61949-83-5

Basic information

• Product Name: 1-Aminoindane hydrochloride
• Synonyms: 1-Aminoindane;1-Indanamine
• CAS NO: 61949-83-5
• Molecular Formula: C₉H₁₁N
• Molecular Weight: 133.19
• EINECS: 252-158-7
• Mol File: 61949-83-5.mol
• Article Data: 34

Chemical Properties

• Melting Point: 15 ºC
• Boiling Point: 96-97 ºC
• Flash Point: 94 ºC
• Appearance: /
• Density: 1.038
• Vapor Pressure: 0.0886mmHg at 25°C
• Refractive Index: 1.561
• PKA: 9.21(at 22℃)
• Water Solubility: insoluble
• CAS DataBase Reference: 1-Aminoindane hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Aminoindane hydrochloride(61949-83-5)
• EPA Substance Registry System: 1-Aminoindane hydrochloride(61949-83-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 61949-83-5(Hazardous Substances Data)

Usage

General Description

1-Aminoindane hydrochloride is a psychoactive designer drug that belongs to the aminoindane class of compounds. It acts as a releasing agent of serotonin, dopamine, and norepinephrine, leading to an increase in their levels in the brain. The compound is known for its stimulant effects and has been found to have potential nootropic and mood-enhancing properties. It has also been reported to induce feelings of euphoria and increased sociability. However, the use of 1-Aminoindane hydrochloride has been associated with potential adverse effects, including cardiovascular complications and neurotoxicity. This substance is not approved for medical use and is considered to be a controlled substance in many jurisdictions due to its potential for abuse and harmful effects.

InChI:InChI=1/C9H11N/c10-9-6-5-7-3-1-2-4-8(7)9/h1-4,9H,5-6,10H2/p+1/t9-/m0/s1

Upstream product

• 34698-41-4 2,3-dihydro-1H-inden-1-amine 
• 95-13-6 1-indene 
• 192461-85-1 (S)-(-)-N-(1-indanamine)diphenylphosphinamide 
• 644997-80-8 (R)-2-((S)-Indan-1-ylamino)-2-phenyl-acetamide 
• 937371-85-2 (E)-indanone O-4-trifluoromethylbenzyl oxime 
• 143-07-7 lauric acid 
• 68253-35-0 (E)-indan-1-one oxime 
• 83-33-0 inden-1-one 
• 644997-81-9 (R)-((S)-Indan-1-ylamino)-phenyl-acetonitrile 
• 644997-79-5 (R)-2-[Indan-(1E)-ylideneamino]-2-phenyl-acetamide 
• 192461-80-6 N-[(1E)-2,3-dihydro-1H-inden-1-ylidene]-P,P-diphenylphosphinic amide 
• 17640-21-0 isopropyl methoxyacetate 
• 1384127-07-4 N-octanoyl dimethyl glycine trifluoroethyl ester 
• 113-24-6 sodium pyruvate 

Downstream Products

• 745783-81-7 (+)-(1S)-indanyl isocyanate 
• 910541-18-3 (S)-2-((S)-Indan-1-ylcarbamoyl)-pyrrolidine-1-carboxylic acid benzyl ester 
• 1213899-46-7 6-hydroxy-(S)-1-aminoindan 
• 218793-71-6 C₂₉H₃₂N₆O₄ 
• 905580-86-1 N-[(1S)-2,3-Dihydro-1H-inden-1-yl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine 
• 905580-80-5 (2R,3R,4S,5R)-5-(6-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-9H-purin-9-yl)-4-fluoro-2-[(trityloxy)methyl]tetrahydrofuran-3-yl benzoate 

Relevant articles and documents

Enantioselective synthesis of 1-aminoindene derivativesviaasymmetric Br?nsted acid catalysis

We describe a catalytic asymmetric iminium ion cyclization reaction of simple 2-alkenylbenzaldimines using a BINOL-derived chiralN-triflyl phosphoramide. The corresponding 1-aminoindenes and tetracyclic 1-aminoindanes are formed in good yields and high enantioselectivities. Further, the chemical utility of the obtained enantiopure 1-aminoindene is demonstrated for the asymmetric synthesis of (S)-rasagiline.

Kinetic Resolution of Racemic Primary Amines Using Geobacillus stearothermophilus Amine Dehydrogenase Variant

A NADH-dependent engineered amine dehydrogenase from Geobacillus stearothermophilus (LE-AmDH-v1) was applied together with a NADH-oxidase from Streptococcus mutans (NOx) for the kinetic resolution of pharmaceutically relevant racemic α-chiral primary amines. The reaction conditions (e. g., pH, temperature, type of buffer) were optimised to yield S-configured amines with up to >99 % ee.

Chemoenzymatic Synthesis of a Chiral Ozanimod Key Intermediate Starting from Naphthalene as Cheap Petrochemical Feedstock

Ozanimod represents a recently developed, promising active pharmaceutical ingredient (API) molecule in combating multiple sclerosis. Addressing the goal of a scalable, economically attractive, and technically feasible process for the manufacture of this drug, a novel alternative synthetic approach toward (S)-4-cyano-1-aminoindane as a chiral key intermediate for ozanimod has been developed. The total synthesis of this intermediate is based on the utilization of naphthalene as a readily accessible, economically attractive, and thus favorable petrochemical starting material. At first, naphthalene is transformed into 4-carboxy-indanone within a four-step process by means of an initial Birch reduction, followed by an isomerization of the C=C double bond, oxidative C=C cleavage, and intramolecular Friedel-Crafts acylation. The transformation of the 4-carboxy-indanone into (S)-4-cyano-1-aminoindane then represents the key step for introducing the chirality and the desired absolute S configuration. When evaluating complementary biocatalytic approaches based on the use of a lipase and transaminase, respectively, the combination of a chemical reductive amination of the 4-carboxyindanone followed by a subsequent lipase-catalyzed resolution turned out to be the most efficient route, leading to the desired key intermediate (S)-4-cyano-1-aminoindane in satisfactory yield and with excellent enantiomeric excess of 99%.