Tolpropamine

Chemical compound

D04AA12 (WHO)

Identifiers

IUPAC name

N,N-dimethyl-3-(4-methylphenyl)-3-phenylpropan-1-amine

CAS Number

5632-44-0 3354-67-4

PubChem CID

72141

ChemSpider

65115^Y

UNII

TBZ8909KFS

KEGG

D07196^Y

ECHA InfoCard100.024.611

Chemical and physical dataFormulaC₁₈H₂₃NMolar mass253.389 g·mol⁻¹3D model (JSmol)

Interactive image

SMILES

c1cc(ccc1C(c2ccccc2)CCN(C)C)C

InChI

InChI=1S/C18H23N/c1-15-9-11-17(12-10-15)18(13-14-19(2)3)16-7-5-4-6-8-16/h4-12,18H,13-14H2,1-3H3^Y
Key:CINROOONPHQHPO-UHFFFAOYSA-N^Y

(verify)

Tolpropamine is an antihistamine and anticholinergic used as an antipruritic.^[1]

References

^ Kutscher B (2000-06-15). "Dermatologicals (D), 2. Antifungals (D01), Emollients and Protectives (D02), and Antipruritics (D04) for Dermatological Use". In Ley C (ed.). Ullmann's Encyclopedia of Industrial Chemistry. pp. 1–24. doi:10.1002/14356007.w08_w01. ISBN 978-3-527-30385-4. S2CID 225510885.

Antipruritics (D04)

Antihistamines for topical use

Anesthetics for topical use

Others

Corticosteroids (e.g., hydrocortisone)
Counterirritants (e.g., mint oil, menthol, camphor)
Difelikefalin
Nalfurafine

Acetylcholine receptor modulators

Muscarinic acetylcholine receptor modulators

mAChRsTooltip Muscarinic acetylcholine receptors

Agonists

77-LH-28-1
AC-42
AC-260,584
Aceclidine
Acetylcholine
AF30
AF150(S)
AF267B
Alvameline
AQRA-741
Arecoline
Bethanechol
Bevonium
Butyrylcholine
Carbachol
CDD-0034
CDD-0078
CDD-0097
CDD-0098
CDD-0102
Cevimeline
Choline
cis-Dioxolane
Clozapine
Desmethylclozapine (norclozapine)
Ethoxysebacylcholine
Itameline
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
Suberyldicholine
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 (+formoterol)
Abediterol
AF-DX 250
AF-DX 384
Ambutonium bromide
Anisodamine
Anisodine
Antihistamines (first-generation) (e.g., brompheniramine, buclizine, captodiame, chlorphenamine (chlorpheniramine), cinnarizine, clemastine, cyproheptadine, dimenhydrinate, dimetindene, diphenhydramine, doxylamine, meclizine, mequitazine, perlapine, phenindamine, pheniramine, phenyltoloxamine, promethazine, propiomazine, triprolidine)
AQ-RA 741
Atropine
Atropine methonitrate
Atypical antipsychotics (e.g., clozapine, fluperlapine, olanzapine (+fluoxetine), rilapine, quetiapine, tenilapine, zotepine)
Benactyzine
Benzatropine (benztropine)
Benzilone
Benzilylcholine mustard
Benzydamine
BIBN 99
Biperiden
Bornaprine
Camylofin
CAR-226,086
CAR-301,060
CAR-302,196
CAR-302,282
CAR-302,368
CAR-302,537
CAR-302,668
Caramiphen
Cimetropium bromide
Clidinium bromide
Cloperastine
CS-27349
Cyclobenzaprine
Cyclopentolate
Darifenacin
DAU-5884
Desfesoterodine
Dexetimide
DIBD
Dicycloverine (dicyclomine)
Dihexyverine
Difemerine
Diphemanil metilsulfate
Ditran
Drofenine
EA-3167
EA-3443
EA-3580
EA-3834
Emepronium bromide
Etanautine
Etybenzatropine (ethybenztropine)
Fenpiverinium
Fentonium bromide
Fesoterodine
Flavoxate
Glycopyrronium bromide (+beclometasone/formoterol, +indacaterol, +neostigmine)
Hexahydrodifenidol
Hexahydrosiladifenidol
Hexbutinol
Hexocyclium
Himbacine
HL-031,120
Homatropine
Imidafenacin
Ipratropium bromide (+salbutamol)
Isopropamide
J-104,129
Hyoscyamine
Mamba toxin 3
Mamba toxin 7
Mazaticol
Mebeverine
Meladrazine
Mepenzolate
Methantheline
Methoctramine
Methylatropine
Methylhomatropine
Methylscopolamine
Metixene
Muscarinic toxin 7
N-Ethyl-3-piperidyl benzilate
N-Methyl-3-piperidyl benzilate
Nefopam
Octatropine methylbromide (anisotropine methylbromide)
Orphenadrine
Otenzepad (AF-DX 116)
Otilonium bromide
Oxapium iodide
Oxitropium bromide
Oxybutynin
Oxyphencyclimine
Oxyphenonium bromide
PBID
PD-102,807
PD-0298029
Penthienate
Pethidine
pFHHSiD
Phenglutarimide
Phenyltoloxamine
Pipenzolate bromide
Piperidolate
Pirenzepine
Piroheptine
Pizotifen
Poldine
Pridinol
Prifinium bromide
Procyclidine
Profenamine (ethopropazine)
Propantheline bromide
Propiverine
Quinidine
3-Quinuclidinyl thiochromane-4-carboxylate
Revefenacin
Rociverine
RU-47,213
SCH-57,790
SCH-72,788
SCH-217,443
Scopolamine (hyoscine)
Scopolamine butylbromide (hyoscine butylbromide)
Silahexacyclium
Sofpironium bromide
Solifenacin
SSRIsTooltip Selective serotonin reuptake inhibitors (e.g., femoxetine, paroxetine)
Telenzepine
Terodiline
Tetracyclic antidepressants (e.g., amoxapine, maprotiline, mianserin, mirtazapine)
Tiemonium iodide
Timepidium bromide
Tiotropium bromide
Tiquizium bromide
Tofenacin
Tolterodine
Tricyclic antidepressants (e.g., amitriptyline (+perphenazine), amitriptylinoxide, butriptyline, cidoxepin, clomipramine, desipramine, desmethyldesipramine, dibenzepin, dosulepin (dothiepin), doxepin, imipramine, lofepramine, nitroxazepine, northiaden (desmethyldosulepin), nortriptyline, protriptyline, quinupramine, trimipramine)
Tridihexethyl
Trihexyphenidyl
Trimebutine
Tripitamine (tripitramine)
Tropacine
Tropatepine
Tropicamide
Trospium chloride
Typical antipsychotics (e.g., chlorpromazine, chlorprothixene, cyamemazine (cyamepromazine), loxapine, mesoridazine, thioridazine)
Umeclidinium bromide (+vilanterol)
WIN-2299
Xanomeline
Zamifenacin

Precursors
(and prodrugs)

See also: Receptor/signaling modulators; Nicotinic acetylcholine receptor modulators; Acetylcholine metabolism/transport modulators

Nicotinic acetylcholine receptor modulators

nAChRsTooltip Nicotinic acetylcholine receptors

Agonists
(and PAMsTooltip positive allosteric modulators)

Antagonists
(and NAMsTooltip negative allosteric modulators)

18-MAC
18-MC
α-Neurotoxins (e.g., α-bungarotoxin, α-cobratoxin, α-conotoxin, many others)
ABT-126
Alcuronium
Allopregnanolone
Amantadine
Anatruxonium
AQW051
Atracurium
Barbiturates (e.g., pentobarbital, sodium thiopental)
BNC-210
Bungarotoxins (e.g., α-bungarotoxin, κ-bungarotoxin)
Bupropion
BW284C51
BW-A444
Candocuronium iodide (chandonium iodide)
Chlorisondamine
Cisatracurium
Coclaurine
Coronaridine
Curare
Cyclopropane
Dacuronium bromide
Decamethonium
Dehydronorketamine
Desflurane
Dextromethorphan
Dextropropoxyphene
Dextrorphan
Diadonium
DHβE
Dihydrochandonium
Dimethyltubocurarine (metocurine)
Dioscorine
Dipyrandium
Dizocilpine (MK-801)
Doxacurium
Encenicline
Enflurane
Erythravine
Esketamine
Fazadinium
Gallamine
Gantacurium chloride
Halothane
Hexafluronium
Hexamethonium (benzohexonium)
Hydroxybupropion
Hydroxynorketamine
Ibogaine
Isoflurane
Ketamine
Kynurenic acid
Laudanosine
Laudexium (laudolissin)
Levacetylmethadol
Levomethadone
Malouetine
ME-18-MC
Mecamylamine
Memantine
Methadone
Methorphan (racemethorphan)
Methyllycaconitine
Metocurine
Mivacurium
Morphanol (racemorphan)
Neramexane
Nitrous oxide
Norketamine
Pancuronium bromide
Pempidine
Pentamine
Pentolinium
Phencyclidine
Pipecuronium bromide
Progesterone
Promegestone
Radafaxine
Rapacuronium bromide
Reboxetine
Rocuronium bromide
Sevoflurane
Stercuronium iodide
Surugatoxin
Thiocolchicoside
Threohydrobupropion
Toxiferine
Tramadol
Trimetaphan camsilate (trimethaphan camsylate)
Tropeinium
Tubocurarine
Vanoxerine
Vecuronium bromide
Xenon

Precursors
(and prodrugs)

See also: Receptor/signaling modulators; Muscarinic acetylcholine receptor modulators; Acetylcholine metabolism/transport modulators

Histamine receptor modulators

H₁

Agonists

Antagonists

First-generation: 4-Methyldiphenhydramine
Alimemazine
Antazoline
Azatadine
Bamipine
Benzatropine (benztropine)
Bepotastine
Bromazine
Brompheniramine
Buclizine
Captodiame
Carbinoxamine
Chlorcyclizine
Chloropyramine
Chlorothen
Chlorphenamine
Chlorphenoxamine
Cinnarizine
Clemastine
Clobenzepam
Clocinizine
Cloperastine
Cyclizine
Cyproheptadine
Dacemazine
Decloxizine
Deptropine
Dexbrompheniramine
Dexchlorpheniramine
Dimenhydrinate
Dimetindene
Diphenhydramine
Diphenylpyraline
Doxylamine
Embramine
Etodroxizine
Etybenzatropine (ethylbenztropine)
Etymemazine
Fenethazine
Flunarizine
Histapyrrodine
Homochlorcyclizine
Hydroxyethylpromethazine
Hydroxyzine
Isopromethazine
Isothipendyl
Meclozine
Medrylamine
Mepyramine (pyrilamine)
Mequitazine
Methafurylene
Methapyrilene
Methdilazine
Moxastine
Orphenadrine
Oxatomide
Oxomemazine
Perlapine
Phenindamine
Pheniramine
Phenyltoloxamine
Pimethixene
Piperoxan
Pipoxizine
Promethazine
Propiomazine
Pyrrobutamine
Talastine
Thenalidine
Thenyldiamine
Thiazinamium
Thonzylamine
Tolpropamine
Tripelennamine
Triprolidine

Second/third-generation: Acrivastine
Alinastine
Astemizole
Azelastine
Bamirastine
Barmastine
Bepiastine
Bepotastine
Bilastine
Cabastinen
Carebastine
Cetirizine
Clemastine
Clemizole
Clobenztropine
Desloratadine
Dorastine
Ebastine
Efletirizine
Emedastine
Epinastine
Fexofenadine
Flezelastine
Ketotifen
Latrepirdine
Levocabastine
Levocetirizine
Linetastine
Loratadine
Mapinastine
Mebhydrolin
Mizolastine
Moxastine
Noberastine
Octastine
Olopatadine
Perastine
Pibaxizine
Piclopastine
Quifenadine (phencarol)
Rocastine
Rupatadine
Setastine
Sequifenadine (bicarphen)
Talastine
Temelastine
Terfenadine
Vapitadine
Zepastine

Others: Atypical antipsychotics (e.g., aripiprazole, asenapine, brexpiprazole, brilaroxazine, clozapine, iloperidone, olanzapine, paliperidone, quetiapine, risperidone, ziprasidone, zotepine)
Phenylpiperazine antidepressants (e.g., hydroxynefazodone, nefazodone, trazodone, triazoledione)
Tetracyclic antidepressants (e.g., amoxapine, loxapine, maprotiline, mianserin, mirtazapine, oxaprotiline)
Tricyclic antidepressants (e.g., amitriptyline, butriptyline, clomipramine, desipramine, dosulepin (dothiepin), doxepin, imipramine, iprindole, lofepramine, nortriptyline, protriptyline, trimipramine)
Typical antipsychotics (e.g., chlorpromazine, flupenthixol, fluphenazine, loxapine, perphenazine, prochlorperazine, thioridazine, thiothixene)

Unknown/unsorted: Azanator
Belarizine
Elbanizine
Flotrenizine
GSK1004723
Napactadine
Tagorizine
Trelnarizine
Trenizine

H₂

Agonists	Amthamine Betazole Dimaprit Histamine HTMT Impromidine L-Histidine UR-AK49
Antagonists	Bisfentidine Burimamide Cimetidine Dalcotidine Donetidine Ebrotidine Etintidine Famotidine Isolamtidine Lafutidine Lamtidine Lavoltidine (loxtidine) Lupitidine Metiamide Mifentidine Niperotidine Nizatidine Osutidine Oxmetidine Pibutidine Quisultazine (quisultidine) Ramixotidine Ranitidine Roxatidine Sufotidine Tiotidine Tuvatidine Venritidine Xaltidine Zolantidine

H₃

Agonists	α-Methylhistamine Cipralisant Histamine Imetit Immepip Immethridine L-Histidine Methimepip Proxyfan
Antagonists	A-349821 A-423579 ABT-239 ABT-652 AZD5213 Bavisant Betahistine Burimamide Ciproxifan Clobenpropit Conessine Enerisant GSK-189254 Impentamine Iodophenpropit Irdabisant JNJ-5207852 NNC 38-1049 PF-03654746 Pitolisant SCH-79687 Thioperamide VUF-5681

H₄

Agonists	4-Methylhistamine α-Methylhistamine Histamine L-Histidine OUP-16 VUF-8430
Antagonists	JNJ-7777120 Mianserin Seliforant Thioperamide Toreforant VUF-6002