Indoramin

Indoramin
Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	C02CA02 (WHO) ;
Identifiers
	IUPAC name N-{1-[2-(1H-indol-3-yl)ethyl]piperidin-4-yl}benzamide;
CAS Number	26844-12-2 ;
PubChem CID	33625;
IUPHAR/BPS	501;
DrugBank	DB08950 ;
ChemSpider	31014 ;
UNII	0Z802HMY7H;
KEGG	D04531 ;
ChEMBL	ChEMBL279516 ;
CompTox Dashboard (EPA)	DTXSID7048370 ;
ECHA InfoCard	100.043.659
Chemical and physical data
Formula	C22H25N3O
Molar mass	347.462 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(c1ccccc1)NC4CCN(CCc3c2ccccc2[nH]c3)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) ; Key:JXZZEXZZKAWDSP-UHFFFAOYSA-N ;
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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]

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

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 February 7, 2018.
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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[pmid3955309-1] 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.