57536-84-2

Usage

Chemical structure

A piperazine derivative with a tetrahydronaphthalenyl group attached to the piperazine ring.

Psychoactive effects

Exhibits potential psychoactive effects due to its interaction with the serotonin system in the brain.

Receptor selectivity

Acts as a selective serotonin receptor agonist, specifically targeting the 5-HT1A and 5-HT1B receptors.

Potential therapeutic applications

Studied for its potential use in the treatment of neurodegenerative and psychiatric disorders, such as depression and anxiety, due to its ability to modulate serotonin levels in the brain.

Recreational drug potential

Investigated for its potential use as a recreational drug, but its use in this context is highly discouraged due to the potential for abuse and harm.

Research status

Further research is needed to fully understand the potential applications and safety profile of 1-(5,6,7,8-tetrahydronaphthalen-1-yl)piperazine.

Legal status

The legal status of THN-PI may vary by country, and it is important to be aware of the regulations in your jurisdiction.

Safety concerns

Due to its psychoactive properties and potential for abuse, the safety and long-term effects of 1-(5,6,7,8-tetrahydronaphthalen-1-yl)piperazine are not well-established, and its use should be approached with caution.

Upstream product

• 821-48-7 bis-(2-chloroethyl)amine hydrochloride 
• 2217-41-6 1-amino-5,6,7,8-tetrahydronaphthalene 
• 29809-14-1 5-nitro-1,2,3,4-tetrahydronaphthalene 

Relevant academic research and scientific papers

AMINO SUBSTITUTED BENZO(HETERO)CYCLIC DERIVATIVES

Use of compounds Formula (I), A = a 5- to 7-membered ring which may contain 1-3 heteroatoms and which may be saturated or partially or completely unsaturated; R= OH, SH, NH2, CN, NO2, halogen, C1-C6-alkyl, C1-C6-haloalkyl; C1-C6- alkoxy, C1-C6-haloalko

2-substituted 1,2-benzisothiazole derivatives and their use as serotonin antagonists (5-HT1A, 5HT1B and 5-HT1D)

where the substituents have the meanings indicated in the description, their preparation and use as serotonin antagonists.

Fused heterocyclic compounds and pharmaceutical applications thereof

The present invention relates to a fused heterocyclic compound of the formula (I) wherein each symbol is as defined in the specification, an optical isomer thereof, a pharmaceutically acceptable salt thereof, a pharmaceutical composition containing a compound of the formula (I), an optical isomer thereof or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable additive, and a medicament containing a compound of the formula (I), an optical isomer thereof or a pharmaceutically acceptable salt thereof. The compound of the present invention is a useful antipsychotic agent effective not only for positive symptoms centering on hallucination and delusion characteristic of the acute stage of schizophrenia, but also negative symptoms of apathy, abulia and autism. The inventive compound is expected to make a highly safe antipsychotic agent associated with less side effects, such as extrapyramidal symptoms and endocrine disturbance, which are observed when a conventional antipsychotic agent having a D2receptor blocking action is administered. Therefore, the inventive compound can be used as a therapeutic agent for the diseases such as schizophrenia.

N4-Unsubstituted N1-Arylpiperazines as High-Affinity 5-HT1A Receptor Ligands

In order to explore the structural requirements for high 5-HT1A affinity, a series of aryl-substituted N1-phenylpiperazines were synthesized and evaluated for their ability to displace -8-OH-DPAT from its specific binding sites in rat frontal cortex homogenates.We found 2-methoxy substitution to be favorable, while 4-methoxy substitution was detrimental for 5-HT1A affinity.Substitution with annelated rings at the 2,3-positions was highly favorable for all investigated compounds, with the exception of a pyrrole ring.All other substitutions, except fluoro, in this class of heterobicyclic phenylpiperazines decreased affinity in the order: ortho>para>meta.The loss of affinity in the ortho and para positions is probably due to steric factors: the substituents either cause steric hindrance with the receptor or prevent the compound from adopting the appropriate conformation for binding to the 5-HT1A receptor.Conformational analysis combined with structure-affinity relationships (SAR) indicates that our arylpiperazines may bind at the 5-HT1A receptor in a nearly coplanar conformation.Observed interactions of the compounds in our 5-HT1A receptor model appeared to be in agreement with SAR data.The aromatic part of the arylpiperazine moiety has ?-? interactions with the aromatic residues Trp161 and Phe362 in helices IV and VI, respectively.The positively charged protonated basic nitrogen forms a hydrogen bond with the negative charged Asp116 in helix III.The ammonium-aspartate complex is surrounded by aromatic residues Trp358 and Phe361 in helix VI.A lipophilic pocket is formed by Phe362, Leu366 (both helix VI), and the methyl group of Thr200 (helix V).In agreement with the model, addition of a methyl substituent to the structure of the benzodioxine analogue 12 in this region, yielding 13, is favorable for 5-HT1A receptor affinity.Unfavorable positions for substitution with bulky groups, like the 3- and 4-positions in the benzofuran compound 14, are explained by steric hindrance with the backbone atoms of helix V.Thus, we were able to rationalize the 5-HT1A SAR of existing N1-phenylpiperazines, as well as a series of newly synthesized bicyclic heteroarylpiperazines, in terms of receptor-ligand interactions.Several of these N4-unsubstituted compounds had affinities in the low-nanomolar range.