Author Topic: Difference between Ephedrine and Psudoephedrine?  (Read 14930 times)

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readyeddie

  • Guest
Re: Difference between Ephedrine and Psudoephedrine?
« Reply #20 on: January 16, 2000, 07:21:00 AM »
Snotbrain that is what i think he is talking about.First of all it must be the good pseudo used in this racimazation.The good pseudo is in the sudafed red hots for sure.The cheaper brands seem to be bullshit or fake.Second 25-30% HCL is used.Third you only have to heat not boil it's about the same way you do when you form a ester for the electro but for alot longer of time.Fourth it needs to be in a closed bottle or something to keep steam out and to keep the HCl from evaporating away.A reflux also is suppose to work fine as long as you keep it to a simmer and not a boil.At about 20 hours you will get around a 30 70 mix at 30 hours you will get like a 50 50 mix.It's real simple but takes alot of time.

Blanka

  • Guest
Re: Difference between Ephedrine and Psudoephedrine?
« Reply #21 on: January 16, 2000, 07:32:00 AM »
can you find the references on that readyeddie? it's the first time I heard it

Blanka

  • Guest
Re: Difference between Ephedrine and Psudoephedrine?
« Reply #22 on: January 16, 2000, 07:43:00 AM »
ephedrine meth vs. psuedo meth (if there is a difference) i don't see that there could be a significant difference that would make experimenting worth the time but you can separate the eph from sudo from the plant by using chloroform which the

Blanka

  • Guest
Re: Difference between Ephedrine and Psudoephedrine?
« Reply #23 on: January 16, 2000, 07:44:00 AM »
can you find the references on that readyeddie? it's the first time I heard it

Zion

  • Guest
Re: Difference between Ephedrine and Psudoephedrine?
« Reply #24 on: January 16, 2000, 07:44:00 AM »
Agreed the red hots have the best in them, but also some myserious bad stuff that fucks the reaction of your reduction, or eXtraction. The non-name brands dont have as much of the good stuff in em. Like Wor said a few weeks ago. Name brand Sudafed has more of the necassary precursors in it but I think more of the B.S. also. But are we really sure what the differance tween E and Psudo is????? sorry about dis'n you earlier this millenium noteph.

Huffalump

  • Guest
Re: Difference between Ephedrine and Psudoephedrine?
« Reply #25 on: January 16, 2000, 08:55:00 AM »
Android,

Did you use pfed or ephidrine in the electro you posted a while back?  I've got quite a bit of purified pfed right now, and have been working towards an electro.  If there's no hope, I'll just shoot for rp. 

Huffalump


readyeddie

  • Guest
Re: Difference between Ephedrine and Psudoephedrine?
« Reply #26 on: January 16, 2000, 08:59:00 AM »
It all depends on what kind of reduction you do some reductions retain others change.Lets take a look at the lithium in ammonia reduction this method retains.So it does not matter if pseudo or ephedrine is used it will give the same product which is d-meth.The same goes for the ester formula and most hydrogenation methods.Now for the red/p and iodine method this one changes but does so in a good way racimazation occures during reflux the boiling acid changes it to a mix of ld meth.So now on to the reductions that change and racimazation doesn't occure their are a few and their not hard to figure out these you will have to do what?Blanka as i told dwarfer i had to get rid of all my photo copies and books the references or out their.Fester if you should happen to read this would you look it up and post it hear for these bees thanks.

Blanka

  • Guest
Re: Difference between Ephedrine and Psudoephedrine?
« Reply #27 on: January 16, 2000, 10:18:00 AM »
damn.. I hate when I lose my connection during a post... I especially hate when part of the post dissappears or when posts appear 3 times.. anyways... eph and pseudo have two chiral centers. they are both at the first 2 carbon sites of the propane cchain. so what the hell does that mean? it means when you make meth, and one of these chiral centers is removed, you will have one of two possiblilities for the meth (-) or (+) meth... so pseudo and eph can yeild both the good meth and useless meth depending on which "kind" of pseudo or ephedrine you use (+ or -) Ok? you still there.. so when I say I don't think there is gonna be a significant difference, i actually mean that if you try to start with OTC shit that contains eph (plants and some pills) or pseudo (pills) there is gonna be a small difference in what you get at the end because what you are starting with to get the meth is not pure... now which do people prefer?? I think the shit from plants is better. And if we are talking about starting with pure products turning into pure meth, it depends on which pseudo and which eph you are talking about (+ or -). If you compare   -(-) ephedrine and +(-) pseudo, there is no difference in the meth you get, they will both be as good... pure (+) meth. I forgot who posted that since the chiral center is removed you will get the same shit no matter what.. or something to that effect... this is totally incorrect as there as 2 not one chiral centers, on of which is removed when the molecule is reduced to meth.

Blanka

  • Guest
Re: Difference between Ephedrine and Psudoephedrine?
« Reply #28 on: January 16, 2000, 10:33:00 AM »
besides the chirality of the tw molecles, I don't think there is a difference... you can find out for sure if there would be any difference by getting a source of l-eph, d-eph, l-pseudo, and d-pseudo and the recemic eph and pseudo to mess around with but you gotta know for sure what you are starting with.. i can't say for sure because I have never made l-meth but it is stated in many books that the d isomer is more potent. this is a waste of time though cuz i'm pretty sure all the people aren't wrong about l-meth (that it is crap).. after reading what eddy put though, i'm wondering if there is a majik method of racemizing l meth like pseudo was easily racemized... not like it would be of any use since they don't use l-meth in vicks... all these bees up in here and we can't find that stupid ref about heating the eph to 100' to recemize it? anyone know what book eddy is talking about? I don't doubt you though mister ed.. talking horse

Sploofer

  • Guest
Re: Difference between Ephedrine and Psudoephedrine?
« Reply #29 on: January 16, 2000, 11:19:00 AM »
Whats it mater man agin why be concerned where the oh group might be had at is it looking like this in all of the concerned shit??? COH and the good shit looking like this???ch and semi good shit like this-chh\

So i yes I fuel such arguments these are all know configereations and end results to known methods metamphetamine the l kind is the reult of what aint now known is know to be not l meth at least mosy of the people uptodate do in fact know the vicks is different then orriginally transcribed the shit is hydrated the entire ring is hydrated however mouthwash even if titled simmiliarly could in fact be a different stuff althgether.................................

the vicks shit real vicks is l - meth do you belive this or do ya think it cost maintains about three to five times the price of the other stuff??

The other stuff its the hydrated stuff mainly proaly the entire central ring is hydrated this is not meth eph or pseudo this is mostly a different thing alltogether hummm>?>>

So we will find that a cyclixzzzation process is relivant to all these concerned w/ isomerization certain cyclizations can be had crystaline like at a given stage in process these are very cutting edge typ crystalizations to be shure  DESCRIPTIVE

Anyways thes CRYSATALS THE PROTECTED FORM WOULD GO INTO metabolized as the rotational varity is seemingly likely who knows??

The cyclating benzeene varity of concerning meth in paticuliar is \potent>>>>>>>>>>>>.................

However the amphetamine is less potent and the sulp less potent still more less impoteniated is finding ephedrine adn pseudo ephedrine this is the grand therum to the rationals are eluted that they are discoved lacking man do ya unc=derstand they dint make s seence???

the pseudo if in fat its methylate dlike ephedrine is the same???

Unless in pseudo we got the oh not attacthed to the side carbon but maybe shit attaches and screws up the ring itself this is pseudo shit????????//  Alhough I think some brands are quite real and they have what is not methylated ephedrine this is also pseudo see non wesern society and laws are not foundation to you r therums I cite the japaneezium rationals in the lit at large it is also finding big differences w/ these western fables pseudo is a bunch of varuios shit not paticullarly usefull shit I say a mixture of shit it is to be shure 600 hundred milligrams produced a metabolic and psycholiogical simmily to twently percent that ammount in the lab rats and humas thus tested why even conside r it was anty more to be eluted see it like ephedrine but its gut shit!


Blanka

  • Guest
Re: Difference between Ephedrine and Psudoephedrine?
« Reply #30 on: January 16, 2000, 03:02:00 PM »
the strange thing about l-meth is that when you have the racemate, even though the levo meth is supposed to be crap, the product is more potent than if it were just dextro meth.. it juss doesn't make sense.. it escapes logical reasoning.. any geniuses wanna help me here cuz I'm not anywhere close to being a expert on this stuff

dwarfer

  • Guest
Re: Difference between Ephedrine and Psudoephedrine?
« Reply #31 on: January 18, 2000, 05:10:00 AM »
Well, all in all the one thing I can agree with with certitude is that plants do the best when they make their blend, as far as future processing goes......-MA, +MA, -AMP, +Amp all designed to make molecules which nestle nicely in my synapse: standing on each other's shoulders they can reach the high cupboards where the cookies are stored.

:< )


PolytheneSam

  • Guest
The article here mentions the RP process with...
« Reply #32 on: January 25, 2003, 03:55:00 PM »
The article here mentions the RP process with ephedrine and gives references to it. 

Post 115871

(Mo Diddly: "Re: Difference between Ephedrine and Psudoephedrine?", Stimulants)

It also shows the absolute configurations of each of the four isomers.


Worlock

  • Guest
Ephedrine vs Pseudo
« Reply #33 on: January 25, 2003, 06:41:00 PM »
Ephedrine from Ma Huang: (-)-ephedrine
 m.p. 35 - 40 °C
 [a]D = -41°
 moderate water solubility

Pseudoephedrine from Ma Huang:(+)-pseudoephedrine
 m.p. 119 °C
 [a]D = +52°
 relatively insoluble in water





http://www.cem.msu.edu/~reusch/VirtualText/sterism3.htm





Rhodium

  • Guest
Hermann Emde's Ephedrine Chemistry Treatise
« Reply #34 on: January 25, 2003, 08:03:00 PM »
Ephedrine/Pseudoephedrine Stereochemistry, Physical Properties and Reduction to Methamphetamine
Hermann Emde

Helvetica Chimica Acta, Vol. 12, pp 365-376 (1929)

(https://www.thevespiary.org/rhodium/Rhodium/djvu/ephedrine-emde-1.djvu)
____ ___ __ _

(Pseudo)Ephedrine Resolution, Racemisation & Interconversion
Hermann Emde

Helvetica Chimica Acta, Vol. 12, pp 377-384 (1929)

(https://www.thevespiary.org/rhodium/Rhodium/djvu/ephedrine-emde-2.djvu)
____ ___ __ _

(Pseudo)Ephedrine Halogenation to the Corresponding Bromo- and Chloroephedrines by reaction with PX5, SOCl2 or conc. aqueous HX, as well as their hydrolysis back to aminoalcohols.
Hermann Emde

Helvetica Chimica Acta, Vol. 12, pp 384-399 (1929)

(https://www.thevespiary.org/rhodium/Rhodium/djvu/ephedrine-emde-3.djvu)
____ ___ __ _

Reaction of (Pseudo)Ephedrine with sulfuric acid to form a cyclic sulfonamide/sulfuric acid ester (Ephedrine betaine), as well as a discussion of common byproducts
Hermann Emde

Helvetica Chimica Acta, Vol. 12, pp 399-405 (1929)

(https://www.thevespiary.org/rhodium/Rhodium/djvu/ephedrine-emde-4.djvu)
____ ___ __ _

Crystal Symmetry and Diastereomeric Properties of (pseudo)Ephedrines, their Hydriodide salts and Betaines latest addition (06-12-04):
Hermann Emde & Fritz Spaenhauer

Helvetica Chimica Acta, Vol. 13, pp 3-9 (1930)

(https://www.thevespiary.org/rhodium/Rhodium/djvu/ephedrine-emde-5.hca_1930_13_3.djvu)



Note: You need a plugin from

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Rhodium

  • Guest
More articles about Ephedrine/Pseudoephedrine
« Reply #35 on: June 29, 2003, 01:15:00 AM »
Über die Synthese der isomeren Ephedrine und ihrer Homologen
Wilhelm Nagajosi Nagai - Seïzo Kanao

None

(https://www.thevespiary.org/rhodium/Rhodium/pdf/ephedrine.isomers.nagai-kanao.pdf)

A landmark article about the synthesis of Ephedrine, Pseudoephedrine and all their respective Nor- and N-methyl homologs as well as both the racemic mixtures and the separate optical isomers of each substance, in total 18 1-Phenyl-2-Amino-1-Propanol homolog isomers. In addition to this, the physical properties for all substances (melting points, boiling points, density, refractive index, specific rotation, solubilities, crystal shapes, elemental analysis, and even the mp for 3-7 different salts/derivatives of each isomer is presented (where applicable).

The only error in the article is the assumption that the pseudo-compounds were 1-Phenyl-1-Amino-2-Propanols  [Formula II, p 157] (as they knew that the ordinary ephedrines were 1-Phenyl-2-Amino-1-Propanols  [Formula I, p 157] ).  75 years ago the concept of stereochemistry was not as developed as it is today, and they had no other analytical tools than to observe melting points and crystal shapes, therefore they could not imagine that ephedrine/pseudoephedrine were diastereomers, and thus all four isomers (d-eph, l-eph, d-pseudo, l-psdeudo) had the exactly same structural formula, just with different 3D-orientation (stereochemistry).


Über eine neue Synthese des -Ephedrine
E. Späth - G. Koller

Chem. Ber. 58, 1268-1271 (1925)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/pseudoephedrine.spath-koller.pdf)

A synthesis of pseudoephedrine using the odd route Benzaldehyde  1-Phenyl-1-propanol Propenylbenzene 1-Phenyl-1,2-dibromopropane 1-Phenyl-1-methoxy-2-bromopropane 1-Phenyl-1-methoxy-2-(methylamino)propane   Pseudoephedrine

Rhodium

  • Guest
Chou: Properties of (pseudo)Ephedrine
« Reply #36 on: December 09, 2003, 06:19:00 PM »
Isolation and Properties of Ephedrine and its Salts
T.-Q. Chou

J. Biol. Chem. 70, 109-115 (1926)

(https://www.thevespiary.org/rhodium/Rhodium/chemistry/ephedrine.chou-jbc.html)
____ ___ __ _

Comparison of Ephedrine and Pseudo-Ephedrine From Ma-Huang (Ephedra vulgaris, var. helvetica)
T.-Q. Chou & B. E. Read

Proc. Soc. Exp. Biol. Med. 618-620 (1926)

(https://www.thevespiary.org/rhodium/Rhodium/chemistry/comparison.ephedrines.html)

Rhodium

  • Guest
Synthesis of all pseudo/ephedrine isomers
« Reply #37 on: January 16, 2004, 01:01:00 PM »
Die Synthesen des Ephedrins, des Pseudoephedrins, ihrer optischen Antipoden und Razemkörper
Ernst Späth und Rudolf Göhring

Monatsh. 41, 319-338 (1920)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/ephedrins.spath.pdf)
____ ___ __ _

Die Konfiguration des Ephedrins
Karl Freudenberg & Fritz Nikolai

Ann. Chem. 510, 223-230 (1934)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/ephedrine.absolute.configuration.pdf)


Rhodium

  • Guest
Synthesis of (1S,2S)-pseudoephedrine
« Reply #38 on: July 02, 2004, 06:17:00 PM »
An enantioselective synthesis of (1S,2S)-pseudoephedrine
G. Vidyasagar Reddy, G. Venkat Rao, V. Sreevani and D. S. Iyengar

Tetrahedron Letters 41(6), 953-954 (2000)

(https://www.thevespiary.org/rhodium/Rhodium/chemistry/pseudoephedrine.oxazolidinone.html)

Abstract
Synthesis of (1S,2S)-pseudoephedrine is described via reduction of an alanine-derived oxazolidinone followed by treating with phenyl magnesium bromide and chemoselective N-methylation in an efficient and practical manner.


In recent years there has been considerable interest in the synthesis of optically pure amino alcohols because of their wide occurrence in several biologically active molecules and also their application as chiral building blocks, auxiliaries and ligands in asymmetric synthesis1-2. Among this class, ephedrine and pseudoephedrine have found wide application for a variety of purposes in organic synthesis. Pseudoephedrine, especially, has been used extensively in asymmetric alkylations of corresponding carboxamides3-4. Recently, we have reported chemoselective reduction of N-protected oxazolidinones to the corresponding lactol derivatives and their application in the synthesis of vicinal amino alcohols5. In this paper, we wish to report a new approach for the synthesis of (1S,2S)-pseudoephedrine by using the synthetic potential of our methodology. The key steps involved in the present synthesis are: (i) reduction of the N-Cbz oxazolidinone derived from alanine (2 to 3); (ii) Grignard addition to the lactol to give the amino alcohol (3 to 4); and (iii) chemoselective N-methylation (4 to 8) as shown in Scheme 1.

The oxazolidinone (2)6, readily obtained from N-Cbz-L-alanine (1) by reacting with paraformaldehyde in the presence of catalytic PTSA, was treated with 1 equiv. of sodium borohydride to give the lactol 3 in excellent yield (95%) as a colourless syrup [?]D -2° (c 1, MeOH). Treatment of lactol (3) with phenyl magnesium bromide afforded an inseparable diastereomeric mixture (4 and 5) in 92% combined yield, ratio 95:5 from 1H NMR. The newly created stereocentre in the major isomer 4 was initially assumed to be S by analogy with our earlier related work5, and was confirmed by conversion into the known title compound. To circumvent the separation problem, the diastereomeric mixture was reacted with paraformaldehyde in the presence of cat. PTSA to furnish oxazolines 6 and 7 in a combined yield of 96%. Oxazoline 6 was easily separated from 7 by using column chromatography in 94% yield (based on crude 6 and 7) as a colourless syrup, [?]D -21.5° (c 1, MeOH). Treatment of oxazoline 6 with NaCNBH3/TMSCl smoothly afforded the N-methyl amino alcohol 8 in 93% yield. Acidic hydrolysis of 8 afforded (1S,2S)-pseudoephedrine hydrochloride as white crystalline solid in 92% yield. M.p. 184–186°C, [?]D +59.8° (c 2, H2O) lit7 m.p. 185–188, [?]D +61° (c 1, H2O), thereby confirming the structure assignment and configurations.

In summary, we have demonstrated an efficient new synthesis of pseudoephedrine in excellent yield. This synthesis will be amenable to the syntheses of analogous compounds with ease. Further work is in progress and will be reported in due course.




Scheme 1.
Reagents and conditions:
(i) (CH2O)n, PTSA, benzene, reflux, 1 h; (ii) 1 equiv. NaBH4, MeOH, 2 h; (iii) PhMgBr, THF, 0°C–rt, 3 h;
(iv) (CH2O)n, PTSA, benzene, reflux, 1 h; (v) NaCNBH3/TMSCl, CH3CN, rt, 30 min; (vi) conc. HCl, reflux, 2 h



References

1. Bycoroft, B.W. Dictionary of Antibiotics and Related Substance; Chapman and Hall: London, 1988.
2. Reetz, M. T.; Rrewes, M. W.; Schmitz, A. Angew. Chem., Int. Ed. Engl. 26, 1141 (1987)
3. Myers, A. G.; Gleason, J. L.; Yoon, T. J. Am. Chem. Soc. 117, 8488 (1995)
4. Myers, A. G.; Yang, B. H.; Chen, H.; Gleason, J. L. J. Am. Chem. Soc. 116, 9361 (1994)
5. Reddy, G. V. S.; Rao, G. V.; Iyengar, D. S. Tetrahedron Lett. 40, 2653 (1999)
6. Ishai, D. B. J. Am. Chem. Soc. 79, 5736 (1957)
7. Aldrich Fine Chemical Catalog, 1998–1999, p. 1441.



Ref #6:
Reaction of Acylamino Acids with Paraformaldehyde
Dov Ben-Ishai

J. Am. Chem. Soc. 79, 5736-5738 (1957)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/aminoacid.oxazolidinone.pdf)


nightshade

  • Guest
is the psuedoephedrine that one extracts from...
« Reply #39 on: July 18, 2004, 10:45:00 PM »