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(-) and (+) explanation needed

our420room

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Sep 28, 2018
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Greetings,
I understand chemistry on a somewhat basic level but I seem to know more than most, at least locally. When I try to talk with friends, they are lost.
My problem is I just can't seem to grasp the meaning of the (-) and (+) symbols related to chemistry.

As an example I know if one was to buy typically used medicines such as sudafed (+)-pseudoephedrine is the active ingredient, or rather the (1S,2R)-form.
What is the difference between (+)-pseudoephedrine and (-)-pseudoephedrine?
I don't care much about the chemistry meaning as much as I wanna know if I can use (-)-pseudoephedrine for my intended purpose.
I see the CAS numbers are different. I have a source for the (-)-pseudoephedrine version and the price is very good.
 
My problem is I just can't seem to grasp the meaning of the (-) and (+) symbols related to chemistry.

they denote which way the compound will rotate plane polarized light.

What is the difference between (+)-pseudoephedrine and (-)-pseudoephedrine?

they are an enantiomeric pair, one is the mirror image of the other, as a result they have different activity in biological systems

the natural isomers, sold as decongestants are 1R,2S-(-)-ephedrine and 1S,2S-(+)-pseudoephedrine.

The enantiomer (-)-(1R,2R)-Pseudoephedrine has fewer side-effects, fewer central nervous system (CNS) stimulatory effects, does not reduce to d-methamphetamine, yet retains its efficacy as a decongestant. However, the patent holder for (-)-Pseudoephedrine (Pfizer/Warner-Lambert) has not yet sought or received government approval for its sale to the public.(US Patent 6,495,529);

and from a patent application US20030119915A1

According to the present invention, at similar doses, (−)-pseudoephedrine binds a1- and a2 adrenergic receptors better than (+)-pseudoephedrine and yet has less adverse effects upon blood pressure and fewer drug interactions. [...] The present invention is directed to a pharmaceutical composition containing (−)-pseudoephedrine and a pharmaceutically acceptable carrier, wherein the pharmaceutical composition is substantially-free of (+)-pseudoephedrine. Surprisingly, the present (−)-pseudoephedrine compositions bind to a-adrenergic receptors with greater affinity than do (+)-pseudoephedrine compositions while causing less adverse effects on blood pressure. Moreover, (−)-pseudoephedrine has decongestant activity which is similar to several known decongestants.

and the affinity at NET/DAT for both is:
(+)-pse: 224 nM @NET/1988 nM @DAT
(-)-pse: 4092 nM @NET/9125 nM @DAT

so, effective as an adrenergic decongestant? sure. but it's useless for methamphetamine/methcathinone synthesis and not even a mild monoamine releaser
 
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Thank you, I'm taking it as I want 1S,2S-(+)-pseudoephedrine would that be correct?
 
The natural enantiomers of either are those used for those with very severely congested nasal passageways which are so badly blocked, the hydroxyl group must bee eliminated, yes.

And don't even THINK of the abominable practice referred to as 'shake and bake'

This is a vile monstrosity which is a heavily bastardized Birch-Benkeser.

Although use of diethyl, diisopropyl or a mix, ethers, in real glassware, bubbling anhydrous GASEOUS NH3 through fine suspension of the alkali metal, it takes longer to form royal blue, I.e the colour of solvated electrons,takes a few hours, under argon (if Li is the chosen alkal metal, nitrogen cannot be used,as alone of the group I metals it freely forms, under atmospheric pressure, a nitride, which is a very strong base, and unstable towards H2O)

But bubbling anhydrous NH3 GAS through a fine suspension of Li or Na chips, rather than condensing and ergo, handling anhydrous liquid NH3 is IMO inherently safer, just not instantaneous formation of royal blue, or Li/Na bronze. as with liquid cryogenic NH3. Note that diisopropyl ether is beloved of peroxidation, far more so than diethyl ether, although at least the highly reducing environment is hostile to those vile alkylidene peroxides.

Na metal, also, is not prone to overreduction to the cyclohexane, assuming a phenyl ring is present in your actual substrate, and you are, I take it on your honour, take it upon trust and good faith, that you use the ephedra alkaloids merely to gain, as examples, a better understanding of isomerism :)

Birch-Benkeser reduction is actually unusually used by meth cooks, an atypical reduction, using it on a benzylic alcohol to yield the aminoalkane. The more usual use is to prepare cyclohexadienes from benzenes, or iif overreduction takes place, full de-aromatization to the corresponding cyclohexane ring takes place, the more usual application of the Birch-B.

Sodium rather than Li is much more mild and far less liable to form the cyclohexadiene or even cyclohexane from a Ph ring or benzene itself.

Note also, a proton donor is requisite,such as anhydrous isopropanol.
 
Limpet_Chicken, I rear your reply earlier and planned to come back later ths evening and reply but it seems both our comments were deleted.
I understand your position better now. The two of you are over my head knowledge wise. You shoot off all this chemistry talk like its nothing at all and I struggle with the basics.
I wish when I was younger I became a chemist or a pharmacist, but it's prolly for the better that I didn't because I would prolly be in jail now. lol
So I take it you don't approve of the SnB method at all. I understand that too but I don't agree. I do have an interest in that and more important to me is methcathinone.
I think the difference is the cook and the quality of the starting ingredients. I try to improve on everything I've been taught and purify or dry everything.
No hard feelings from before and I hope to learn from you possibly.
 
Just a note to all that personal attacks should be avoided if you don't want the nice post you just typed up to disappear. Sometimes the mods don't have the time to surgically remove just the naughty bits.

Also, replies to removed posts will also frequently be removed, even if not necessarily rule-breaking in and of themselves, in order to maintain thread coherency.
 
What I mean by 'shake and bake', is basically chucking in a layer of a nonpolar solvent, and at the bottom, a mix of strong base and ammonium salt, to form a bilayer in a pop bottle, along with the pseudo/ephedrine in the nonpolar, and the ammonia generated by means of the stronger base (usually something like caustic soda, NaOH/sodium hydroxide) displacing the weaker base, NH3, ammonia, to replace the cation, say if one started with ammonium sulfate and sodium hydroxide, one would get ammonia and sodium sulfate (ammonium hydroxide is a bit of a misnomer, it is often referred to as such, but in aqueous solution it doesn't form to any great extent as an actual molecular species) anyhow, that is what happens, strong base kicks out the weaker base and forms the corresponding salt, liberating the weaker base.

This in an ammonium salt, means ammonia liberation. H2O is added, as I understand the process, in a very small amount to get it to proceed.

And this horror, with the suspended Li bits, is then stuck in a capped plastic bottle, which the crazy buggers that do it have to periodically 'fart', I.e release part of the building up pressure. Otherwise the pressure makes the whole thing explode due to overpressure, spraying caustic alkali everywhere, filling the place with ammonia, flammable nonpolar fuel, such as ether, along with an alkali metal which has a chance to cause the fuel vapor to ignite.

Basically, shake and bake is a redneck way of rigging up a bomb that they hope won't actually blow up in their face, and that includes pseudoephedrine as a filling. In the hopes that, assuming it doesn't explode and cover the poor sod in 3rd degree burns and pepper them with hot corrosives, they might then extract the meth from the nonpolar after addition of a proton donor, an alcohol, to allow the reaction to finish, and assist in quenching it, as the wastes are dangerously water-reactive, such as lithium amide. Alkali metal amides are water sensitive and quite violently reactive in such a case, get very hot very quickly and blast ammonia from here to the gates 'o'hell.

It's a really, really ghetto-ed version of a legitimate technique of reduction of pseudoephedrine/ephedrine to methamphetamine known as a Birch-Benkeser reduction.

In the case of PSE/ephedrine then it's an unusual application. Usually the B-B reduction reduces a phenyl (benzene) ring to a cyclohexadiene, or else is employed to entirely de-aromatize an aromatic ring, such as full reduction of benzene to cyclohexane. Lithium being the more aggressive, but less physically violent, compared to sodium, whilst Na, sodium, is MUCH more liable to ignite, if things go tits up, than lithium is. Li can be pretty calm, in terms of spontaneous fire, I've even held a slice of lithium metal in tongs, run it under the kitchen tap (not making meth at the time), and then even dunked it into a pan of water and held it there, as well as allowed it to surface.

It fizzed, it shot around the surface of the water, on it's cloud of evolved hydrogen gas, it ran around the place like a squirrel on a crack bender, but never did it actually take flame or spark. Nor ignite the H2 evolved. I TRIED to get it to do so, tried pretty hard with several pieces of lithium, why? for fun basically=D

But no success in that respect.

A little piece of sodium about the size of a BB pellet on the other hand, chuck that in water and you'll almost certainly get at least a spark, a pop and an orange flame (from the sodium D line in the visual spectrum of it's emissions, just like street lights). That could ignite the hydrogen, easily, and then that would probably take the flammable nonpolar solvent with it, result of the botched shake and bake? boom! ARRGGHWHERESMYFACE!'

And a bigger bit of sodium, it can be downright violent. Say, a one inch cubed size specimen, if that were tossed into H2O then it WOULD go off with a loud crack and shoot off in flames.

Bits around 1cm....especially if they heat up enough to become molten in reaction with the water, then when molten its another beastie entirely, take one of my past electrolytic cells, running on NaOH (caustic soda, molten, heated electrically, water-free of course), once had an argon tank run dry, that was being used as a protective inert atmosphere.

I got cut off from the lab power supply, because the cell was interposed between it, and the wall socket, so I couldn't cut the power, even wearing a blast shield, little blobs, between BB size and at largest single blob, about 1.5-2cm, were forming and immediately reacting with the air, to a sound like machinegun fire rate-wise, constant stream of crackling, popping loud bangs, every so often, interspersed with a single, or a couple of loud sharp reports, as a big blob of molten Na coalesced together before exploding in a flying ball of bright orange dripping flaming metal.

Even with thick gloves, goggles and a blast shield over the top covering from forehead to torso, thick leather trench over my body, I couldn't even get close, I had to leg it in the opposite direction and kill the power supply at the source, turning the house mains supply off at the fuse box.

Quite a fun 4-5 AM little excursion into incidental pyrotechnics, and to me, in that circumstance, most amusing.

But had that been in a bottle of ether, it'd have blown up in a seriously dangerous way. Especially pressurized, full of caustic alkali, full of pressurized ammonia gas, and dependent upon the reactions of the person conducting such a procedure being fast enough in judging exactly when to 'burp' the bottle and stop it exploding in their face....another matter altogether.

Thats the kind of worst case scenario in a shake and bake. Third degree burns, an explosion, alkali metal serving as shrapnel, whilst molten and exploding in wound cavities (not fun, I once got a bit up my nose as a teen, in some initial clumsy attempts at molten caustic electrolysis. A bit of sodium went 'WHUMP!', shot off through the air, and right up my right nostril, before going off again, on meeting all that wetness generally found inside a human nose. Of course, I was wearing goggles, but one generally doesn't think 'hm, maybe I should have stuffed bog roll, tampons, or both, up each nostril whilst presiding over a spitting, crackling electrolytic cell.

Eyes, first thing, but up the nose?

(and no, for the record, I didn't use tampons, I used bog roll, wadded up and stuffed up my hooter to prevent any further inadvertent insufflation of molten sodium and any more than the one little crater blasted into my nasal septum, like a male daniella westbrook, but far better looking, but with the nasal trauma condensed into a matter of seconds=D)
 
I understand like 20% of what you say, I'm just some old retired guy with a background in business, certainly not chemistry. Although it certainly interests me.
I read a lot, being disabled that's something I do every day is read. I do get the point your making though, and I've heard it before.
We have a real problem and the biggest problem is people doing this method who have no idea what they are doing.

Even in SnB, it isn't one method called SnB, there are many takes on it, maybe a better word would be tek.
I've done it before, in another world and there was no water used at all and every chemical/solvent/fuel was dry.
It was a very basic recipe with like 3 ingredients I believe.
Water (and air) is certainly the enemy. This method only needed to be burped like 3 times I think, maybe 4.

We've had people blow up all around here, it's scary for sure.
Thanks for the chat Limpet_Chicken !!
 
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