Indoramin

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Indoramin
Indoramin.svg
Systematic (IUPAC) name
N-{1-[2-(1H-indol-3-yl)ethyl]piperidin-4-yl}benzamide
Clinical data
AHFS/Drugs.com International Drug Names
Identifiers
CAS Registry Number 26844-12-2 N
ATC code C02CA02
PubChem CID: 33625
IUPHAR/BPS 501
DrugBank DB08950 N
ChemSpider 31014 YesY
UNII 0Z802HMY7H YesY
KEGG D04531 YesY
ChEMBL CHEMBL279516 YesY
Chemical data
Formula C22H25N3O
Molecular mass 347.454 g/mol
 N (what is this?)  (verify)

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]

Dosage[edit]

Indoramin is commonly prescribed as 20mg 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 occuring indole ethylamino compounds with pronounced phamacological activities. They have served as the inspiration for synthesis of numerous analogues.

α1-Adrenergic blocking agent with antihypertensive and bronchodilating activity. Prepn:[6][7]

One such study involved alkylation of 4-benzamidopyridine (2) with 3-(2-Bromoethyl)-1H-indole (1) to give quaternary salt (4); this intermediate was in turn hydrogenated with a Raney nickel catalyst to give indoramine (4).

References[edit]

  1. ^ 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. 
  2. ^ "Indoramin 20mg tablets". Medicines.org.uk. April 20, 2011. Retrieved September 30, 2012. 
  3. ^ Ullman's encyclopedia of Industrial Chemistry, Sixth Edition, 2002.
  4. ^ "Indoramin hydrochloride". National Health Service (UK). Retrieved September 30, 2012. 
  5. ^ "Indoramin 20mg tablets". Medicines.org.uk. Retrieved September 30, 2012. 
  6. ^ J. L. Archibald, J. L. Jackson, ZA 6803204 ; eidem, U.S. Patent 3,527,761 (1969, 1970 both to Wyeth).
  7. ^ doi:10.1021/jm00293a009
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