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ISOMERS of mdma...

skittlepig

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Joined
Jun 2, 2001
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1
VALANCIES of mdma...

Hey i heard that even pure MDMA can be different each time you take it simply cos it can change its 'charge' or something. And each time its made it can end up with different valencies. Is this true? Wouldnt that really make it a different substance? How many different MDMA molecules can you get?
[This message has been edited by skittlepig (edited 03 June 2001).]


[Edit: Title renamed "Isomers of MDMA" from original (incorrect ) title "Valancies of MDMA"; p_d]
 
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32. 32 different valancies.. this is something not many people know about id be interested in knowing where you heard it..
its not something that just occurs in every MDMA discussion..
cant chat.. ill be back with more.
and NO none are any less dangerous than any other MDMA molecule...
 
I've read something similar about K... Can't wait till the dodgy dealers get hold of this info... Great selling point!!!
 
I searched for nearly THREE HOURS for the site I found this recorded on, in vain. But I DO have a tape of a talkback radio debate that I joined in on one day where a chick came on later and stated all this shit about the 'charges'(?!) of the MDMA, that there were to her knowledge 32 possibles, and that it meant each different one could 'fry' a different set of neurons each time (she was very 'ANTI').. Im inclined to agree with the data (but not the 'frying') as i did find independant of her, a page saying almost the same thing. and the general chem of it all was sound. Can anyone help me find that page!?
Feelin stupid now, made statement, cant firmly back it up. : (
=K9=
 
PP - the thing about K is that is can come as either a Potassium salt (k), or a sodium salt (na).... I here one has slightly more kick than the other.
 
Valency normally refers to the charge on an ion i.e. how many electrons the neutral atom is missing or has extra. In the HCl form, the amine part of MDMA gains a + charged hydrogen from the H-Cl to give the amine a + charge, which forms an ionic bond with the negative Cl- ion.

I suggest reading some basic organic chemistry regarding isomers. Pick a book/online page etc that details isomers with good pictures. You don't have to learn it all, but a non in-depth reading will allow you to understand the terminology.


Several different types of isomers exist but not all are relevant to MDMA.


Molecules termed enantiomers, are stereoisomeric forms (isomers) related to each other as are your right and left hands. They are non superimposable images because of the shape resulting from 4 different groups attached to a chiral carbon centre.

Chirality_with_hands.jpg
Pic from wiki page on chirality


An example of a chirality is the second carbon on the alkyl branch of MDMA (yellow in below pic) that is bonded to:

1) a Nitrogen with 1 Hydrogen & a CH3 ( -NH-CH3 )
2) a Carbon with 3 hydrogens ( -CH3 )
3) a Carbon with 2 Hydrogens ( -CH2- )
4) a Hydrogen (-H )

Spatially, these 4 groups may be positioned differently. Steric repulsion allows by rotation, certain positions to be favoured, so placement of the chiral carbon and the attached groups is not random.

MDMAenantiomers.gif



The l and d or (-) and (+) designation is arrived at by by passing polarised light through one pure form. Positions of different groups will effect direction and angle of deflection. Determining this direction assigns a character L or (-) for levorotatory (lefthand ), and D or (+) for dextrorotatory ( righthand )


Another type of isomer configuration, resulting in the assignment of an R or S, is determined by priority placement of the groups attached. Viewing the carbon and attached groups as a tetrahedral with the lowest value group at the top, the order of the other three groups (lowest value to highest value priority) determines R for a right hand circular direction and S for a left.
Note that with many molecules, the R or S assignment may exist in either the (-) or (+) from. However with MDMA the (-) is the R form and the (+) is the S form.

Shulgin states as does the CRC handbook on enantiomers, that the S(+) isomer is the most potent empathy producing form in humans, by quite a degree.


Pihkal #109 MDMA

With MDMA, the usual assignments of activity to optical isomers is reversed from all of the known psychedelic drugs. The more potent isomer is the "S" isomer, which is the more potent form of amphetamine and methamphetamine. This was one of the first clear distinctions that was apparent between MDMA and the structurally related psychedelics (where the "R" isomers are the more active).

Most MDMA is (assumed to be) made from the ketone, an achiral group with a double bond to oxygen [ >C=O ] and planer in form. The N (amine)group is attached to C2 via a process known as reductive amination, givng [ >CH-NH-CH3 ]. Several variations of this reaction exist, using different reducing agents or catalysts.

Other methods that arrive at the target via different mechanisms produce a single enantiomer. Isomers can be separated by chromatography and with some enantiomer resolving agents, but it is unlikely this would be done with street intended product.


As to 32 different forms - I would think - not isomers. And although isomers possess different properties, if it ain't an isomer of MDMA it ain't MDMA. It is definitely possible there could be any of 32 different compounds (more even) in pills. Most likely things are binders, substitutes, unreacted precursors, and products of bad lab routine or side reactions occurring during the synthesis.
 
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My head hurts anyone else ??
well you sound like you know what your talking about ;P
 
The queue to have phase_dancer's children starts here, take a number. No cutting in front.
BigTrancer
biggrin.gif

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Load universe into cannon. Aim at brain. Shoot.
 
Thank you phase_dancer. *digs out second year organic chem memory*.... uhuh.
 
I grovel at thy feet...
*two words*
You Rock..
"Stereoisomeric"s make for an interesting hunt on any search engine... try it and see.
Thanks for that but. Im gonna have myself a great week sifting through pages of text..
 
it's bizzare, i am doing 2nd year organic chem at the moment, and most of tht words that are being sprouted in here are actually making sense... this is crazy... i may actually pass my chem exam... well... maybe...
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Drugs are not the answer... Drugs? is the question... Yes is the answer.
 
Give me more S-isomer MDMA!
I know the same thing is with K - one form, i think its the l-form induces a "psychotic" state and the d-form has the anaesthetic "power" or something like that - i did it in lecture not long ago, and everyone was wondering why i was giggling - "isnt it used in animals??" they all asked .............
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SMILE :) - it's the second best thing you can do with your lips ;)
 
consfusered:
i have an organic chemistry major to my credit and have a wild guess at what got me through and made me interested.
Its amazing how much attention u pay to a lecturer who is prattling on about excruciatingly boring and difficult topics, when they explain many facets of the chemistry and biochemistry of the molecules we love
smile.gif

Plus u will find yourself reading rather complicated material on the net and in journals as it is drug related and then walk into the class and realise u know exactly what is going on!
I have NEVER heard of valancies to describe large molecules.
Enantiomers are surely whats been referred to, and P-D has said everything that needs to be
smile.gif
 
ChEmIcaL_NiGhT said:
PP - the thing about K is that is can come as either a Potassium salt (k), or a sodium salt (na).... I here one has slightly more kick than the other.
Sounds like you're actually referring to GHB, which commonly comes as one of two salts, Potassium GammaHydroxyButyrate and Sodium GammaHydroxyButyrate, the metals being the bases and the GHB being the acid. The base and the acid combine to form the salt.

Ketamine is a base AFAIK, so to form the salt it is combined with an acid, which I'm pretty sure is always HCl.
Next time you see a vial have a looksee, I'm 99% positive it'll say Ketamine Hydrochloride.

Hmm, I just realised this thread was two years old.
How did I get here?
/me goes off to find out what I'm on...
 
^^^ Yeah but it does come in other forms, I'm no chemistry buff but I do remember reading about how you used to be able to import ketamine from china legally, but you had to convert it to HCI.

Also, you can reverse the isomer on K which changes the experience somewhat.
 
God I hate chemistry, but this thread is *so* interesting!!!

I've been wondering about this for a while; I'd never heard about the different valencies (didn't even know that word existed till I read this thread) but I wanted to know why there's such a variation in effects of ecstasy... I know a lot has to do with setting and the state that you're in (emotionally, physically etc) as well as the strength of the pill, but I've noticed that effects don't always seem to be linked to strength - e.g. you can get serious jaw clenching/eye wigs on a pill that's not even that strong. Just the other night I was wondering why, and was about to post here on BL asking why..

But now I kind of have an idea, before I even asked my question. So... thanks guys! :3
 
killarava2day said:
^^^ Yeah but it does come in other forms, I'm no chemistry buff but I do remember reading about how you used to be able to import ketamine from china legally, but you had to convert it to HCI.
Probably being sold in it's freebase form.
 
I seem to remember two variants of MDMA which are dependent on the precursor Safrole being used: MDMA-b and MDMA-d. Correct Phase Dancer? And is this related to isomers?
 
Cis & Trans Isomers

What you may be thinking of is isosafrole which can exist as two isomers, cis isosafrole and trans isosafrole. This form of isomer results from substitution across a double bond. Basically it may stick out left or right in direction. If the other end substitute is orientated in the same direction, the molecule is said to be the cis isomer. If in the opposite position it is known as the trans isomer

When the isomerisation is done to safrole both isomers are produced, but the trans isomer is more stable so is the dominant component (70:30).

From here on, whether the iso used is one isomer or the other becomes irrelevant as conversion to the ketone also produces a planer molecule which only exists in one form.

When the final reductive amination occurs, 2 isomers are produced; the (+) or d or -in this case- the S isomer, and the (-) or l or R in a 50:50 ratio.

This route, or a variation of, is the usual method used to produce MDMA. While routes and methods exist for producing a single isomer of MDMA, this is hardly ever done IMO as it would be far from economically justifiable and the market, given the choice, would prefer the 50:50 mixture anyway.
 
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