Amosulalol

Chemical compound From Wikipedia, the free encyclopedia

Amosulalol (INN) is an antihypertensive drug. It has much higher affinity for α1-adrenergic receptors than for β-adrenergic receptors.[1] It is not approved for use in the United States.

AHFS/Drugs.comInternational Drug Names
Routes of
administrationOral
ATC code
  • none
Legal status
  • In general: ℞ (Prescription only)
Quick facts Clinical data, AHFS/Drugs.com ...
Amosulalol
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
  • (RS)-5-[1-hydroxy-2-[2-(2-methoxyphenoxy)ethylamino]ethyl]-2-methylbenzenesulfonamide
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC18H24N2O5S
Molar mass380.46 g·mol−1
3D model (JSmol)
  • CC1=C(C=C(C=C1)C(CNCCOC2=CC=CC=C2OC)O)S(=O)(=O)N
  • InChI=1S/C18H24N2O5S/c1-13-7-8-14(11-18(13)26(19,22)23)15(21)12-20-9-10-25-17-6-4-3-5-16(17)24-2/h3-8,11,15,20-21H,9-10,12H2,1-2H3,(H2,19,22,23) checkY
  • Key:LVEXHFZHOIWIIP-UHFFFAOYSA-N checkY
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Synthesis

Guaiacol (1) reacts with ethylene oxide to give 2-(2-methoxyphenoxy)ethanol (2). Halogenation with thionyl chloride converts the alcohol group to a chloride, (3), which is used to alkylate benzylamine (4) to give the secondary amine (5). This forms a tertiary amine (7) when combined with 5-bromoacetyl-2-methylbenzenesulfonamide (6). The reduction of the carbonyl group with sodium borohydride produces (8) and catalytic hydrogenation removes the benzyl group, yielding amosulalol.[2][3][4]

References

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