Tryptamines The Big & Dandy Bufotenine (5-HO-DMT) Thread - The Truth is Out There

[Morninggloryseed]

I think I see where you are going wioth it. I thought you meant "4-O-DMT" stays that way if reacted. I don't think it can exist without either an H, or something like a Ca or as the Acetyl ester. I'd bet 5-AcO-DMT would be active.

It’s a well known fact that phenolic compounds behave like this. You do know about phenol right? Bufotenin is based on phenol. If you react calcium hydroxide with phenol, you get calcium phenoxide. It loses the H and forms a salt with calcium. The same thing happens with morphine, psilocin, and bufotenin is no exception to this rule. Look up phenoxide and phenol, and you'll see what I'm talking about.

How is it possible for this rule not to apply with bufotenine when it clearly applies to phenol, morphine and psilocin? Can someone please explain how bufotenine could be the one exception to this rule?

 

[Morninggloryseed]

F%B, can you comment?

 

[Anadenanthera]

I think I see where you are going wioth it. I thought you meant "4-O-DMT" stays that way if reacted. I don't think it can exist without either an H, or something like a Ca or as the Acetyl ester. I'd bet 5-AcO-DMT would be active.

I'm not a chemist, but I have a few friends who are.

One of my chemist friends says it will be stable once 5-O-DMT combines with Ca to become 5-CaO-DMT. I do know about calcium oxide being pretty stable until reacted with water (which forms calcium hydroxide). I can see how 5-CaO-DMT would be stable because the DMT side would prevent the calcium oxide at the 5 position from reacting with the water.

I met one person on-line claiming that 5-CaO-DMT will convert to DMT if reacted with the antioxidant Vitamin C. He said Vitamin C will pull off the calcium, forming calcium ascorbate and 5-O-DMT, and then pull of the oxygen forming DMT. If true, this should also work for psilicon (4-HO-DMT). I never heard of this before and I wonder if it is true. I started a thread about this called "Free Base DMT from Bufotenine via Vitamin C?" here:

http://www.bluelight.ru/vb/showthread.php?t=337835

 

[vecktor]

I think I see where you are going wioth it. I thought you meant "4-O-DMT" stays that way if reacted. I don't think it can exist without either an H, or something like a Ca or as the Acetyl ester. I'd bet 5-AcO-DMT would be active.

a phenoxide is an ion PhO-
so bufotenin in its phenoxide form is -O-DMT the thing being negatively charged so it has a positive counter ion in this case allegedly calcium Ca 2+, equally it could be sodium or potassium or whatever. phoxides convert readily back into phenols. the calcium is not covalently attached to the O it is merely a positively entity which is attracted to the negative charge. there are not CaO-DMTs rather there are possibly Ca2+ and -ODMTs.

IMHO this whole idea of calcium bufotenate is BS.

one possibility is that adding lime and heating causes the formation of dehydrobufoetenine a three ring compound where the amino tail ends up joined back to the phenyl ring, this supposedly is active. I am not certain how dehydrobuftenine arises it is quite common in analysis, I think it might be heat and base.

 

[Anadenanthera]

a phenoxide is an ion PhO-
so bufotenin in its phenoxide form is -O-DMT the thing being negatively charged so it has a positive counter ion in this case allegedly calcium Ca 2+, equally it could be sodium or potassium or whatever. phoxides convert readily back into phenols. the calcium is not covalently attached to the O it is merely a positively entity which is attracted to the negative charge. there are not CaO-DMTs rather there are possibly Ca2+ and -ODMTs.

IMHO this whole idea of calcium bufotenate is BS.

one possibility is that adding lime and heating causes the formation of dehydrobufoetenine a three ring compound where the amino tail ends up joined back to the phenyl ring, this supposedly is active. I am not certain how dehydrobuftenine arises it is quite common in analysis, I think it might be heat and base.

I'm not a chemist, nor do I claim to be very knowledgeable in that area. My chemist buddy insists that 5-CaO-DMT is indeed created and that this is what calcium bufotenate is.

All I know is that bufotenine treated with calcium hydroxide is stronger than free-base bufotenine. Something is indeed happening to it. So if it doesn’t convert to calcium bufotenate, is it converting to dehydrobufotenine as is postulated above?

Does anyone else agree with Vecktor on this?

 

[vecktor]

I'm not a chemist, nor do I claim to be very knowledgeable in that area. My chemist buddy insists that 5-CaO-DMT is indeed created and that this is what calcium bufotenate is.

All I know is that bufotenine treated with calcium hydroxide is stronger than free-base bufotenine. Something is indeed happening to it. So if it doesn’t convert to calcium bufotenate, is it converting to dehydrobufotenine as is postulated above?

Does anyone else agree with Vecktor on this?

ask your chemistry buddy what valency calcium always has?
then ask him what valency it appears to have in 5-CaO-DMT?

 

[retired_chemist]

On the whole Calcium blood brain barrier thing - every reference I've seen about so far had, well, no references. Show me the scientific studies that this hypothesis is based on and I'll reconsider.


One thing I am in no uncetain terms absolutely sure about is the foillowing statement is just not true:

What’s even more interesting is that because 5-O-DMT is not bufotenin, it should be legal in nearly all countries, even in the US.:D However, if you react 5-O-DMT with an acid, like the acid in your stomach, hydrochloric acid, the reaction is reversed and it becomes 5-OH-DMT hydrochloride (bufotenine hydrochloride), which is illegal only in the US (as far as I know).

Read the letter of the schedules:

http://a257.g.akamaitech.net/7/257/...cess.gpo.gov/cfr_2004/aprqtr/21cfr1308.11.htm

(d) Hallucinogenic substances. Unless specifically excepted or unless listed in another schedule, any material, compound, mixture, or preparation, which contains any quantity of the following hallucinogenic substances, or which contains any of its salts, isomers, and salts of isomers whenever the existence of such salts, isomers, and salts of isomers is possible within the specific chemical designation (for purposes of this paragraph only, the term ``isomer'' includes the optical, position and geometric isomers):

...

(15) Bufotenine.................................................. 7433

The law does not specify "amine salts" versus "phenoxide salts", it simply specifies "salt".

This is most definitely a "salt":

Ca[5-O-DMT]2

And thereby most definitely a Schedule I material by US Federal Codes 21CFR1308.11

 

[Solipsis]

Yeah Vecktor is right.
Calcium Oxide is indeed a stable solid under dry conditions, dissolved in water you get:

CaO + H2O -> Ca(OH)2

However this is only formal because in water Ca(OH)2 cannot exist just as Ca(ODMT)2 cannot exist. They both are salts which ionize in water to form the separated positive and negative part. Ca2+ OH- and DMT-O- (that last - is a minus) are ions, charged incomplete parts which compose salts if the water is removed. CaODMT is absolutely wrong because Ca is 2+ and ODMT / DMT-O is 1-, they have to add up so 2 DMT-O's are neccessary for every Calcium: Ca(ODMT)2 is therefor correct. It can indeed be produced by adding Ca(OH)2 or CaO to water and 5-HO-DMT. A part of 5-HO-DMT in water breaks down to H+ (or H3O+) and DMT-O- , the H3O+ will meet the OH- and change into water which is of course lost in the whole body of water. Upon evaporation, Ca(ODMT)2 is obtained.

Where I get confused is why would this compound be any less toxic or more psychedelic? Because it may present limited dissolving properties? Even if this is true - suppose one imbibes the material.
It would sit in his stomache until it dissolves in water, and when it does the calcium loses sight of the bufotenate to meet up with other anions. Like I said earlier, salts decompose... their respected parts react dynamically and gradually in the environment.
So the only effect this compound may have is a selfproviding delayed release as it dissolves. I say forget calcium bufotenate.

 

[retired_chemist]

In stomach acid I feel pretty confident that the Ca[5-ODMT]2 while probably water insoluble, would dissolve very rapidly in HCl solution by virtue of the 2 alkyldimethylamine groups present in the complex, and the calcium salt at the phenolic groups would be immediately decomposed to CaCl2, so orally there should be no difference than bufotenine hydrochloride.

I think the argument is that the Ca[5-ODMT]2 form is more active by either insufflation (of the snuff) or by smoking. I remain skeptical of the whole theory without some meaningful references to studies.

 

[Morninggloryseed]

Someone changed the wikipedia entry to reflect this "Ca-O-DMT" as if it were fact. Was that you Anadenanthera? Change it back until something can be confirmed.

 

[Morninggloryseed]

Anyone have access to this? I no longer have university access.

Bufo toads and bufotenine: fact and fiction surrounding an alleged psychedelic.

Journal of Psychoactive Drugs
Vol 28 (No. 3) July 1996, 267-290
by T. Lyttle; D. Goldstein; J. Gartz

 

[Anadenanthera]

Someone changed the wikipedia entry to reflect this "Ca-O-DMT" as if it were fact. Was that you Anadenanthera? Change it back until something can be confirmed.

I checked on http://en.wikipedia.org/wiki/Bufotenin

I can't find Ca-O-DMT or anything like that there.

It does mention calcium bufotenate though.

I'd like to edit it. That would be COOL! How can I edit it? When I press "Edit this page" it says "You have been blocked from editing". It gives the reason as "open proxy".

 

[Anadenanthera]

In stomach acid I feel pretty confident that the Ca[5-ODMT]2 while probably water insoluble, would dissolve very rapidly in HCl solution by virtue of the 2 alkyldimethylamine groups present in the complex, and the calcium salt at the phenolic groups would be immediately decomposed to CaCl2, so orally there should be no difference than bufotenin hydrochloride.

I think the argument is that the Ca[5-ODMT]2 form is more active by either insufflation (of the snuff) or by smoking. I remain skeptical of the whole theory without some meaningful references to studies.

Yes, it would convert back into bufotenin hydrochloride if you took it orally.

Friends of mine vaporize it and take it sublingually and say its more active that way.

There are a lot of possible salts of bufotenin that aren't documented. I've been trying to find references to it and I can't. I have been able to find references showing some esters of bufotenin are more psychoactive, but nothing on any basic salts, not even sodium bufotenate.

I know bufotenin hydrochloride is HORRIBLE! Its documented in only one publication that I am aware of.

I have a friend who says bufotenin ascorbate is very pleasant, but causes nausea. I can't even find bufotenin ascorbate documented anywhere. There is so little out there on bufotenin.

 

[Anadenanthera]

On the whole Calcium blood brain barrier thing - every reference I've seen about so far had, well, no references. Show me the scientific studies that this hypothesis is based on and I'll reconsider.


One thing I am in no uncetain terms absolutely sure about is the foillowing statement is just not true:



Read the letter of the schedules:

http://a257.g.akamaitech.net/7/257/...cess.gpo.gov/cfr_2004/aprqtr/21cfr1308.11.htm

(d) Hallucinogenic substances. Unless specifically excepted or unless listed in another schedule, any material, compound, mixture, or preparation, which contains any quantity of the following hallucinogenic substances, or which contains any of its salts, isomers, and salts of isomers whenever the existence of such salts, isomers, and salts of isomers is possible within the specific chemical designation (for purposes of this paragraph only, the term ``isomer'' includes the optical, position and geometric isomers):

...

(15) Bufotenine.................................................. 7433

The law does not specify "amine salts" versus "phenoxide salts", it simply specifies "salt".

This is most definitely a "salt":

Ca[5-O-DMT]2

And thereby most definitely a Schedule I material by US Federal Codes 21CFR1308.11

Yeah, it’s a salt, but its a salt of 5-O-DMT, not 5-HO-DMT. Just like phenoxide is not phenol. It has different properties. They are not the same exact compound. It all depends on the interpretation of the law, so even though 5-O-DMT is not explicitly mentioned in the law, you could possible interpret it as being covered. My interpretation is NO, its not covered by the law mentioned above because its actually a different compound in my eyes. But law is left to interpretation, and US drug laws are so vague. I wouldn't play around with it in the US. Chances are, even if the law doesn't cover it, you'd get in trouble in some way or another.

Its always better to assume any drug is illegal and don't do any research with it unless you get a silence from the government specifically allowing the research to be conducted.

 

[Anadenanthera]

Yeah Vecktor is right.
Calcium Oxide is indeed a stable solid under dry conditions, dissolved in water you get:

CaO + H2O -> Ca(OH)2

However this is only formal because in water Ca(OH)2 cannot exist just as Ca(ODMT)2 cannot exist. They both are salts which ionize in water to form the separated positive and negative part. Ca2+ OH- and DMT-O- (that last - is a minus) are ions, charged incomplete parts which compose salts if the water is removed. CaODMT is absolutely wrong because Ca is 2+ and ODMT / DMT-O is 1-, they have to add up so 2 DMT-O's are neccessary for every Calcium: Ca(ODMT)2 is therefor correct. It can indeed be produced by adding Ca(OH)2 or CaO to water and 5-HO-DMT. A part of 5-HO-DMT in water breaks down to H+ (or H3O+) and DMT-O- , the H3O+ will meet the OH- and change into water which is of course lost in the whole body of water. Upon evaporation, Ca(ODMT)2 is obtained.

Where I get confused is why would this compound be any less toxic or more psychedelic? Because it may present limited dissolving properties? Even if this is true - suppose one imbibes the material.
It would sit in his stomache until it dissolves in water, and when it does the calcium loses sight of the bufotenate to meet up with other anions. Like I said earlier, salts decompose... their respected parts react dynamically and gradually in the environment.
So the only effect this compound may have is a selfproviding delayed release as it dissolves. I say forget calcium bufotenate.

Great material A very different view from others I’ve seen.

Ca(ODMT)2? Very interesting indeed. That type of bond doesn't happen to phenoxide. Why would it happen to bufotenin?

It’s my understanding that if you take calcium bufotenate orally, it doesn't work well. It’s the same as bufotenin hydrochloride. If you snuff it, it works very well.

Some people say it's just converting back into free-base bufotenin in the nose. But then, why the increased potency? This is what I don't understand. People I know say it’s stronger in calcium salt form. Is it just placebo effect? That’s always possible, especially when talking about hallucinogens. But these people are long time users of Yopo and Vilca, so I doubt its just placebo effect.

Could the calcium be doing something to aide in absorption when it converts back into free base bufotenine in the nose, if that happens?

Any ideas?

 

[vecktor]

Yeah, it’s a salt, but its a salt of 5-O-DMT, not 5-HO-DMT. Just like phenoxide is not phenol. It has different properties. They are not the same exact compound. It all depends on the interpretation of the law, so even though 5-O-DMT is not explicitly mentioned in the law, you could possible interpret it as being covered. My interpretation is NO, its not covered by the law mentioned above because its actually a different compound in my eyes. But law is left to interpretation, and US drug laws are so vague. I wouldn't play around with it in the US. Chances are, even if the law doesn't cover it, you'd get in trouble in some way or another.

Its always better to assume any drug is illegal and don't do any research with it unless you get a silence from the government specifically allowing the research to be conducted.

it is not a salt of 5-O-DMT
a simple analogies

Hydrochloric acid is HCL
Sodium Chloride Na+ Cl- is a salt of hydrochloric acid
the anion is (Cl)-
HCl is the parent acid not Cl

Phenol is HO-C5H5
Sodium phenoxide Na+ O-C5H5 is a salt of phenol
the anion is (O-C5H5)-
Phenol HO-C5H5 is the parent acid

Bufotenin is 5-HO-DMT
calcuim bufotenate is a salt of bufotenin
the anion is (5-O-DMT)-
Bufotenin is the parent acid of the 'bufotenates' not (5-O-DMT)-

We refer to things as being salts of their parent acid. whether you are a lawyer a chemist or whatever,
This is not a matter of interpretation it is a fact.

A phenoxide salt of something is charged, things which are charged tend to be very poor at crossing the blood brain barrier unless they are transported by carriers, and I doubt there is a carrier or transporter for bufotenin as there isn't for serotonin.

I call bullshit on the whole calcium bufotenate thing.

 

[swilow]

I read in TIHKAL that amanita muscaria contains 5-OH-DMT....this stuff seems to be popping up everywhere.

 

[Coolio]

Wait, amanitas have tryptamines in them as well as muscimol?

 

[squerll]

I was always under the impression it was mildly psychedelic with harsh and possibly deadly side affects.
Things that a mildly or possibly usually don’t turn out to be much use, combined with possible deadly side affects make this one seem like a dangerous place with no rewards.
There seems to always be someone who likes to try things like this, I am interested in hearing more about it. But I don’t want any until the info changes, if it ever does.

My definition of psychedelic is a substance that has the ability to produce insights and life changing experiences. Which I haven’t heard any of that about 5-ho-dmt.

Some people use the definition of mind manifesting but that is so broad it can include about anything. Unleaded gas and rubber cement can make you hallucinate images from your mind and make you feel like total garbage with no insights afterwards (which seems to sum up most of the 5-o-dmt experience reports) but I wouldn't classify them as psychedelic. I would classify them as toxic garbage. Which seems like what 5-ho-dmt falls under.

 

[squerll]

...