Indoramin
Clinical data
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
  • N-{1-[2-(1H-indol-3-yl)ethyl]piperidin-4-yl}benzamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
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UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.043.659 Edit this at Wikidata
Chemical and physical data
FormulaC22H25N3O
Molar mass347.462 g·mol−1
3D model (JSmol)
  • O=C(c1ccccc1)NC4CCN(CCc3c2ccccc2[nH]c3)CC4
  • InChI=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) checkY
  • Key:JXZZEXZZKAWDSP-UHFFFAOYSA-N checkY
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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]

Dosage

Indoramin is commonly prescribed as 20 mg tablets when used in BPH.[4]

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.[5]

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.

α1-Adrenergic blocking agent with antihypertensive and bronchodilating activity. Prepn:[6][7]
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 (3); this intermediate was in turn hydrogenated with a Raney nickel catalyst to give indoramine (4).

References

  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 February 7, 2018.
  6. ^ J. L. Archibald, J. L. Jackson, ZA 6803204 ; eidem, U.S. Patent 3,527,761 (1969, 1970 both to Wyeth).
  7. ^ 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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