Alimemazine

{{Short description|Chemical compound}}

{{Use dmy dates|date=April 2025}}

{{cs1 config |name-list-style=vanc |display-authors=6}}

{{Infobox drug

| Watchedfields = changed

| verifiedrevid = 477317349

| image = Alimemazine.svg

| alt =

| image2 = Alimemazine Tartrate 10mg.jpg

| alt2 =

| USAN=trimeprazine

| BAN=trimeprazine

| tradename =

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

| DailyMedID = Trimeprazine

| MedlinePlus =

| pregnancy_AU = C

| routes_of_administration = By mouth

| class = Anti-allergic agent

| ATC_prefix = R06

| ATC_suffix = AD01

| ATC_supplemental =

| legal_AU =

| legal_UK = POM

| legal_US = Rx-only

| legal_US_comment = {{cite web | title=Trimeprazine tartrate powder | website=DailyMed | date=14 March 2019 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=44b6cea3-21d4-4164-830b-91fa1fab6510 | access-date=15 July 2024}}

| metabolism = Liver

| elimination_half-life = 4.78 ± 0.59 hours{{cite journal | vauthors = Hu OY, Gfeller E, Perrin JH, Curry SH | title = Relative bioavailability of trimeprazine tablets investigated in man using HPLC with electrochemical detection | journal = The Journal of Pharmacy and Pharmacology | volume = 38 | issue = 3 | pages = 172–6 |date=March 1986 | pmid = 2871150 | doi = 10.1111/j.2042-7158.1986.tb04539.x| s2cid = 506087 }}

| IUPHAR_ligand = 7237

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 84-96-8

| PubChem = 5574

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB01246

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

| ChemSpiderID = 5373

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

| UNII = 76H78MJJ52

| UNII2 = 362NW1LD6Z

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

| KEGG = D07125

| KEGG2 = D02245

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

| ChEMBL = 829

| synonyms = trimeprazine

| IUPAC_name = N,N,2-trimethyl-3-phenothiazin-10-yl-propan-1-amine

| C=18 | H=22 | N=2 | S=1

| smiles = S2c1ccccc1N(c3c2cccc3)CC(C)CN(C)C

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

| StdInChI = 1S/C18H22N2S/c1-14(12-19(2)3)13-20-15-8-4-6-10-17(15)21-18-11-7-5-9-16(18)20/h4-11,14H,12-13H2,1-3H3

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

| StdInChIKey = ZZHLYYDVIOPZBE-UHFFFAOYSA-N

}}

Alimemazine (INN), also known as trimeprazine, commonly provided as a tartrate salt, is a phenothiazine derivative that is used as an antipruritic (it prevents itching from causes such as eczema or poison ivy, by acting as an antihistamine).{{Cite web|url=https://pubchem.ncbi.nlm.nih.gov/compound/78032|title=(3R,4R)-3,4-dihydroxyhexane-2,5-dione;N,N,2-trimethyl-3-phenothiazin-10-ylpropan-1-amine|website=pubchem.ncbi.nlm.nih.gov}} It also acts as a sedative, hypnotic, and antiemetic for prevention of motion sickness.

Despite being structurally related to the molecule chlorpromazine, it is not used as an antipsychotic.{{cite web|url=https://go.drugbank.com/drugs/DB01246 |title=Alimemazine|access-date=2007-09-15|archive-date=2006-12-30|archive-url=https://web.archive.org/web/20061230231431/http://redpoll.pharmacy.ualberta.ca/drugbank/cgi-bin/getCard.cgi?CARD=APRD00258.txt|url-status=live}}