pimethixene

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477508648

| IUPAC_name = 1-Methyl-4-(9H-thioxanthen-9-ylidene)piperidine

| image = Pimethixene.png

| tradename =

| Drugs.com = {{drugs.com|international|pimethixene}}

| pregnancy_category =

| legal_status =

| routes_of_administration = Oral, nasal

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 314-03-4

| ATC_prefix = R06

| ATC_suffix = AX23

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 152408

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = NZLVRVYNQYGMAB-UHFFFAOYSA-N

| PubChem = 4822

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = T46J20J26F

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D07406

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 4656

| smiles = S2c1ccccc1/C(c3c2cccc3)=C4/CCN(C)CC4

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C19H19NS/c1-20-12-10-14(11-13-20)19-15-6-2-4-8-17(15)21-18-9-5-3-7-16(18)19/h2-9H,10-13H2,1H3

| C=19 | H=19 | N=1 | S=1

}}

Pimethixene is an antihistamine and anticholinergic of the thioxanthene chemical class originally developed to treat hyperactivity,{{cite journal | vauthors = Chefneux A | title = [New treatment of hyperkinesis in the child: pimethixene] | journal = Revue Médicale de Liège | volume = 33 | issue = 14 | pages = 500–3 | date = July 1978 | pmid = 674966 }} anxiety, sleep disorders, and allergy. It is also used for anesthesia and as a bronchodilator (to dilate the bronchi and bronchioles for more airflow).

In combination with pholcodine, it was sold in France by Laboratoires Salvoxyl in the 1970s as the antitussive Salvodex.{{cite web | url = https://www.oncowitan.com/2020/12/08/salvodex-9-1-methyl-4-piperylidenylthiaxanthene-and-pholcodine-from-laboratoires-salvoxyl-orleans-1971 | title = Salvodex® (9-(1-methyl, 4-piperylidenyl)thiaxanthene and pholcodine), from Laboratoires Salvoxyl (Orléans), 1971 | last = Bailly | first = Christian | publisher = Oncowitan | date = 8 December 2020 | accessdate = 4 January 2022}} Pimethixene alone is still available in Brazil under the trade name Muricalm.

In addition to its other activities, it is a highly potent but non-selective serotonin 5-HT_2B receptor antagonist.{{cite journal | vauthors = Schmitz B, Ullmer C, Segelcke D, Gwarek M, Zhu XR, Lübbert H | title = BF-1--a novel selective 5-HT2B receptor antagonist blocking neurogenic dural plasma protein extravasation in guinea pigs | journal = Eur J Pharmacol | volume = 751 | issue = | pages = 73–80 | date = March 2015 | pmid = 25666387 | doi = 10.1016/j.ejphar.2015.01.043 | url = }} The selective serotonin 5-HT_2B receptor antagonist BF-1 was derived from pimethixene.