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All 14 posts Subject: Phenmetrazine synth from propiophenone Please login to post Down

ztion
(Stranger)
03-10-02 23:19
No 280265
      Phenmetrazine synth from propiophenone
(Rated as: good read)

Hi,

Someone I know has been thinking about synthing phenmetrazine.
This is how that person has planned to do it:

First we react propiphenone with bromine.

C6H5-C=OCH2CH3 + Br2 --> C6H5-C=OCHBrCH3

Next we reduce that carbonyl group to an alcohol.

C6H5-C=OCHBrCH3 + NaBH4 --> C6H5-HCOHCHBrCH3

Then we react that with ethanolamine.

C6H5-HCOHCHBrCH3 + OHCH2CH2NH2 --> C6H5-HCOHCH(NHCH2CH2OH)CH3

And finaly we cyclolize it with some sulphuric acid.

C6H5-HCOHCH(NHCH2CH2OH)CH3 + H2SO4 --> phenmetrazine [1]

During a trial in Sweden (~1965) where the doctors prescribed drugs for addicts, the speed freaks apparently prefered phenmetrazine over both amphetamine
and methamphetamine! It is of lower potency than amphetamine, but the euphoria was apparenly MUCH better. So when they had free drugs they could just solve the potency problem by taking more of the drug. From what I've heard 100mg phenmetrazine == 50mg amphetamine.

So what do you think, could the synth be done this way?

References:

1. Patent US2835669

foxy2
(Distinctive Doe)
03-11-02 00:15
No 280299
      Re: Phenmetrazine synth from propiophenone

Might bee interesting.
When I have some spare time I will compile a load of info I have found on this compound. But it might take me a WHILE.
Make a Difference Donate Now!! (http://www.lp.org/drugwar/)

PrimoPyro
(Hive Prodigy)
03-11-02 00:24
No 280303
      Re: Phenmetrazine synth from propiophenone

You could also make the alpha-hydroxy-beta-bromopropane by reacting propenylbenzene with NBS and water, there is a procedure on Rhodium's site for this reaction.

   PrimoPyro
Vivent Longtemps La Ruche!

Fuchicoma
(Ghost In the Shell)
03-11-02 15:09
No 280655
      Re: Phenmetrazine synth from propiophenone

Phenmetrazine and Phendimetrazine can both be easily made from l-ephredrine and psuedoephedrine by reacting with ethylene oxide. This epoxide is made from hydrolysis of ethyl chlorohydrin which is in turn made from ethylene and a hypochlorite like bleach, wouldn't this be an easier route to Phenmetrazine?

Rhodium
(Chief Bee)
03-11-02 18:04
No 280689
User Picture       Re: Phenmetrazine synth from propiophenone

Fu: That sounds good, do you have any references or reaction specifications for that transformation?

psychokitty
(Her Majesty, Stoni's Kitty)
03-11-02 21:43
No 280794
      Re: Phenmetrazine synth from propiophenone

I do. Several. I guess I'll add this to my list of things to post so that I can get that color added to my name.

I'm compliling that list for you, Rhodium. Do I HAVE to type up all the experimental details? Or can I just type up the references with a summary of the paper's contents? It's just that some of the stuff I have is too long and has alot of incorporated chemistry symbolism that I can't replicate for you in text form. And I don't know how to scan items to send them over the internet. Advice would be good in that area.

Rhodium
(Chief Bee)
03-12-02 00:16
No 280848
User Picture       Re: Phenmetrazine synth from propiophenone

Summary is fine for references from common journals - but I would appreciate an experimental part if the journal is obscure in any way, such as being more than 100 years old, or if it is russian/asian - because it is often impossible to find those even in large libraries.

Fuchicoma
(Ghost In the Shell)
03-15-02 16:26
No 283000
      Re: Phenmetrazine synth from propiophenone

There are some specific references sited in the Merck Ed. 12th Ed. and maybe some patents. Has anyone tasted this substance? Are there any side effects? (lesser or more worse than the other common stimulants?) What is the potency ratio between Phenmetrazine and Phendimetrazine?

Mountain_Girl
(Hive Bee)
03-25-02 13:41
No 287622
      Phenmetrazine synth from propiophenone'
(Rated as: good read)

I can't help with the synth, except to say that the references the Merck mentions are (Phenmetrazine):
Patent US3018222,
Clark, J. Org. Chem. 27, 3251 (1962) and,
Klosa, J. Prakt. Chem. 21, 12 (1963).

I know almost nothing about this compound but have recently been wondering if its psychedelic analogues have ever been tested, eg. 2,5 dimethoxy phenmetrazine or something ?

GlaseIs
(Stranger)
03-26-02 02:04
No 287865
      PhenDImetrazine

   For those that don't know, Phendimetrazine is the weight loss drug Bontril (ick who made that name?), and its only scedule 3. With the extra N-methyl, one would think that Phenmetrazine is to Phendimetrazine as Amphetamine is to Methamphetamine? Anyhow, these stimulate the release of Norepinephine like U4Euh does (notice the structural similarities there also)
On the 6th day God created man. On the 7th day, man returned the favor.

ztion
(Stranger)
03-26-02 06:48
No 287976
      Actually I think that phendimetrazine is weaker ...

Actually I think that phendimetrazine is weaker than phenmetrazine. I have not researched this seriously yet but i will soon. (There's an article in Läkartidningen which deals with phendimetrazine, 1974 jun sometime).
But think about this: Preludin (phenmetrazine) was discontinued because of the massive abuse. Now they instead make Prelu-2 (phenDImetrazine), why would they do that if phendimetrazine would be even better to abuse?
Also I saw on the web some list of amounts of different medications you could take into some country. You could take in x mg of phenmetrazine, but the amount for dimetrazine was actually x * 3 mg or something. This indicates to me that it is much weaker.
This is somewhat annoying, since phendimetrazine is much easier to make. If the amine is tertiary you don't have to reduce the propiphenone to an alcohol to cyclize it. You can just reflux it in formic acid. Presto! (GB862198 but it is only in GB791416 they mention that it only works for a tertiary amine). I wonder though if a hydroxy group "counts" to make a tertiary amine.. then we could use n-hydroxyetanolamine and just cyclize with formic as above... If we interpolate all other amines the n-hydroxy version should be just as active.

ztion
(Stranger)
03-26-02 16:41
No 288130
      Ok, now I've read that article in Läkartidningen.

Ok, now I've read that article in Läkartidningen.

They say that the recomended dose (by the medical company?), 35mg 2-3 times a day, doesn't differ between phenmetrazine and dimetrazine. Also the acute tox. is the same, the central stimulating effect is also the same, registered as the effect on spontanous movement in rats. Later they find that fenmetrazine increases the blood pressure but phendimetrazine doesn't. At first they speculate that this may be because the n-methyl group, but a bit later they mentition that it may be because the phenmetrazine was d,l while the dimetrazine was d-.(!) It seems obvious to me that THAT was the reason it didn't have any blood presure increasing effects, and maybe also why they seem to think it is equipotent.
They also say that phenmetrazine is a metabolite of dimetrazine, with dimetrazine being dominanit in urin samples up to 5 hours after an injection, while phenmetrazine is in majority afterwards. Also there is some n-hydroxy metabolite.

Look up these references to find out for yourself:

Toxicol Appl Pharmacol 2: 589-601 1960: Pharm. and tox. studies of phendimetrazine.
Läkartidningen 1974 Jun 5; 71(23) 2385-2387

Rhodium
(Chief Bee)
09-03-04 16:18
No 529372
User Picture       Phendimetrazine: 2-Phenyl-3,4-Dimethyl-morpholine
(Rated as: good read)

Optisch Aktives 2-Phenyl-3,4-Dimethyl-morpholin
Walter Otto
Angew. Chem. 68(5), 181-182 (1956) (https://www.rhodium.ws/pdf/phendimetrazine.isomers.pdf)

^{The Hive - Clandestine Chemists Without Borders}

Rhodium
(Chief Bee)
09-15-04 01:56
No 531357
User Picture       Phenmetrazine synthesis references
(Rated as: excellent)

The Phenmetrazine synthesis references from Post 287622 (Mountain_Girl: "Phenmetrazine synth from propiophenone'", Stimulants)

Cis- and trans-3-Methyl-2-phenylmorpholine
Frank H. Clarke
J. Org. Chem. 27, 3251-3253 (1962) (https://www.rhodium.ws/pdf/phenmetrazine.clarke.pdf)
____ ___ __ _

_{Über Synthese spasmolytisch wirksamer Körper. XIX.}
Synthese von Estern der Benzil- und Mandelsäure mit 2-Phenyl-3-methyl-4-(β-oxyäthyl)-morpholin
Joseph Klosa
Journal für Praktische Chemie 12-17 (1963) (https://www.rhodium.ws/pdf/phenmetrazine-klosa.pdf)

^{The Hive - Clandestine Chemists Without Borders}

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	All 14 posts		Subject: Phenmetrazine synth from propiophenone		Please login to post		Down


		ztion (Stranger) 03-10-02 23:19 No 280265				Phenmetrazine synth from propiophenone (Rated as: good read)
						Hi, Someone I know has been thinking about synthing phenmetrazine. This is how that person has planned to do it: First we react propiphenone with bromine. C6H5-C=OCH2CH3 + Br2 --> C6H5-C=OCHBrCH3 Next we reduce that carbonyl group to an alcohol. C6H5-C=OCHBrCH3 + NaBH4 --> C6H5-HCOHCHBrCH3 Then we react that with ethanolamine. C6H5-HCOHCHBrCH3 + OHCH2CH2NH2 --> C6H5-HCOHCH(NHCH2CH2OH)CH3 And finaly we cyclolize it with some sulphuric acid. C6H5-HCOHCH(NHCH2CH2OH)CH3 + H2SO4 --> phenmetrazine [1] During a trial in Sweden (~1965) where the doctors prescribed drugs for addicts, the speed freaks apparently prefered phenmetrazine over both amphetamine and methamphetamine! It is of lower potency than amphetamine, but the euphoria was apparenly MUCH better. So when they had free drugs they could just solve the potency problem by taking more of the drug. From what I've heard 100mg phenmetrazine == 50mg amphetamine. So what do you think, could the synth be done this way? References: 1. Patent US2835669



		foxy2 (Distinctive Doe) 03-11-02 00:15 No 280299				Re: Phenmetrazine synth from propiophenone
						Might bee interesting. When I have some spare time I will compile a load of info I have found on this compound. But it might take me a WHILE. Make a Difference Donate Now!! (http://www.lp.org/drugwar/)



		PrimoPyro (Hive Prodigy) 03-11-02 00:24 No 280303				Re: Phenmetrazine synth from propiophenone
						You could also make the alpha-hydroxy-beta-bromopropane by reacting propenylbenzene with NBS and water, there is a procedure on Rhodium's site for this reaction. PrimoPyro Vivent Longtemps La Ruche!



		Fuchicoma (Ghost In the Shell) 03-11-02 15:09 No 280655				Re: Phenmetrazine synth from propiophenone
						Phenmetrazine and Phendimetrazine can both be easily made from l-ephredrine and psuedoephedrine by reacting with ethylene oxide. This epoxide is made from hydrolysis of ethyl chlorohydrin which is in turn made from ethylene and a hypochlorite like bleach, wouldn't this be an easier route to Phenmetrazine?



		Rhodium (Chief Bee) 03-11-02 18:04 No 280689				Re: Phenmetrazine synth from propiophenone
						Fu: That sounds good, do you have any references or reaction specifications for that transformation?



		psychokitty (Her Majesty, Stoni's Kitty) 03-11-02 21:43 No 280794				Re: Phenmetrazine synth from propiophenone
						I do. Several. I guess I'll add this to my list of things to post so that I can get that color added to my name. I'm compliling that list for you, Rhodium. Do I HAVE to type up all the experimental details? Or can I just type up the references with a summary of the paper's contents? It's just that some of the stuff I have is too long and has alot of incorporated chemistry symbolism that I can't replicate for you in text form. And I don't know how to scan items to send them over the internet. Advice would be good in that area.



		Rhodium (Chief Bee) 03-12-02 00:16 No 280848				Re: Phenmetrazine synth from propiophenone
						Summary is fine for references from common journals - but I would appreciate an experimental part if the journal is obscure in any way, such as being more than 100 years old, or if it is russian/asian - because it is often impossible to find those even in large libraries.



		Fuchicoma (Ghost In the Shell) 03-15-02 16:26 No 283000				Re: Phenmetrazine synth from propiophenone
						There are some specific references sited in the Merck Ed. 12th Ed. and maybe some patents. Has anyone tasted this substance? Are there any side effects? (lesser or more worse than the other common stimulants?) What is the potency ratio between Phenmetrazine and Phendimetrazine?



		Mountain_Girl (Hive Bee) 03-25-02 13:41 No 287622				Phenmetrazine synth from propiophenone' (Rated as: good read)
						I can't help with the synth, except to say that the references the Merck mentions are (Phenmetrazine): Patent US3018222, Clark, J. Org. Chem. 27, 3251 (1962) and, Klosa, J. Prakt. Chem. 21, 12 (1963). I know almost nothing about this compound but have recently been wondering if its psychedelic analogues have ever been tested, eg. 2,5 dimethoxy phenmetrazine or something ?



		GlaseIs (Stranger) 03-26-02 02:04 No 287865				PhenDImetrazine
						For those that don't know, Phendimetrazine is the weight loss drug Bontril (ick who made that name?), and its only scedule 3. With the extra N-methyl, one would think that Phenmetrazine is to Phendimetrazine as Amphetamine is to Methamphetamine? Anyhow, these stimulate the release of Norepinephine like U4Euh does (notice the structural similarities there also) On the 6th day God created man. On the 7th day, man returned the favor.



		ztion (Stranger) 03-26-02 06:48 No 287976				Actually I think that phendimetrazine is weaker ...
						Actually I think that phendimetrazine is weaker than phenmetrazine. I have not researched this seriously yet but i will soon. (There's an article in Läkartidningen which deals with phendimetrazine, 1974 jun sometime). But think about this: Preludin (phenmetrazine) was discontinued because of the massive abuse. Now they instead make Prelu-2 (phenDImetrazine), why would they do that if phendimetrazine would be even better to abuse? Also I saw on the web some list of amounts of different medications you could take into some country. You could take in x mg of phenmetrazine, but the amount for dimetrazine was actually x * 3 mg or something. This indicates to me that it is much weaker. This is somewhat annoying, since phendimetrazine is much easier to make. If the amine is tertiary you don't have to reduce the propiphenone to an alcohol to cyclize it. You can just reflux it in formic acid. Presto! (GB862198 but it is only in GB791416 they mention that it only works for a tertiary amine). I wonder though if a hydroxy group "counts" to make a tertiary amine.. then we could use n-hydroxyetanolamine and just cyclize with formic as above... If we interpolate all other amines the n-hydroxy version should be just as active.



		ztion (Stranger) 03-26-02 16:41 No 288130				Ok, now I've read that article in Läkartidningen.
						Ok, now I've read that article in Läkartidningen. They say that the recomended dose (by the medical company?), 35mg 2-3 times a day, doesn't differ between phenmetrazine and dimetrazine. Also the acute tox. is the same, the central stimulating effect is also the same, registered as the effect on spontanous movement in rats. Later they find that fenmetrazine increases the blood pressure but phendimetrazine doesn't. At first they speculate that this may be because the n-methyl group, but a bit later they mentition that it may be because the phenmetrazine was d,l while the dimetrazine was d-.(!) It seems obvious to me that THAT was the reason it didn't have any blood presure increasing effects, and maybe also why they seem to think it is equipotent. They also say that phenmetrazine is a metabolite of dimetrazine, with dimetrazine being dominanit in urin samples up to 5 hours after an injection, while phenmetrazine is in majority afterwards. Also there is some n-hydroxy metabolite. Look up these references to find out for yourself: Toxicol Appl Pharmacol 2: 589-601 1960: Pharm. and tox. studies of phendimetrazine. Läkartidningen 1974 Jun 5; 71(23) 2385-2387



		Rhodium (Chief Bee) 09-03-04 16:18 No 529372				Phendimetrazine: 2-Phenyl-3,4-Dimethyl-morpholine (Rated as: good read)
						Optisch Aktives 2-Phenyl-3,4-Dimethyl-morpholin Walter Otto Angew. Chem. 68(5), 181-182 (1956) (https://www.rhodium.ws/pdf/phendimetrazine.isomers.pdf) ^{The Hive - Clandestine Chemists Without Borders}



		Rhodium (Chief Bee) 09-15-04 01:56 No 531357				Phenmetrazine synthesis references (Rated as: excellent)
						The Phenmetrazine synthesis references from Post 287622 (Mountain_Girl: "Phenmetrazine synth from propiophenone'", Stimulants) Cis- and trans-3-Methyl-2-phenylmorpholine Frank H. Clarke J. Org. Chem. 27, 3251-3253 (1962) (https://www.rhodium.ws/pdf/phenmetrazine.clarke.pdf) ____ ___ __ _ _{Über Synthese spasmolytisch wirksamer Körper. XIX.} Synthese von Estern der Benzil- und Mandelsäure mit 2-Phenyl-3-methyl-4-(β-oxyäthyl)-morpholin Joseph Klosa Journal für Praktische Chemie 12-17 (1963) (https://www.rhodium.ws/pdf/phenmetrazine-klosa.pdf) ^{The Hive - Clandestine Chemists Without Borders}

All 14 posts	End of thread	Top