Amosulalol
Chemical compound
- none
- In general: ℞ (Prescription only)
- (RS)-5-[1-hydroxy-2-[2-(2-methoxyphenoxy)ethylamino]ethyl]-2-methylbenzenesulfonamide
- 85320-68-9
Y
- 2169
- 2084 Y
- C69JI1BAU8
- D07451 Y
- ChEMBL152231 Y
- DTXSID90868893
- Interactive image
- 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)Y
- Key:LVEXHFZHOIWIIP-UHFFFAOYSA-NY
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.
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
- ^ 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.
- ^ US patent 4217305, Kazuo Imai, et al., "Phenylethanolamine derivatives", issued 1980-08-12, assigned to Yamanouchi Pharmaceutical Co. Ltd.
- ^ Arima, H.; Tamazawa, K.; Synthesis of 14C-labeled 5-[1-hydroxy-2-[2-(o-methoxyphenoxy)ethylamino]ethyl]-2-methylbenzenesulfonamide hydochloride (YM-09538). J Label Compd Radiopharm 1983, 20, 7, 803-811.
- ^ "Amosulalol". Pharmaceutical Substances. Thieme. Retrieved 2024-07-12.
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- See also: Receptor/signaling modulators
- Dopaminergics
- Serotonergics
- Monoamine reuptake inhibitors
- Monoamine releasing agents
- Monoamine metabolism modulators
- Monoamine neurotoxins
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