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spicybrown
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| Joined: 26 Jun 2005 |
| Posts: 19 |
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725.22 Points
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2-Fluoro and 3-fluoro substituted amphetamines
Thu Jun 30, 2005 8:57 am |
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Does anybody know of any reports on the activity of these two isomers of 4-fluoroamphetamine? The benzaldehydes of both are available to a friend, but nitroethane is apparently in very limited supply and so they don't want to use it unless there's precedented potential.
-SpicyBrown |
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re: 2-Fluoro and 3-fluoro substituted amphetamines
Thu Jun 30, 2005 2:32 pm |
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Un friend m'a said le 2-fluoroamphétamine est active et about le same activité like amphétamine. Je don't remember what was le dosage level.
Why use le nitroethane, when maybe vous could use l' aldol with MEK, followed by le Baeyer-Villiger, non? Ou perhaps le Darzen condensation?
It would be very interesting to look into l'activité des two compounds. |
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spicybrown
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| Joined: 26 Jun 2005 |
| Posts: 19 |
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725.22 Points
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re: 2-Fluoro and 3-fluoro substituted amphetamines
Thu Jun 30, 2005 5:40 pm |
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Nitroethane simply isn't that uh.. simple to make. There was a huge thread on the Hive about how basically all of the methods SUCK.
Charles: Going through MEK aldol is too lenghtly and steppy for my friend's tastes, and I think there's a lot of potential there for low yields and what-not. The Darzen condensation is however a very good potential for when my friend is a little less busy.
-SpicyBrown |
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re: 2-Fluoro and 3-fluoro substituted amphetamines
Thu Jun 30, 2005 9:39 pm |
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>> Charles: Going through MEK aldol is too len...
Le propre title est 'Mon général' 
To preparé le nitroethane il y a un excellent suggestion posté by Nicodem au Sciencemadness:
https://sciencemadness.org/talk/viewthread.php?tid=909
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As already briefly mentioned by Kinetic, there is also another efficient OTC oxime-to-nitro oxidant, for those of us who can't get Oxone. Sodium perborate in acetic acid oxidizes oximes of many types into their nitro counterparts. Like usually happens when I search for something in the mess of my files I couldn’t find the paper but I think the reference (found in another paper) is Synlett (1992) 337. I remember that the method worked on aliphatic oximes as well.
Anyway, what’s maybe new and more important, pyruvic acid oxime should be as useful (or even more) as a substrate to be oxidized to nitroethane. Pyruvic acid is much more accessible than acetaldehyde or its trimer. It can be made by pyrolisis of tartaric acid in the presence of H2SO4 (a glycol rearrangement to HOOC-CH2-CO-COOH, followed by decarboxylation to Me-CO-COOH). I see no special reason why the perborate oxidation would not work on Me-C(=NOH)-COOH just as it works on other oximes. The beauty is that both the oxime formation and its oxidation can probably be made in one pot. The intermediate 2-nitropropionic acid easily decarboxylates to nitroethane. So you already get your favorite product at the end. Off course, pyruvic acid must be used as an alkali salt in order to form hydroxylamine from H2NOH hydrochloride or sulphate. Alternatively sodium acetate can be used as a base. Luckily calcium pyruvate can be bought online if you look hard enough on the net, so for some there is even no need to make pyruvic acid at all. The reactions involved would be:
Ca(MeCOCOO)2 + 2NH2OH×HCl =[AcOH]=> CaCl2 + 2H2O + 2Me-C(=NOH)-COOH
Me-C(=NOH)-COOH + NaBO3×4H2O =[AcOH]=> Me-CH(NO2)-COONa + H3BO3 + 3H2O
Me-CH(NO2)-COONa + HCl =[AcOH]=> Et-NO2 + CO2
Unfortunately I never was so desperate to try the reaction myself (who needs nitroethane anyway ), but if I would I would do it like this:
I would dissolve the calcium pyruvate in acetic acid solvent and add two equivalents of hydroxylamine hydrochloride. I would then let it reflux for a few hours in order to assure the conversion to the oxime, then add the sodium perborate and continue the reaction by the instructions from the paper (which I can’t find at the moment). At the end I would however add as much of conc. HCl as it is needed to acidify the reaction and continue the reflux for one hour more (a 20% excess in relation to sodium perborate should do). This is because 2-nitro-propionic acid is a considerably stronger acid than acetic acid and is therefore mostly deprotonated due to the formed borate being basic. Its deprotonation would inhibit the decarboxylation step, so the addition of HCl is in order to assure all of the acid decarboxylate to the nitroethane. The work up should be a simple dilution with cold water, separation of the EtNO2 layer (extraction with CH2Cl2 or ether is also advisable), washing with water, NaHCO3, brine and distillation.
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Le pyruvate de calcium et sodium are cheap and OTC, they are commonly used to help relieve les disproportionées horizontales.. |
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64bandil
Busy Bee
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| Joined: 22 Mar 2005 |
| Posts: 35 |
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1508.72 Points
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re: 2-Fluoro and 3-fluoro substituted amphetamines
Mon Jul 04, 2005 12:35 am |
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2-fluoroamphetamine is active as an stimulant / hallucunogenic compound at app. 1 mg/kg. It feels like amphetamine, except theres a really nice hallucinogen like effect lurking in the back ground.... Lasts a bit shorter than 4-fluoroamphetamine.
Only tried it once at 75 mg's which was a fine dosage level. |
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