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Captodiame

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Captodiame
Clinical data
AHFS/DrugsInternational Drug Names
Routes of
administration		Oral
ATC code
Legal status
Legal status
  • BR:Class C1(Other controlled substances)[1]
  • In general: ℞ (Prescription only)
Pharmacokineticdata
ExcretionRenal
Identifiers
  • 2-[(4-butylsulfanylphenyl)-phenyl-methyl]sulfanyl-N,N-dimethylethanamine
CAS Number
PubChemCID
DrugBank
ChemSpider
UNII
KEGG
CompTox Dashboard(EPA)
ECHA InfoCard100.006.936Edit this at Wikidata
Chemical and physical data
FormulaC21H29NS2
Molar mass359.59g·mol−1
3D model (JSmol)
  • S(c1ccc(cc1)C(SCCN(C)C)c2ccccc2)CCCC
  • 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,4-5,15-17H2,1-3H3checkY
  • Key:IZLPZXSZLLELBJ-UHFFFAOYSA-NcheckY
☒NcheckY(what is this?)(verify)

Captodiame(INN), also known ascaptodiamine,is anantihistaminesold under the trade namesCovatine,Covatix,andSuvrenwhich is used as asedativeandanxiolytic.The structure is related todiphenhydramine.[2]

A 2004 study suggested captodiame may be helpful in preventingbenzodiazepine withdrawal syndromein people discontinuingbenzodiazepinetreatment.[2]

In addition to its actions as an antihistamine, captodiamine has been found to act as a5-HT2Creceptorantagonistandσ1receptorandD3receptoragonist.[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 thehypothalamusbut not in thefrontal cortexorhippocampus.[3]This unique action may be related to its ability to attenuatestress-inducedanhedoniaandcorticotropin-releasing factor(CRF) signaling in the hypothalamus.[3]

Synthesis

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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-Craftsacylation of the n-butyl ether of thiophenol withbenzoyl chloridegives the correspondingbenzophenone.Reduction of the ketone with zinc/NaOH followed by treatment with HCl in ether affords the benzhydryl chloride. Displacement of the halogen withthioureagives, by reaction of the last at its most nucleophilic center, theisothiouroniumsalt. 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.

See also

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References

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  1. ^Anvisa(2023-03-31)."RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial"[Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese).Diário Oficial da União(published 2023-04-04).Archivedfrom the original on 2023-08-03.Retrieved2023-08-16.
  2. ^abMercier-Guyon C, Chabannes JP, Saviuc P (2004). "The role of captodiamine in the withdrawal from long-term benzodiazepine treatment".Curr Med Res Opin.20(9): 1347–55.doi:10.1185/030079904125004457.PMID15383182.S2CID32561767.Free full text with registration
  3. ^abcdRing RM, Regan CM (October 2013). "Captodiamine, a putative antidepressant, enhances hypothalamic BDNF expression in vivo by synergistic 5-HT2c receptor antagonism and sigma-1 receptor agonism".J. Psychopharmacol. (Oxford).27(10): 930–9.doi:10.1177/0269881113497614.hdl:10197/4383.PMID23863923.
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