Prothipendyl

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| ImageFile=Prothipendyl.svg

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| PIN=N,N-Dimethyl-3-(10H-pyrido[3,2-b][1,4]benzothiazin-10-yl)propan-1-amine

| OtherNames=

|Section1={{Chembox Identifiers

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 5O6VWA87VA

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| CASNo=303-69-5

| PubChem=14670

| EINECS = 214-958-4

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| ChemSpiderID = 14002

| SMILES = CN(C)CCCN1C2=CC=CC=C2SC3=C1N=CC=C3

| 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

| InChIKey = JTTAUPUMOLRVRA-UHFFFAOYAL

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| StdInChI = 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

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| StdInChIKey = JTTAUPUMOLRVRA-UHFFFAOYSA-N

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|Section2={{Chembox Properties

| Formula=C₁₆H₁₉N₃S

| MolarMass=285.40716

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|Section6={{Chembox Pharmacology

| ATCCode_prefix = N05

| ATCCode_suffix = AX07

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|Section7={{Chembox Legal status

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| legal_BR = C1

| legal_BR_comment = {{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-16 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-04-04}}

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|Section8={{Chembox Hazards

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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.{{cite book|author=J. Elks|title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA1038|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=1038–}}{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA893|year=2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=893–}}{{Cite web |url=https://www.drugs.com/international/prothipendyl.html |title=Archived copy |access-date=2017-09-27 |archive-date=2017-09-27 |archive-url=https://web.archive.org/web/20170927160324/https://www.drugs.com/international/prothipendyl.html |url-status=dead }}{{cite book|author1=D. Leigh|author2=C.M. Pare|author3=J. Marks|title=A Concise Encyclopaedia of Psychiatry|url=https://books.google.com/books?id=o-bzCAAAQBAJ&pg=PA396|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-011-5913-5|pages=396–}} It differs from promazine only by the replacement of one carbon atom with a nitrogen atom in the tricyclic ring system. Prothipendyl is said to not possess antipsychotic effects, and in accordance, appears to be a weaker dopamine receptor antagonist than other phenothiazines.{{cite book|title=Psychotropic Agents: Part I: Antipsychotics and Antidepressants|url=https://books.google.com/books?id=oK7tCAAAQBAJ&pg=PA131|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-3-642-67538-6|pages=131–}}