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Amosulalol

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Chemical compound

Pharmaceutical compound
Amosulalol
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
IUPAC name
  • (RS)-5-ethyl]-2-methylbenzenesulfonamide
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC18H24N2O5S
Molar mass380.46 g·mol
3D model (JSmol)
SMILES
  • CC1=C(C=C(C=C1)C(CNCCOC2=CC=CC=C2OC)O)S(=O)(=O)N
InChI
  • 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)
  • Key:LVEXHFZHOIWIIP-UHFFFAOYSA-N

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

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.

References

  1. Sponer G, Bartsch W, Hooper RG (1990). "Drugs acting on multiple receptors: β-blockers with additional properties.". Pharmacology of antihypertensive therapeutics. Handbook of Experimental Pharmacology. Vol. 93. Berlin, Heidelberg: Springer. pp. 131–226 (183). doi:10.1007/978-3-642-74209-5_5. ISBN 978-3-642-74209-5.
  2. US patent 4217305, Kazuo Imai, et al., "Phenylethanolamine derivatives", issued 1980-08-12, assigned to Yamanouchi Pharmaceutical Co. Ltd. 
  3. Arima, H.; Tamazawa, K.; Synthesis of 14C-labeled 5-ethyl]-2-methylbenzenesulfonamide hydochloride (YM-09538). J Label Compd Radiopharm 1983, 20, 7, 803-811.
  4. "Amosulalol". Pharmaceutical Substances. Thieme. Retrieved 2024-07-12.


Adrenergic receptor modulators
α1
Agonists
Antagonists
α2
Agonists
Antagonists
β
Agonists
Antagonists


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