Indoramin

Indoramin

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 Number	26844-12-2 N
ATC code	C02CA02 (WHO)
PubChem	CID: 33625
IUPHAR/BPS	501
DrugBank	DB08950 N
ChemSpider	31014 Y
UNII	0Z802HMY7H Y
KEGG	D04531 Y
ChEMBL	CHEMBL279516 Y
Chemical data
Formula	C22H25N3O
Molecular mass	347.454 g/mol
SMILES O=C(c1ccccc1)NC4CCN(CCc3c2ccccc2nc3)CC4
InChI 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) Y Key:JXZZEXZZKAWDSP-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

Indoramin (trade names Baratol and Doralese) is a piperidine antiadrenergic agent.

It is an alpha-1 selective adrenoceptor antagonist with direct myocardial depression action; therefore, it results in no reflex tachycardia. It is also used in benign prostatic hyperplasia (BPH).

It is commonly synthesized from tryptophol.

Dosage

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

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.

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:

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).