Thiazinamium metilsulfate

Chemical compound
  • R06AD06 (WHO)
Identifiers
  • N,N,N-trimethyl-1-(10H-phenothiazin-10-yl)propan-2-aminium
CAS Number
  • 58-34-4 checkY
  • thiazinamium: 2338-21-8 checkY
PubChem CID
  • 6015
ChemSpider
  • 5793
UNII
  • IA16WBX317
  • thiazinamium: 666W2P28N2 checkY
ECHA InfoCard100.017.320 Edit this at WikidataChemical and physical dataFormulaC18H23N2S+Molar mass299.46 g·mol−13D model (JSmol)
  • Interactive image
  • CC(CN1C2=CC=CC=C2SC3=CC=CC=C31)[N+](C)(C)C
InChI
  • 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)

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

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

  • Phenothiazine
  • Promethazine

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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Benzimidazoles (*)DiarylmethanesEthylenediaminesTricyclicsOthers
For topical use
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Receptor/signaling modulators
Nicotinic acetylcholine receptor modulators
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nAChRsTooltip Nicotinic acetylcholine receptors
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(and PAMsTooltip positive allosteric modulators)
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(and NAMsTooltip negative allosteric modulators)
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Receptor/signaling modulators
Muscarinic acetylcholine receptor modulators
Acetylcholine metabolism/transport modulators
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H1
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  • Belarizine
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  • GSK1004723
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H4
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Antidepressants
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