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Isopropylbenzylamine

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Isopropylbenzylamine
Ball-and-stick model of the isopropylbenzylamine molecule
Names
Preferred IUPAC name N-Benzylpropan-2-amine
Other names N-(Phenylmethyl)propan-2-amine
Isopropylbenzylamine
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.789 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C10H15N/c1-9(2)11-8-10-6-4-3-5-7-10/h3-7,9,11H,8H2,1-2H3Key: LYBKPDDZTNUNNM-UHFFFAOYSA-N
  • InChI=1/C10H15N/c1-9(2)11-8-10-6-4-3-5-7-10/h3-7,9,11H,8H2,1-2H3Key: LYBKPDDZTNUNNM-UHFFFAOYSA-N
SMILES
  • N(C(C)C)Cc1ccccc1
Properties
Chemical formula C10H15N
Molar mass 149.237 g·mol
Pharmacology
Legal status
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

N-isopropylbenzylamine is a compound that has appeared in chemical literature often playing an intermediary role in applications of experimental synthesis and novel organic transformations. Despite having limited documented uses, it is most well known for having previously come to the attention of the DEA due to being used by illicit methamphetamine manufacturers as a diluent of or substitute for methamphetamine, with many recorded sightings occurring in the years 2007–2008. It not known to be a controlled substance in any other jurisdiction. Isopropylbenzylamine is not thought to have any stimulant effects in its own right, though anecdotal reports suggest that it may be associated with side effects such as headaches and confusion which are not typically associated with methamphetamine itself. The toxicity of N-isopropylbenzylamine has been studied as of 2022 and it has been found to produces toxicity via increasing nitric oxide in vitro. In this study, in vitro toxicity of N-isopropylbenzylamine and its toxicity-related targets were investigated in SN4741, SH-SY5Y or PC12 cell lines that model neurons. The study sounds an alarm for methamphetamine abusers and warns of the dangerousness of N-isopropylbenzylamine for public health.

Isopropylbenzylamine hydrochloride crystals seized by DEA.

References

  1. Anvisa (24 July 2023). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 25 July 2023). Archived from the original on 27 August 2023. Retrieved 27 August 2023.
  2. Xu, Peng; Li, Haijie; Qiu, Qiyang; Xiao, Xiao; Qiu, Yi; Li, Xiangyu; Wang, Youmei; Zhou, Wenhua; Shen, Haowei; Cui, Wei (1 October 2022). "N-isopropylbenzylamine, a methamphetamine mimics, produces toxicity via increasing nitric oxide in vitro". Toxicology. 480: 153337. doi:10.1016/j.tox.2022.153337. PMID 36162621. S2CID 252500676.
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