123039-93-0

Usage

Uses

Used in Pharmaceutical Industry:
DIHYDREXIDINE HYDROCHLORIDE is used as a therapeutic agent for treating Parkinson's disease, as it exhibits antiparkinson effects by targeting the dopamine D1 and D5 receptors.
Used in Mental Health Applications:
DIHYDREXIDINE HYDROCHLORIDE is used as a cognitive enhancer for individuals with schizophrenia and schizotypal disorder, helping to improve cognitive and working memory deficits by modulating the dopaminergic system.
Used in Neurological Research:
DIHYDREXIDINE HYDROCHLORIDE serves as a research tool in understanding the role of dopamine D1 and D5 receptors in various neurological conditions, including Parkinson's disease and cognitive impairments in mental health disorders.

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

• 126296-10-4 trans-10,11-dimethoxy-5,6,6a,7,8,12b-hexahydrobenzophenanthridine hydrochloride 
• 126296-09-1 trans-6-benzyl-10,11-dimethoxy-5,6,6a,7,8,12b-hexahydrobenzophenanthridine hydrochloride 
• 166591-12-4 1,2-dihydro-6,7-dimethoxy-3-nitronaphthalene 
• 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 
• 132814-55-2 (((2-bromobenzyl)oxy)methanetriyl)tribenzene 
• 406499-03-4 (6aR,12bS)-(+)-10,11-dimethoxy-5,6,6a,7,8,12b-hexahydrobenzophenanthridine 

Downstream Products

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

Relevant academic research and scientific papers

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

A novel and efficient synthesis of dihydrexidine

An efficient synthesis of the dopamine D1 selective full agonist dihydrexidine has been achieved in high yields and requiring no chromatographic separations via a facilitated intramolecular Henry cyclization of a (nitropropyl)benzophenone and subsequent diastereomerically selective reduction of the resulting tricyclic ni- troalkene. Georg Thieme Verlag Stuttgart.

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.

METHOD OF ADMINISTRATION OF DOPAMINE RECEPTOR AGONISTS

Methods for treating a patient having pulmonary edema are described. The methods include administering to the lung endobronchial space of the airways of the patient an effective amount of a dopamine D1 receptor agonist. Dopamine D1 receptor agonists, including hexahydrobenzophenanthridine, hexahydrothienophenanthridine, phenylbenzodiazepine, chromenoisoquinoline, naphthoisoquinoline dopamine receptor agonists, and their pharmaceutically acceptable salts, formulated as aerosols and dry powders are also described.

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

A new approach for the synthesis of (±)-trans-10,11-dihydroxy-5,6,6a,7,8,12b-hexahydrobenzo[a]phenanthrid ine (dihydrexidine)

A novel method is reported for the synthesis of (±)-trans-10,11-dihydroxy-5,6,6a,7,8,12b-hexahydrobenzo[a]phenanthrid ine (dihydrexidine, 6b) employing as a key step the cyclization of the acid chloride of 3b, via decarbonylation, to the hexahydrobenzo[a]phenanthridine 4b.

Dopaminergic benzo[a]phenanthridines: Resolution and pharmacological evaluation of the enantiomers of dihydrexidine, the full efficacy D1 dopamine receptor agonist

Racemic trans-10,11-dihydroxy-5,6,6a,7,8,12b- hexahydrobenzo[a]phenanthridine (2, dihydrexidine) was shown previously to be the first bioavailable full efficacy agonist at the D1 dopamine receptor. In addition to its full D1 agonist

trans-10,11-Dihydroxy-5,6,6a,7,8,12b-hexahydrobenzophenanthridine: A Highly Potent Selective Dopamine D1 Full Agonist

trans-10,11-Dihydroxy-5,6,6a,7,8,12b-hexahydrobenzophenanthridine (4a, dihydrexidine) has been found to be a highly potent and selective agonist of the dopamine D1 receptor in rat brain.Dihydrexidine had an EC50 of approximately 7