captodiame captodiame captodiame (inn), also known as captodiamine, is an antihistamine sold under the trade names covatine, covatix, and suvren which is used as a sedative and anxiolytic. the structure is related to diphenhydramine. captodiameclinical dataahfs/drugs.cominternational drug namesroutes ofadministrationoralatc coden05bb02 (who) legal statuslegal status in general: ℞ (prescription only) pharmacokinetic dataexcretionrenalidentifiers iupac name 2-sulfanyl-n,n-dimethylethanamine cas number486-17-9 ypubchem cid10240drugbankdb09014 nchemspider9823 yuniih93k9455ddkeggd07316 yecha infocard100.006.936 chemical and physical dataformulac21h29ns2molar mass359.59 g·mol−13d model (jsmol)interactive image smiles s(c1ccc(cc1)c(sccn(c)c)c2ccccc2)cccc inchi inchi=1s/c21h29ns2/c1-4-5-16-23-20-13-11-19(12-14-20)21(24-17-15-22(2)3)18-9-7-6-8-10-18/h6-14,21h,4-5,15-17h2,1-3h3 ykey:izlpzxszllelbj-uhfffaoysa-n y ny (what is this?) (verify) a 2004 study suggested captodiame may be helpful in preventing benzodiazepine withdrawal syndrome in people discontinuing benzodiazepine treatment. in addition to its actions as an antihistamine, captodiamine has been found to act as a 5-ht2c receptor antagonist and σ1 receptor and d3 receptor agonist. it produces antidepressant-like effects in rats. however, captodiamine is unique among antidepressant-like drugs in that it increases brain-derived neurotrophic factor (bdnf) levels in the hypothalamus but not in the frontal cortex or hippocampus. this unique action may be related to its ability to attenuate stress-induced anhedonia and corticotropin-releasing factor (crf) signaling in the hypothalamus. synthesis the oxygen atom in these molecules can in many cases be dispensed with as well; substitution of sulfur for nitrogen affords a molecule whose salient biologic properties are those of a sedative and tranquilizer. captodiamine synthesis: hubner oluf herman, petersen povl viggo. u.s. patent 2,830,088 (1958). friedel-crafts acylation of the n-butyl ether of thiophenol with benzoyl chloride gives the corresponding benzophenone. reduction of the ketone with zinc/naoh followed by treatment with hcl in ether affords the benzhydryl chloride. displacement of the halogen with thiourea gives, by reaction of the last at its most nucleophilic center, the isothiouronium salt. hydrolysis of the salt leads to the sulfur analog of a benzhydrol. alkylation of the sodium salt of this last with n-(2-chloroethyl)dimethylamine affords captodiame.