123039-93-0

Basic information

• Product Name: DIHYDREXIDINE HYDROCHLORIDE
• Synonyms: DIHYDREXIDINE HYDROCHLORIDE;(+/-)-TRANS-10,11-DIHYDROXY-5,6,6A,7,8,12B-HEXAHYDROBENZO[A]PHENANTHRIDINE HYDROCHLORIDE;DihydrexidineHCl;DIHYDROXIDINE HYDROCHLORIDE
• CAS NO: 123039-93-0
• Molecular Formula: C17H18ClNO2
• Molecular Weight: 303.78
• Product Categories: Dopamine receptor
• Mol File: 123039-93-0.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 488.3°Cat760mmHg
• Flash Point: 190.5°C
• Appearance: /solid
• Density: 1.267g/cm³
• Vapor Pressure: 3.7E-10mmHg at 25°C
• Storage Temp.: 2-8°C
• CAS DataBase Reference: DIHYDREXIDINE HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: DIHYDREXIDINE HYDROCHLORIDE(123039-93-0)
• EPA Substance Registry System: DIHYDREXIDINE HYDROCHLORIDE(123039-93-0)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 123039-93-0(Hazardous Substances Data)

Usage

Uses

Dihydrexidine is a moderately selective full agonist at the dopamine D1 and D5 receptors (1,2). It has been shown to have antiparkinson effects. It also has the ability to improving the cognitive and working memory deficits in schizophrenia and schizotypal disorder.

Biological Activity

A potent, full efficacy dopamine D 1 agonist which shows no agonist activity at peripheral D 2 receptors or adrenoceptors at doses which cause maximal stimulation of D 1 sites. The compound appears to be fully bioavailable in brain and exhibits profound antiparkinsonism effects in vivo .

InChI:InChI=1/C17H17NO2.ClH/c19-15-7-10-5-6-14-17(13(10)8-16(15)20)12-4-2-1-3-11(12)9-18-14;/h1-4,7-8,14,17-20H,5-6,9H2;1H/t14-,17-;/m1./s1

Upstream product

• 406499-03-4 (6aR,12bS)-(+)-10,11-dimethoxy-5,6,6a,7,8,12b-hexahydrobenzophenanthridine 
• 126296-09-1 trans-6-benzyl-10,11-dimethoxy-5,6,6a,7,8,12b-hexahydrobenzophenanthridine hydrochloride 
• 126296-10-4 trans-10,11-dimethoxy-5,6,6a,7,8,12b-hexahydrobenzophenanthridine hydrochloride 
• 406174-94-5 (1R,2S)-6,7-Dimethoxy-1-phenyl-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid 2,6-di-tert-butyl-4-methoxy-phenyl ester 
• 406174-96-7 N-(6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydro-naphthalen-2-yl)-N-methoxymethyl-4-methyl-benzenesulfonamide 
• 406174-97-8 (6aR,12bS)-10,11-Dimethoxy-6-(toluene-4-sulfonyl)-5,6,6a,7,8,12b-hexahydro-benzo[a]phenanthridine 
• 406174-93-4 6,7-dimethoxy-3,4-dihydro-naphthalene-2-carboxylic acid 2,6-di-tert-butyl-4-methoxy-phenyl ester 
• 406174-95-6 N-((1R,2R)-6,7-Dimethoxy-1-phenyl-1,2,3,4-tetrahydro-naphthalen-2-yl)-4-methyl-benzenesulfonamide 
• 406174-92-3 (1R,2R)-6,7-Dimethoxy-1-phenyl-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid 
• 406174-91-2 (1R,2R)-6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydronaphthalen-2-ylamine 
• 675872-23-8 (1S,2R)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-nitro-1-(2-trityloxymethylphenyl)naphthalene 
• 675872-24-9 {2-[(1S,2R)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-nitronaphthalen-1-yl]phenyl}methanol 

Downstream Products

• 137417-08-4 5,6,6a,7,8,12b-hexahydrobenzo(a)phenanthridine-10,11-diol 
• 126327-49-9 (+/-)-10,11-dihydroxy-5,6,6a,7,8,12b-hexahydrobenzophenanthridine hydrochloride 
• 137417-08-4 (+)-Dihydrexidine hydrochloride 

Relevant articles and documents

Improved asymmetric synthesis of dopamine D1 full agonist, dihydrexidine, employing chiral ligand-controlled asymmetric conjugate addition of aryllithium to a nitroalkene

Asymmetric conjugate addition of 2-trityloxymethylpheyllithium to a nitroalkene was mediated by a chiral ligand to give the key intermediate for dopamine D1 full agonist dihydrexidine 1. The shortcut of both Curtius rearrangement and Pictet-Spengler type

Co-administration of dopamine-receptor binding compounds

Methods for treating a patient having neurological, psychotic, and psychiatric disorders are described comprising the steps of administering to the patient an effective amount of a partial and/or full dopamine D1 receptor agonist, and administering to the patient an effective amount of a dopamine D2 receptor antagonist. Pharmaceutical compositions comprising a dopamine D1 receptor agonist and a dopamine D2 receptor antagonist are also described. The D1 dopamine receptor agonist and the D2 dopamine receptor antagonist can be administered to the patient in the same or in a different composition or compositions.

The first asymmetric synthesis of a dopamine D1 agonist, dihydrexidine, employing asymmetric conjugate addition technology

The first asymmetric synthesis of benzophenanthridine dopamine D1 full agonist, dihydrexidine, was accomplished employing three key processes, external chiral ligand-controlled conjugate addition of phenyllithium, Curtius conversion of a carboxylic group