4-Methylaminorex
Title: 4-Methylaminorex
CAS Registry Number: 3568-94-3
CAS Name: 4,5-dihydro-4-methyl-5-phenyl-2-oxazolamine
Additional Names: 2-amino-4-methyl-5-phenyl-2-oxazoline; 4-MAX
Molecular Formula: C10H12N2O
Molecular Weight: 176.22
Percent Composition: C 68.16%, H 6.86%, N 15.90%, O 9.08%
Literature References: Indirect acting sympathomimetic agent related to amphetamine, q.v.. Exists as four isomers, (±)-trans and (±)-cis; the latter being the drug of abuse. Prepn: G. I. Poos et al., J. Med. Chem. 6, 266 (1963); G. I. Poos, US 3161650 (1964 to McNeil Labs). Synthesis and chemical properties of isomers: R. F. X. Klein et al., J. Forensic Sci. 34, 962 (1989). Structure-activity comparison of isomers: R. A. Glennon, B. Misenheimer, Pharmacol. Biochem. Behav. 35, 517 (1990). Mechanism of action study with behavioural effects: K. Batsche et al., J. Pharmacol. Exp. Ther. 269, 1029 (1994). Metabolism in rats: G. L. Henderson et al., J. Anal. Toxicol. 19, 563 (1995). Neurochemical effects: Y. Zheng et al., J. Pharm. Pharmacol. 49, 89 (1997).
 
Derivative Type: (±)-cis Form
CAS Registry Number: 29493-77-4
Additional Names: EU4EA; U4Euh; Ice
Manufacturers' Codes: McN-822
Properties: Crystals from benzene, mp 154.5-156° (Poos, 1963). Also reported as mp 139-142° (Glennon). [a]D25 -244.7° for (-)-form; [a]D25 +240.9° for (+)-form.
Melting point: mp 154.5-156°; mp 139-142° (Glennon)
Optical Rotation: [a]D25 -244.7° for (-)-form; [a]D25 +240.9° for (+)-form
 
NOTE: The (±)-cis isomers are controlled substances (stimulant): 21 CFR, 1308.11.

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