18085-03-5

Basic information

• Product Name: Naphthalenylisopropylamine
• Synonyms: Naphthalenylisopropylamine;alpha-Methyl-2-naphthaleneethanamine;PAL 287
• CAS NO: 18085-03-5
• Molecular Formula: C₁₃H₁₅N
• Molecular Weight: 185.268
• Mol File: 18085-03-5.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• Density: 1.047
• CAS DataBase Reference: Naphthalenylisopropylamine(CAS DataBase Reference)
• NIST Chemistry Reference: Naphthalenylisopropylamine(18085-03-5)
• EPA Substance Registry System: Naphthalenylisopropylamine(18085-03-5)

Safety Data

• Hazardous Substances Data: 18085-03-5(Hazardous Substances Data)

Usage

General Description

Naphthalenylisopropylamine, also known as N-isopropyl-1-napthylamine, is a chemical compound with potential applications in the field of medicine. It is a derivative of naphthalene and isopropylamine, and is thought to have potential as a serotonin-dopamine activity modulator. Research has shown that Naphthalenylisopropylamine may have potential therapeutic effects in the treatment of various conditions, including depression, anxiety and other mood disorders. It has also been investigated for its potential as a neuroprotective agent and as a treatment for certain neurodegenerative diseases. However, further research is needed to fully understand its mechanism of action and potential therapeutic applications. Due to its biological activity, it has also received attention as a potential drug of abuse and has been included in the list of controlled substances in some countries.

Upstream product

• 66-99-9 β-naphthaldehyde 
• 37629-58-6 (E)-2-(2-nitroprop-1-en-1-yl)naphthalene 
• 59832-12-1 1-(β-naphthyl)-2-nitro-1-propene 

Downstream Products

• 133795-81-0 (1-Methyl-2-naphthalen-2-yl-ethyl)-(3-phenyl-propyl)-amine 

Relevant articles and documents

Development of a rationally designed, low abuse potential, biogenic amine releaser that suppresses cocaine self-administration

Convergent lines of evidence support a dual deficit model of stimulant withdrawal, where reductions in synaptic dopamine (DA) and 5-hydroxytryptamine (serotonin) (5-HT) contribute to dysphoria, drug craving, and relapse. Thus, we predicted that a nonamphetamine compound with substrate activity at DA and 5-HT transporters (i.e., a dual DA/5-HT releaser) would be an effective medication for treating stimulant addictions. Ideally, this type of medication would alleviate withdrawal symptoms, suppress cocaine self-administration, and lack side effects commonly associated with central nervous system stimulants. In the present work, more than 350 compounds were screened in vitro for activity as substrate-type releasing agents at DA, 5-HT, and norepinephrine transporters. These efforts identified PAL-287 (1-napthyl-2-aminopropane) as a nonamphetamine compound with potent substrate activity at biogenic amine transporters. In vivo microdialysis in rats demonstrated that PAL-287 (1-3 mg/kg i.v.) increased extracellular DA and 5-HT in frontal cortex, but effects on 5-HT were somewhat greater. PAL-287 induced substantially less locomotor stimulation than (+)-amphetamine, a drug that increases only extracellular DA. Administration of high-dose (+)-methamphetamine or (±)-3,4-methylenedioxymethamphetamine to rats produced long-lasting depletion of cortical 5-HT, whereas PAL-287 (18 mg/kg i.p. × 3) did not. PAL-287 displayed little or no reinforcing properties in rhesus monkeys trained to self-administer cocaine, yet PAL-287 produced a dose-dependent decrease in responding for cocaine when infused at a dose of 1.0 mg/kg/h. Collectively, the findings reported here demonstrate that nonamphetamine monoamine releasing agents such as PAL-287 might be promising candidate medications for the treatment of stimulant dependence.