This is a nice precursor to meta-methoxylated amphetamines
And why would you make that ?? not much fun in m-metoxyamphetamin.
There's something about 3-methoxy-4-methylamphetamine in http://www.erowid.org/library/books_online/pihkal/pihkal123.shtml (http://www.erowid.org/library/books_online/pihkal/pihkal123.shtml)
, it could be close to 4-bromo. Who knows?
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 (http://l2.espacenet.com/dips/viewer?PN=US4419367&CY=gb&LG=en&DB=EPD)
. Happy hornieness! Hope you have a girlfriend! ;D
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 ;D - 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.
(https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000327957-file_krnw.gif)
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, IMHO ;D 8) ;D 8) :-[ ).
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 :)
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 (http://l2.espacenet.com/dips/viewer?PN=US3798271&CY=gb&LG=en&DB=EPD)
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 (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!
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!
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 (http://salmon.psy.plym.ac.uk/year1/psy128sexual_behaviour/sexbehav.htm#female_motivation_rat)
Those who give up essential liberties for temporary safety deserve neither liberty nor safety
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:
(https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000327957-file_ez4u.gif)
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 (https://www.thevespiary.org/talk/index.php?topic=11502.msg32275000#msg32275000)
(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.
PrimoPyro
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 (http://l2.espacenet.com/dips/viewer?PN=US4755613&CY=gb&LG=en&DB=EPD)
) 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.