Chemistry:Captodiame

Short description: Chemical compound

Captodiame

Clinical data
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	N05BB02 (WHO)
Legal status
Legal status	BR: Class C1 (Other controlled substances) In general: ℞ (Prescription only)
Pharmacokinetic data
Excretion	Renal
Identifiers
IUPAC name 2-[(4-butylsulfanylphenyl)-phenyl-methyl]sulfanyl-N,N-dimethylethanamine
CAS Number	486-17-9 Y
PubChem CID	10240
DrugBank	DB09014 N
ChemSpider	9823 Y
UNII	H93K9455DD
KEGG	D07316 Y
Chemical and physical data
Formula	C21H29NS2
Molar mass	359.59 g·mol−1
3D 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 Y Key:IZLPZXSZLLELBJ-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

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.

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-HT_2C 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.

See also

• Hydroxyzine
• Cyproheptadine