4,5-Dimethoxyphthalide

The title compound, C(25)H(18)N(4)O, is a non-planar bipolar ligand containing triphenyl-amine and 1,3,4-oxadiazole units. In the mol-ecule, the benzene ring, the 1,3,4-oxadiazole ring, and the pyridine ring are twisted slightly with respect to each other [dihedral angle between the benzene and 1,3,4-oxadiazole rings = 9.4 (4) and between the 1,3,4-oxadiazole and pyridine rings = 3.0 (4)°]. Moreover, the dihedral angles between the two phenyl rings and the benzene ring are 88.2 (4) and 113.3 (4)°, and that between the two phenyl rings is 67.9 (4)°. The closest distances between the pyridine ring and the 1,3,4-oxadiazole and benzene rings in adjacent mol-ecules are 3.316 and 3.363 Å, respectively, indicating the existence of π-π inter-actions.

In the title compound, C(38)H(36)F(2)N(4)O(4), the pyrazole rings form dihedral angles of 50.02 (4) and 18.05 (4)° with their attached fluorobenzene rings, and make dihedral angles of 76.08 (4) and 73.54 (5)° with the aromatic ring of the attached phen-oxy group. In the crystal, the molecules are connected by weak C-H⋯π inter-actions.

Objective: 4-Methyl-5-(4-methylphenyl)-4,5-dihydrooxazol-2-amine (4,4'-dimethylaminorex (4,4'-DMAR)) is a derivative of the controlled substances aminorex and 4-methylaminorex marketed as a potential novel psychoactive substance. This paper brings together the published scientific and 'grey' literature to understand 4,4'-DMAR as a novel psychoactive substance. Methods: Searches of the published scientific and 'grey' literature, using the keywords '4-methyl-euphoria', '4-methyl-U4Euh', '4-M-4-MAR', '4,4-dimethylaminorex', '4,4'-DMAR', 'para-methyl-4-aminorex' and 'Serotoni', were undertaken to identify information on the availability, prevalence of use and desired/unwanted effects of 4,4'-DMAR. Results: No studies have reported the prevalence of use of 4,4'-DMAR. Internet snapshot studies in April and May 2014 showed availability of 4,4'-DMAR from one and two Internet suppliers respectively. Price decreased with increasing purchase amounts from €12/g for a 1-g purchase to €2.20/g for a 100-g purchase in April 2014. Internet discussion fora suggest that the desired and unwanted effects of 4,4'-DMAR are similar to those seen with other sympathomimetic drugs such as 3,4-methylenedioxy-methamphetamine and mephedrone, although the duration of unwanted effects and 'comedown' appear to be longer. Unwanted effects were reported at doses of 5-200 mg, which overlaps with the reported doses (10-200 mg) associated with desired effects. 4,4'-DMAR has been detected, along with other drugs, in 27 deaths in Europe; the contribution of the 4,4'-DMAR in these deaths has not been established. Conclusions: Currently, there appears to limited availability of 4,4'-DMAR; therefore, use is likely to be low. Its desired and unwanted effects appear similar to other sympathomimetic recreational drugs such as methylenedioxy-methamphetamine or mephedrone.