From Wikipedia, the free encyclopedia
Prothipendyl
Names
Preferred IUPAC name
N ,N -Dimethyl-3-(10H -pyrido[3,2-b ][1,4]benzothiazin-10-yl)propan-1-amine
Identifiers
ChemSpider
ECHA InfoCard
100.132.989
EC Number
UNII
InChI=1S/C16H19N3S/c1-18(2)11-6-12-19-13-7-3-4-8-14(13)20-15-9-5-10-17-16(15)19/h3-5,7-10H,6,11-12H2,1-2H3
N Key: JTTAUPUMOLRVRA-UHFFFAOYSA-N
N InChI=1/C16H19N3S/c1-18(2)11-6-12-19-13-7-3-4-8-14(13)20-15-9-5-10-17-16(15)19/h3-5,7-10H,6,11-12H2,1-2H3
Key: JTTAUPUMOLRVRA-UHFFFAOYAL
CN(C)CCCN1C2=CC=CC=C2SC3=C1N=CC=C3
Properties
C16 H19 N3 S
Molar mass
285.40716
Pharmacology
N05AX07 (
WHO )
Legal status
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Prothipendyl (brand names Dominal , Timovan , Tolnate ), also known as azapromazine or phrenotropin , is an
anxiolytic ,
antiemetic , and
antihistamine of the
azaphenothiazine group which is marketed in
Europe and is used to treat
anxiety and
agitation in
psychotic syndromes .
[2]
[3]
[4]
[5] It differs from
promazine only by the replacement of one
carbon atom with a
nitrogen atom in the
tricyclic
ring system .
[2]
[3] Prothipendyl is said to not possess
antipsychotic effects, and in accordance, appears to be a weaker
dopamine receptor
antagonist than other phenothiazines.
[6]
[5]
Synthesis
See also:
Pipazetate .
Synthesis:
[7]
[8] Patents:
[9]
[10]
1-Azaphenothiazine [261-96-1] (1 )
3-Dimethylaminopropyl chloride [109-54-6] (2 )
Sodium hydride suspension
References
^
Anvisa (2023-03-31).
"RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese).
Diário Oficial da União (published 2023-04-04).
Archived from the original on 2023-08-03. Retrieved 2023-08-16 .
^
a
b J. Elks (14 November 2014).
The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies . Springer. pp. 1038–.
ISBN
978-1-4757-2085-3 .
^
a
b
Index Nominum 2000: International Drug Directory . Taylor & Francis. 2000. pp. 893–.
ISBN
978-3-88763-075-1 .
^
"Archived copy" . Archived from
the original on 2017-09-27. Retrieved 2017-09-27 . {{
cite web }}
: CS1 maint: archived copy as title (
link )
^
a
b D. Leigh; C.M. Pare; J. Marks (6 December 2012).
A Concise Encyclopaedia of Psychiatry . Springer Science & Business Media. pp. 396–.
ISBN
978-94-011-5913-5 .
^
Psychotropic Agents: Part I: Antipsychotics and Antidepressants . Springer Science & Business Media. 6 December 2012. pp. 131–.
ISBN
978-3-642-67538-6 .
^ von Schlichtegroll, Proc. 1st Int. Congr. Neuro-Pharm. 1958, 408 (1959), C.A. 54, 13400g (1960).
^ Yale, Harry L.; Sowinski, Francis (1958). "10-(Dialkylaminoalkyl)-pyrido[3,2-b][1,4]benzothiazine (1-Azaphenothiazine) and Related Compounds". Journal of the American Chemical Society 80 (7): 1651–1654. doi:10.1021/ja01540a035.
^ Yale, Bernstein,
U.S. patent 2,943,086 (1960 to Olin Mathieson).
^
FR 1173134 (1959 to
Rhône-Poulenc ).
H1
Agonists Antagonists
Others:
Atypical antipsychotics (e.g.,
aripiprazole ,
asenapine ,
brexpiprazole ,
brilaroxazine ,
clozapine ,
iloperidone ,
olanzapine ,
paliperidone ,
quetiapine ,
risperidone ,
ziprasidone ,
zotepine )
Phenylpiperazine
antidepressants (e.g.,
hydroxynefazodone ,
nefazodone ,
trazodone ,
triazoledione )
Tetracyclic antidepressants (e.g.,
amoxapine ,
loxapine ,
maprotiline ,
mianserin ,
mirtazapine ,
oxaprotiline )
Tricyclic antidepressants (e.g.,
amitriptyline ,
butriptyline ,
clomipramine ,
desipramine ,
dosulepin (dothiepin) ,
doxepin ,
imipramine ,
iprindole ,
lofepramine ,
nortriptyline ,
protriptyline ,
trimipramine )
Typical antipsychotics (e.g.,
chlorpromazine ,
flupenthixol ,
fluphenazine ,
loxapine ,
perphenazine ,
prochlorperazine ,
thioridazine ,
thiothixene )
H2
H3
H4