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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).

• Norepinephrine reuptake inhibitors
• Antidepressants
• Imidazolines