• Neuroscience & Pharmacology Discussion Welcome Guest
    Posting Rules Bluelight Rules
    Recent Journal Articles Chemistry Mega-Thread
    FREE Chemistry Databases! Self-Education Guide

  • N&PD Moderators: Skorpio

Lefetamine???

Lefetamine is just N,N-dimethyl-1,2-diPEA, and 1,2-diPEA is, well, alpha-phenyl-PEA.

Let me state this again: classic stimulants like cocaine, amphetamine and meth and more unusual ones like mcat and whatever else ARE NOT DA agonists (if they are, it's only very weak). DA agonists induce lots and lots of vomiting. Not to say they aren't abused. Apparently monkeys will self inject, especially ones w/ history of cocaine abuse.

I'm not sure about aPPEA, but lefetamine is a DARI and a mu agonist and apparently has some NMDA-antagonistic properties.
 
haribo1 said:
CAS: 10016-75-8
CAS: 451-40-1
Name: 1,2-Diphenyl-ethanone
Name: Benzyl phenyl ketone
Name: Deoxybenzoin

This, dimethylamine and a borohydride will yield raecemic product. Then it's down to partial crystalisation to produce an optically pure product. I don't think it's production that is the problem but rather bang per buck...
Click to expand...

I almost forgot about this thread! Just a question, not to get to deep into synth, but would borohydride be needed because the secondary amine nucleophile forms an enamine with 1,2-Diphenylethanone - which subsequently needs to be reduced with a hydride? I'm sorta new with using N nucleophiles, :(
 
Correct, yes. This is reductive amination. You can do both steps in one pot, if you use a selective reducing agent (selective for reducing imines, not aldehydes and ketones) such as NaCNBH3 or STAB. Can't give you more information than this though, Bluelight is not the place for such discussions.
 
Similar structure to amphetamine, mu receptor affinity, AND an NMDA receptor antagonist?
holy shit, this stuff must be like liquid Jesus.

And just a quesiton, why is synth discussion so taboo? i mean erowid has plenty of synth articles and the authorities seem to tolerate it
 
SpunkySkunk347 said:
And just a quesiton, why is synth discussion so taboo? i mean erowid has plenty of synth articles and the authorities seem to tolerate it
Click to expand...

because it rapidly degrades into the hive, shake n bake, how do I k00K m3th.
it doesn't fit with the harm reduction idea, the potential for harm from people getting a synthesis from teh interweb is quite large.
It is better to have no practical synthetic discussion, its pretty black and white and easy to enforce.
 
MattPsy said:
Correct, yes. This is reductive amination. You can do both steps in one pot, if you use a selective reducing agent (selective for reducing imines, not aldehydes and ketones) such as NaCNBH3 or STAB. Can't give you more information than this though, Bluelight is not the place for such discussions.
Click to expand...

But would the selective reducing agents work on imines AND enamines? Because if one were to go the dimethylamine route, the secondary amine would form an enamine - (E)-N,N-dimethyl-1,2-diphenylethenamine - instead of a primary amine nucleophile forming the imine. Or does both exist in equilibrium with their enol tautomers (that being the enamine and imine)?
 
Yes they're tautomeric pairs, and the equilibrium lies more toward the imine side, afaik.
 
MattPsy said:
Yes they're tautomeric pairs, and the equilibrium lies more toward the imine side, afaik.
Click to expand...

Hey, matt! Just curious, when a secondary amine attacks a carbonyl group to form an enamine, wouldn't the equilibrium lie towards the enamine since the imine would cause the N to be positively charged? I think it would be different with a primary amine attacking the carbonyl because the imine that would be formed could have a H(+) pulled off letting the equilibrium lie more towards the imine. The secondary amine after forming an enamine doesn't have this 'loose' proton so I think that this would shift the equilibrium towards the enamine - that being because it's lower in energy. Phew! anyways, let me know what you think!
 
Sorry yeah you're absolutely right, I was thinking for primary amines!
Nonetheless, the iminium species will exist in equilibrium with the enamine :) .
So I expect the reaction would be a bit slow (sluggish reaction between the ketone and secondary amine, this part is the rate-limiting part) but it would still work sweet.
 
could piperidine or pyrrolidine be used in place of the amine in the same reductive amination of deoxybenoin to give a,b-diphenylp__idine? perhaps the new compound will retain da/nmda/ fx but have greater potency?
 
...another idea, It would seem lefetamine analogs can retain the same basic activity with subs on the N pos.. What about other subs, that would be real dope if it would retain it's nmda,da, and even maybe mu activity while adding a nice 5ht element. Some examples might be...

N-methyl-3,4-methylenedioxy-a,b-diphenethylamine
3,4,5-trimethoxy-a,b-diphenethylamine
^^^..-a,b-dibenzylethylamine
2-thio/fluoro-..^^^
...etc... u get the idea
I would assume however you wouldnt want to have it analog any of the more potent 5HT PEAs as you'd want all the different receptor types to be evenly activated.

kinda like a simpler phenethylamine ibogaine
 
Here's some interesting info on lefetamine:

[...] There is also the much stronger Lephetamine derivative, where the -N(CH3)2 group is replaced by an 1-(4-cyclohexyl)piperazine functionality (2), with the dextro-(+)-isomer being the stronger one, almost equipotent to morphine. If an OH group is placed in the 3-position of the benzene ring furthest from the amine (3), the activity increases more than twentyfold.

Comparative effective dose (Morphine = 1)
l-(-)-Amine 1 = 19.5
d-(+)-Amine 2 = 1.3
l-(-)-Amine 3 = 0.3
d-(+)-Amine 3 = 0.023

References
Nippon Yakurigaku Zasshi 56, 514 (1960)
J. Med. Chem. 18, 1240 (1975); 21, 1265 (1978); 22, 58 (1979)
J. Pharm. Pharmacology. 32, 635 (1980)
Click to expand...
 
I'd like to seen it become like an ultra psychedelic rather than opiate
 
There is an interesting article on lefetamine in J.Med.Chem.:
Studies on Morphine-like Compounds. V.1 Absolute Configuration and Conformations of Optically Active 1,2-Diphenylethylamine Derivatives
Tadashi Sasaki, Ken Kanematsu, Yojiro Tsuzuki, Katsumi Tanaka
J. Med. Chem.; 1966; 9(6); 847-850. DOI: 10.1021/jm00324a015
Click to expand...
First (free) page: http://pubs.acs.org/cgi-bin/abstract.cgi/jmcmar/1966/9/i06/f-pdf/f_jm00324a015.pdf

According to them it's 0.33-0.5 times as potent as morphine. They also came up with some interesting findings on the stereochemistry.
 
Last edited:
If the R Isomer is the active one on the mu receptors and the S more responsible for its stimulant and NMDA activity,one might conclude that the racemate could be even more recreational!?
 
The R enantiomer is responsible for both the opioid and the NMDA/stimulant activity.
 
I've read about lefetamine being neurotoxic in several places. Does anyone know of any references where I can read more about this? Exactly how neurotoxic is it really? And does it apply to analogues of it also?
 
You must log in or register to reply here.
Top