nuke
Bluelighter
- Joined
- Nov 7, 2004
- Messages
- 4,190
Sorry, simple question, what does SD stand for?
Standard deviation from a number of different trials. Usually it is the mean standard deviation if I'm recalling right (sd/(# trials)^1/2))
N&PD Moderators: Skorpio
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Stimulants of the Future II
nuke
Bluelighter
Sorry, simple question, what does SD stand for?
Standard deviation from a number of different trials. Usually it is the mean standard deviation if I'm recalling right (sd/(# trials)^1/2))
dread
Bluelighter
No not the imine (=N-), but the weird amine (-NH2) group on top of the imine
Well, IIRC in the case of Aminorex the amine and imine tautomerize... so the imine becomes amine and the amine becomes imine...
So if you only remove the nitrogen that's sticking out, and leave it with the imine, I think it could well have a fully aromatic metabolite a la MPTP -> MPP+...
So I'd rather just remove the nitrogen and the double bond, giving a phenyloxazolidine.
/navarone/
Bluelighter
You're fearing the formation of a oxazole ring right?
Though how dangerous could that be since the nitrogen wont become charged like MPP+?
BTW your post drove me into a very interesting wiki page on heterocyclic compounds that filled my head with curiosities.
http://en.wikipedia.org/wiki/Simple_aromatic_ring(look at the table)
Just think about how many interesting analogues you could get by swiching the methylenedioxy ring of MDXX with any of those heterocyclic rings.....
As I cited a few weeks ago on this thread, Shulgin made an indole amphetamine analogue (5-IT) that showed great potentials (with activity at 20 mg and duration of about 12 hours).
Just think.... The curiosity is overwhelming me now...
dread
Bluelighter
You're fearing the formation of a oxazole ring right?
Though how dangerous could that be since the nitrogen wont become charged like MPP+?
I don't know... I only know I wouldn't be taking the chance, lol!
Just think about how many interesting analogues you could get by swiching the methylenedioxy ring of MDXX with any of those heterocyclic rings.....
I know! For a while I've been contemplating on the benzothiophene-analogue of 5-IT... Either fully aromatic or the dihydro-version, which would be the thio analogue of the weirdly named "desoxy-MDA"...
/navarone/
Bluelighter
Or a benzoxazole analogue!
That would be awfully similar to MDMA by shape and polarity and the high aromaticity gives it high stability too.
fastandbulbous
Bluelight Crew
^ Yeah just what we need, another 4-methyl substiututed stimulant based on a phenylisopropylamine
When will someone get busy and make 2-phenyl-3,6-dimethylmorpholine (aka 6-methylphenmetrazine). Me & the rats loved it years ago
dread
Bluelighter
I'd be happy for almost any phenmetrazine analogue...
3',4'-Methylenedioxy and 3-ethyl seem like substitution worthy of exploring, I just hope they'll hit the RC market some day...
/navarone/
Bluelighter
Ya, I would understand your interests on the MD analogue since phenmetrazine seems to have scarse serotonergic activity compared to other common amphetamines.
However, 3-ethyl? Could you explain this substitution proposition?
daddysgone
Bluelighter
I'd be happy for almost any phenmetrazine analogue...
3',4'-Methylenedioxy and 3-ethyl seem like substitution worthy of exploring, I just hope they'll hit the RC market some day...
But phenmetrazine is Schedule II, which would make any analog, fall under the analog act. Am i missing something?
/navarone/
Bluelighter
^ Yeah just what we need, another 4-methyl substiututed stimulant based on a phenylisopropylamine
When will someone get busy and make 2-phenyl-3,6-dimethylmorpholine (aka 6-methylphenmetrazine). Me & the rats loved it years ago
I assume you mean phemetrazine with a methyl group right above the oxygen.
Interesting! Do you mind sharing some words about it?
dread
Bluelighter
But phenmetrazine is Schedule II, which would make any analog, fall under the analog act. Am i missing something?
not everyone lives in the US... is what you're missing probably
c0rt3x
Bluelighter
I was very interested in a nearer description it's effects, too!
It's structure remembers me somewhat of ideas of mine I posted some time ago:
(6-methoxy-3,4-dimethyl-5-phenyl-1,3-oxazinan-2- amine)
it considered it as a strutural mix of MDMA, Methylphenidate, as well as 4-Methylaminorex... :D
I'd love to be the first trying it! (No Risk - No Fun...)
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c0rt3x
Bluelighter
not everyone lives in the US... is what you're missing probably
Strictly speaking there are only a few countries beside the USA that prohibited almost every derivatives of scheduled substances in advance... The only other country with a similar analog law is Australia - as far as I know... 8)
fastandbulbous
Bluelight Crew
I was very interested in a nearer description it's effects, too!
It's structure remembers me somewhat of ideas of mine I posted some time ago:
(6-methoxy-3,4-dimethyl-5-phenyl-1,3-oxazinan-2- amine)
it considered it as a strutural mix of MDMA, Methylphenidate, as well as 4-Methylaminorex... :D
I'd love to be the first trying it! (No Risk - No Fun...)
The oxygens have the configuration of an acetal and the ring will open in water to leave an aldehyde group attached to the beta carbon of the ethylamine side chain
fastandbulbous
Bluelight Crew
I assume you mean phemetrazine with a methyl group right above the oxygen.
Interesting! Do you mind sharing some words about it?
Nope methyl attached to the carbon attached to oxygen on other side or the ring to the phenyl group. I've tried it and it's good (it has considerable anorectic activity, not much less potent than phenmetrazine and very like the parent drug). Only problem is it requires norephedrine as a starting product, which makes things a tad complicated (as norephedrine is watched as it's also the starting point for 4-methylaminorex and potentially a source of amphetamine a la ephedrine to meth)
/navarone/
Bluelighter
Yeah that's what I meant (by right above the oxygen I didn't mean right 'on' the oxygen).
Would you consider it better than Phen?
BTW a few posts back i posted something about beta-methoxymethamphetamine that really interested me as a phenmetrazine substitute (citing one of your old posts from SotF I):
WTF... how come i cant find any info about simple beta methoxy amphetamine on chemspider or google.
This is absurd....i'm dissapointed.
Thank gof F&B always comes up with some info (gotta love that guy):
-From Stimulants of the Future I:
Beta-methoxyamphetamine is O-methylcathine (O-methylphenylpropanolamine) and beta-methoxy methamphetamine is O-methylephedrine. O-methylephedrine is like phenmetrazine with the ring cleaved between the ethylene bridge between the O and N atoms. Years ago it was on my to do list, but never got around to it. It looks very promising.
The beta-methyleneamphetamines (cathenine as Vanadium called it) is the basic structure I suggested would be possibly a more potent 5HT2a agonist when ring substituted than the corresponding amphetamines (see ;Acid, dragonflies & the 5HT2a receptor')
^^^
By the way, the O-methylepherdrine mentioned by F&B does really seem promising as a phenmetrazine substitute.
However it seems that its pretty tricky to make it as a pure enatiomer (R,R) and unlikely to come out from home labs.
Methylating ephedrine is not reccomended due to high chances of E2 Elimination. Shulgin used nitrostyrene to make such componds but separating the 4 different enatiomers would be another bitch.
Too bad..
Another problem with that synth is the high chances of methylating or 'amphetaminating' the amine on the ephedrine.
Yah it's a bitch, PPA is controlled also over here (it can be prescribed only in very small doses), however ephedrine isn't truly controlled here (most pills are prescribed, but a few nasal drops products aren't). In fact some dude who isn't /navarone/ gave me some phendimetrazine and I pretty much liked it.
Some other phen analogues that I am curious to read about is the 5 memebred and the 7 membered ring analoges.
One would have the functional groups (ether & amine) more streched in and the other more streched out. It would be interesting to see how this affects the activity.
I'm usually too shy to write anything in ADD, but I have a particular interest in these substituted phenmetrazines, so here goes...
Yeah that's what I meant (by right above the oxygen I didn't mean right 'on' the oxygen).
You're still not getting it right, mate. The 6 position on the morpholine moiety is next to the nitrogen, not the oxygen. The two methyls are placed on the carbons either side of the nitrogen.
Another problem with that synth is the high chances of methylating or 'amphetaminating' the amine on the ephedrine.
I'm not quite sure what you mean by 'amphetaminating', but anyway, there are ways to avoid N-methylation or other unwanted reactivity at the nitrogen, i.e. use appropriate protecting groups. (Yes I know, no synth discussion)
The ethyl analogue of phenmetrazine (3-ethyl-2-phenylmorpholine) was mentioned by dread a bit further up. It's an interesting substance and in fact it has been made and assayed by a former colleague of mine. Its synthesis may seem fairly straightforward, but since you're building two stereogenic centres from achiral starting materials, you'll end up with a mixture of four isomers; two enantiomeric pairs, of which I believe only the cis isomers are active (and one more so than the other). It might still be worthwhile, but the 3,6-dimethyl makes a lot more sense if you have PPA to start from.
Just my tuppence worth.
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/navarone/
Bluelighter
I thought so too assuming that the nitrogen had the priority but soon after I discovered that the counting starts from the oxygen thus phenmetrazine's IUPAC name is 3-methyl-2-phenylmorpholine.
Reference:
http://en.wikipedia.org/wiki/Morpholine