Misplaced Pages

This is an old revision of this page, as edited by Mo18ekula (talk | contribs) at 15:13, 17 December 2024 (←Created page with '{{Infobox drug | drug_name = Dazadrol | image = Dazadrol.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 = <!-- Pharmaco...'). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Dazadrol

Clinical data
Other names	Sch 12650
Identifiers
IUPAC name (4-chlorophenyl)-(4,5-dihydro-1H-imidazol-2-yl)-pyridin-2-ylmethanol
CAS Number	47029-84-5 25387-70-6
ChemSpider	30497
Chemical and physical data
Formula	C15H14ClN3O
Molar mass	287.75 g·mol
3D model (JSmol)	Interactive image
SMILES C1CN=C(N1)C(C2=CC=C(C=C2)Cl)(C3=CC=CC=N3)O
InChI InChI=1S/C15H14ClN3O/c16-12-6-4-11(5-7-12)15(20,14-18-9-10-19-14)13-3-1-2-8-17-13/h1-8,20H,9-10H2,(H,18,19) Key:DITYEPYMBCHKLF-UHFFFAOYSA-N

Antidepressant.

Noradrenaline reuptake inhibitor and gastric acid secretion inhibitor.

Synthesis

Patent (Ex 12): #3 substance:

The reaction between p-chlorophenylacetonitrile (1) and 2-bromopyridine (2) in the presence of a suitable base gives (3). Reaction with ethylenediamine forms the imidazoline ring giving PC20361737 (4). Air oxidation then affords the tertiary carbinol by attack at the highly activated, multiply benzylic carbon. There is thus obtained the antidepressant dazadrol (5).

References

1. Schmitt H, Petillot N. Propriétés pharmacologiques d'un nouvel antidépresseur potentiel: le ((p-chlorophényl)-2-(pyridyl)-hydroxyméthyl) imidazoline (SCH 12.650 . Therapie. 1971 Jul-Aug;26(4):805-21. French. PMID: 5119131.
2. Lippmann, W. (1970). "Blockade of noradrenaline uptake and inhibition of gastric acid secretion by 2- imidazoline maleate (Sch-12650)". Journal of Pharmacy and Pharmacology. 22 (5): 387–388. doi:10.1111/j.2042-7158.1970.tb08548.x.
3. Walter Lewis A, DE1905353A1 (1969 to Scherico Ltd).
4. Lewis A. Walter, US4081544 (1978 to Merck Sharp and Dohme Corp).
5. Lewis A. Walter, US3932431 (1976 to Merck Sharp and Dohme Corp).

Lua error in Module:Navbox_with_collapsible_groups at line 6: attempt to call field 'with collapsible groups' (a nil value).

• Norepinephrine reuptake inhibitors
• Antidepressants
• Imidazolines