Indoramin
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| Systematic (IUPAC) name | |
|---|---|
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N-{1-[2-(1H-indol-3-yl)ethyl]piperidin-4-yl}benzamide
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| Clinical data | |
| Drugs.com | International Drug Names |
| Identifiers | |
| CAS Number | 26844-12-2  |
| ATC code | C02CA02 (WHO) |
| PubChem | CID 33625 |
| IUPHAR/BPS | 501 |
| DrugBank | DB08950 |
| ChemSpider | 31014  |
| UNII | 0Z802HMY7H |
| KEGG | D04531 |
| ChEMBL | CHEMBL279516 |
| Chemical data | |
| Formula | C22H25N3O |
| Molar mass | 347.454 g/mol |
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Indoramin (trade names Baratol and Doralese) is a piperidine antiadrenergic agent.
It is an alpha-1 selective adrenoceptor antagonist[1] with direct myocardial depression action; therefore, it results in no reflex tachycardia. It is also used in benign prostatic hyperplasia (BPH).[2]
It is commonly synthesized from tryptophol.[3]
Contents
Dosage[edit]
Indoramin is commonly prescribed as 20 mg tablets when used in BPH.[4]
Side Effects[edit]
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.[5]
Synthesis[edit]
Tryptamine and serotonin are naturally occurring indole ethylamino compounds with pronounced pharmacological activities. They have served as the inspiration for synthesis of numerous analogues.
One such study involved alkylation of 4-benzamidopyridine (2) with 3-(2-Bromoethyl)-1H-indole (1) to give quaternary salt (3); this intermediate was in turn hydrogenated with a Raney nickel catalyst to give indoramine (4).
References[edit]
- ^ Pierce V, Shepperson NB, Todd MH, Waterfall JF (February 1986). "Investigation into the cardioregulatory properties of the alpha 1-adrenoceptor blocker indoramin". Br. J. Pharmacol. 87 (2): 433–441. doi:10.1111/j.1476-5381.1986.tb10834.x. PMC 1916533. PMID 3955309.
- ^ "Indoramin 20mg tablets". Medicines.org.uk. April 20, 2011. Retrieved September 30, 2012.
- ^ Ullman's encyclopedia of Industrial Chemistry, Sixth Edition, 2002.
- ^ "Indoramin hydrochloride". National Health Service (UK). Retrieved September 30, 2012.
- ^ "Indoramin 20mg tablets". Medicines.org.uk. Retrieved September 30, 2012.
- ^ J. L. Archibald, J. L. Jackson, ZA 6803204; eidem, U.S. Patent 3,527,761 (1969, 1970 both to Wyeth).
- ^ Archibald, J. L.; Alps, B. J.; Cavalla, J. F.; Jackson, J. L. (1971). "Synthesis and hypotensive activity of benzamidopiperidylethylindoles". Journal of Medicinal Chemistry 14 (11): 1054. doi:10.1021/jm00293a009. PMID 5115203.
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