Author Topic: Synthesis of 4-Fluoroamphetamine  (Read 19392 times)

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Whizard

  • Guest
Re: Synthesis of 4-Fluoroamphetamine
« Reply #20 on: August 10, 2001, 12:28:00 PM »
My main interest in pursuing this was 4-Fluoromethamphetamine. Which is potentially a more active compound then it's unsubstituted derivative. I understand that the aldehyde is not very reactive to Nitroethane. Does anyone have data on 4-Fluoromethamphetamine activity or the aldehyde's reactivity?

I dunno, but I been told ... You never slow down, you never grow old!

Rhodium

  • Guest
Re: Synthesis of 4-Fluoroamphetamine
« Reply #21 on: August 10, 2001, 01:05:00 PM »
From the JMC reference given above:

4-fluorobenzaldehyde (24.8g, 0.2 mol), nitroethane (30g, 0.4 mol), 20ml of isopropanol and 1 ml butylamine were heated under reflux for 5h. The reaction mixture was allowed to cool to room temperature overnight while crystallization occured. The crude yellow product was filtered and recrystallized from methanol to afford 20g (55%, 0.11 mol) of pale yellow crystals (mp 64-66°C).

obituary

  • Guest
Re: Synthesis of 4-Fluoroamphetamine
« Reply #22 on: August 10, 2001, 03:09:00 PM »
is the sub. bz.aldehyde watched at all? 

is there any pharma info for 4-F-Meth?

Rhodium

  • Guest
Re: Synthesis of 4-Fluoroamphetamine
« Reply #23 on: August 10, 2001, 04:08:00 PM »
The aldehyde is completely unwatched. Pharmacological information can be found in Eur.J.Pharmacol., EN, 287:2, 1995, p105-114, which largely says it is a stimulant similar to amphetamine, and is not similar to serotonergic agents like MDMA, and therefore is not toxic to serotonergic neurons like the other 4-haloamphetamines.

A subjective test by Mobius can be read at

https://www.thevespiary.org/rhodium/Rhodium/pharmacology/pfa.txt


Whizard

  • Guest
Re: Synthesis of 4-Fluoroamphetamine
« Reply #24 on: August 10, 2001, 11:08:00 PM »
Thanks for the details of the JMC citation. Your write up "Ethylenediammonium diacetate - a mild and effective Henry reaction catalyst" led me to have little hope of this aldehyde's cooperative nature.
BTW is JMC available to online? :)

I dunno, but I been told ... You never slow down, you never grow old!

Rhodium

  • Guest
Re: Synthesis of 4-Fluoroamphetamine
« Reply #25 on: August 11, 2001, 10:30:00 AM »
JMC is available online, but you will have to pay per credit card for all articles you want to access.

Whizard

  • Guest
Re: Synthesis of 4-Fluoroamphetamine
« Reply #26 on: August 12, 2001, 10:28:00 PM »
So are you offering me the use of your credit card (OFOM!). Seriously, I started my quest investigating the preparation and (possible) activity of 4-fluoromethampetamine after the citation in "Future Synthetic Drugs of Abuse" which I believe you are familiar with...

Alternatively, the use of 1-(4-fluorophenyl)propan-2-one, in place of P2P, would almost certainly give a product with adrenomimetic properties, and may in fact be considerably more potent than methamphetamine.

The underlying question is: Is there a compound which is stronger (as a stimulant as defined LOC CIT) than Methamphetamine?


I dunno, but I been told ... You never slow down, you never grow old!

Rhodium

  • Guest
Re: Synthesis of 4-Fluoroamphetamine
« Reply #27 on: August 13, 2001, 07:00:00 AM »
I really don't know, and I have asked this myself earlier. I think slappy had a QSAR on stimulants, and I hope he will be posting the reference soon.

slappy

  • Guest
Re: Synthesis of 4-Fluoroamphetamine
« Reply #28 on: August 14, 2001, 04:20:00 AM »
Rhod, I am currently away from all of my ref's, and will remain so for the rest of the month. When I get access to a local university library, and Beistien & CAS I can find it for you.

I seem to recall them mentioning that electron injecting substituents maintained or (rarely) increased potency, and electron withdrawing substituents usually decresed potency (especially -NO2). Electron density at the aromatic ring is also important along with even electron distrobution, and unreactivity. Replacment of the benzene ring with similar aromatic heterocycles resulted in reduced potency. The furan, thiophene, pyrrole, pyridine, and pyrimidine analouges were explored.

randolph_carter

  • Guest
Re: Synthesis of 4-Fluoroamphetamine
« Reply #29 on: August 28, 2001, 06:07:00 AM »
well well ..
hey now....
ye bee a talkin about my ole favourite da fluorinated amphez...
i've did a lil research in this arena and i can most certainly comment on the READY availablity of 2 fluoro p2p (think acros...sig/flu/ald...)which i can assure you is a MUCH more pleasant dream than the 4 fluoro varietal...a lil pricey tho i.e. $3-$6/g but it is "puriss" grade...
neurotoxicity is lower than other halogens by a mile....
although on perusing da sig catalog i find 4 cl MeAmp available uncontrolled and served neat @ $150/g also noted some 4-fluoro cmpds as well...
they do taste great and they are much less filling...
R_C

"remember little ones, love is real,not fade away, so pass some ammo on today......"

Rhodium

  • Guest
Re: Synthesis of 4-Fluoroamphetamine
« Reply #30 on: August 28, 2001, 08:22:00 AM »
Are you saying you have actually tried any fluoroamphetamines? In that case I would be VERY interested in hearing about your syntheses and bioassays.

Do you have any pharmacological/chemical references pertaining to other fluorinated (meth)amphetamines than 4-fluoroamphetamine?

4-Chloroamphetamines are serotonergic neurotoxins and are not stimulants.

randolph_carter

  • Guest
Re: Synthesis of 4-Fluoroamphetamine
« Reply #31 on: August 28, 2001, 04:10:00 PM »
WELL OF COURSE!!!
i wuz a inquirin around here about 2 years ago about said compounds and really didn't get much except some old nichols quotes and some sasha redux...
so as they say inquirin m indz have GOT to know...
so on europa's farthest shore lizards obtained 2-fluoro-P2P neat via sigmoidz for some experiments...a lil leucart wallach with a dash of everyones fave n-methylformamide and voila..
what ya seek..
MUCH longer cycle to metabolize to nada than the non sub....

more raves to come later....
gotta go get some lilith bootie now....
hope to bee back soon.....



"remember little ones, love is real,not fade away, so pass some ammo on today......"

Bwiti

  • Guest
Flourine + Amphetamine?
« Reply #32 on: August 15, 2002, 05:51:00 AM »
Rather than synthing it from 4-fluorophenyl-2-nitropropene: Dissolve freebase amphetamine in ether and gas it with flourine?? I'm probably completely off base, but it doesn't hurt to ask. Peace! 8)

Love my country, fear my government.

Cyrax

  • Guest
Bwitti, fluorine gas is very, very, very ...
« Reply #33 on: August 15, 2002, 08:26:00 AM »
Bwiti, that yellow fluorine gas is very, very, very reactive.  It is one of the most vicious chemicals I know (if you do not take phosgene into account).  Trust me: you do not want to mess with it.  There is no way to get a regioselective reaction (mabey just a regioselective death of all the dudes that stand in the vicinity of the reaction vessel).

This comes from Advanced Inorganic Chemistry, 5th ed, Cotton F.A. p 546:  "Fluorine is the chemically most reactive of all the elements and combines directly at ordinary or elevated temperatures with all the elements other than nitrogen, oxygen, and the lighter noble gases, often with extreme vigor (whow !!!).  It also attacks many other compounds, particulary organic compounds, breaking them down to fluorides; organic materials often inflame and burn in the gas."

If some laboratory operator is broken down to fluorides, he must have been working with F2 gas  ::) .

SPISSHAK

  • Guest
What I want to know is
« Reply #34 on: August 15, 2002, 02:03:00 PM »
where that guy that posted in novel forum on catalytic transfer hydrogenation of p2p's got that 4-fluorophenylacetone from?

Dr_Heckyll

  • Guest
CAS#: 459-03-0
« Reply #35 on: August 15, 2002, 07:27:00 PM »
4-FLUOROPHENYLACETONE
CAS#: 459-03-0

Available from ACROS and Lancaster. Cost ~ $10/g

DrH



http://lyricsdomain.com/lyrics/26021/


Barium

  • Guest
I guess that guy would be me..
« Reply #36 on: August 16, 2002, 06:32:00 AM »
I have made my 2- and 4-FP-2-P myself of course.

They are quite easily made from the benzaldehydes and nitroethane, then reducing/hydrolysing the nitropropene by any of the routes I´ve also suggested in the novel forum.

Or, they can very easily be made by the Darzen route, also in the novel forum.

UTFSE

randolph_carter

  • Guest
2 f p2p sources...
« Reply #37 on: October 15, 2002, 06:58:00 AM »

Antoncho

  • Guest
Fluorinated BA's - in the kitchen?
« Reply #38 on: January 26, 2003, 11:19:00 PM »
This is certainly very very intriguing... All these funny fluoro-substituted stims.... Fluorinated 4-MAR also has to bee worthwhile...

So decided i'd dig up smth for the OTCbees like me so that they have a hope of making some at some very very :)  distant future...


Here goes:

Patent US5227531



175 g (1 mol) of 2,4-dichlorobenzaldehyde were heated together with 1,000 g of sulfolane and 151 g (2.6 mol) of potassium fluoride for 15 h at 210 DEG-215 DEG C. The reaction mixture was thoroughly mixed during the entire duration of the reaction by a powerful stirring mechanism in order to prevent the insoluble salts settling. Cooling was then carried out to room temperature and the inorganic constituents were separated off by means of a suction filter covered with a blanket of nitrogen. Rinsing was carried out twice using 100 g of fresh sulfolane in each case. From the filtrate 96.6 g=68% of theory of 2,4-difluorobenzaldehyde with a boiling point of 70.5 DEG C. (40 mbar) was obtained by rectification under reduced pressure in a column containing approx. 20 theoretical trays. Solidification point: approximately 2 DEG C.



Sulfolane ain't exactly OTC, but they also say that:


The reaction is able to proceed in a wide temperature range. Expediently, temperatures between about 120 DEG and 250 DEG C., in particular between about 180 DEG and 230 DEG C., are employed.

Suitable as solvents for the reaction are in principle all the possible dipolar aprotic solvents, preferably tertiary carboxylic acid amides such as dimethylformamide, dimethylacetamide, N-methylpyrrolidone, N,N,N',N'-tetramethylurea, N,N'-dimethylimidazolidin-2-one, sulfoxides such as dimethylsulfoxide and sulfones such as dimethylsulfone, diphenylsulfone and sulfolane. Particularly preferred are N-methylpyrrolidone, dimethylsulfoxide and dimethylsulfone, in particular, however, sulfolane.



And there's also diethylacetamide (bp 185 C) which can bee easily made from next-to-OTC materials.



Antoncho

Rhodium

  • Guest
4-Fluoroamphetamine
« Reply #39 on: January 27, 2003, 12:14:00 AM »
Good, that complements

Post 380478

(pHarmacist: "p-F-benzaldehyde from p-Cl-benzaldehyde", Methods Discourse)
nicely.

I have also uploaded a 4-Fluoroamphetamine pharmacology article to my page:

Eur. J. Pharmacol. 287, 105-113 (1995)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/4-fluoroamphetamine.pdf)