THENALIDINE

Thenalidine
Clinical data
ATC code	D04AA03 ( WHO) R06AX03 ( WHO) ; R06AX53 ( WHO) (combinations);
Identifiers
	IUPAC name 1-Methyl-N-phenyl-N-(2-thienylmethyl)piperidin-4-amine;
CAS Number	86-12-4 ;
PubChem CID	27901;
DrugBank	DB04826 ;
ChemSpider	25957 ;
UNII	6U94N2D00F;
KEGG	D07194 ;
CompTox Dashboard ( EPA)	DTXSID1048835 ;
ECHA InfoCard	100.001.501
Chemical and physical data
Formula	C17H22N2S
Molar mass	286.44 g·mol−1
3D model ( JSmol)	Interactive image;
	SMILES s1c(ccc1)CN(c2ccccc2)C3CCN(C)CC3;
	InChI InChI=1S/C17H22N2S/c1-18-11-9-16(10-12-18)19(14-17-8-5-13-20-17)15-6-3-2-4-7-15/h2-8,13,16H,9-12,14H2,1H3 ; Key:KLOHYVOVXOUKQI-UHFFFAOYSA-N ;
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Thenalidine is an antihistamine with anticholinergic properties used as an antipruritic drug.^[1] It was withdrawn from the US, Canadian, and UK markets in 1963 due to a risk of neutropenia.^[2]

References

^ Getzler NA, Ereaux LP (March 1959). "Evaluation of thenalidine tratrate (sandostene) in dermatological disorders". Canadian Medical Association Journal. 80 (6): 445–8. PMC 1830689. PMID 13629433.
^ "Thenalidine". DrugBank.

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[1] Getzler NA, Ereaux LP (March 1959). "Evaluation of thenalidine tratrate (sandostene) in dermatological disorders". Canadian Medical Association Journal. 80 (6): 445–8. PMC 1830689. PMID 13629433.

[2] "Thenalidine". DrugBank.

[1]

[2]

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

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

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

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

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Clinical data

ATC code	D04AA03 ( WHO) R06AX03 ( WHO) R06AX53 ( WHO) (combinations)
Identifiers
IUPAC name 1-Methyl-N-phenyl-N-(2-thienylmethyl)piperidin-4-amine
CAS Number	86-12-4^Y
PubChem CID	27901
DrugBank	DB04826^Y
ChemSpider	25957^N
UNII	6U94N2D00F
KEGG	D07194^Y
CompTox Dashboard ( EPA)	DTXSID1048835
ECHA InfoCard	100.001.501
Chemical and physical data
Formula	C₁₇H₂₂N₂S
Molar mass	286.44 g·mol⁻¹
3D model ( JSmol)	Interactive image
SMILES s1c(ccc1)CN(c2ccccc2)C3CCN(C)CC3
InChI InChI=1S/C17H22N2S/c1-18-11-9-16(10-12-18)19(14-17-8-5-13-20-17)15-6-3-2-4-7-15/h2-8,13,16H,9-12,14H2,1H3^N Key:KLOHYVOVXOUKQI-UHFFFAOYSA-N^N
^NY (what is this?) (verify)