# Dazepinil

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Dazepinil
> Markdown URL: https://mediated.wiki/source/Dazepinil.md
> Source: https://en.wikipedia.org/wiki/Dazepinil
> Source revision: 1264570171
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{Short description|Antidepressant}}

{{Infobox drug
| drug_name = Dazepinil
| image = Dazepinil.svg
| width = 250px
| caption = 

<!-- Clinical data -->
| pronounce = 
| tradename = 
| Drugs.com = 
| MedlinePlus = 
| licence_CA = 
| licence_EU = 
| DailyMedID = 
| licence_US = 
| pregnancy_AU = 
| pregnancy_category = 
| dependency_liability = 
| addiction_liability = 
| routes_of_administration = 
| class = 
| ATC_prefix = 
| ATC_suffix = 

<!-- Legal status -->
| legal_status = 

<!-- Pharmacokinetic data -->
| bioavailability = 
| protein_bound = 
| metabolism = 
| metabolites = 
| onset = 
| elimination_half-life = 
| duration_of_action = 
| excretion = 

<!-- Identifiers -->
| CAS_number = 75991-50-3
| CAS_supplemental = 75241-19-9
| PubChem = 53432
| IUPHAR_ligand = 
| DrugBank = 
| ChemSpiderID = 48264
| UNII = 730EPY2HSM
| KEGG = 
| ChEBI = 
| ChEMBL = 117042
| NIAID_ChemDB = 
| PDB_ligand = 
| synonyms = HRP 543

<!--Chemical data-->
| C=17 | H=18 | N=2
| IUPAC_name = 2,3-dimethyl-4-phenyl-4,5-dihydro-1,3-benzodiazepine 
| StdInChI=1S/C17H18N2/c1-13-18-16-11-7-6-10-15(16)12-17(19(13)2)14-8-4-3-5-9-14/h3-11,17H,12H2,1-2H3
| StdInChIKey = STDYWHYUOSSCBO-UHFFFAOYSA-N 
| smiles = CC1=NC2=CC=CC=C2CC(N1C)C3=CC=CC=C3
}}
'''Dazepinil''', classified as a [tricyclic antidepressant](/source/tricyclic_antidepressant), is a pharmacological compound that has never been approved for medical use. Its mechanism of action involves inhibiting the reuptake of [norepinephrine](/source/norepinephrine) and serotonin at the [synaptic](/source/Synapse) cleft, thereby enhancing [neurotransmitter](/source/neurotransmitter) availability in the brain.

Dazepinil is a 1,3-[benzodiazepine](/source/benzodiazepine) derivative that has been reported to have marked anti-[tetrabenazine](/source/tetrabenazine) activity, to inhibit neurotransmitter uptake into rat brain [synaptosome](/source/synaptosome)s and to lack [anticholinergic](/source/anticholinergic) activity as evidenced by negligible displacement of [3H][quinuclidinyl benzylate](/source/3-quinuclidinyl_benzilate) from rat brain [muscarinic receptor](/source/muscarinic_receptor)s, and by negligible antagonism of the cholinergic stimulation produced by [physostigmine](/source/physostigmine) or [oxotremorine](/source/oxotremorine). This suggests that HRP 534 might be clinically useful as a novel antidepressant which is devoid of anticholinergic side-effects.<ref>{{cite book | vauthors = Ankier SI | date= 1986 | chapter=Progress in Medicinal Chemistry | title=4 Recent Progress in the Development of New Antidepressant Drugs | series= Progress in Medicinal Chemistry | publisher=Elsevier | volume=23 | pages=121–185 | pmid = 3310107  | url=https://linkinghub.elsevier.com/retrieve/pii/S0079646808703424 | doi=10.1016/S0079-6468(08)70342-4| isbn= 978-0-444-80802-8 }}</ref>

==Synthesis==

The chemical synthesis has been reported:<ref>{{cite journal | vauthors = Geyer HM, Martin LL, Crichlow CA, Dekow FW, Ellis DB, Kruse H, Setescak LL, Worm M | display-authors = 6 | title = (+/-)-4-Aryl-4,5-dihydro-3H-1,3-benzodiazepines. 1. Synthesis and evaluation of (+/-)-4,5-dihydro-2,3-dimethyl-4-phenyl-3H-1,3-benzodiazepine and analogues as potential antidepressant agents | journal = Journal of Medicinal Chemistry | volume = 25 | issue = 4 | pages = 340–346 | date = April 1982 | pmid = 7200144 | doi = 10.1021/jm00346a003 }}</ref><ref>{{cite journal | vauthors = Martin LL, Setescak LL, Worm M, Crichlow CA, Geyer HM, Wilker JC | title = (+/-)-4-Aryl-4,5-dihydro-3H-1,3-benzodiazepines. 2. Nuclear-substituted analogues of (+/-)-4,5-dihydro-2,3-dimethyl-4-phenyl-3H-1,3-benzodiazepine and (+/-)-4,5-dihydro-2-ethyl-3-methyl-4-phenyl-3H-1,3-benzodiazepine as potential antidepressant agents | journal = Journal of Medicinal Chemistry | volume = 25 | issue = 4 | pages = 346–351 | date = April 1982 | pmid = 7069712 | doi = 10.1021/jm00346a004 }}</ref>

center|500px|Dazepinil synthesis
The base catalyzed reaction between N-Boc-o-toluidine [74965-31-4] ('''1''') and N-Benzylidenemethylamine [622-29-7] ('''2''') gives PC20452101.<ref>{{cite web | title = PC20452101 | url = https://pubchem.ncbi.nlm.nih.gov/compound/20452101 | work = PubChem | publisher = U.S. National Library of Medicine }}</ref> The removal of the Boc protecting group by treatment with [trifluoroacetic acid](/source/trifluoroacetic_acid) afforded 2-[2-(Methylamino)-2-phenylethyl]aniline, PC10857157 ('''3''').<ref>{{cite web | title = PC10857157 | url = https://pubchem.ncbi.nlm.nih.gov/compound/10857157 | work = PubChem | publisher = U.S. National Library of Medicine }}</ref> Reaction of the resulting diamine with methyl orthoacetate adds the required extra carbon atom and leads to the formation of dazepinil ('''4''').

== References ==
{{reflist}}

{{Antidepressants}}
{{Anxiolytics}}
{{Neuropathic pain and fibromyalgia pharmacotherapies}}
{{Monoamine reuptake inhibitors}}

{{DEFAULTSORT:Serotonin Norepinephrine Reuptake Inhibitor}}

Category:Serotonin–norepinephrine reuptake inhibitors
Category:Benzodiazepines

---
Adapted from the Wikipedia article [Dazepinil](https://en.wikipedia.org/wiki/Dazepinil) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Dazepinil?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.