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</ref> #3 substance:<ref>Lewis A. Walter, US4081544 (1978 to Merck Sharp and Dohme Corp).</ref><ref>Lewis A. Walter, US3932431 (1976 to Merck Sharp and Dohme Corp).</ref> </ref> #3 substance:<ref>Lewis A. Walter, US4081544 (1978 to Merck Sharp and Dohme Corp).</ref><ref>Lewis A. Walter, US3932431 (1976 to Merck Sharp and Dohme Corp).</ref>
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The reaction between p-chlorophenylacetonitrile (1) and ] (2) in the presence of a suitable base gives (3). Reaction with ethylenediamine forms the imidazoline ring giving (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). The reaction between p-chlorophenylacetonitrile (1) and ] (2) in the presence of a suitable base gives (3). Reaction with ethylenediamine forms the imidazoline ring giving (4). Air oxidation then affords the tertiary carbinol by attack at the highly activated benzylic carbon giving dazadrol (5).
==See also==
*]
== References == == References ==
{{reflist}} {{reflist}}
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{{Antidepressants}} {{Antidepressants}}
{{Monoamine reuptake inhibitors}} {{Monoamine reuptake inhibitors}}
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Latest revision as of 22:09, 19 December 2024

Dazadrol
Clinical data
Other namesSch 12650
Identifiers
IUPAC name
  • (4-chlorophenyl)-(4,5-dihydro-1H-imidazol-2-yl)-pyridin-2-ylmethanol
CAS Number
ChemSpider
Chemical and physical data
FormulaC15H14ClN3O
Molar mass287.75 g·mol
3D model (JSmol)
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.

It's mode of action is stated to be Noradrenaline reuptake inhibitor and it is a 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 benzylic carbon giving dazadrol (5).

See also

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).
Antidepressants (N06A)
Specific reuptake inhibitors and/or receptor modulators
SSRIsTooltip Selective serotonin reuptake inhibitors
SNRIsTooltip Serotonin–norepinephrine reuptake inhibitors
NRIsTooltip Norepinephrine reuptake inhibitors
NDRIsTooltip Norepinephrine–dopamine reuptake inhibitors
NaSSAsTooltip Noradrenergic and specific serotonergic antidepressants
SARIsTooltip Serotonin antagonist and reuptake inhibitors
SMSTooltip Serotonin modulator and stimulators
Others
Tricyclic and tetracyclic antidepressants
TCAsTooltip Tricyclic antidepressants
TeCAsTooltip Tetracyclic antidepressants
Others
Monoamine oxidase inhibitors
Non-selective
MAOATooltip Monoamine oxidase A-selective
MAOBTooltip Monoamine oxidase B-selective
Adjunctive therapies
Miscellaneous
Monoamine reuptake inhibitors
DATTooltip Dopamine transporter
(DRIsTooltip Dopamine reuptake inhibitors)
NETTooltip Norepinephrine transporter
(NRIsTooltip Norepinephrine reuptake inhibitors)
SERTTooltip Serotonin transporter
(SRIsTooltip Serotonin reuptake inhibitors)
VMATsTooltip Vesicular monoamine transporters
Others
See also: Receptor/signaling modulators • Monoamine releasing agents • Adrenergics • Dopaminergics • Serotonergics • Monoamine metabolism modulators • Monoamine neurotoxins