Thiazinamium metilsulfate

Thiazinamium metilsulfate

Thiazinamium
Systematic (IUPAC) name
N,N,N-trimethyl-1-(10H-phenothiazin-10-yl)propan-2-aminium
Identifiers
CAS Number	2338-21-8
ATC code	R06AD06
PubChem	CID 6016
UNII	IA16WBX317
Chemical data
Formula	C18H23N2S^+
Molar mass	299.45 g/mol
SMILES CC(CN1C2=CC=CC=C2SC3=CC=CC=C31)[N+](C)(C)C
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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^[1]

Thus, reaction of the well-known antihistaminic drug promethazine with methylchloride leads to thiazinamium chloride.

See also

• Phenothiazine
• Promethazine

References

1. Lewis, A.J.; Dervinis, A.; Carlson, R.P.; Rosenthale, E.; Daniel, W.C. (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.