N-Isopropylbenzylamine

Chemical properties

CLEAR VERY SLIGHTLY YELLOW TO YELLOW LIQUID

The Uses of N-Isopropylbenzylamine

N-Isopropylbenzylamine, can be used as an intermediate in the synthesis of pharmaceutical compounds,and as a precursor to the manufacture of some drugs. Due to it’s similarity in appearance and physical properties to methamphetamine, it has been recently come under consideration of DEA.

Preparation

N-benzylisopropylamine is synthesized by the reduction reaction of N-isopropylbenzamide or prepared from benzylamine and acetone by reductive amination reaction.

What are the applications of Application

N-Isopropylbenzylamine was used as ligand in the preparation and characterization of bis(cyclopentadienyl)magnesium. It was also used in the synthesis of N-benzylideneisopropylamine-N-oxide.

General Description

N-isopropylbenzylamine is a structural isomer of methamphetamine, is one of the most common adulterants. It forms amine adducts with magnesocene at ambient temperature in toluene.

Authentication

The N-Isopropylbenzylamine (N-IBA) compound is an isomer of methamphetamine (MA), which is often misused as an additive to methamphetamine or marketed as counterfeit methamphetamine material. To identify fake methamphetamine, the Marquis test does not show a colour reaction, while the methamphetamine test shows a colour change to brownish-orange. In the Simon test, both show a blue colour. The white crystals were dissolved in methanol and then identified using gas chromatography-mass spectrometry (GC-MS), the compound N-Isopropylbenzylamine had an m/z of 134 and a base peak of m/z = 91. Using Raman spectroscopy, only the methamphetamine compound was detected and not N-Isopropylbenzylamine. When FTIR spectroscopy was used for identification, both compounds were detected with the same results.

Cytotoxicity

The toxicity of N-isopropylbenzylamine was evaluated in SH-SY5Y, PC12, and SN4741 cell lines. Cells were treated with 0.3–10 mM N-isopropylbenzylamine for 24 hours, and cell viability was measured using MTT assay. N-isopropylbenzylamine concentration-dependently reduced cell viability in these cells. The IC50 values of N-isopropylbenzylamine on cell viability were 3.47, 1.49, and 3.21 mM for SH-SY5Y cells, PC12 cells, and SN4741 cells, respectively. N-isopropylbenzylamine produced toxicity in cell lines that model neurons. Moreover, the activation of nNOS and the production of intracellular NO might be involved in N-isopropylbenzylamine-induced toxicity in SN4741 cells[1].

References

[1] Peng Xu . “N-isopropylbenzylamine, a methamphetamine mimics, produces toxicity via increasing nitric oxide in vitro.” Toxicology 480 (2022): Article 153337.