Safrole to MDA in the human body

[The Holy Quadruplty]

safrole can eventually become 3,4-methylenedioxyphenyl in the human body which then can turn into mda.

Safrole is isomerized into Isosafrole i beleive, then Isosafrole into Methylenedioxyphenyl, than that into MDA, or somethimg like that is how.

if im wrong please lmk as that's why im posting this.

 

[emkee_reinvented]

Good morning, The Holy Quadruplty

well assuming you are investigating it, i don t know if you plan ingesting it.
For the reason you mentioned, the in-vivo transformation to MDA.
And assume you are aware that in small quantity like we ingest via spices.
Is safe, but large am-mount s are considered unsafe, and Carcinogen s.

So be safe, don t ingest a load of Safrole, for that reason!
[US Safrole-oil don t contain it, it is de-Safrolised !]

https://www.ncbi.nlm.nih.gov/books/NBK590823/

eMKee

 

[The Holy Quadruplty]

Good morning, The Holy Quadruplty

well assuming you are investigating it, i don t know if you plan ingesting it.
For the reason you mentioned, the in-vivo transformation to MDA.
And assume you are aware that in small quantity like we ingest via spices.
Is safe, but large am-mount s are considered unsafe, and Carcinogen s.

So be safe, don t ingest a load of Safrole, for that reason!
[US Safrole-oil don t contain it, it is de-Safrolised !]

https://www.ncbi.nlm.nih.gov/books/NBK590823/

eMKee

Ive heard it may actually have the opposite of carcinogenic effects, but idk which is true
?!

 

[Docta]

Isosafrole into Methylenedioxyphenyl, than that into MDA

Why do you believe safrole would isomerize? do you have a reference?

"Methylenedioxyphenyl" is chemically ambiguous, I assume you mean 1,3-Benzodioxole or close radical intermediate.

Thing is 1,3-Benzodioxole would be many steps down the metabolic pathway, I don't see how it would then get back to 3,4-Methylenedioxyamphetamine in any significant quantity making that path unlikely.

heard it may actually have the opposite of carcinogenic effects

If any of these compounds could protect cells from other carcinogens I'm pretty sure the science journals would be leading with that story.

 

[The Holy Quadruplty]

Why do you believe safrole would isomerize? do you have a reference?

While searching on Googlr i read that it cam be isomerized into isosafrole in the body, if I find it again ill share it.

 

[The Holy Quadruplty]

I read a few different places about the anticarciogenic effects, imcluding here in Bluelight.

 

[The Holy Quadruplty]

No im talking about Safrole being isomerized in the human body into Isosafrole, and them Isosafrole metabolizing to Methelyenedioxyphenyl, and them to MDA like i said.

 

[Docta]

No im talking about Safrole being isomerized in the human body into Isosafrole,

Yeah I get that, regarding interest in your source for that statement. Pretty much all peer reviewed papers on the subject find dominant safrole metabolites such as 1'-hydroxysafrole and 3'-hydroxysafrole excreted in urine. Oxidation of safrole by the P450 enzyme appears the dominant pathway, any in vivo isosafrole derivatives would be quite minor players.

It appears as though you're focusing on a very minor component that may or may not result in MDA, when the main result of eating safrole is its transformation into proximate carcinogens.

Isosafrole metabolizing to Methelyenedioxyphenyl, and them to MDA like i said.

Ok lets say with "Methelyenedioxyphenyl" they actually mean 4-methylenedioxyphenyl-2-propanone (MDP2P) a very probable oxidation product, how do we get to an amine?
Putting the A in MDA is the question you're asking and I gotta say that looks an unlikely outcome. MAP2P is kinda unstable so readily undergoes further oxidation losing mass.

The image is for illustration purposes only and is missing some steps. [ theoretical ]

 

[The Holy Quadruplty]

I read it does, but so ykaur answer is no it does not?

 

[The Holy Quadruplty]

And is Methelenedioxymethyl recreational at all I wonder?!

 

[Docta]

I read it does, but so ykaur answer is no it does not?

Maybe I didn’t explain myself well enough. There is no evidence to support isomerized of safrole to isosafrole in the body.

While the isomerization of safrole under hot alkaline conditions (Bert, 1941; Naves and Ardizio, 1957) gives isosafrole as a product of synthetic chemistry these conditions don’t exist within the human body. It’s a possibility that minor amounts of isosafrole might be formed from safrole in the body, but it's not the main metabolic pathway.

Think of it this way: If you drink a beer keg full of safrole, theses’ a very slim possibility of ending up with a thimble full of isosafrole, the remainder would be all oxidation products safrole. So, we’re talking very low to trace amount yields in vivo. Making the whole idea highly unlikely.

And is Methelenedioxymethyl recreational at all I wonder?!

Assuming you mean Methylenedioxyphenyl

Yeah, like I said before the term “Methylenedioxyphenyl” is chemically ambiguous, that’s a nice way of saying Bull Shit chemistry. Methylenedioxyphenyl as a compound would be a radial therefore unstable. Even the use of the term makes me think whom ever was telling this story is an unreliable narrator with little to no understanding of how things work.

The closest compound is benzodioxole and that doesn’t do much, so lets say no.

 

[The Holy Quadruplty]

Is Benzodioxol recreational?

 

[4DQSAR]

Is Benzodioxol recreational?

No.

The human body is mostly an oxidative instument and for safrole to become MDA would require a reduction.

@Docta has demostrated what I believe to be a reasonble pathway for the metabolism of safrole. Note that it's oxidative all the way down.

Is 'oxidative amination' a thing? Why, yes it is. Does it occur in vivo? Not that I'm aware of. It's still a relatively new field in organic chemistry but so far it appears to be a highly endothermic reaction requiring some quite unusual catalysts and conditions.

I think someone DID publish a paper showing that safrole could undergo oxidative amination but the conditions were bizarre and it was more of 'look what I can do' than a 'here is a facile new route'. But it's 25+ years since I read the paper and I admit, it's blurry in my memory so if I'm wrong, blame time.

 

[Deleted member 576750]

I read it does, but so ykaur answer is no it does not?

whether something happens or not may be irrelevant if it only happens 1 in 1000000 enzymatic reactions

i think youre focusing too much on the binary "does it happen or not" and ignoring "does it reach a meaningful concentration" where the answer is no

also if you read something on google, rather than just telling us you read it on google please go back and find the link to the web page where you read it and then link it here

 

[The Holy Quadruplty]

I read myristicin can metabolize into myristicin alcohol

Is myristin alcohol simular to alohol or not?! I hope not honestly. Lol

Also ill try to find that link for you.

 

[4DQSAR]

'myristicin'

Do you mean nutmeg AKA 'the sailors high'?

It's unclear if myristicin binds to the same class of receptors as it's amine containing derivatives do, but the fact that the BEST source of information are journals of forensic medicine SHOULD be a warning.

The reports given by survivors hardly gives nutmeg any good reviews.

I hear in jails, prisoners have figured out that grinding and smoking IBS medications contaning scopolomine (hyoscine) butyl bromide will produce a scopolomine trip, but every time a prison system bans a medication, someone will find something else and each time it's a worse option.

 

[emkee_reinvented]

Ive heard it may actually have the opposite of carcinogenic effects, but idk which is true
?!

Read that also adding the confusion, better safe then sorry.

Or turn it in some proper old skool MD[M]A, if you are a chemist.

 

[Deleted member 576750]

I read myristicin can metabolize into myristicin alcohol

Is myristin alcohol simular to alohol or not?! I hope not honestly. Lol

Also ill try to find that link for you.

an alcohol just means that is has on OH group it has nothing to do with ethanol, the drinking alcohol besides the fact that ethanol has an OH group

 

[The Holy Quadruplty]

Ok so random, but even tho i do notice some slight stimulant, and pretty strong psycadelic like hallucinagenic effects from Nutmeg, but i get tested every month, amd never had amphetamines come up in my system.

 

[The Holy Quadruplty]

Another slightly off topic question, has anyone tried nutmeg with opioids, and benzos?

I can't find any information anywhere.