Prothipendyl

Prothipendyl (brand names Dominal, Timovan, Tolnate), also known as azaphenothiazine 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.[1][2][3][4] It differs from promazine only by the replacement of one carbon atom with a nitrogen atom in the tricyclic ring system.[1][2] Prothipendyl is said to not possess antipsychotic effects, and in accordance, appears to be a weaker dopamine receptor antagonist than other phenothiazines.[5][4]

Prothipendyl
Names
Preferred IUPAC name
N,N-Dimethyl-3-(10H-pyrido[3,2-b][1,4]benzothiazin-10-yl)propan-1-amine
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.132.989
EC Number
  • 214-958-4
PubChem CID
UNII
InChI
  • 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
SMILES
  • CN(C)CCCN1C2=CC=CC=C2SC3=C1N=CC=C3
Properties
Chemical formula
 C16H19N3S
Molar mass 285.40716
Pharmacology
N05AX07 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Synthesis

The same precursor also used for Pipazethate.

Synthesis:[6][7] Patents:[8][9]

1-Azaphenothiazine [261-96-1] (1) 3-Dimethylaminopropyl chloride [109-54-6] (2)

References
  1. 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.
  2. Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 893–. ISBN 978-3-88763-075-1.
  4. 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.
  5. Psychotropic Agents: Part I: Antipsychotics and Antidepressants. Springer Science & Business Media. 6 December 2012. pp. 131–. ISBN 978-3-642-67538-6.
  6. von Schlichtegroll, Proc. 1st Int. Congr. Neuro-Pharm. 1958, 408 (1959), C.A. 54, 13400g (1960).
  7. 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.
  8. Yale, Bernstein, U.S. Patent 2,943,086 (1960 to Olin Mathieson).
  9. FR 1173134 (1959 to Rhône-Poulenc).


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