big limiting factor we run into when speculating on compounds is crowding- too many carbons stuffed too close to that active nitrogen renders the compound inactive or simply physically impossible. Most of the -tBT variations are thus, probably unlikely. I am going to arbitrarily guess that the crowding becomes too much for the molecule or the body to handle past having an ethyl group next door. There exists zero information on effects a cyclobutyl group would have in a tryptamine, and it is for now impossible to predict as there are no structural-activity relationships recorded that would even offer hints as to how those might behave- but more likely such molecules would be unstable or exceedingly difficult to produce. If the effects of a cyclobutyl group are to be studied, it should be done with a much simpler substitution on the nitrogen, so I am tossing anything past an ethyl group into the reject pile for now too. Furthermore, it seems that the longer the chains are and the more carbons are involved in the overall formula, the less active and less potent the chemical will be. So the shorter we keep it, the more promising everything is. With this in mind, it's likely that we cannot expect much from the following compounds:
BiBT, BtBT, DiBT, iBiPT, iBsBT, iBtBT, sBiPT, tBsBT, PtBT, DtBT, tBiPT, tBALT, PcBT, BcBT, DcBT, cBiPT, cBiBT, sBcBT, tBcBT, cBALT, and cBcPT.
 |
| The (probable) rejects |
I'm not saying that these should all be dismissed as inactive or impossible, but they are more likely than not going to be subpar experiences that require extremely high doses and may have a litany of uncomfortable side effects. And some may indeed be physically impossible to make.
Despite the fact that the rule seems to be the less carbons, the more promising the effects, the N-x tryptamines with the lowest amount of carbons out of this series are also fairly lackluster in effects. NBT is questionably active, NsBT may perhaps be interesting as an empathogen, and NtBT was barely active. The activity of NiBT is still unknown. Whether these substances yield interesting substituted analogues is unknown, as substituted N-x-tryptamines have never been made, even with simpler variations like NMT, NET, or NPT (with the exception of 5-MeO-NMT, whose effects in people are still undocumented). Nonetheless, substitutions of N-x-tryptamines should be explored in ones with something simpler than weird butyl groups first.
NsBT or some substituted analogue may be interesting however.
So the next step up from there is likely the most promising, the Methyl-Butylated tryptamines.
 |
| friends perhaps? |
Shulgin had already demonstrated that MBT was active, albeit in very high doses. To gauge the effects of the other variations, we can look to the tryptamines a step down- the propyl tryptamines. Dipropyltryptamine, DPT, with two straight chains the least potent of the base tryptamines commonly available, dosing into the 100s of mgs. Diisopropyltryptamine, DiPT, meanwhile, has the same amount of carbons but in a much tighter arrangement, and is considerably more potent (with extremely unique auditory effects). So perhaps having a long straight chain involved does something to the potency. Perhaps MiBT, MsBT, and MtBT may be more potent than MBT due to the this effect, but this is just raw speculation and I don't know for sure. But in general, many base tryptamines are less recreational, potent, or interesting than their 4-HO and 4-AcO counterparts, and in the world of butylated tryptamines, I think these substitutions are where they would shine the most. Ethyl substitutions may also prove fruitful. The one standing example of mixing an ethyl group with a higher order of carbon chain is EPT, which has two very interesting and useful analogues in 4-HO-EPT and 4-AcO-EPT. Ethylisopropyltryptamine (EiPT) has also been attempted, and though little information exists on it, the few reports show promise. As mentioned before, the effect of a cyclobutyl group is completely unknown and nearly impossible to predict, so that's a big question mark for now. However, there exists one 4-HO substituted tryptamine that has a cyclopropyl group in its base structure 4-HO-McPT, which is a fairly lackluster and higher dosing psychedelic. I wonder if the extremely tense cyclopropyl group would be hydrolized into an isopropyl, serving as prodrug to 4-HO-MiPT, in which case a cyclobutyl would be hydrolyzed into a sec-butyl group. For now I am leaving McBT and EcBT out of consideration, until any information on such compounds at all is attained.
Nevertheless, based on that, out of all the butylated tryptamines that are possible, I believe the following compounds may prove the most interesting psychedelics of the bunch:
4-HO-MBT, 4-AcO-MBT, 4-HO-MiBT, 4-AcO-MiBT, 4-HO-MsBT, and 4-AcO-MsBT
and with the ethyl variants,
4-HO-EBT, 4-AcO-EBT, 4-HO-EsBT, and 4-AcO-EsBT.
or if you want to see it illustrated:
 |
| The goods |
I didn't include 4-HO or 4-AcO analogues of MtBT or EtBT, because the stability and activity of the tert-butyl groups in tryptamines in any context is still almost entirely unknown. The only one to ever have been manufactured and tested was NtBT (which doesn't have another carbon stuck to the nitrogen to worry about) (and which was also found to be brief and lackluster). All of the others have never been manufactured in human history, and of course have never been tested under any circumstance, and the one that was made and tested did not show much promise.
EiBT analogues were also not included for the sake of being thoroughly crowded around the nitrogen.
Also seen as possible substitutions are the various butyl groups combined with an Allyl group and a cyclopropyl group. For both Allyl Tryptamines and Cyclopropyltryptamines, no examples exist of other substitutions beyond a methyl group (namely in the MALT series and the McPT series), so it is entirely unknown what effect paring them with even longer and more complex chains may have. For both examples, the products are considered fairly mild and lackluster, so it follows that building them up with even longer and more complex chains may further reduce interesting effects. But of course it cannot be known or predicted until it is tried.
Of course, the base structures for most of these have never been manufactured in human history or been tested, so their baseline activity is simply not known for now. Some unforseen structural anomaly in one of these benign seeming compounds could end up rendering it and all of its analogues completely inactive. Once again, we don't know until we make it and try.
As the various carbon chains get longer, it can be expected that activity and potency will further decrease, though not to the point where they are rendered totally inactive. They might just prove to not be particularly fun or interesting.
Now looking at the effects of known Butyl tryptamines, one might think "They dose so high and they don't sound particularly exciting. Why bother?" Well, a lot of the compounds explored in this entry are speculation based on structure or animal trials, we really don't know what truly unique effects in humans will arise from these chemicals until we try them. Who could've predicted the unique auditory effects of DiPT just by looking at the molecule? All sorts of idiosyncratic effects could be hiding in this infinite variety, just waiting to be discovered. Furthermore, the low potency seems a curse, but it could perhaps be a blessing- in a world of irresponsible researchers who don't use scales or misuse scales, perhaps it could prove helpful to have high-dosing failsafe psychedelics that have a broad margin of error, where a 20-30 mg discrepancy in dose won't really be noticeable.
It's unlikely that we will ever encounter these however- from a market perspective, there really isn't much payoff. Large amounts of product are needed for the desired effects, meaning it will likely be more expensive for the end user. Production of some, especially the sterically fussy ones that crowd around the nitrogen may be very difficult and complicated, and the products may be fairly unstable or difficult to work with (indeed 4-HO-DsBT is an oily liquid at room temperature)2. And furthermore, the effects may be so lackluster that they don't really have much broad appeal to market beyond their novelty for intrepid psychonauts. I would personally love to see and sample some of these, but perhaps that is just a pipe dream.
Sources and Further Reading:
1-Shulgin A, Shulgin A (1997) DBT. TiHKAL: The Continuation
2-Shulgin A, Shulgin A (1997) 4-HO-DBT. TiHKAL: The Continuation
3-Shulgin A, Shulgin A (1997) 4-HO-MBT. TiHKAL: The Continuation
4-Brimblecombe RW, Downing DF, Green DM, Hunt RR (1964) Some pharmacological effects of a series of tryptamine derivatives. Br J Pharmacol Chemother 23(1): 43–54.
5-Leonard BE, Shallice SA (1972) The effects of some tryptamine derivatives on brain monoamines and their precursor amino acids. Neuropharmacology 11(3):373‐384.
6-Mckenna DJ, Repke DB, Lo L, Peroutka SJ (1990) Differential interactions of indolealkylamines with 5-hydroxytryptamine receptor subtypes. Neuropharmacology, 29(3): 193-198
2-Shulgin A, Shulgin A (1997) 4-HO-DBT. TiHKAL: The Continuation
3-Shulgin A, Shulgin A (1997) 4-HO-MBT. TiHKAL: The Continuation
4-Brimblecombe RW, Downing DF, Green DM, Hunt RR (1964) Some pharmacological effects of a series of tryptamine derivatives. Br J Pharmacol Chemother 23(1): 43–54.
5-Leonard BE, Shallice SA (1972) The effects of some tryptamine derivatives on brain monoamines and their precursor amino acids. Neuropharmacology 11(3):373‐384.
6-Mckenna DJ, Repke DB, Lo L, Peroutka SJ (1990) Differential interactions of indolealkylamines with 5-hydroxytryptamine receptor subtypes. Neuropharmacology, 29(3): 193-198
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