Just had a dream and a jeanie granted me a tub of m-methoxyphenylacetic acid. The jeanie has given me one day to bake something with it or it will perish. Can someone help me with a recipe?  

Mix it with acetic anhydride and anhydrous sodium or potassium acetate and reflux it several hours. Yield should be about 50 percent meta-methoxyphenylacetone. This is a nice precursor to meta-methoxylated amphetamines.

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This is a nice precursor to meta-methoxylated amphetamines

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And why would you make that ?? not much fun in m-metoxyamphetamin.

This could be right, but that's the only target compound (AFAIK) with somewhat CNS activity. If you have a better idea, please let it me know, I want to learn from other bees.

In the X-methoxyamphetamine series, only 4-methoxyamphetamine (4-MA, PMA) has a certain "desired" effect (but on the other hand, it is reported to be responsible for lethal overdoses - PMA taken as XTC). The 2- and 3-methoxyamphetamines are much less potent. I think I've even read that one of these two has been used as a pharmaceutical drug for a while.

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-[ A Friend With W33D Is A Friend Indeed ]-

What would the effects of 3-Methoxy-4-Bromoamphetamine be?

There's a thread on conversion to pea's from paa's.  is the pea analog worthwhile?

There's something about 3-methoxy-4-methylamphetamine in

http://www.erowid.org/library/books_online/pihkal/pihkal123.shtml

, it could be close to 4-bromo. Who knows?

If you can turn it into 2-(3-Methoxy-phenyl)-ethylamine you have a supposedly very powerful sex stimulant, better than any Viagra.

At a dose of 1 mg/kg/day this compound gets male mice to mount 20 times more often then controls on females, and females 5 times more often to show lordosis.

So it might spice up your sex life significantly, if that's of any use for you

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Dr. Heckyll & Mr. Jive by Men at Work
...tells my tale.

Could you please post the reference? If this is true and transferable to humans, it would be very nice.

I know it is in a US patent, but I have forgotten which one.

Shit, everyone wants references: when I apply for I job they want references I don't have, and now they even want references at The Hive. Life really suck. Should have stayed away from the place   .

Well, at least the references required at The Hive I have, and even beat the Chief Bee with my archive. Rhodium was right, though. It's in a patent:

Patent US4419367

. Happy hornieness! Hope you have a girlfriend!  

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Dr. Heckyll & Mr. Jive by Men at Work
...tells my tale.

WOWWWWWWW!!!!!!!!!!!

Un-fucking-believable!!!

I think i just acquired another 'goal of my life'!

Sorry if i sound like an underscrewed science geek  - for i am not. But this is just SOOOOOOOOOOOOOOO awesome!

I mean, i always thought that making sexual stimulants like Viagra was far out-of-reach for an amateur chemist, and now it turns out it's fucking POSSIBLE - and, moreover, it's a phenethylamine!

Just let me quote some passages.

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According to the present invention there are provided pharmaceutical and veterinary compositions for use as sex stimulants in male and female mammals comprising as active ingredient a compound of the general formula where X designates --OCH3.--SCH3 or a halogen, the substituent being either in ortho or in meta position, as well as the salts and complexes of these. The term halogen in this context designates chlorine or bromine ... The ortho-chloro, meta-chloro, ortho-bromo and meta-bromo compounds were tested on animals and all of these were found to be effective sex stimulants.

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https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000327957-file_krnw.gif" title="View this image">

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Preliminary tests with human volunteers have shown that the pharmaceutical compositions of the present invention exert a pronounced effect on human males. Tests have shown that o-methoxy- and o-methylthiophenylethylamine are effective in dosages of 35 to 50 mg when given per os as the hydrochloride salt. A preferred dose is in the range of from 5 to 10 mg, a number of times per day. The drug is advantageously administered per os in the form of capsules. The effect is obtained after a few hours to a few days.

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So, the only downside (as compared to sildanefil) is the relatively long latency period, but WTF (20x increase in sexual activity is well worth a few hrs wait, IMHO         ).

Another question - can someone explain me what they meant by 'female lordosis/mount coefficient'? I.e., is there a chance that it could have a similar activity for ladies? That'd bee really cool

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Now, to the synthetic ideas.

Ortho-MeO-PEA seems to bee the most potent of them all. To make the aldehyde which would bee converted by standard means into the PEA, one could:

a) Nitrate toluene (a la Cheapskate).

b) Reduce to toluaniline (again a la Cheapskate, but

Patent US3798271

has this rxn in its most perfect form , yield circa quantitative) and steam-distill the ortho-isomer out.

c) Diazotize/methanolize the amino group (or Sandmeyer it to smth else, if desired)

d) Oxidize the methyl group to aldehyde by any known way, e.g. w/Na peroxodisulfate/FeSO4; or chromic anhydride/PTC




Alternatively, one could try to make the aminobenzaldehyde directly from nitrotoluene, similarly to

http://orgsyn.org/orgsyn/prep.asp?prep=cv4p0031

- there they make para-amino-BA from p-nitrotoluene w/Na2S; can anyone suggest if the same route would bee applicable to ortho-isomer? Seems likely.

Another Q: how does one separate o- and p- nitrotoluenes resulting after intration? Will simple fractional distillation do?

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Does anyone have better/shorter ideas? Of course, o-MeO-BA could bee easily bought from a chem supply company. Moreover, ortho-cresol, which is also widely available and cheap (not for SWIM, but anyway) would serve as an excellent precursor.


Dr. Heckyll, my HUGE thanks to you!





Antoncho

P.S. Another idea......that has just occurred to me is actually MUCH simpler:

a) Brominate plain benzaldehyde

b) Methoxylate the haloid (the rxn will run much more smoothly than in case of vanillin beecause of the absense of electron-donating substituents on the ring) or, alternatively, hydroxylate/methylate it.


Voila! - here's your meta-MeO-benzaldehyde!

o-methoxybenzaldehyde (non-watched and quite cheap) is reacted with methyl 2-chloroacetate (Darzen) to o-methoxyphenylacetaldehyde + hydroxylamine --> o-methoxyphenylacetaldoxime which can be dehydrated to the nitrile with acetic anhydride, or reduced as it is to the amine.

Oil of Wintergreen = Methyl Salicylate (o-OH.C6H4.COCH3)
1) Methylate with MeI
2) Reduce to benzylic alcohol with Na/EtOH
3) Oxidize to o-MeO-BA with MnO2
?

& what about aspirin as possible precursor ?

(I would personally just buy the o-MeO-BA but it's fun to think of the options)

Receptivity: the females ability to copulate. The lordosis score measures this by expressing the number of times a female emits the lordosis posture as a percentage of the number of times she is mounted by a sexually experienced and vigorous male. Notice that lordosis does not measure the female's willingness to copulate. Indeed the small test cages used in most studies prevent females escaping from sexually vigorous males.

http://salmon.psy.plym.ac.uk/year1/psy128sexual_behaviour/sexbehav.htm#female_motivation_rat

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Those who give up essential liberties for temporary safety deserve neither liberty nor safety

Better sex through chemistry.

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A friend with speed is a friend indeed

Wow, so many replies in no time - thank you!

Special thanks go out to Foxy2

Still, the meaning of the misterious 'mount coefficient' remains unclear.
Well, from what i read in that article the link to which Foxy gave, female rats DO give a fuck  about having/not having sex, and, although they still get raped occasionally, as it seems , their wish to copulate does play a role


So it looks good for the ladies thus far


Another question that haunts me - why in the world they never began marketing it? Instead we have that monstrous Viagra, which is probably 100+ times more expensive to synthesize.

There are three possibilities i can think of:

1) Not as strong as it should bee to effectively counteract impotence in males.

2) Some medically undesirable side-effects.

3) Recreationally psychoactive properties (at larger doses, maybee?)


What do you think, fellow bees?

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As for the chemistry - why, it never appeared to me bee4 that by simply Reimer-Tiemanning plain old phenol, one can get ~25% yield of ortho-hydroxy-benzaldehyde aka salicylaldehyde. Separation of isomers is real easy in this case: very different acidities (they isolate it by acidifing the mixtr to a controlled pH); plus, IIRC, the para-isomer doesn't steam-distill, while ortho- does.

Then just methylate the hydroxy.

How d'you like it - four steps total from phenol, huh? Looks quite good to SWIM .






Antoncho

Why didn't Shulgin mention this?
Damn, if this really works... Pfizer will go belly up without Viagra  

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I'm not fat just horizontally disproportionate.

>Another question that haunts me - why in the world they never began marketing it? Instead we have that monstrous Viagra, which is probably 100+ times more expensive to synthesize.

Well, these compounds make males (and seems that females too) willing to have sex, Viagra (and other PDE5 inhibitors) addresses different medical problem - when guy already is willing, but cannot get his stick up because of old age, diabetes or whatever.