Talk:Propylhexedrine/Archive 1

Archive 1

Bottom part reads like a how-to for extracting propylhexedrine from inhalers

The section in chemistry starting from "Propylhexadrine is an amine" to the end of that section looks to me like practical instruction on how to do an acid/base extraction to seperate propylhexedrine from the other stuff in inhalers. Such how-to information isn't supposed to be in wikipedia, and the information on the properties of amines should probably not be here at all - otherwise we'd be justified in having that mention on every article about an amine. 68.186.246.165 (talk) 01:55, 5 May 2009 (UTC)

It certainly wasn't intended to be a "how to" guide for extracting propylhexedrine from benzedrex inhalers; if, however, it reads that way to a lot of folks, I wouldn't be opposed to its removal (I added that part and by this I mean if it was removed due to consensus I wouldn't try to add it back / start and edit war).

Personally, I feel the info I added would be completely insufficient to do a proper extraction for somebody without pre-existing chemistry knowledge (and those with that knowledge don't count, since they know how to do it already without any help from the internet).

I simply wanted to clarify the nature of the propylhexedrine contained in benzedrex (that it is the freebase, a volatile oily substance, which allows for a small amount to be inhaled when used as directed as a nasal decongestant); additionally, I felt that stating that the propylhexedrine in benzedrex is racemic was good information to have in an article about this substance (though ... a source would be nice ... I had a source for this information that I cannot track down now for some reason - help would be much appreciated - I'm VERY sure that the propylhexedrine in benzedrex is racemic, though).

You have a point about the generic information about simple amines. Perhaps the simple protonation-deprotonation examples were unnecessary because in a way you're correct - why should propylhexedrine have that info while the tons of other amines on wiki don't - perhaps a link to the amine article would be better for people who want to know the basics of amine chemistry.

As far as the description of the salt form propylhexedrine hydrochloride - I don't see what the problem is with that. It's a known substance that is definitely made by people who use this substance recreationally and is certainly made in legitimate labs also (I believe the anoretic drug Eventin was propylhexedrine HCl 25 mg). Also, the comment that PHX HCl can be vaporized is there because this is done among those who abuse the drug - I think articles about drugs that are recreational can delve into routes of administration (the different routes, their respective dangers, differing bioavailabilities, etc...) and still be completely encyclopedic.

This part may need some changes, but I'd like to wait for more input if everybody is alright with that. If there's a desire to trim that part I added down, I won't try to revert it back to its current state.

However I must again mention that .... I'm not seeing how it's a "how to" guide for extracting this drug from the inhalers. The only people who would be able to pick up and do an extraction after reading that part already have prior understanding of acid-base separation of chemicals IMO.

I'm not logged in I just realized. This is thesmallprint189 posting. 98.15.227.105 (talk) 02:40, 25 May 2009 (UTC)

I'm sorry but you don't have any idea what you'r talking about. This drug is HIGHLY abused. Just google it and I'm sure you'll find hundreds of posts and "how to" guides on extracting the drug from the inhaler. I look at Wikipedia as a place to find ANY & ALL information on a subject. This substance is absolutely and 100% an amphetamine like drug with similar effects to Methamphetamine. I personally take Adderoll and I have seen this chemical in action and its MUCH stronger than the "max dose" of Adderoll my doctor gives me every month. Please don't rant about information being shown when its nothing more than the truth. Who are you to say what people should or should not know? If something is true, and in this case, very popular I believe Wikipedia should let it be known. If there are sources, link them. I agree that this is not a "how to" place to find information but if there is information to be found, I see no reason it should not be on the page. It can be found all over the Internet anyway so if Wikipedia can sort out the truth and have a accurate page of information on a subject? Let it be known. Just my thoughts.

PS: IV'ing this drug will most likely kill anyone. The properties of this substance should never be injected into the blood stream. I tell you this and I have personally shoved just about every substance known to man into my arm but even I would never inject something with the properties of this chemical. Knowledge of this could and most likely will prevent idiots from trying such a thing. ( No I do not do drugs anymore ) — Preceding unsigned comment added by 3o22dj (talk • contribs) 07:20, 3 November 2012 (UTC)

As a chemist and advocate of the overall "harm reduction" ideas, I have to say that excluding information may actually be more harmful than including it. Anyone with basic, organic chemistry knowledge is not going to need any "how-to" to accomplish extraction. Those with less knowledge may try to extract using things like charcoal lighter or nail polish remover, among other things that have been tried, and all those alternatives are worse than doing it correctly. I'm not suggesting a "cookbook", but only that relevant information not be excluded. The way it is written now is not bad. -The Original Abraxas 01:52, 12 November 2014 (UTC)

More info on Eventin?

This article would benefit from some cited info on the prescription use of this drug as an anorectic. I see that mention is made of "Eventin", but I'm having serious trouble finding a reference to said pharmaceutical brand name anywhere on the Net. Can anybody provide some more information on prescription use of this drug? It might well also provide useful dose comparisons between the recreational internal use and the "official" internal prescribed dose. Bullzeye ^contribs 23:50, 18 August 2009 (UTC)

Apparently it's no longer on the market in any Western countries (which explains the lack of information). I found one reference that described a 25mg dose for the UK preparation, but it's nothing you can cite. From my experience, 25-50mg of PHD once or twice daily would be fairly tolerable and wouldn't strongly effect a user's mood. As for its effectiveness, your guess is as good as mine. 74.178.245.217 (talk) 18:32, 20 August 2009 (UTC)

Recreational use underestimated

The section on recreational abuse potential needs to go. For starters it suggest that menthol and lavendor oil can't be removed from benzedrex when in reality this is a very simple process(just put it in water). Then it starts warning people away from using it. I can tell you this drug has a HUGE following and you can find all sorts of discussions about it among meth and adderall users. YVNP (talk) 04:17, 20 November 2009 (UTC)

Also, It lists benadryl as having a higher recreational value, even though it is considered one of the worst drugs to use for recrational purposes. Muchotreeo (talk) 00:53, 1 May 2014 (UTC)

Stereochemistry section incorrect

Under the chemistry section, it currently states:

"Propylhexedrine, like amphetamine and methamphetamine, is a chiral compound (the α-carbon is chiral, like in its amphetamine cousins). Like other monoamine releasing stimulants with the amphetamine type backbone, the dextrorotatory isomer of propylhexedrine is much more active as a norepinephrine and dopamine releaser in the central nervous system than the levorotatory isomer is. The propylhexedrine contained in Benzedrex inhalers is racemic d,l-propylhexedrine as the freebase. It is likely that pure d-propylhexedrine would have a higher abuse potential and less undesirable side effects than the racemic compound."

The author of this makes the assumption that orientation of the alpha carbon in D-methamphetamine and D-propylhexedrine are analogus, but this is incorrect. When the orientation of the alpha carbon of propylhexedrine matches the orientation of the alpha carbon of D-methamphetamine, it is referred to as the levo isomer of propylhexedrine, levopropylhexedrine. In fact, levopropylhexedrine is synthesized from dextromethamphetamine (source). According to this study, it was concluded that l-N-Methyl-β-cyclohexylisopropylamine HCl (a.k.a. levopropylhexedrine) and d-N-Methyl-β-phenylisopropylamine HCl (a.k.a. d-methamphetamine) were the more active of the stereo isomers regarding pressor and excitatory actions.

I think using the R/S notation for stereo isomers would help illustrate this point. When using the R/S notation for stereo-chemistry, then it is true that (S)-methamphetamine corresponds to (S)-propylhexedrine, and that the S isomer of both drugs is the more pharmacologically active of the pair. —Preceding unsigned comment added by 198.189.58.254 (talk) 00:52, 16 November 2010 (UTC)

IV injection risks section should be relooked at if even necessary or correct.

Seeing as "transient diplopia" is being a technical term for double vision, it makes me wonder the broadness of interpretation that is undertaken with the phrase "and brainstem dysfunction"? Isn't any non-endogenous chemical effecting receptors in the human brainstem also technically a dys-function (if not even 'mal-function'; dys- as something foreign to the usual functioning of a bodily organ rather than a negative or bad "mal-" functioning?). So shooting propylhexedrine seems no more dangerous than shooting methamphetamine and the section seems a bit overblown in my opinion. Most sources of any drug of abuse seem to overplay the seriousness of their IV route of administration, but in comparing to other drugs are dubious in why the drug subject topic is so much worse generally; really it seems mostly the one writing is just doing some ethical duty that outweighs that authors own value set on forthright information bearing to the intended audience by making their drug of discussion out to be avoided by any rationalizing means. Even if improperly comparing to the risks of other similar drugs the audience may have experience with or desensitization to the fear of the use of a particular route with. Nagelfar (talk) 04:17, 25 December 2010 (UTC)

Propylhexedrine is a serious vasoconstrictor, I think it's the same reason you don't IV epinephrine. Unless cerebral hemorrhage is your thing. C6541 (T↔C) 19:26, 8 September 2012 (UTC)

3D structure

This is this a racemate. 3D structure is one specific configuration (one enantiomer). Thus, the 3D structure is wrong and should be eliminated. Best regards, --Jü (talk) 11:21, 24 February 2011 (UTC)

The standard for medical (and other chemical) articles about racemic compounds is for the JSmol 3D renderer to pick one arbitrarily (an image of one of a pair is better than no image at all), and ideally for a Wikipedia editor to create separate static images of each. DMacks (talk) 01:54, 28 March 2024 (UTC)

I added the other enantiomer's image. DMacks (talk) 02:08, 28 March 2024 (UTC)

I was wondering since cyclohexane is a "chair structure" would the final result or properties of the molecule be different depending on on which carbon is starting point? Or is cyclohexane still symmetrical in that regard? — Preceding unsigned comment added by Lurkerofalltrades (talk • contribs) 05:06, 1 March 2012 (UTC)

The chair is symmetric. The group attached to the chair is always "the only thing on the only corner that has anything other than H".DMacks (talk) 01:54, 28 March 2024 (UTC)

Dose

It would be good to include some information about the therapeutic and medical doses of this. — Preceding unsigned comment added by Testem (talk • contribs) 16:32, 17 March 2012 (UTC)

I'll add that, the dosage is 800 ml of air per inhalation delivering 0.4 to 0.5 mg (400 μg to 500 μg) of propylhexedrine (the recommended dosage is two inhalations) C6541 (T↔C) 16:29, 22 November 2012 (UTC)

Alternate synthesis confusion

I removed the following from the article:

In addition propylhexedrine can be synthesized starting with cyclohexylacetone using N-Methylformamide, sulfuric acid and sodium hydroxide.

and its accompanying image. The image was not cyclohexylacetone, and the sentence makes no sense. Mixing anything with "sulfuric acid and sodium hydroxide" is just dissolving it in neutral aqueous sodium (bi)sulfate. I suspect there are some key steps or details omitted and there is no cite to help the reader or other editors figure it out. Is it actually a Leuckart reaction, where the acid is part of the actual amination and then the base neutralizes the ammonium product of it? DMacks (talk) 18:16, 22 November 2012 (UTC)

I apologize for the confusion, I really phrased it badly. The synthesis is read as:

Merck Index
Step 1	Step 2	Step 3	References
33.6 grams of cyclohexylacetone, a compound known to the art, dissolved in 13 grams of 85% formic acid is caused to interact with 72.0 grams of N-methylformamide at 160º-18OºC for 4 hours. This results in the formation of the formyl derivative of the amine.	The formyl derivative is then hydrolyzed by refluxing with 50% sulfuric acid for about 4 hours, after which the hydrolysate is extracted with ether to remove the acid-insoluble material and the aqueous solution made strongly alkaline with any suitable alkalizing agent, for example, sodium hydroxide, to liberate the amine.	The amine is then taken up in ether, dried over potassium hydroxide and purified by distillation, preferably under reduced pressure. β-cycohexylisopropylmethylamine thus obtained boils at 90º-92ºC at 22mmHg.	Merck Index 7761 Kleeman & Engel p.774 OCDS Vol.1 p.37 (1977) I.N. p.817

C6541 (T↔C) 21:10, 22 November 2012 (UTC)

I also made the cyclohexylacetone image based on what I was able to dig up on the internet. C6541 (T↔C) 21:12, 22 November 2012 (UTC)

Okay, that synthesis is in line with what I suspected. I would be interested in knowing what site provided this structure of the compound, so we know not to consider is WP:RS and/or to talk to its maintainers about publishing incorrect information. DMacks (talk) 05:56, 23 November 2012 (UTC)

I see my problem, I had an extra oxygen. I should have realized it was the cyclohexyl form of phenylacetone. I'll fix the structure. C6541 (T↔C) 20:10, 24 November 2012 (UTC)

Does that look better? C6541 (T↔C) 20:16, 24 November 2012 (UTC)

Chemical classification

Is propylhexedrine a substituted amphetamine? If so I will add it to the amphetamines category. Clr324 02:52, 9 December 2014 (UTC) — Preceding unsigned comment added by Clr324 (talk •

Archive 1

contribs)

It doesn't seem like it, per the definition given in Substituted amphetamine; in particular, the ring is cyclohexyl not phenyl (name-detail of amphetamine). There are several sentences about that in Propylhexedrine#Chemistry already. DMacks (talk) 04:05, 9 December 2014 (UTC)

Thank you Clr324 05:53, 9 December 2014 (UTC) — Preceding unsigned comment added by Clr324 (talk • contribs)

recreational use section integrity

The information in the recreational use section is lacking citation making it ambiguous and untrustworthy. Namely the claim that due to its interaction with catecholamines, and specifically serotinin, make it any more neurotoxic than other CNS stimulant. The effects are poorly researched, but only two case studies have been reported to have observed brain stem dysfunction caused by propylhexedrine. Not-Patrick (talk) 16:47, 16 November 2021 (UTC)