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)[1] 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
PubChemCID	10240
DrugBank	DB09014 N
ChemSpider	9823 Y
UNII	H93K9455DD
KEGG	D07316 Y
CompTox Dashboard(EPA)	DTXSID50862014
ECHA InfoCard	100.006.936
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 ascaptodiamine, is anantihistamine sold under the trade namesCovatine,Covatix, andSuvren which is used as asedative andanxiolytic. The structure is related todiphenhydramine.^[2]

A 2004 study suggested captodiame may be helpful in preventingbenzodiazepine withdrawal syndrome in people discontinuingbenzodiazepine treatment.^[2]

In addition to its actions as an antihistamine, captodiamine has been found to act as a5-HT_2C receptorantagonist andσ₁ receptor andD₃ receptoragonist.^[3] It producesantidepressant-like effects in rats.^[3] However, captodiamine is unique among antidepressant-like drugs in that it increasesbrain-derived neurotrophic factor (BDNF) levels in thehypothalamus but not in thefrontal cortex orhippocampus.^[3] This unique action may be related to its ability to attenuatestress-inducedanhedonia andcorticotropin-releasing factor (CRF) signaling in the hypothalamus.^[3]

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.

Friedel-Crafts acylation of the n-butyl ether of thiophenol withbenzoyl chloride gives the correspondingbenzophenone. Reduction of the ketone with zinc/NaOH followed by treatment with HCl in ether affords the benzhydryl chloride. Displacement of the halogen withthiourea gives, by reaction of the last at its most nucleophilic center, theisothiouronium salt. Hydrolysis of the salt leads to the sulfur analog of a benzhydrol. Alkylation of the sodium salt of this last withN-(2-chloroethyl)dimethylamine affords captodiame.

• Hydroxyzine
• Cyproheptadine

• 5-HT2C antagonists
• Antihistamines
• Anxiolytics
• Dopamine agonists
• H1 receptor antagonists
• Muscarinic antagonists
• Sedatives
• Sigma agonists
• Thioethers

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