Methdilazine

Methdilazine
Clinical data
AHFS/Drugs.com	Monograph
ATC code	R06AD04 (WHO) ;
Identifiers
	IUPAC name 10-[(1-methylpyrrolidin-3-yl) methyl]- 10H-phenothiazine;
CAS Number	1982-37-2 ;
PubChem CID	14677;
IUPHAR/BPS	7231;
DrugBank	DB00902 ;
ChemSpider	14009 ;
UNII	4Q13LY9Z8X;
KEGG	D04979 ;
ChEMBL	ChEMBL1200959 ;
CompTox Dashboard (EPA)	DTXSID6023282 ;
ECHA InfoCard	100.016.220
Chemical and physical data
Formula	C18H20N2S
Molar mass	296.43 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES S2c1ccccc1N(c3c2cccc3)CC4CCN(C)C4;
	InChI InChI=1S/C18H20N2S/c1-19-11-10-14(12-19)13-20-15-6-2-4-8-17(15)21-18-9-5-3-7-16(18)20/h2-9,14H,10-13H2,1H3 ; Key:HTMIBDQKFHUPSX-UHFFFAOYSA-N ;
	(verify)

Methdilazine (Dilosyn, Tacaryl) is a first-generation antihistamine with anticholinergic properties of the phenothiazine class.

Synthesis

Methdilazine synthesis:^[1] R. F. Feldkamp and Y. H. Wu; Mead Johnson & Company; U.S. Patent 2,945,855 (1960).

Rani Basu L, Mazumdar K, Dutta N, Karak P, Dastidar S (2005). "Antibacterial property of the antipsychotic agent prochlorperazine, and its synergism with methdilazine". Microbiol Res. 160 (1): 95–100. doi:10.1016/j.micres.2004.10.002. PMID 15782943.
Chattopadhyay D, Mukherjee T, Pal P, Saha B, Bhadra R (1998). "Altered membrane permeability as the basis of bactericidal action of methdilazine". J Antimicrob Chemother. 42 (1): 83–6. doi:10.1093/jac/42.1.83. PMID 9700532.
Chattopadhyay D, Dastidar S, Chakrabarty A (1988). "Antimicrobial properties of methdilazine and its synergism with antibiotics and some chemotherapeutic agents". Arzneimittelforschung. 38 (7): 869–72. PMID 2905130.

The ring-contracted analog, methdilazine shows only very weak activity as a tranquilizer; instead, that agent constitutes an important antihistamine.