Thiazinamium metilsulfate

Thiazinamium metilsulfate (INN) or thiazinam is an antihistamine. The USAN is thiazinamium chloride (with a different counterion).

Thiazinamium metilsulfate
Thiazinamium
Clinical data
ATC code
Identifiers
  • N,N,N-trimethyl-1-(10H-phenothiazin-10-yl)propan-2-aminium
CAS Number
PubChem CID
ChemSpider
UNII
ECHA InfoCard100.017.320
Chemical and physical data
FormulaC18H23N2S+
Molar mass299.46 g·mol−1
3D model (JSmol)
  • CC(CN1C2=CC=CC=C2SC3=CC=CC=C31)[N+](C)(C)C
  • InChI=1S/C18H23N2S.CH4O4S/c1-14(20(2,3)4)13-19-15-9-5-7-11-17(15)21-18-12-8-6-10-16(18)19;1-5-6(2,3)4/h5-12,14H,13H2,1-4H3;1H3,(H,2,3,4)/q+1;/p-1
  • Key:BVIDQAVCCRUFGU-UHFFFAOYSA-M
 ☒NcheckY (what is this?)  (verify)

Synthesis

Since many of the uses of antihistamines involve conditions such as rashes, which should be treatable by local application, there is some rationale for developing drugs for topical use. The known side effects of antihistamines could in principle be avoided if the drug were functionalized to avoid systemic absorption. The known poor absorption of quat salts make such derivatives attractive for nonabsorbable antihistamines for topical use.

Thiazinamium chloride synthesis from promethazine and chloromethane.[1]

See also

References
  1. Lewis AJ, Dervinis A, Carlson RP, Rosenthale E, Daniel WC (1982). "Thiazinamium chloride: A bronchodilator with antiallergic activity in animals". Journal of Allergy and Clinical Immunology. 69: 155. doi:10.1016/S0091-6749(62)80531-4.
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