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4-Methylaminorex Pseudo FAQ
by Eleusis [eleusis@netcom.com]
html by Erowid
v 1.2 - Oct, 1995
Erowid Note: This FAQ was not authored by Erowid. It may include out-of-date and/or incorrect information. Please check the version date to see when it was most recently revised. It appears on Erowid as part of our historical archives. For current information, see Erowid's summary pages in the substance's main vault.
INDEX
Introduction
Disclaimer
Basic Q & A
Cognate Preparation
References
Revision History


INTRODUCTION
Due to strangely increased demand for information on 4-methylaminorex chemistry and synthesis that I have received by mail, I decided to compile a short document with the cognate preparation of this interesting compound. This may become a full-fledged FAQ in the future, depending on user response and outside input donated where this will undoubtedly be deficient.


DISCLAIMER
This is for informational purposes only. It is being produced in order to illustrate the novel structure and effects of the aryloxazolines. Use this information at your own risk, I cannot be held responsible for what you do with it, etc... and so on.


BASIC Q & A

Q1. What is 4-methylaminorex?

A1. 4-methylaminorex (also called "Ice") is a potent norepinephrine modulator, increasing it's effect. It has a characteristic look and feel, like white opaque ice, hence the name. Ice is currently a Schedule I drug as designated by the DEA (Drug Enforcement Agency) which means it is felt to have NO medical use whatsoever. It was originally researched for appetite suppressant ability, but never pursued, probably because it's too much fun. It is important to know that the slang term 'ice' is also used to refer to methamphetamine.


Q2. Can 4-methylaminorex be made from amphetamine/methamphetamine?

A2. It is *technically* possible, but requires some backwards motions to get back to a sec. alcohol. At least one individual, in a personal communication to me, indicated that "they knew of someone who could convert crank [methamphetamine] into ice by washing it with something". This is not possible.


Q3. What kind of chemical is it?

A3. In drug parlance, which is notoriously Non-IUPAC compliant, Ice is synonymous with "Euphoria" (U4Euh), 4-Methylaminorex, or, chemically speaking: dl-cis-2-amino-4-methyl-5-phenyl-2-oxazoline. This is a tongue twister of a name, so I will explain and illustrate it with a cheap floozie of an ascii drawing.

     //\
    //  \____ _____ ____CH3
    |   ||   |     |
    |   ||   |     |
    \\  /    O     N
     \\/      \  //
               \//
                |
                N
               / \
              H   H
The numbering starts at the heterocyclic Oxygen and goes counter-clockwise. So the amine is at the 2 position, the methyl is at the 4 position, a phenyl ring is tacked on at the 5 position. Also, the 2-oxazoline part is often merely called oxazoline, as the double bond to the heterocyclic Nitrogen is implied.

It is interesting to note that all of the stereoisomers of 4-MAR are centrally active [1] (ie - it is not stereospecific in action).


Q4. What does 4-methylaminorex do?

A4. Anecdotally, it is said to help concentration and thinking - a sort of "make-you-smarter" drug, with a minor speed-like component to it. Time of action is around 4-6 hours (some say 14-16). Dosage varies but a good start is 20 mg for a 150 lb individual. It is smoked as the free base or the hydrochloride salt - both have relatively low melting points.


COGNATE PREPARATION

Reagents
  • Phenylpropanolamine HCl
  • Methanol
  • Cyanogen Bromide
  • Sodium Acetate
  • Sodium Carbonate
  • Water
  • Benzene (or similar)
  • Ether
Extraction of Phenylpropanolamine from OTC preparations
  1. Extract Phenylpropanolamine HCl (PPA) from OTC diet pills by crushing and dissolving in 10 mL methanol per gram of PPA. Decant solution onto the Buchner funnel and repeat with 2 more volumes of methanol. Use methanol instead of water because it has less tendency to form a colloid with any cellulosic binders present which would otherwise severely clog the filter paper.

  2. Distill off most of the methanol then add cold water to dissolve all of the PPA solids. Basify to approximately pH 9 with 10% Sodium Carbonate or Sodium Hydroxide solution. Extract out PPA base using 3 volumes of ether of approximately 1/3 the volume of water. The methanol will follow into the ether as well, but very little of the formed salt will.

  3. Distill off ether/methanol for later recovery of the solvents and weigh the amount of solid PPA base, mp 101C. The amount you process here determines, obviously, the amounts of everything else to use later on.

Forming the Oxazoline Ring
The ideal ratio of all the reagents is as follows [2]:

1.0 Mole Phenylpropanolamine (MW: 151.2)
1.1 Moles Cyanogen Bromide (MW: 105.93)
3.0 Moles of Sodium Acetate (MW: 82.04)

The Sodium Acetate may be prepared by carefully adding an equinormal amount of Sodium Hydroxide to glacial Acetic Acid and drying the resultant salt at 120C for 15 minutes.

The preparation of Cyanogen Bromide is covered in another document of mine.

This compound should only be prepared in an area of *adequate* ventillation. A full covering fume hood is ideal (geez - make one, I did) or outside with the wind blowing away from you. Cyanogen Bromide acts on cytochrome oxidase just like any other cyanide and will kill you quite effectively. Also, it has been known to decompose spontaneously when impure.

  1. Dissolve 15g (.142M) of Cyanogen Bromide in 50 mL of Methanol at 0C.

  2. Dissolve 19.5g (.129M) of Phenylpropanolamine and 31.8g (.387M) of Sodium Acetate in 300 mL of Methanol at 0C. Place this in a round bottom flask equipped with a stirrer magnet and addition funnel.

  3. Add the Cyanogen Bromide solution to the flask though the addition funnel over a period of 15 minutes with stirring.

  4. React for an additional 45 minutes at 0C.

  5. Evaporate solvents at reduced pressure and with gentle water bath heat (50C tops) - do not attempt to recover!

  6. Dissolve the oily residue in water and then add saturated Sodium Carbonate solution until a white solid precipitates.

  7. Filter this cake of white solid on the Buchner, then wash twice with ice cold water and dry in a vacuum dessicator.

  8. Recrystallize the crude dried product from Benzene to yield ~63%.

  9. *OPTIONAL* - Form the hydrochloride salt by bubbling HCl gas though the Benzene until white crystals fall out or shaking with 5% HCl and evaporating the water off.


REFERENCES

  1. Journal of Forensic Sciences, v34, #4, 1989, "The Stereoisomers of 4-Methylaminorex", pp 963-979, Klein, Sperling, Cooper & Kram

  2. Journal of Medicine Chemistry, v6, 1963, "2-Amino-5-Aryl-2-Oxazolines. Potent New Anorectic Agents", pp 266-272, Poos, Carson, Rosenau, Roszkowski, Kelley & McGowin


REVISION HISTORY

v 1.0 - Original
v 1.1 - (Oct 1995) I can't believe no one caught my special atomic modification of Nitrogen that takes 4 bonds! What, are you people asleep out there??? Anyway, a couple of modifications, slightly revised question/answers and a CORRECTED ascii drawing are in this rev. This makes the FAQ reasonably accurate but still not what I'd call a definitive source by any means. Thanks to all who have sent comments thus far.
v 1.2 - (Feb 2000) This is a slight modification by Erowid, primarily put into html and organized.