Draft:Dazadrol

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−1
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;

Dazadrol is an antidepressant first quoted in the literature in 1971.^[1]

It's mode of action is stated to be Noradrenaline reuptake inhibitor and it is a gastric acid secretion inhibitor.^[2]

Synthesis

Patent (Ex 12):^[3] #3 substance:^[4]^[5]

The reaction between p-chlorophenylacetonitrile [140-53-4] (1) and 2-bromopyridine [109-04-6] (2) in the presence of a suitable base gives [5005-37-8] (3). Reaction with ethylenediamine forms the imidazoline ring giving PC20361737 (4). Air oxidation then affords the tertiary carbinol by attack at the highly activated benzylic carbon giving dazadrol (5).

References

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

[1] Schmitt H, Petillot N. Propriétés pharmacologiques d'un nouvel antidépresseur potentiel: le ((p-chlorophényl)-2-(pyridyl)-hydroxyméthyl) imidazoline (SCH 12.650 [Pharmacological properties of a new potential antidepressant: ((p-chlorophenyl)-2-(pyridyl)-hydroxymethyl) 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-[p-chlorophenyl-2-(pyridyl)-hydroxymethyl] 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).

[1]

[2]

[3]

[4]

[5]

Draft:Dazadrol

Synthesis

See also

References