103028-81-5

Basic information

• Product Name: 6-METHOXY-1-INDANAMINE
• Synonyms: 6-METHOXY-INDAN-1-YLAMINE;6-METHOXY-1-INDANAMINE;1-AMINO-6-METHOXY INDAN;6-Methoxy-2,3-dihydro-1H-inden-1-aMine;2,3-Dihydro-6-methoxy-1H-inden-1-amine;6-Methoxyindan-1-amine;1H-Inden-1-amine,2,3-dihydro-6-methoxy
• CAS NO: 103028-81-5
• Molecular Formula: C₁₀H₁₃NO
• Molecular Weight: 163.22
• EINECS: 604-604-1
• Mol File: 103028-81-5.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 266℃
• Flash Point: 119℃
• Appearance: /
• Density: 1.087
• Vapor Pressure: 0.009mmHg at 25°C
• Refractive Index: 1.562
• PKA: 9.18±0.20(Predicted)
• CAS DataBase Reference: 6-METHOXY-1-INDANAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-METHOXY-1-INDANAMINE(103028-81-5)
• EPA Substance Registry System: 6-METHOXY-1-INDANAMINE(103028-81-5)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 103028-81-5(Hazardous Substances Data)

Usage

General Description

6-Methoxy-1-indanamine, also known as 6-MeO-1-indanamine or MIA, is a psychoactive compound and a substituted phenethylamine. It is an analog of alpha-methyltryptamine (AMT), and it is also closely related to 5-MeO-AMT. MIA acts as a selective serotonin releasing agent and a monoamine oxidase inhibitor, meaning it affects the levels of serotonin and other neurotransmitters in the brain. It has been studied for its potential use in the treatment of various psychiatric disorders and has been found to have hallucinogenic effects. Additionally, 6-Methoxy-1-indanamine has also been identified as an impurity in illegal drug preparations, making it a substance of concern in the field of drug enforcement and forensic toxicology.

InChI:InChI=1/C10H13NO/c1-12-8-4-2-7-3-5-10(11)9(7)6-8/h2,4,6,10H,3,5,11H2,1H3

Upstream product

• 180915-76-8 6-methoxyindan-1-one oxime 
• 3469-07-6 5-methoxy-1H-indene 
• 13623-25-1 6-methoxy-2,3-dihydro-1H-inden-1-one 
• 64-19-7 acetic acid 

Downstream Products

• 133497-57-1 1-amino-6-hydroxyindan 

Relevant articles and documents

Synthesis and Reactivity of 6- and 7-Methoxyindanoaziridines

The synthesis,spectral, and reactivity properties of 6-methoxy- and 7-methoxyindanoaziridines (8 and 9,respectively) are detailed.Hydrolysis of each aziridine produced the corresponding trans and cis-2-amino-1-indanols in approximately 1:2 ratio, respectively.The 7-methoxy adduct 9 underwent hydrolysis approximately 250 times faster then the isomeric 6-methoxyaziridine 8 at pH 8.88.Both the product profiles and the kinetic rate data for the hydrolysis of 8 and 9 are consistent with a mechanism in which protonation of the aziridine precedes the rate-determining ring-opening step to generate the corresponding benzylic cation.The products generated in these reactions paralleled those reported for the hydrolysis of the antineoplastic agent mitomycin C under reductive conditions.The implications of these findings in relation to the mode of action of mitomycin C are discussed.

Deconstructive Oxygenation of Unstrained Cycloalkanamines

A deconstructive oxygenation of unstrained primary cycloalkanamines has been developed for the first time using an auto-oxidative aromatization promoted C(sp3)?C(sp3) bond cleavage strategy. This metal-free method involves the substitution reaction of cycloalkanamines with hydrazonyl chlorides and subsequent auto-oxidative annulation to in situ generate pre-aromatics, followed by N-radical-promoted ring-opening and further oxygenation by 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) and m-cholorperoxybenzoic acid (mCPBA). Consequently, a series of 1,2,4-triazole-containing acyclic carbonyl compounds were efficiently produced. This protocol features a one-pot operation, mild reaction conditions, high regioselectivity and ring-opening efficiency, broad substrate scope, and is compatible with alkaloids, osamines, and peptides, as well as steroids.

Process for the synthesis of indanylamine or aminotetralin derivatives and novel intermediates

A process for preparing indanylamine and aminotetralin derivatives from indanone or tetralone oximes by acylating the oximes with an organic anhydride, followed by catalytic hydrogenation in the presence of an organic anhydride with subsequent hydrolysis is described. The process is commercially feasible providing indanylamine and aminotetralin derivatives in high yield that are useful as intermediates in the production of therapeutically active compounds. Also described are novel intermediates, 1-indanone O-acetyl oximes and 1-tetralone O-acetyl oximes.