7234-65-3

Usage

Molecular structure

A complex structure with a hexahydro-2H-pyrido[1,2-b]isoquinoline core.

Class

Hetrocyclic compounds

Derivative

A derivative of the naturally occurring alkaloid harman.

Psychoactive properties

Known for its psychoactive properties.

Therapeutic effects

Studied for its potential therapeutic effects on the central nervous system.

Neurological disorders

Investigated for its potential role in neurological disorders.

Effects on mood, cognition, and behavior

Known to have effects on mood, cognition, and behavior.

Neurotransmitter and receptor modulation

Implicated in the modulation of various neurotransmitters and receptors in the brain.

Pharmacological research

A subject of interest for pharmacological research.

Implications

Has potential implications for neuropharmacology and neurochemistry.

Upstream product

• 15912-12-6 3,4,11,11a-tetrahydro-2H,6H-pyrido[1,2-b]isoquinolin-1-one 
• 138351-01-6 2-(tert-butoxycarbonyl)-3-(4-chloro-1-n-butyl)1,2,3,4-tetrahydroisoquinoline 
• 138351-00-5 1-<2-((tert-butoxycarbonyl)aminomethyl)phenyl>-6-chloro-2-hexanone 
• 75821-59-9 trans-benzoquinolizidine N-oxide 
• 90329-77-4 1,2,3,4,11,11a-hexahydro-6H-pyrido[1,2-b]isoquinolin-6-one 
• 7803-57-8 hydrazine hydrate 
• 112-27-6 2,2'-[1,2-ethanediylbis(oxy)]bisethanol 
• 137650-02-3 (1-benzylpiperidin-2-yl)methanol 
• 2563-84-0 3-phenylhexahydro-1H-oxazolo[3,4-a]pyridine 
• 522-33-8 Tripiperidin 
• 175857-65-5 2-(diphenylphosphinoyl)piperidine 
• 184356-17-0 (2-Methylene-piperidin-1-yl)-phenyl-methanone 
• 89-93-0 ortho-methylbenzylamine 
• 15912-58-0 2-(3-ethoxycarbonyl-propyl)-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

Synthesis and Evaluation of 6,11-Ethanohexahydrobenzoquinolizidines: A New Class of Noncompetitive N-Methyl -D-aspartate Antagonists

The synthesis and in vitro and in vivo evaluation of 12,13-cycloalkyl-6,11-ethanobenzoquinolizidines, a new class of noncompetitive N-methyl-D-aspartate (NMDA) antagonists acting at the PCP site on the NMDA receptor complex, is reported.Structure-activity relationship studies led to the identification of 10-hydroxy-(6α,11α,11aβ,12R*,13S*)-1,3,4,6,11,11a,13,14,15,16-decahydro-12H-6,11-endo-cyclopenta-2H-pyridoisoquinoline hydrobromide (5h) and 9-hydroxy-(6α,11α,11aβ,12R*,13S*)-1,3,4,6,11,11a,13,14,15,16-decahydro-12H-6,11-endo-cyclopenta-2H-pyridoisoquinoline hydrobromide (5i), the most potent members of this series with Ki values of 2.3 +/- 0.2 and 2.3 +/- 0.5 nM, respectively.Molecular modeling studies revealed that this series of compounds occupies both lipophilic sites of the Andrews PCP receptor model and shares structural features which are common to other classes of known noncompetitive NMDA antagonists such as MK-801.

The photolysis of berbine N-oxides

Photolysis of trans-canadine N-oxide (3) leads to lactam 5 and formamide 7. Similarly, photolysis of trans-xylopinine N-oxide (12) supplies lactam 14 and amide 15. Oxaziridine 4 is a probable intermediate in these transformations, so that selective oxidation of the berbine nucleus at C-6 has been achieved, accompanied by fission of the N-7-C-14 bond. LAH reduction of lactam 5 gives rise to dibenzazecine 8, while similar treatment of amide 7 generates dibenzazonine 10. Alternatively, acid hydrolysis of 7 furnishes dibenzazonine 11.

Diastereoselective electrophilic substitution of α-amino-substituted benzylic organometallics

Reductive metallation of a diastereoisomeric bicyclic 2-phenyloxazolidine derived from 2-hydroxymethylpiperidine occurs with racemization at the benzylic carbon atom. Reaction of intermediate organometallics with alkyl halides affords substituted amino alcohols in a highly syn-selective fashion. Observed diastereoselectivities are rationalized in terms of rapidly equilibrating epimeric intermediate organometallics, one of which reacts preferentially under appropriate reaction conditions. Deuteration of the same intermediates usually leads to deuterated amino alcohols with low diasteroselectivities, unless lithium is employed as the reducing agent and the resulting mixture is allowed to equilibrate before deuteration.

Dramatically different photochemical behaviour of 1-aroyl-2-methylene piperidine and pyrrolidine derivatives. An expeditious synthesis of ruspolinone

Upon irradiation in neutral solvent, the diversely substituted 1-aroyl-2-methylenepiperidines 6a-f give rise to photocyclized products 4a-f while their pyrrolidine congeners 7a,c,d afford enaminoketones 18a,c,d products of photo-Fries rearrangement.

Heteroatom-directed lateral lithiation: Synthesis of isoquinoline derivatives from N-(tert-butoxycarbonyl)-2-methylbenzylamines

Methodology for the preparation of isoquinoline derivatives from N-(tert-butoxycarbonyl)-2-methylbenzylamines (1) was developed. Conversion of 1 to the dilithio species followed by condensation with DMF afforded Boc-3-hydroxy-1,2,3,4-tetrahydroisoquinolin

PREPARATION OF TETRAHYDROISOQUINOLINES FROM N-(TERT-BUTOXYCARBONYL)-2-METHYLBENZYLAMINES

Dilithiation of N-(tert-butoxycarbonyl)-2-methylbenzylamine (1a) followed by treatment with N,N-dimethylformamide affords 2-(tert-butoxycarbonyl)-3-hydroxy-tetrahydroisoquinoline (3a).Dehydration and reduction of 3a afford BOC-tetrahydroisoquinoline (5a).The methodology is also applicable to synthesis of chloro and fluoro substituted tetrahydroisoquinolines (5b,c), 3 and 4-substituted derivatives (8,10), and the hexahydro-2H-benzoquinolizine ring system (13).