2-Aminoindane (2-AI) is a stimulant of the 2-aminoindane family which has been sold as a designer drug.
Pharmacology Pharmacodynamics 2-AI is a monoamine releasing agent acting as a selective substrate for NET and DAT. It partially substitutes for amphetamine in rodent drug discrimination tests.
+ Compound Monoamine release (, nM) Ref Serotonin Norepinephrine Dopamine 2-AI >10,000 86 439 MDAI 114 117 1,334 MMAI 31 3,101 >10,000 MEAI 134 861 2,646 d-Amphetamine 698–1,765 6.6–7.2 5.8–24.8 MDA 160–162 47–108 106–190 MDMA 50–85 54–110 51–278 3-MA 58.0 103 Notes: The smaller the value, the more strongly the compound produces the effect. The assays were done in rat brain synaptosomes and human potencies may be different. See also Monoamine releasing agent § Activity profiles for a larger table with more compounds. Refs:
Chemistry Synthesis The chemical synthesis of 2-aminoindane was reported. For example, a 79% yield was reported from indene and ammonia precursors. The older method uses 1-indanone as the starting material.
Analogues 2-AI is a rigid analogue of amphetamine and has similar effects in rodents. Other related homologues and rigid analogues of amphetamine include 2-aminotetralin (2-AT), 2-amino-1,2-dihydronapthalene (2-ADN), 1-naphthylaminopropane (1-NAP), 2-naphthylaminopropane (2-NAP), 1-phenylpiperazine (1-PP), , and .
Derivatives
A number of derivatives of 2-aminoindane, also known as substituted 2-aminoindanes, are known, including 5-IAI, aprindine, BFAI, BFMAI, DHAI, DOM-AI ETAI, indantadol, MDAI, MEAI (5-MeO-2-AI), MDMAI, MMAI, NM-2-AI, PNU-99,194, Pyr-AI, and TAI, among others. Rexaceract (c.f. GT-02287) contains the 2-AI pharmacophore.
Society and culture Legal status China As of October 2015 2-AI is a controlled substance in China.
Finland Scheduled in the "Government decree on psychoactive substances banned from the consumer market".
Sweden Sweden's public health agency suggested classifying 2-AI as a hazardous substance, on June 24, 2019.
United States 2-Aminoindane is not scheduled at the federal level in the United States, but may be considered an analog of amphetamine, in which case purchase, sale, or possession could be prosecuted under the Federal Analog Act.
See also Substituted 2-aminoindane Cyclized phenethylamine 1-Aminoindane 1-Aminomethylindane 2-Aminotetralin
References
External links 2-AI (2-Aminoindane) - Isomer Design 2-Aminoindane - PsychonautWiki 2-Aminoindan - Erowid