How psychedelic is MDMA?

[Jabberwocky]

Hi there! I've been a casual drug user for 5 or 6 years and last night at a party I had the chance to try pure MDMA for the first time. I bought my gram which came as a bag of off white slightly brown powder which i eyeballed into a cup and kicked back with a little warm water (which is how the guy recommended i take it)

I want to start by saying everyone at the party was on this stuff and maybe it's my inexperience with the drug talking but it seemed to me that everyone was tripping. this MDMA was extremely psychedelic, like full blown visuals that i'd normally experience off 2 tabs of acid and on top of that after the visuals went away it kept me stimulated for 12+ hours which goes against everything i've read about molly. it also didn't give me that in love with everyone feeling that I got when I took an ecstasy pill a few years ago and while dancing felt good i was much more interested in just talking to people, nobody at the party was really dancing.

Basically i'm just wondering if that's normal for pure MDMA? I'm thinking i was actually sold some weird RC or something like 4-aco-dmt mixed with meth. I still have a good amount of the bag left and it was a fun time but if I do it again with friends I don't want to be telling them it's molly if it's not

Thanks!

No - it isn't in any way shape or form. Psychedelic effects from substances not known to be psychedelic (as stated in earlier posts) are almost certainly modulated by some form of Hallucinogen Persisting Perception Disorder -- where the cortical pathways are highly overstimulated by any 5HT2 agonism -- and respond as if true psychedelics had been ingested. This is common in long term high cumulative dose users.


One can search the erowid website to find substances that are psychedelic and have a duration of 12+ hours at a dose of ( ?? 100-200 mg i'm guessing)

Of interest are the beta-ketone analogues of the 2-C family of psychedelic phenethylamines -- this family of substances produce full-blown CEV and OEV (which isn't happening of a normal does of MDMA) morphing, melting, breathing, tracers, color saturation, etc


Anyway -- if it was 4-aco-dmt the ridiculous auditory hallucinations are a hallmark -- absence of which points to it wasn't

 

[MagickalKat777]

No - it isn't in any way shape or form. Psychedelic effects from substances not known to be psychedelic (as stated in earlier posts) are almost certainly modulated by some form of Hallucinogen Persisting Perception Disorder -- where the cortical pathways are highly overstimulated by any 5HT2 agonism -- and respond as if true psychedelics had been ingested. This is common in long term high cumulative dose users.


One can search the erowid website to find substances that are psychedelic and have a duration of 12+ hours at a dose of ( ?? 100-200 mg i'm guessing)

Of interest are the beta-ketone analogues of the 2-C family of psychedelic phenethylamines -- this family of substances produce full-blown CEV and OEV (which isn't happening of a normal does of MDMA) morphing, melting, breathing, tracers, color saturation, etc


Anyway -- if it was 4-aco-dmt the ridiculous auditory hallucinations are a hallmark -- absence of which points to it wasn't

You got so much of it wrong I don't even know where to start.

First off, 4-AcO-DMT is not known for auditory hallucinations, DiPT and it's hydroxylated analogs are. I've have 4-AcO-DMT and I've had mushrooms and neither gave me any form of auditory distortion. I only ever got it from DMT and 5-MeO-AMT outside of MDA (which is known for all kinds of hallucinogenic aberrations that nobody can tie a SAR relationship to) or DiPT (the diarrhea and steep dose curve of 5-MeO-DiPT kept even me away from it. 4-AcO-DMT is not known for that effect at all, you flat out don't know what you're talking about.

Next up, beta-ketones are ALWAYS weaker than their parent chemicals. 2C-B is unequivocally better than bk-2C-B. Beta-ketones were invented to get around the law but by your logic, methylone would be better than MDMA. Unfortunately beta-ketones tend to lose most of their psychedelic activity so unless you've take 2C-B and kb-2C-B at the same dose and found bk to be superior, shut your mouth and stop giving misinformation.

Third, did you seriously say that there are substances that last 12+ hours and suggested over a 100mg dose?! The ones that last 12+ hours have defenses against the body breaking it down. For example, 5-MeO-AMT. It's also known as alpha,O-dimethylserotonin and it's a molecule that was made to cross the blood brain barrier, something serotonin can not do because MAO goes to town on it. 100mg would be death. 1.5mg is active for most. Anything that makes you trip that hard for a long time? It's generally very potent. LSD, DOx series, etc.

Lastly, MDMA is classified as a psychedelic amphetamine - it is well known for being psychedelic. In fact it's psychedelic activity is why it's being investigated with PTSD patients because it has the strange effect where the psychedelic experience is not scary even if the content itself would normally be scary.

Stop giving reckless advice. I don't care if you're trolling or just ignorant, either way you could hurt someone.

 

[Jabberwocky]

You got so much of it wrong I don't even know where to start.

First off, 4-AcO-DMT is not known for auditory hallucinations, DiPT and it's hydroxylated analogs are. I've have 4-AcO-DMT and I've had mushrooms and neither gave me any form of auditory distortion. I only ever got it from DMT and 5-MeO-AMT outside of MDA (which is known for all kinds of hallucinogenic aberrations that nobody can tie a SAR relationship to) or DiPT (the diarrhea and steep dose curve of 5-MeO-DiPT kept even me away from it. 4-AcO-DMT is not known for that effect at all, you flat out don't know what you're talking about.

Next up, beta-ketones are ALWAYS weaker than their parent chemicals. 2C-B is unequivocally better than bk-2C-B. Beta-ketones were invented to get around the law but by your logic, methylone would be better than MDMA. Unfortunately beta-ketones tend to lose most of their psychedelic activity so unless you've take 2C-B and kb-2C-B at the same dose and found bk to be superior, shut your mouth and stop giving misinformation.

Third, did you seriously say that there are substances that last 12+ hours and suggested over a 100mg dose?! The ones that last 12+ hours have defenses against the body breaking it down. For example, 5-MeO-AMT. It's also known as alpha,O-dimethylserotonin and it's a molecule that was made to cross the blood brain barrier, something serotonin can not do because MAO goes to town on it. 100mg would be death. 1.5mg is active for most. Anything that makes you trip that hard for a long time? It's generally very potent. LSD, DOx series, etc.

Lastly, MDMA is classified as a psychedelic amphetamine - it is well known for being psychedelic. In fact it's psychedelic activity is why it's being investigated with PTSD patients because it has the strange effect where the psychedelic experience is not scary even if the content itself would normally be scary.

Stop giving reckless advice. I don't care if you're trolling or just ignorant, either way you could hurt someone.

Can you actually read -- I said there are substances that last 12 hours that are dose between 100 and 200 mg --> BK-2CB

GO look up the substance

Bk-2CB has several trip reports on erowid that identify 12-18 + hours -- for some reason the beta-ketone version of 2-CB lasts much longer -- and the dose is 100-300 mg


You can apologize after you read the reports

https://erowid.org/experiences/exp.php?ID=105075

30 hours from 150 mg

https://erowid.org/experiences/exp.php?ID=105314

20 hours from 3 (110 mg) capsules


Of interest --

If the liver manages to replace oxygen of the ketone with an hydroxy then Catechol-O-methyltransferase can convert the hydroxy to a methyl group -- like the dopamine to 3-Methoxy tyramine conversion

We know that MDMA is metabolized by Catechol-O-methyltransferase

The result from bk-2C-B is BOB -- https://en.wikipedia.org/wiki/BOB_(psychedelic) (dose 10-20 mg -- duration 10-20 hours)

It is interesting that the addition of the beta-ketone allows the possible path

 

[Black]

Of interest --

If the liver manages to replace oxygen of the ketone with an hydroxy then Catechol-O-methyltransferase can convert the hydroxy to a methyl group -- like the dopamine to 3-Methoxy tyramine conversion

We know that MDMA is metabolized by Catechol-O-methyltransferase

you mean methoxy group instead of methyl group?
comt normally acts on the aromatic hydroxyl groups at the 3 or 4 positions of the ring. i don't see any reason to believe that it would do something with the aliphatic beta hydroxyl group on a pea. especially since ephedrine (which has that pea backbone and a beta hydroxyl; so it'd be the ideal target for comt if it would do what you suppose) is basically excreted unchanged with the remainer being dihydroxy derivatives or benzoic acid [source]. there are no beta methoxy- (or methyl- for that matter) metabolites here.

 

[Jabberwocky]

you mean methoxy group instead of methyl group?
comt normally acts on the aromatic hydroxyl groups at the 3 or 4 positions of the ring. i don't see any reason to believe that it would do something with the aliphatic beta hydroxyl group on a pea. especially since ephedrine (which has that pea backbone and a beta hydroxyl; so it'd be the ideal target for comt if it would do what you suppose) is basically excreted unchanged with the remainer being dihydroxy derivatives or benzoic acid [source]. there are no beta methoxy- (or methyl- for that matter) metabolites here.

Yes methoxy (methyl replacing the hydrogen to give methoxy instead of the alcohol)

The ketone could possibly be reduced to the alcohol by the HCl in the stomach (acid mediated hydrolysis) (heck trigylcerides are hydrolyzed)

Whether the COMT enzyme or the liver methylates the hydroxyl to a methoxy -- or the liver does is immaterial

 

[Black]

it's not hydrolysis. the reaction from ketone to alcohol is a simple reduction — and we know (from the metabolism of methylone for example) that this happens in vivo. HCl is not a reducing agent.
how is it now immaterial if the hydroxyl group is metabolised to a methoxy when what you proposed above is exactly that?

 

[bvrd man]

there are mild visuals throughout but some visuals seem to come in at the end and increase as it leaves the body.

 

[Jabberwocky]

it's not hydrolysis. the reaction from ketone to alcohol is a simple reduction — and we know (from the metabolism of methylone for example) that this happens in vivo. HCl is not a reducing agent.
how is it now immaterial if the hydroxyl group is metabolised to a methoxy when what you proposed above is exactly that?

immaterial in regard to the exact mechanism of hydroxy - methoxy.

I still posit that acid mediated hydrolysis (HCl in stomach acid) can reduce the ketone to the alcohol

 

[Black]

I still posit that acid mediated hydrolysis (HCl in stomach acid) can reduce the ketone to the alcohol

you know a lot about chemistry. i really don't understand why you would propose something impossible.
which is going to be the reducing agent?
H+? that cannot be oxidised further (having less than zero electrons is impossible). you would need H-.
Cl-? that means C=O + 2 Cl- +2H+ -> CH-0H + Cl2. if you get that to work then congratulations. you now have access to unlimited energy.

 

[Jabberwocky]

you know a lot about chemistry. i really don't understand why you would propose something impossible.
which is going to be the reducing agent?
H+? that cannot be oxidised further (having less than zero electrons is impossible). you would need H-.
Cl-? that means C=O + 2 Cl- +2H+ -> CH-0H + Cl2. if you get that to work then congratulations. you now have access to unlimited energy.

I shouldn't have used term reduce.

aqueous acid catalyzed nucleophilic addition

a nucleophile attacks the partially positive carbon breaking the p bond of the electrophilic carbon and attaching to the carbon (no leaving group for the substitution)

H+ is key --> I don't need it to oxidize, in acid conditions the H+ from the hydronium protonates the oxygen left from the broken ketone into an alcohol

I'm still figuring out the exact way to replace the nucleophile with a hydrogen

_________*************************


Actually, Lewis Acids will directly protonate the oxygen of the ketone to the hydroxy -- I don't even need to worry about nucleophilic addition --

The Hydronium ( H3O+) in stomach acid is a Lewis Acid and will protonate the ketone of bk-2C-B directly to the hydroxy

 

[Black]

of course the ketone can be protonated, but that doesn't give you the alcohol. the resulting molecule has a positive charge and will lose the proton once the pH reaches neutral values again.

the term reduction is correct, because the reaction you proposed is a reduction. and you do need some sort of reducing agent to perform a reduction.

 

[Jabberwocky]

of course the ketone can be protonated, but that doesn't give you the alcohol. the resulting molecule has a positive charge and will lose the proton once the pH reaches neutral values again.

the term reduction is correct, because the reaction you proposed is a reduction. and you do need some sort of reducing agent to perform a reduction.

For a nucleophilic attack on the Carbon, yes. But for an electrophilic attack on the O, actually you don't. All you need is an acid and water.


Electrophilic attack on the carbonyl oxygen is sufficient.

The carbonyl oxygen is a weak Lewis Base, as such it will gladly accept an H+ from the Lewis Acid Hydronium (H3O+) -- which is formed by HCl and Water.

Because the carbonyl has a slightly polar double bond between the C=O the electrophile can attack either the pi or sigma bond.

The electrons in the carbonyl pi bond are highly distorted toward the Oxygen (because O is much more electro-negative than C)

When the H+ electrophile attacks the pi bond, the electrons that were shared with the Carbon bond to the H+ the result is a hydroxyl with lone pairs balanced on either side of the O and a single bond (sigma) between the O and C.

The resulting group is resonance stabilized.

 

[Black]

you just described the same thing from above in more detail. it's still not an alcohol, but a protonated ketone. the "resulting" molecule is charged and will react back to the unprotonated ketone at physiological pH.

 

[Jabberwocky]

you just described the same thing from above in more detail. it's still not an alcohol, but a protonated ketone. the "resulting" molecule is charged and will react back to the unprotonated ketone at physiological pH.

actually it wont.

It is not the ketone any longer -- the hydrogen bonds with the carbonyl pi bond -- so only 1 bond between the C and O

It is a resonance stabilized molecule. Look it up.

 

[aced126]

actually it wont.

It is not the ketone any longer -- the hydrogen bonds with the carbonyl pi bond -- so only 1 bond between the C and O

It is a resonance stabilized molecule. Look it up.

Are you serious?!? You've actually got around 4-5 people knowledgeable in chemistry telling you that you're plain wrong yet you're being completely adamant in defending a ridiculously incorrect theory! Truly unbelievable...
http://www.bluelight.org/vb/threads/776091-The-Small-amp-Handy-BOHB-(beta-hydroxy-2C-B)-thread

 

[Yeetbeat]

It's borderline Hitchens's razor at times.

 

[Black]

actually it wont.

It is not the ketone any longer -- the hydrogen bonds with the carbonyl pi bond -- so only 1 bond between the C and O

It is a resonance stabilized molecule. Look it up.

bullshit. i challenge you to produce a equation for the reaction that results in a neutral alcohol.

you might say that a molecule with a positive charge is fine. but that's just plain wrong. look at this table. the pka of a protonated ketone is -7.3 (in words: MINUS seven point three). even when there a phenyl ring adjacent and you get some resonance stabilisation (let's say it moves the pka up by 6; i'm being generous here), then you get in stomach acid (ph=2) roughly something like 0.001% (-1 to 2 is 4 log units) of the ketone protonated. at physiological ph it's basically nothing. there is a reason that reactions that depend of ketones being protonated are usually performed in concentrated acids like H2SO4...

the reaction you are thinking of is (probably) the formation of a hydrate. it doesn't stop at the protonated ketone, but water acts as a nucleophile, forming the hydrate. but since you need stronly electron pulling groups in the vicinity for the hydrate to be stable which we don't have here, the equilibrium lies on the side of the ketone.

 

[Jabberwocky]

bullshit. i challenge you to produce a equation for the reaction that results in a neutral alcohol.

you might say that a molecule with a positive charge is fine. but that's just plain wrong. look at this table. the pka of a protonated ketone is -7.3 (in words: MINUS seven point three). even when there a phenyl ring adjacent and you get some resonance stabilisation (let's say it moves the pka up by 6; i'm being generous here), then you get in stomach acid (ph=2) roughly something like 0.001% (-1 to 2 is 4 log units) of the ketone protonated. at physiological ph it's basically nothing. there is a reason that reactions that depend of ketones being protonated are usually performed in concentrated acids like H2SO4...

the reaction you are thinking of is (probably) the formation of a hydrate. it doesn't stop at the protonated ketone, but water acts as a nucleophile, forming the hydrate. but since you need stronly electron pulling groups in the vicinity for the hydrate to be stable which we don't have here, the equilibrium lies on the side of the ketone.

The pi bond of the ketone donates 2 electrons to the Hydrogen -- resulting the the resonance stabilized oxygen detailed in the link below.

"Some oxonium ions are resonance stabilized, in which case not all resonance forms of the species fit the above definition."


eg:

http://www.ochempal.org/index.php/alphabetical/o-p/oxonium-ion/

Not to mention that ketones will spontaneously tautomerize to the enol(ate) -- in water but more readily in aqueous acid. The bk-2c-b is not the free-base, it is HCl -- adding more acid

Then there is the fact of bk-2c-b dimerization.

The dissociation reactions of the bk-2c-b dimer upon reaction with stomach acid is not completely characterized.

I am researching the possibility of a dimer dissociation directly to the enol (because it is in acid) with the adoption of a Hydrogen resulting in the completely stable alcohol. The readiness of electron pairs to be shared between the alpha and beta carbon due to tautomerization may allow for the adoption of H+, especially in an over-saturated H3O+ and HCl environment.

 

[aced126]

The HCl salt of bk-2-CB isn't going to dimerise because all the components are crystallised and cannot move. You need a reaction medium i.e. a solvent where different components of the reaction mixture are free to move around and react with one another. If you dissolved bk-2-CB in acidified water (similar to if you were to orally ingest it via the stomach) then you might need to consider what could happen.

In fact, 2 things could happen. Firstly, imine formation could take place causing dimerisation. However this is a reversible process so the imine dimer can convert back to its monomers before being absorbed. But more importantly the rate of formation will be very slow due to the extremely low pH causing almost all of the molecules to be protonated at the nitrogen, which then makes it impossible for the nitrogen to attack the carbonyl carbon. Imine formation has the fastest rate at a slightly low pH (6 is good) where not a significant proportion of the amine is protonated, but every so often a carbonyl oxygen is protonated making the carbonyl carbon susceptible to attack by the amine. Also the ketone is quite bulky slowing down the rate and reducing the equilibrium constant but that factor is small compared to the low pH one.

The second possibility of dimerisation is acid catalysed self aldol condensation. This, once again will not happen in acidic solution. Consider the reaction between acetone and elemental bromine catalysed by acetic acid. The acetone is only brominated once. This is because for bromination to occur, the alpha carbon needs to stabilise a delta positive charge in the transition state. The bromine on the alpha carbon withdraws electron density and destabilises that carbon so no further than one time bromination occurs. With a base catalysed bromination of acetone, the alpha carbon now needs to stabilise a delta negative charge which in fact the bromine helps with so bromination occurs multiple times (this is the basis of the iodoform test; iodination occurs 3 times on the alpha carbon and, once the ketone is attacked by a hydroxide, the tetrahedral intermediate collapses expelling CI3- which then deprotonates the resulting carboxylic acid, forming iodoform). In the case of bk-2-CB in highly acidic environments, the amine (on the alpha carbon) is protonated and even more electron withdrawing than say bromine, so it destabilises the transition state required for the enol to attack an unenolised molecule of bk-2-CB. This aldol reaction will not occur.

Don't bother trying to study aldol self condensations or imine formation though. Instead figure out what oxidation and reduction is for a start lol. You can't just jump in the deep end without first trawling through the basics. Take my advice and read that book instead of pointlessly wasting time "researching dimer dissociation".

 

[Black]

The pi bond of the ketone donates 2 electrons to the Hydrogen -- resulting the the resonance stabilized oxygen detailed in the link below.

"Some oxonium ions are resonance stabilized, in which case not all resonance forms of the species fit the above definition."


eg:

http://www.ochempal.org/index.php/alphabetical/o-p/oxonium-ion/

Not to mention that ketones will spontaneously tautomerize to the enol(ate) -- in water but more readily in aqueous acid. The bk-2c-b is not the free-base, it is HCl -- adding more acid

i already factored in the resonance stabilisation in my estimate above. all my points from that post above still stand, as well as the challenge for the corresponding equation that actually leads to an alcohol.

You can't just jump in the deep end without first trawling through the basics

exactly what i was thinking.