Thonzylamine

Last updated: 2025-07-25 07:38:57

Thonzylamine

Thonzylamine
Clinical data

Other names	Neohetramine
AHFS/Drugs.com	International Drug Names
ATC code	D04AA01 (WHO) R01AC06 (WHO) R06AC06 (WHO)
Identifiers
IUPAC name N-(4-methoxybenzyl)-N',N'-dimethyl-N-pyrimidin-2-ylethane-1,2-diamine
CAS Number	91-85-0^N 63-56-9
PubChem CID	5457
ChemSpider	5258^Y
UNII	R79646H5Z8
KEGG	D08587^Y
ChEMBL	ChEMBL1623738^N
CompTox Dashboard (EPA)	DTXSID8043864
ECHA InfoCard	100.001.913
Chemical and physical data
Formula	C₁₆H₂₂N₄O
Molar mass	286.379 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES n1cccnc1N(CCN(C)C)Cc2ccc(OC)cc2
InChI InChI=1S/C16H22N4O/c1-19(2)11-12-20(16-17-9-4-10-18-16)13-14-5-7-15(21-3)8-6-14/h4-10H,11-13H2,1-3H3^Y Key:GULNIHOSWFYMRN-UHFFFAOYSA-N^Y
^NY (what is this?) (verify)

Thonzylamine (or neohetramine)^[1] is an antihistamine and anticholinergic used as an antipruritic.

Synthesis

Thonzylamine synthesis: H. L. Friedman and A, V. Tolstouhov, U.S. patent 2,465,865 (1949).

References

↑ Arminio JJ, Sweet CC (December 1949). "The prophylaxis and treatment of the common cold with neohetramine (thonzylamine hydrochloride)". Industrial Medicine & Surgery. 18 (12): 509–11. PMID 15393969.

v t e Antipruritics (D04)
Antihistamines for topical use	Bamipine Chloropyramine Chlorphenoxamine Clemastine Dimetindene Diphenhydramine Isothipendyl Mepyramine Pheniramine Promethazine Thenalidine Thonzylamine Tolpropamine Tripelennamine
Anesthetics for topical use	Benzocaine Cinchocaine Dibucaine Lidocaine Oxybuprocaine Pramocaine Quinisocaine Tetracaine
Others	Corticosteroids (e.g., hydrocortisone) Counterirritants (e.g., mint oil, menthol, camphor) Difelikefalin Doxepin Nalfurafine

Decongestants and other nasal preparations (R01)

Topical

Sympathomimetics, plain	Amidephrine Cyclopentamine Ephedrine Epinephrine Fenoxazoline Iproheptine Levmetamfetamine Methylephedrine Metizoline Naphazoline Oxymetazoline Phenylephrine Propylhexedrine Tetryzoline Tramazoline Tuaminoheptane Tymazoline Xylometazoline
Antiallergic agents, excluding corticosteroids	Spaglumic acid histamine antagonists (Levocabastine Antazoline Thonzylamine) mast cell stabilizer (some are also antihistamines) (Cromoglicic acid Nedocromil Azelastine Olopatadine Lodoxamide)
Corticosteroids	Beclometasone dipropionate Betamethasone^# Budesonide Ciclesonide Dexamethasone Flunisolide Fluticasone (Fluticasone furoate, Fluticasone propionate) Mometasone furoate Prednisolone^# Tixocortol Triamcinolone Triamcinolone acetonide
Other nasal preparations	Cafaminol Calcium hexamine thiocyanate Eucalyptus oil Framycetin Hexamidine Hyaluronan Ipratropium bromide Mupirocin Retinol Ritiometan Saline water
Combination products	Olopatadine/mometasone

Systemic use:
Sympathomimetics

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

v t e Antihistamines (R06)
Benzimidazoles (*)	Astemizole Azelastine Bilastine Emedastine Mizolastine Talastine
Diarylmethanes	Diarylmethoxyalkylamines: Bromazine (bromodiphenhydramine) Carbinoxamine Chlorphenoxamine Clemastine Diphenhydramine (+naproxen) Diphenylpyraline Doxylamine Ebastine Orphenadrine Diphenylmethanolpiperidines: Fexofenadine Terfenadine Diphenylmethylpiperazines: Buclizine Cetirizine Levocetirizine Chlorcyclizine Cinnarizine Cyclizine Etodroxizine Hydroxyzine Meclizine Oxatomide Phenylpyridinylpropanamines: Brompheniramine Chlorphenamine Dexbrompheniramine (+pseudoephedrine) Dexchlorpheniramine (+betamethasone) Pheniramine Others: Acrivastine Bamipine Dimetindene Phenyltoloxamine Pyrrobutamine Quifenadine Triprolidine
Ethylenediamines	Antazoline Chloropyramine Histapyrrodine Mepyramine (pyrilamine) Methapyrilene Phenbenzamine Thenalidine Tripelennamine (pyribenzamine)
Tricyclics	Dibenzocycloheptenes: Antidepressants (e.g., amitriptyline) Azatadine Cyproheptadine Deptropine Desloratadine Ketotifen Loratadine Rupatadine Phenothiazines: Alimemazine Fenethazine Hydroxyethylpromethazine Isothipendyl Mequitazine Methdilazine Oxomemazine Promethazine Others: Antidepressants (e.g., doxepin, mirtazapine, trimipramine) Epinastine Latrepirdine Mebhydrolin Olopatadine Perlapine Phenindamine Pimethixene
Others	Phenylpiperazines: Antidepressants (e.g., trazodone) Phenbenzamine
For topical use	Bamipine Chloropyramine Chlorphenoxamine Clemastine Dimetindene Diphenhydramine Doxepin Isothipendyl Mepyramine (pyrilamine) Promethazine

Acetylcholine receptor modulators

Muscarinic acetylcholine receptor modulators

mAChRs

Agonists

Antagonists

Precursors
(and prodrugs)

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

Nicotinic acetylcholine receptor modulators

nAChRs

Agonists
(and PAMs)

Antagonists
(and NAMs)

Precursors
(and prodrugs)

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

Histamine receptor modulators

H₁

Agonists

Antagonists

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)

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

See also: Receptor/signaling modulators; Monoamine metabolism modulators; Monoamine reuptake inhibitors

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Thonzylamine

Synthesis

See also

References