{{short description|Chemical compound}} {{Drugbox | IUPAC_name = ''N''-<nowiki/>{1-[2-(1''H''-indol-3-yl)ethyl]piperidin-4-yl}benzamide | image = Indoramin.svg | image_class = skin-invert-image
<!--Clinical data--> | tradename = | Drugs.com = {{drugs.com|international|indoramin}} | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_US = <!-- A / B / C / D / X --> | pregnancy_category = | legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S8 --> | legal_UK = <!-- GSL / P / POM / CD --> | legal_US = <!-- OTC / Rx-only --> | legal_status = | routes_of_administration =
<!--Pharmacokinetic data--> | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =
<!--Identifiers--> | CAS_number_Ref = {{cascite|correct|CAS}} | CAS_number = 26844-12-2 | ATC_prefix = C02 | ATC_suffix = CA02 | PubChem = 33625 | IUPHAR_ligand = 501 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB08950 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 31014 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 0Z802HMY7H | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = D04531 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 279516
<!--Chemical data--> | C=22 | H=25 | N=3 | O=1 | smiles = O=C(c1ccccc1)NC4CCN(CCc3c2ccccc2[nH]c3)CC4 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C22H25N3O/c26-22(17-6-2-1-3-7-17)24-19-11-14-25(15-12-19)13-10-18-16-23-21-9-5-4-8-20(18)21/h1-9,16,19,23H,10-15H2,(H,24,26) | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = JXZZEXZZKAWDSP-UHFFFAOYSA-N }} '''Indoramin''' (trade names '''Baratol''' and '''Doralese''') is a piperidine antiadrenergic agent.
It is an alpha-1 selective adrenoceptor antagonist<ref name="pmid3955309">{{cite journal | vauthors = Pierce V, Shepperson NB, Todd MH, Waterfall JF | title = Investigation into the cardioregulatory properties of the alpha 1-adrenoceptor blocker indoramin | journal = British Journal of Pharmacology | volume = 87 | issue = 2 | pages = 433–441 | date = February 1986 | pmid = 3955309 | pmc = 1916533 | doi = 10.1111/j.1476-5381.1986.tb10834.x }}</ref> with direct myocardial depression action; therefore, it results in no reflex tachycardia. It is also used in benign prostatic hyperplasia (BPH).<ref>{{cite web|url=http://www.medicines.org.uk/Guides/indoramin%20hydrochloride/prostatic%20hyperplasia%20(benign)|title=Indoramin 20mg tablets|publisher=Medicines.org.uk|date=April 20, 2011|access-date=September 30, 2012|archive-date=July 25, 2022|archive-url=https://web.archive.org/web/20220725151921/https://www.medicines.org.uk/Guides/indoramin%20hydrochloride/prostatic%20hyperplasia%20(benign)|url-status=dead}}</ref>
It is commonly synthesized from tryptophol.<ref>Ullman's encyclopedia of Industrial Chemistry, Sixth Edition, 2002.</ref>
==Dosage== Indoramin is commonly prescribed as 20 mg tablets when used in BPH.<ref>{{cite web|url=http://www.nhs.uk/medicine-guides/pages/MedicineOverview.aspx?condition=Prostatic%20hyperplasia%20(benign)&medicine=indoramin%20hydrochloride|title=Indoramin hydrochloride|publisher=National Health Service (UK)|access-date=September 30, 2012}}</ref>
==Side Effects== Drowsiness, dizziness, dry mouth, nasal congestion, headache, fatigue, weight gain, hypotension, postural hypotension, depression, problems with ejaculation, diarrhoea, nausea, increased need to pass urine, and palpitations.<ref>{{cite web|url=https://www.medicines.org.uk/emc/product/6666|title=Indoramin 20mg tablets|publisher=Medicines.org.uk|access-date=February 7, 2018}}</ref>
==Synthesis== Tryptamine and serotonin are naturally occurring indole ethylamino compounds with pronounced pharmacological activities. They have served as the inspiration for synthesis of numerous analogues.
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One such study involved alkylation of 4-benzamidopyridine (2) with a bromoethyy compound (1) derived from tryptophol, to give a quaternary pyridinium salt (3); this intermediate was in turn hydrogenated with a Raney nickel catalyst to give indoramine.<ref>{{Cite patent | inventor = Archibald JL, Jackson JO |country=ZA|number=6803204}}; eidem, {{US patent|3527761}} (1969, 1970 both to Wyeth).</ref><ref>{{cite journal | vauthors = Archibald JL, Alps BJ, Cavalla JF, Jackson JL | title = Synthesis and hypotensive activity of benzamidopiperidylethylindoles | journal = Journal of Medicinal Chemistry | volume = 14 | issue = 11 | pages = 1054–1059 | date = November 1971 | pmid = 5115203 | doi = 10.1021/jm00293a009 }}</ref>
==Product withdrawal== On May 31, 2013, the French National Agency for the Safety of Medicines and Health Products (ANSM) concluded that the benefit/risk ratio of this product was unfavorable and withdrew Vidora's marketing authorization and recalled its batches from the market on June 3, 2013.<ref>{{Cite web |title=Actualités |url=https://ansm.sante.fr/actualites/a-la-une |access-date=2023-04-17 |website=ANSM |language=fr}}</ref>
== References == {{reflist}}
{{Antihypertensives and diuretics}} {{Adrenergic receptor modulators}} {{Tryptamines}}
Category:Alpha-1 blockers Category:Benzamides Category:N,N-Dialkyltryptamines Category:Piperidines
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