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549-18-8

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Multiple organolithium generation in the continuous flow synthesis of amitriptyline
A continuous flow protocol for the preparation of the tricyclic antidepressant (TCA) amitriptyline is reported. The advantages of flow chemistry when handling organometallic agents as well as when performing reaction with gases are demonstrated. Continuous multilithiation combined with carboxylation and the Parham cyclization, a Grignard addition and thermolytic water elimination by inductive heating are key features of the multistep protocol. Copyright
Kupracz, Lukas,Kirschning, Andreas
p. 3375 - 3380
(2013/12/04)

Discovery of diphenyl amine based sodium channel blockers, effective against hNav1.2
The development of new therapies for chronic pain is an area of unmet medical need. Central to pathways of chronic pain is the upregulation of voltage-gated sodium channels. The use of tricyclic antidepressants, which also have sodium channel activity, in chronic pain therapy prompted us to develop novel compounds from this scaffold. Herein, we show that the tricyclic moiety is not needed for effective inhibition of the [3H]-BTX binding site and sodium currents of hNav1.2. Our lead compound 6, containing a diphenyl amine motif, demonstrated a 53% inhibitory block of Nav1.2 currents at 10 μM, which is greater than 50% increase in current block in comparison to the amitriptyline standard. Altogether our study establishes that the tricyclic motif is unnecessary for hNav1.2 activity and modification of the amine portion is detrimental to sodium channel block.
Hudgens, Debjani P.,Taylor, Catherine,Batts, Timothy W.,Patel, Manoj K.,Brown, Milton L.
p. 8366 - 8378
(2008/02/05)

ONE-STEP GRIGNARD REACTIONS WITH DIMETHYLAMINOPROPYL CHLORIDE: APPLICATION TO THE SYNTHESIS OF TRICYCLIC DRUGS
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Miodownik, A.,Kreisberger, J.,Nussim, M.,Avnir, D.
p. 241 - 246
(2007/10/02)

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Chemical Properties

Appearance/Colour :white crystalline powder
Melting Point: 196-197 °C
Boiling Point: 398.2 °C at 760 mmHg
Flash Point:174 °C
Density: 1.076g/cm3
Solubility:H2O: soluble
Storage Temp.:2-8°C
Vapor Pressure: 1.5E-06mmHg at 25°C
PKA: 9.4(at 25℃)
Merck: 14,487
PSA: 3.24000
LogP: 4.97060

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