dr_dolittle (Stranger)
07-02-02 12:17
No 327957
      m-methoxyphenylacetic acid-------->  Bookmark   

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? frown
07-02-02 12:47
No 327962
      m-methoxyphenylacetone  Bookmark   

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.
(Hive Addict)
07-02-02 13:18
No 327968
      Re: This is a nice precursor to meta-methoxylated ...  Bookmark   

This is a nice precursor to meta-methoxylated amphetamines

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

07-02-02 16:10
No 327996
      Better idea ?  Bookmark   

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.
07-02-02 18:29
No 328014
      In the X-methoxyamphetamine series, only ...  Bookmark   

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.

-[ A Friend With W33D Is A Friend Indeed ]-
(Chief Bee)
07-02-02 19:11
No 328021
      What would the effects of ...  Bookmark   

What would the effects of 3-Methoxy-4-Bromoamphetamine be?
(Hive Bee)
07-02-02 21:43
No 328046
      phenethylamines  Bookmark   

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

(Hive Bee)
07-03-02 01:07
No 328115
      MMA  Bookmark   

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?
07-17-02 22:26
No 333755
      m-MEO-PEA  Bookmark   

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 :)

Dr. Heckyll & Mr. Jive by Men at Work
...tells my tale.
(Hive Bee)
07-18-02 12:50
No 334066
      reference ...  Bookmark   

Could you please post the reference? If this is true and transferable to humans, it would be very nice.
(Chief Bee)
07-19-02 00:03
No 334277
      I know it is in a US patent, but I have forgotten ...  Bookmark   

I know it is in a US patent, but I have forgotten which one.
07-19-02 05:01
No 334400
      Shit, everyone wants references  Bookmark   

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 mad.

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! laugh

Dr. Heckyll & Mr. Jive by Men at Work
...tells my tale.
(Official Hive Translator)
07-19-02 09:03
No 334488
      OH MY GOD !!!!!!!  Bookmark   



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

Sorry if i sound like an underscrewed science geeklaugh - 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.

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.

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.

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, IMHOlaughcoollaughcoolblush).

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 coolsmile

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?

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!


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!
(Hive Bee)
07-19-02 09:26
No 334494
      Or...  Bookmark   

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.
(Hive Bee)
07-19-02 10:05
No 334509
      For o-MeO-BA maybe ...  Bookmark   

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)
(Distinctive Doe)
07-19-02 10:36
No 334521
      Receptivity: the females ability to copulate.  Bookmark   

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.


Those who give up essential liberties for temporary safety deserve neither liberty nor safety
(Hive Bee)
07-19-02 10:44
No 334523
      Better sex through chemistry. :-)  Bookmark   

Better sex through chemistry.smile

A friend with speed is a friend indeed
(Official Hive Translator)
07-19-02 12:11
No 334543
      Thank you!  Bookmark   

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

Special thanks go out to Foxy2wink

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 fucksmile about having/not having sex, and, although they still get raped occasionally, as it seemssmile, their wish to copulate does play a rolesmile

So it looks good for the ladies thus farwink

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?

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 SWIMwink.

(Stoni's sexual toy)
07-19-02 12:36
No 334546
      Why didn't Shulgin mention this?  Bookmark   

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

I'm not fat just horizontally disproportionate.
(Hive Bee)
07-19-02 16:44
No 334591
      Why Viagra?  Bookmark   

>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.
(Chief Bee)
07-19-02 21:41
No 334668
      If you start with common ortho-cresol ...  Bookmark   

If you start with common ortho-cresol (o-Me-Phenol), you methylate the phenol, and either make the benzaldehyde or benzyl chloride through any common route, and from there proceed either via the nitrostyrene or benzyl cyanide to the PEA...

...or oxidize the methyl to the acid and then to the alcohol and then as above either via benzyl halide or benzaldehyde.

The funny part is that common aspirin also is a good precursor :)
07-20-02 04:04
No 334873
      This is the beginning...  Bookmark   

On July 17, 2002, at 22:26, a stranger nicknamed Dr. Heckyll started the revolution with a carefully launched post:
the love drugs wave was borne.

Make love not war becomes a reality.

And this is only the beginning. The good Dr. Heckyll has more on store, so much more. Just be patient...

{Make sure you notice that the post is marked with a wink}

Dr. Heckyll & Mr. Jive by Men at Work
...tells my tale.
(HyperLab Bee)
07-20-02 14:46
No 335038
      aspirin  Bookmark   

And what do you suggest we should do to aspirin to make it o-meo... etc.?

When I die bury me upside down so the world can kiss my ass.
(Chief Bee)
07-20-02 14:49
No 335041
      Hydrolyse the acetyl ester with aqueous base, ...  Bookmark   

Hydrolyse the acetyl ester with aqueous base, yielding o-hydroxy-benzoic acid. Reduce the acid to the alcohol, methylate the phenol, and then make either the benzaldehyde or the benzyl halide from the o-methoxy-benzylalcohol.
(Hive Prodigy)
07-20-02 15:05
No 335044
      Aromatic Nitroso groups  Bookmark   

Can one react an aromatic nitroso group (Ar-N=O) With hydroxylamine and HCl to form a diazonium salt?

Ar-N=O + H2N-OH --> Ar-N=N-OH + H2O
Ar-N=N-OH + HCl --> Ar-N#N+Cl- (ionic salt) (# = triple bond)

This could prove useful on a larger scale manufacture of your ortho-methoxyphenylalkyl derivatives, by utilizing the following series:

Baudisch Reaction:

Followed by methylation of the free phenol form, then diazotization of the nitroso via the method proposed above.

The final step would be conversion of the phenyl-diazonium salt to the benzaldehyde via the method in Post 322750 (Tricky: "Benzaldehydes from diazonium salt, OTC!", Novel Discourse) which is supplemented by information in OrgSyn.

Benzene --> o-(OH)(NO)PhH --> o-(OMe)(NO)PhH --> o-(OMe)(NNCl)PhH --> o-(OMe)(CHO)PhH

And from the benzaldehyde its all familiar territory for the rest of the syntheses.

(Hive Prodigy)
07-20-02 15:10
No 335046
      On Second Thought  Bookmark   

Hahahaha, forget all that crap. I totally misses the obvious:

Phenol + reimer-tiemann + DMS methylation. Man, thats a lot simpler.

Phenol is cheap, CHCl3 is cheap, KOH is cheap. DMS can be made from cheap MeOH and H2SO4. Cheap cheap cheap! A lot cheaper and easier than the prior post of mine.

Yeah the reimer tiemann yield isnt so hot from phenol, and some of it will be the wrong isomer, but the ingedients are so cheap, easy to get, and its such an easy reaction, that one shouldnt be stopped by this imperfection. Just my opinion.

07-20-02 17:23
No 335078
      Cheap  Bookmark   

When calculating the cost, you'll have to consider the effort to clean up the aldehyde and subsequent intermediates till you arrive at the o-methoxybenzaldehyde. Even an optimized Reimer-Tiemann (Patent US4755613) yields only about 77% of the desired isomer. The p-isomer can be extracted with Et2O. How laborious is the methylation and the clean-up?

How compares that to a price of ~$450 for 2.5 kg of o-methoxybenzaldehyde? Assuming an all-over by-weight yield of 50% based on the o-methoxybenzaldehyde, and a dose of 10 mg of o-methoxyphenylethylamine, this is only $0.0036 for the o-methoxybenzaldehyde per dose, which in my opinion is insignificant.

Dr. Heckyll & Mr. Jive by Men at Work
...tells my tale.
(HyperLab Bee)
07-20-02 20:10
No 335123
      reducing acid  Bookmark   

Rhodium: How would we reduce acid to alcohol...EDIT:oops?crazy

When I die bury me upside down so the world can kiss my ass.
(Chief Bee)
07-20-02 20:20
No 335127
      LAH, Na/EtOH, NaBH4/I2, NaBH4/H2SO4 etc...  Bookmark   

LAH, Na/EtOH, NaBH4/I2, NaBH4/H2SO4 etc...
08-05-02 23:46
No 341824
      2-methoxy-phenethylamine *dud*
(Rated as: excellent)


2-methoxy-phenethylamine = *dud*

sorry to burst the bubble but i saw this exciting patent
a couple of years ago and forged ahead with the 2-methoxy-pea.
was even so fortunate to find that it's available commercially!
unfortunatly its effects were
nothing like described in the patent (for myself [male] and
also a female experimentor friend). If I recall correctly we
Worked it up to 75-100mg in a single dose and also tried 5-10mg
several times a day as described in the patent. I have
since lost my notes on this subject so I must resort to
memory with regards to the activity or lack there of. 
There was definitely something going on but not sexually
stimulating, mentally stimulating, or otherwise interesting
to this experienced lab rat.  no idea about the other subs,
we chose not to pursue them due to the lack
of positive results with 2-meo and the fact that
that we would have to spend a lot of time/effort/money
to synth the 3-meo ourselves. We ended up throwing all
the remaining 2-meo material away...
yet another case of wishful patenting... or perhaps
the other subs are better than the 2-meo???
seems there are *a lot* of patents like this, where
the baby just doesn't live up to it's billing.

hope this saves a few bees some valuable time/effort/money.

keep digging and dreaming !



master of the alchemikal arts
(Hive Bee)
08-06-02 04:30
No 341915
      Patents  Bookmark   

Just because something is patented doesn't mean it's real and working! One of my "favourite" patents is a way of treating tumors by irradiating its antimatter. In practice, they put a mirror next to the patient in about 1 m distance. Then they irradiate with some hard radiation the virtual mirror image of the tumor, i.e. a point about 1 m behind the mirror, some 2 m away from the actual tumor, where they claim is the antimatter part of the tumor, and by destroying it's antimatter, the patient gets cured... crazy. (I'm citing from memory; if you're curious, just search patents for "antimatter", there isn't much popping up, and one of the few is it laugh.)

So no, a patents doesn't guarantee the validity of a technology. But a reputable company, let's say Merck & Co., is less likely than individual inventors or small companies/institutes to patent some weird dreams.

Happiness, health and wealth through chemistry...