Old Compounds.. info appreciated.

[djsim]

Hey all, was looking through this book of Pharmaceutical Manfacturing I found at a book store and they describe PENTOREX TARTATE

It's basically amphetamine, with a methyl at the alpha and beta position ... 2-amino-2-methyl-3-phenylbutane
CAS numbers are given as "Chemical Abstracts Registry No.: 434-43-5 (Base); 22876-60-4"

References: "Brevet Special de Medicament 931,804, April 17, 1963; Assigned to Nordmak Werke Gesellschaft mit Beschraenkter Haftung, residant en Allemagne"

Also under methods for dextroempahetamine it describes separating the optical isomers (d) of amphetamine using tartaric acid. Can someone remind me how this works?

Also, anyone heard of Amfecloral? 1-Phenyl-N-(2,2,2-trichlorethylidene)-2-propylamine
It's amphetamine double bonded at nitrogen to CH2C(Cl)3. Is this just one of those prodrug compounds like benzphetamine (or even like todays Vyvanse)?

Thanks for any input guys

 

[nuke]

The more common name for 2-amino-2-methyl-3-phenylbutane is phenpentermine. Given its similarity to phentermine I doubt you could expect much potential in the way of a CNS stimulant.

To separate enantiomers with tartaric acid you usually salt one of the enantiomers of tartaric acid with an enantioner of your compound and the resolved salt is stereospecific (eg l-(+)-tartaric acid and r,s-ketamine yields the tartrate salt of s-ketamine).

The planar bond at the CN and the trichloro methane attached to it is enough to make me want to stay away from the second one.

 

[Jamshyd]

^ That's ingenious!

 

[Hammilton]

it's pretty easy to do, actually, and tartaric acid is nothing watched.

 

[vecktor]

The more common name for 2-amino-2-methyl-3-phenylbutane is phenpentermine. Given its similarity to phentermine I doubt you could expect much potential in the way of a CNS stimulant.

To separate enantiomers with tartaric acid you usually salt one of the enantiomers of tartaric acid with an enantioner of your compound and the resolved salt is stereospecific (eg l-(+)-tartaric acid and r,s-ketamine yields the tartrate salt of s-ketamine).

The planar bond at the CN and the trichloro methane attached to it is enough to make me want to stay away from the second one.

its just a stabilised imine, the material will metabolise to a small amount of chloral and instantly to the hydrate which is pretty innocuous in the expected quantities.

 

[djsim]

OK, so can someone explain the tartaric acid resolution to me?
Basically the synthesis method from the book says the racemic amphetamine base is mixed with d-tartaric acid making dl-alpha-methylphenethylamine d-tarate, a neutral salt. Substance dissolved in 1L abs ethanol, crystal form... crystals formed are mainly levo. repeat and repeat until all that is left is dextro.

OK, how does this work? Why does levo precipitate into crystals first? If l-tartaric acid was used, would the dextro cystals of amphetamine form first (ie opposite effect to that seen) Is it always the way that dextro tartaric acid will make levo crystals come out first? or is it just like polarised light... you dont know til you do the experiement?

Finally, the DEA microgram said years ago that they busted meth coming from Mexico @ 99% purity. However it was the tarate salt. Is this most likely because:
a) its Mexico. they'll use whatever salt they can get
b) they resolved racemic meth into the dextro isomer and didnt bother reforming the freebase then redoing the salt as HCl as per normal mexican meth

 

[dread]

That's beta-methyl-phentermine, right?

 

[djsim]

That's beta-methyl-phentermine, right?

yeh, thats right.
I just found it interesting because I searched the CAS numbers, and nothing. Same with patents etc. Not on Wikipedia etc, so was curious

 

[MurphyClox]

OK, how does this work? Why does levo precipitate into crystals first? If l-tartaric acid was used, would the dextro cystals of amphetamine form first (ie opposite effect to that seen) Is it always the way that dextro tartaric acid will make levo crystals come out first? or is it just like polarised light... you dont know til you do the experiement?

No, IMO you can not predict which salt will precipitate first.

The reason that one salt precipitates earlier than it's enatiomeric congener is mainly solubility, which isn't the same for both stereoisomers (otherwise you wouldn't be able to separate it by this technique).

Murphy

 

[MurphyClox]

...double-post, please delete... (SORRY!)

 

[MurphyClox]

Research-paper on Pentorex:

"The pharmacology of 2-phenyl-3-methyl-3-aminobutane, an anorexigenic substance."
Behrendt, Wilhelm A.; Deininger, Rolf (Nordmark-Werke G.m.b.H., Hamburg, Germany)
Arzneimittel-Forschung 1963, 13(8 ), p.711

"Stimulation of sodium excretion and diuresis by appetite-inhibiting amphetamine derivatives."
Opitz, Klaus.
Klinische Wochenschrift 1965, 43(4), p.225

"Comparative studies of the potency of several anorexiants."
Opitz, Klaus; Kemper, Fritz; Loeser, Arnold.
Arzneimittel-Forschung 1965, 15(3), p.278

"Effect of anorexigenic compounds on the metabolism of carbohydrates and fatty acids."
Herold, Elisabeth; Kemper, Fritz; Opitz, Klaus.
Arzneimittel-Forschung 1965, 15(6), p.657


Patents:

"Aromatic-aliphatic amines."
Bockmuhl, Max; Stein, Leonhard; Ehrhart, Gustav (Farbwerke Hoechst AG), 1952, DE 849695

"Appetite depressants based on DL-, D-, and L-2-phenyl-3methyl-3-butylamine."
Nordmark-Werke GmbH, 1964, 17 pp., FR M2594

"Drug composition for weight reduction."
Kopf, Roland, 1986, 14 pp., DE 3430389 A1

PEACE! Murphy