β-methylamphetamine, β-methylmethamphetamine,

[Limpet_Chicken]

I searched and found next to nothing on the former and nothing at all on beta-methylmethamphetamine.

Anyone know much about the effects profile of either of these, or of beta-methyl-N-ethylamphetamine?

 

[sekio]

Presumably these would be less-selective stimulants comparable to amphetamine? You do have the issue of chirality to consider, though, as you'll have erythro/threo pairs in addition to +/-.

I know b-methylphenethylamine has been put in "workout supplements" and I think it's got amphetaminoid effects. I'll look on Reaxys later and tell you.

10.1039/C39880001503 has synthesis of B-methyl amphetamines of all sorts via a Grignard rxn yielding the N-hydroxy compounds
10.1021/ja01255a017 via alkylation of phenylacetone, has some of the physiology in dogs and rabbits, apparently b-methyl amphetamines are less toxic than those with no b-alkylation, they retain pressor activity but amphetamine and b-methylamphetamine are stronger than b-methylmethamphetamine or b-ethylamphetamien/b-propylamphetamine/b-dimethylamphetamine
also a patent: Haarmann and Reiner; DE833042 1948

I'd rather try B-methylamphetamine than the fucking alpha-hexyl cathinones, I'll say...

 

[Limpet_Chicken]

What do you mean by less selective? that is to say, less selective in what manner?

Interesting to see they are less toxic than methamphetamine. Are they likely to also be lesser adrenergic pressors? because I HATE that kind of stuff. If they do turn out to be ephedrine-like rather than amphetamine-like then I'd just have wasted time and effort.

Chiral resolution of the racemate is possible, to the extent of separating dextrorotatory from laevorotatory isomers via selective crystallization with chiral aminoacids, or the old chestnut, D-tartaric acid or L-tartaric acid


Since it neither involves creating a drug, nor altering the structure of an existing one, is it permissible to enquire as to how one would resolve threo/erythro isomers?
Could they be selectively bound in a chiral metal-based chelant, perhaps? or are there other means? because thats a little out of my experience range.Or of course I could just resolve D/L and let the rest do what the hell it feels like.

And alpha-cyclohexyl? well have heard that alpha-phenylmethamphetamine is worth it. Might try that one first actually.since its so close to lefetamine, it has a certain appeal to it.

 

[sekio]

is it permissible to enquire as to how one would resolve threo/erythro isomers?

I think it says in the paper - selective crystallization as the salts have different solubility. And different melt points.

All of them will be pressors to some extent; exactly how much I don't know.

The paper describes N-cyclohexyl, not alpha-cyclohexyl, BTW

 

[Dresden]

fastandbulbous tried them and said they were worthless as stimulants.

 

[Limpet_Chicken]

The beta-methylated amphetamines? or cathinones with a big ugly cyclohexane ring carbuncle sprouting off the amine?

Not surprised those are utter shit. Afterall, look what happens with the likes of N-butylated amphetamines, whilst I am not as familar with cathinones as I am with the amphetamines and phenethylamines the area the amine binds in of the binding pockets of DAT/VMAT/NET/SERT obviously have limited space in which to accept a binding ligand. But if the likes of sec-butyl and tert-butyl don't come up smelling of roses, that surely has to come up covered in manure and probably worse besides. Sod that for a lark. And Dresden-thanks-you just saved me from some effort and money spent. On to more interesting things.

 

[simstimstar]

I'm a bit confused by your wording. Are you asking about alpha, beta, N - trimethyl phenethylamine, or beta, N-dimethylphenethylamine (a sort of normethamphetamine if you will), or something else entirely?

Beta methyl phenethylamine is a known TAAR agonist and pressor. I think much less of a dopamine releasing agent compared to the alpha methyl version (amphetamine), and not really abusable.

According to Wikipedia beta phenyl methamphetamine is a long acting and potent stimulant. I would imagine SAR would be closer to 2-Diphenylmethylpyrrolidine or desoxypipradol. That's just my guess though. The only thing I have to support it structural similarities. I haven't bioassayed either any of those myself.

Cheers!
-SB

 

[simstimstar]

2-D2PM, and desoxypipradrol being closer to pheniditic acid derivatives than amphetamine (therefore closer to MDPV or even methylphenidate in mechanism of action since they are potent reuptake inhibitors and possibly also releasers rather than straight up amphetamine style releasers).

Someone please correct me if I'm incorrect here.
Cheers!
-SB

 

[Limpet_Chicken]

Beta,alpha-methylphenethylamine. and beta,alpha-N-methylphenethylamine.

Don't fancy the pressor bit . And 'nor-' refers specifically to the removal of a group from a nitrogen, comes from the german 'N-ohne [without] radical', the correct terminology in the case you mentioned would be 'desmethyl'

Its not beta-phenylmethamphetamine, beta-Ph-amphetamine or beta-Ph-ethamphetamine, but the amphetamine through N-ethylamphetamines with a phenyl group replacing the alpha-methyl. As well as beta-methyl-apphetamine, to coin a term for the alpha-phenyldesmethylphenethylamines.