4-Methyl-aminorex

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4-Methyl-aminorex
Systematic (IUPAC) name
4-methyl-5-phenyl-2-amino-oxazoline
Identifiers
CAS number	3568-94-3 29493-77-4 - (±)-cis isomers
ATC code	?
PubChem	?
Chemical data
Formula	C₁₀H₁₂N₂O
Mol. mass	176.21
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	?
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status	Schedule III(CA) Schedule I(US)
Routes	Oral, Vaporized, Insufflated, Injected

4-Methyl-aminorex is a stimulant drug of the 2-Amino-5-Aryloxazoline class. Commonly called "Euphoria," "U4EA,", "U4Euh", "4MA", "Intellex", "4-MAX", or "methylaminorex"; 4-Methylaminorex has also been termed "ice" due to the appearance of pure 4MA as large, white crystals, although the street name "ice" is more commonly used for pure crystalline methamphetamine. The US Government, by statute, defines "ice" as methamphetamine with a purity of 80% or greater.

4-Methylaminorex has effects comparable to methamphetamine but with a much longer duration. Some contend it has fewer side effects.^{[citation needed]} It is banned in many countries as a stimulant.

1 Chemistry
2 Dosage
3 Effects
4 Legal Status in the United States
5 See also
6 Works Cited
7 External links
- 7.1 Programs
  - 7.1.1 Television

[edit] Chemistry

4-methylaminorex exists as four stereoisomers - (±)-cis and (±)-trans. The (±)-cis isomers are the form used recreationally. The (±)-cis isomers are generally synthesized from dl-phenylpropanolamine in one step by cyclization with cyanogen bromide (sometimes prepared in situ by reacting sodium cyanide with bromine). Alternate synthesis routes generally involve more steps, such as replacing cyanogen bromide with sodium or potassium cyanate to form an intermediate and then reacting it with concentrated hydrochloric acid. The (±)-trans isomers are synthesized in the same manner above but dl-norpseudoephedrine is used as the starting material instead.

[edit] Dosage

4-methylaminorex can be smoked, insufflated or taken orally.

As an anorectic, the ED50 is 8.8mg/kg in rats for the (±)-cis isomers. The (±)-trans isomers are slightly more potent at 7.0mg/kg. As a recreational drug, the effective dosage ranges from 5-25mg [1].

[edit] Effects

It produces long-lasting effects, generally up to 16 hours in duration if taken orally and up to 12 hours if smoked or insufflated. Large doses have been reported anecdotally to last up to 36 hours. The effects are stimulant in nature, producing euphoria, an increase in attention, and increased cognition. It has been reported to produce effects similar to nootropics.^{[citation needed]}

[edit] Legal Status in the United States

Under Federal law, (±)-cis-4-methylaminorex was placed in Schedule I as in the Controlled Substances Act on. It is curious that only the cis isomer was controlled, making it the first and to date the only time a specific diastereomer has been listed as a controlled substance¹. Manufacturing the trans isomer required a different process that those encountered when the substance was first scheduled, and was believed less potent than the cis isomer with a much lower abuse potential.²

However, studies revealing the abuse potential of the 'trans' isomer, coupled with the development of new clandestine synthetic methods that would produce the trans created a potential loophole in the law, which covered only the 'cis' isomer.

To clarify the situation, the US Drug Enforcement Administration published a paper in its DEA Microgram Journal, regarding interpretation of the relevant statutory law as it relates to the status of trans-4-methylaminorex. In summary, according to this non-legally binding descision, trans-4-methylaminorex is not currently a controlled substance, but a potential analog. In fact, the report explicitly states:

"The United States [Drug Enforcment Administration has the following opinion on the legality of the positional isomer "trans"-4-methylaminoaminorex, which, unlike its 'cis' isomer was never placed in any schedule under the Controlled Substances Act.

However, the opinion does say that the agency considers the substance a potential controlled substance analog, making the substance identical to a Schedule I substance if intended for human consumption, according to the analog act In fact, the report gives an account of a successful conviction under the analog act of an offense involving the 'trans' isomer. The full text, very detailed, sound legalistic interpretation, along with advances in clandestine chemistry than increased the production of the trans isomer can be read on the DEA Microgram 2005, Vol. 3 [2]

[edit] See also

[edit] Works Cited

1. Rodriguez, Walter R., and Russell A. Allred. "DEA Resources, Microgram Journal, Volume 3, July-December 2005." Drug Enforcement Administration. Dec. 2005. Drug Enforcement Administration. 27 Dec. 2006 2. 'ibid'