Alimemazine

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Alimemazine


Systematic (IUPAC) name
N,N,2-trimethyl-3-phenothiazin-10-yl-propan-1-amine
Clinical data
AHFS/Drugs.com	International Drug Names
MedlinePlus	a600010
Pregnancy cat.	C (AU)
Legal status	?
Routes	Oral
Pharmacokinetic data
Metabolism	Hepatic
Half-life	4.78 ± 0.59 hours^[1]
Identifiers
CAS number	84-96-8^Y
ATC code	D04AA10 R06AD02, R06AD05
PubChem	CID 5574
DrugBank	DB01246
ChemSpider	5373^Y
UNII	76H78MJJ52^Y
KEGG	D07125^Y
ChEMBL	CHEMBL829^Y
Chemical data
Formula	C₁₈H₂₂N₂S
Mol. mass	298.447 g/mol
SMILES	eMolecules & PubChem
InChI InChI=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^Y Key:ZZHLYYDVIOPZBE-UHFFFAOYSA-N^Y
Y (what is this?) (verify)

Alimemazine (INN), also known as trimeprazine (former BAN and USAN; brand names Nedeltran, Panectyl, Repeltin, Therafene, Theraligene, Theralen, Theralene, Vallergan, Vanectyl, and Temaril), 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).^[2] It also acts as a sedative, hypnotic and antiemetic for prevention of motion sickness. Although it is structurally related to drugs such as chlorpromazine, it is not used as an antipsychotic treatment.^[3]

In veterinary use, the combination of alimemazine and prednisolone is licensed as an antipruritic and antitussive in dogs.

References

^ Hu OY, Gfeller E, Perrin JH, Curry SH (March 1986). "Relative bioavailability of trimeprazine tablets investigated in man using HPLC with electrochemical detection". The Journal of Pharmacy and Pharmacology 38 (3): 172–6. PMID 2871150.
^ "PubChem CID 78032". http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=78032.
^ "Drugbank:Trimeprazine". http://redpoll.pharmacy.ualberta.ca/drugbank/cgi-bin/getCard.cgi?CARD=APRD00258.txt.

Cholinergics

Receptor ligands

mAChR	Agonists: 77-LH-28-1 AC-42 AC-260,584 Aceclidine Acetylcholine AF30 AF150(S) AF267B AFDX-384 Alvameline AQRA-741 Arecoline Bethanechol Butyrylcholine Carbachol CDD-0034 CDD-0078 CDD-0097 CDD-0098 CDD-0102 Cevimeline cis-Dioxolane Ethoxysebacylcholine LY-593,039 L-689,660 LY-2,033,298 McNA343 Methacholine Milameline Muscarine NGX-267 Ocvimeline Oxotremorine PD-151,832 Pilocarpine RS86 Sabcomeline SDZ 210-086 Sebacylcholine Suberylcholine Talsaclidine Tazomeline Thiopilocarpine Vedaclidine VU-0029767 VU-0090157 VU-0152099 VU-0152100 VU-0238429 WAY-132,983 Xanomeline YM-796 Antagonists: 3-Quinuclidinyl Benzilate 4-DAMP Aclidinium Bromide Anisodamine Anisodine Atropine Atropine Methonitrate Benactyzine Benzatropine (Benztropine) Benzydamine BIBN 99 Biperiden Bornaprine CAR-226,086 CAR-301,060 CAR-302,196 CAR-302,282 CAR-302,368 CAR-302,537 CAR-302,668 CS-27349 Cyclobenzaprine Cyclopentolate Darifenacin DAU-5884 Dimethindene Dexetimide DIBD Dicyclomine (Dicycloverine) Ditran EA-3167 EA-3443 EA-3580 EA-3834 Etanautine Etybenzatropine (Ethylbenztropine) Flavoxate Himbacine HL-031,120 Ipratropium bromide J-104,129 Hyoscyamine Mamba Toxin 3 Mamba Toxin 7 Mazaticol Mebeverine Methoctramine Metixene N-Ethyl-3-Piperidyl Benzilate N-Methyl-3-Piperidyl Benzilate Orphenadrine Otenzepad Oxybutynin PBID PD-102,807 PD-0298029 Phenglutarimide Phenyltoloxamine Pirenzepine Piroheptine Procyclidine Profenamine RU-47,213 SCH-57,790 SCH-72,788 SCH-217,443 Scopolamine (Hyoscine) Solifenacin Telenzepine Tiotropium bromide Tolterodine Trihexyphenidyl Tripitamine Tropatepine Tropicamide WIN-2299 Xanomeline Zamifenacin; Others: 1st Generation Antihistamines (Brompheniramine chlorphenamine cyproheptadine dimenhydrinate diphenhydramine doxylamine mepyramine/pyrilamine phenindamine pheniramine tripelennamine triprolidine, etc) Tricyclic Antidepressants (Amitriptyline doxepin trimipramine, etc) Tetracyclic Antidepressants (Amoxapine maprotiline, etc) Typical Antipsychotics (Chlorpromazine thioridazine, etc) Atypical Antipsychotics (Clozapine olanzapine quetiapine, etc)

nAChR	Agonists: 5-HIAA A-84,543 A-366,833 A-582,941 A-867,744 ABT-202 ABT-418 ABT-560 ABT-894 Acetylcholine Altinicline Anabasine Anatoxin-a AR-R17779 Butyrylcholine Carbachol Cotinine Cytisine Decamethonium Desformylflustrabromine Dianicline Dimethylphenylpiperazinium Epibatidine Epiboxidine Ethanol Ethoxysebacylcholine EVP-4473 EVP-6124 Galantamine GTS-21 Ispronicline Lobeline MEM-63,908 (RG-3487) Nicotine NS-1738 PHA-543,613 PHA-709,829 PNU-120,596 PNU-282,987 Pozanicline Rivanicline Sazetidine A Sebacylcholine SIB-1508Y SIB-1553A SSR-180,711 Suberylcholine TC-1698 TC-1734 TC-1827 TC-2216 TC-5214 TC-5619 TC-6683 Tebanicline Tropisetron UB-165 Varenicline WAY-317,538 XY-4083 Antagonists: 18-Methoxycoronaridine α-Bungarotoxin α-Conotoxin Alcuronium Amantadine Anatruxonium Atracurium Bupropion (Amfebutamone) Chandonium Chlorisondamine Cisatracurium Coclaurine Coronaridine Dacuronium Decamethonium Dextromethorphan Dextropropoxyphene Dextrorphan Diadonium DHβE Dimethyltubocurarine (Metocurine) Dipyrandium Dizocilpine (MK-801) Doxacurium Duador Esketamine Fazadinium Gallamine Hexafluronium Hexamethonium (Benzohexonium) Ibogaine Isoflurane Ketamine Kynurenic acid Laudexium (Laudolissin) Levacetylmethadol Malouetine Mecamylamine Memantine Methadone Methorphan (Racemethorphan) Methyllycaconitine Metocurine Mivacurium Morphanol (Racemorphanol) Neramexane Nitrous Oxide Pancuronium Pempidine Pentamine Pentolinium Phencyclidine Pipecuronium Radafaxine Rapacuronium Rocuronium Surugatoxin Suxamethonium (Succinylcholine) Thiocolchicoside Toxiferine Trimethaphan Tropeinium Tubocurarine Vecuronium Xenon

Reuptake inhibitors

Plasmalemmal

CHT Inhibitors	Hemicholinium-3 (Hemicholine; HC3) Triethylcholine

Vesicular

VAChT Inhibitors	Vesamicol

Enzyme inhibitors

Anabolism

ChAT inhibitors	1-(-Benzoylethyl)pyridinium 2-(α-Naphthoyl)ethyltrimethylammonium 3-Chloro-4-stillbazole 4-(1-Naphthylvinyl)pyridine Acetylseco hemicholinium-3 Acryloylcholine AF64A B115 BETA CM-54,903 N,N-Dimethylaminoethylacrylate N,N-Dimethylaminoethylchloroacetate

Catabolism

AChE inhibitors	Reversible: Carbamates: Aldicarb Bendiocarb Bufencarb Carbaryl Carbendazim Carbetamide Carbofuran Chlorbufam Chloropropham Ethienocarb Ethiofencarb Fenobucarb Fenoxycarb Formetanate Furadan Ladostigil Methiocarb Methomyl Miotine Oxamyl Phenmedipham Pinmicarb Pirimicarb Propamocarb Propham Propoxur; Stigmines: Ganstigmine Neostigmine Phenserine Physostigmine Pyridostigmine Rivastigmine; Others: Acotiamide Ambenonium Donepezil Edrophonium Galantamine Huperzine A Minaprine Tacrine Zanapezil Irreversible: Organophosphates: Acephate Azinphos-methyl Bensulide Cadusafos Chlorethoxyfos Chlorfenvinphos Chlorpyrifos Chlorpyrifos-Methyl Coumaphos Cyclosarin (GF) Demeton Demeton-S-Methyl Diazinon Dichlorvos Dicrotophos Diisopropyl fluorophosphate (Guthion) Diisopropylphosphate Dimethoate Dioxathion Disulfoton EA-3148 Echothiophate Ethion Ethoprop Fenamiphos Fenitrothion Fenthion Fosthiazate GV Isofluorophate Isoxathion Malaoxon Malathion Methamidophos Methidathion Metrifonate Mevinphos Monocrotophos Naled Novichok agent Omethoate Oxydemeton-Methyl Paraoxon Parathion Parathion-Methyl Phorate Phosalone Phosmet Phostebupirim Phoxim Pirimiphos-Methyl Sarin (GB) Soman (GD) Tabun (GA) Temefos Terbufos Tetrachlorvinphos Tribufos Trichlorfon VE VG VM VR VX; Others: Demecarium Onchidal (Onchidella binneyi)

BChE inhibitors	Cymserine * Many of the acetylcholinesterase inhibitors listed above act as butyrylcholinesterase inhibitors.

Others

Precursors	Choline (Lecithin) Citicoline Cyprodenate Dimethylethanolamine (DMAE, deanol) Glycerophosphocholine Meclofenoxate (Centrophenoxine) Phosphatidylcholine Phosphatidylethanolamine Phosphorylcholine Pirisudanol

Cofactors	Acetic acid Acetylcarnitine Acetyl-coA Vitamin B₅ (Pantethine Pantetheine Panthenol)

Others	Acetylcholine releasing agents: α-Latrotoxin β-Bungarotoxin; Acetylcholine release inhibitors: Botulinum toxin (Botox); Acetylcholinesterase reactivators: Asoxime Obidoxime Pralidoxime

Histaminergics

Receptor
ligands

H₁	Agonists: 2-Pyridylethylamine Betahistine Histamine HTMT UR-AK49 Antagonists: "1st generation": 4-Methyldiphenhydramine Alimemazine Antazoline Azatadine Bamipine Benzatropine (Benztropine) Bepotastine Bromazine Brompheniramine Buclizine Captodiame Carbinoxamine Chlorcyclizine Chloropyramine Chlorothen Chlorphenamine Chlorphenoxamine Cinnarizine Clemastine Clobenzepam Clocinizine Cyclizine Cyproheptadine Dacemazine Deptropine Dexbrompheniramine Dexchlorpheniramine Dimenhydrinate Dimetindene Diphenhydramine Diphenylpyraline Doxylamine Embramine Etybenzatropine (Ethylbenztropine) Etymemazine Histapyrrodine Homochlorcyclizine Hydroxyethylpromethazine Hydroxyzine Isopromethazine Isothipendyl Meclozine Mepyramine (Pyrilamine) Mequitazine Methafurylene Methapyrilene Methdilazine Moxastine Niaprazine Orphenadrine Oxatomide Oxomemazine Phenindamine Pheniramine Phenyltoloxamine Pimethixene Piperoxan Promethazine Propiomazine Pyrrobutamine Talastine Thenalidine Thenyldiamine Thiazinamium Thonzylamine Tolpropamine Tripelennamine Triprolidine; "2nd generation": Acrivastine Astemizole Azelastine Cetirizine Clemizole Clobenztropine Ebastine Emedastine Epinastine Ketotifen Latrepirdine Levocabastine Loratadine Mebhydrolin Mizolastine Olopatadine Rupatadine Setastine Terfenadine; "3rd generation": Desloratadine Fexofenadine Levocetirizine; Miscellaneous: Tricyclic antidepressants (Amitriptyline Doxepin Trimipramine, etc) Tetracyclic antidepressants (Mianserin Mirtazapine, etc) Serotonin antagonist and reuptake inhibitors (Trazodone Nefazodone) Typical antipsychotics (Chlorpromazine Thioridazine, etc) Atypical antipsychotics (Clozapine Olanzapine Quetiapine, etc)

H₂	Agonists: Amthamine Betazole Dimaprit Histamine HTMT Impromidine UR-AK49 Antagonists: Burimamide Cimetidine Ebrotidine Famotidine Lafutidine Lavoltidine/Loxtidine Lupitidine Metiamide Niperotidine Nizatidine Oxmetidine Ranitidine Roxatidine

H₃	Agonists: α-Methylhistamine Cipralisant Histamine Imetit Immepip Immethridine Methimepip Proxyfan Antagonists: A-349,821 A-423,579 ABT-239 Betahistine Burimamide Ciproxifan Clobenpropit Conessine GSK-189,254 Impentamine Iodophenpropit JNJ-5,207,852 MK-0249 NNC-38-1,049 PF-03654746 Pitolisant SCH-79,687 Thioperamide VUF-5,681

H₄	Agonists: 4-Methylhistamine Histamine VUF-8,430 Antagonists: JNJ-7,777,120 Thioperamide VUF-6,002

Reuptake
inhibitors

Vesicular

VMAT inhibitors	Ibogaine Reserpine Tetrabenazine

Enzyme
inhibitors

Anabolism

HDC inhibitors	Catechin Meciadanol Naringenin Tritoqualine

Catabolism

HNMT inhibitors	Amodiaquine Diphenhydramine Harmaline Metoprine Quinacrine SKF-91,488 Tacrine

DAO inhibitors	Aminoguanidine

Others

Precursors	L-Histidine

Cofactors	Vitamin B6 (pyridoxine pyridoxamine pyridoxal → Pyridoxal phosphate)

v t e Tricyclics

Classes	Acridine Anthracene Dibenzazepine Dibenzocycloheptene Dibenzodiazepine Dibenzothiazepine Dibenzothiepin Dibenzoxazepine Dibenzoxepin Phenothiazine Pyridazinobenzoxazine Pyridinobenzodiazepine Thioxanthene

Antidepressants	7-OH-Amoxapine Amezepine Amineptine Amitriptyline Amitriptylinoxide Amoxapine Aptazapine Azepindole Azipramine Butriptyline Cianopramine Ciclazindol Ciclopramine Clomipramine Cotriptyline Cyanodothiepin Demexiptiline Depramine/Balipramine Desipramine Dibenzepin Dimetacrine Dosulepin/Dothiepin Doxepin Enprazepine Esmirtazapine Fluotracen Hepzidine Homopipramol Imipramine Imipraminoxide Intriptyline Iprindole Ketipramine Litracen Lofepramine Losindole Loxapine Maprotiline Mariptiline Mazindol Melitracen Metapramine Mezepine Mianserin Mirtazapine Naranol Nitroxazepine Nortriptyline Noxiptiline Octriptyline Opipramol Oxaprotiline Pipofezine Pirandamine Propizepine Protriptyline Quinupramine Setiptiline/Teciptiline Tandamine Tampramine Tianeptine Tienopramine Trimipramine

Antihistamines	Alimemazine Azatadine Clobenzepam Cyproheptadine Dacemazine Deptropine Desloratadine Epinastine Etymemazine Hydroxyethylpromethazine Isopromethazine Isothipendyl Ketotifen Latrepirdine Loratadine Mebhydrolin Mequitazine Methdilazine Olopatadine Oxomemazine Phenindamine Pimethixene Promethazine Propiomazine Rupatadine Thiazinamium

Antipsychotics	Acetophenazine Amoxapine Asenapine Butaclamol Butaperazine Carphenazine Carpipramine Chlorpromazine Chlorprothixene Ciclindole Clocapramine Clomacran Clorotepin Clotiapine Clozapine Cyanothepin Doclothepin Docloxythepin Erizepine Flucindole Flumezapine Fluotracen Flupentixol Fluphenazine Gevotroline Homopipramol Isofloxythepin Levomepromazine/Methotrimeprazine Loxapine Maroxepin Meperathiepin Mesoridazine Metitepine Metoxepin Mosapramine Naranol Octomethothepin Olanzapine Oxyclothepin Oxyprothepin Peradithiepin Perathiepin Perazine Perphenazine Periciazine Piperacetazine Pipotiazine Piquindone Prochlorperazine Promazine Prothipendyl Quetiapine Sulforidazine Thiethylperazine Thiopropazate Thioridazine Thiothixene Tilozepine Trifluoperazine Triflupromazine Trifluthepin Zotepine Zuclopenthixol

Others	Atiprosin Carbamazepine Carvedilol Cyclobenzaprine Darenzepine Elanzepine Eslicarbazepine acetate Etazepine Licarbazepine Methylene Blue Monatepil Nuvenzepine Oxcarbazepine Oxitriptyline Pirenzepine Pirolate Pitrazepin Pizotifen Profenamine Rispenzepine Serazapine Siltenzepine Telenzepine Zolenzepine

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Alimemazine

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