According to the third scheme, nortriptyline is synthesized by reacting methylamine with 5-(3-bromopropyliden)-10,11-dihydro-5H-dibenz[a,d]cycloheptene (7.1.6) .
A few modifications of the described methods have been suggested for making nortripty-line [27-32]. Nortriptyline is a drug with a relatively short latent period of action. It is practically devoid of sedative effects. It is used in manic-depressive psychoses, in all forms of endogenous depression, and also in major depressive conditions. The most common synonyms of nortriptyline are aventyl, nortrilen, motival, vivactil, and pamelor.
Protriptyline: Protriptyline, N-methyl-5-H-dibenzo[a,d]cyclohepten-5-propylamine (7.1.22), differs from all of the drugs described above in that there is present a double bond at the C10-C11 position of the central 7-membered ring of the tricyclic part of the molecule. At the same time, a free electron pair on C5 belonging to either a nitrogen atom or an exo-cyclic double bond are excluded, which undoubtedly changes both the architecture of the whole molecule as well as, the collocation of pharmacophore groups.
Protriptyline is synthesized by alkylation of 5-H-dibenzo[a,d]cycloheptene with 3-(N-phormyl-N-methylamino)propylchloride (7.1.20), which is synthesized from compound (7.1.19). The resulting intermediate product (7.1.21) undergoes alkaline hydrolysis, which leads to the formation of protriptyline (7.1.21) [33-38].
HO-CH2-CH2-CH2-NH—ch3 + h2ncho ho-ch2-ch2-ch2-n (
Was this article helpful?