Tiamenidine

Chemical compound From Wikipedia, the free encyclopedia

Tiamenidine (BAN, USAN, INN, also known as thiamenidine, Hoe 440) is an imidazoline compound that shares many of the pharmacological properties of clonidine. It is a centrally-acting α2 adrenergic receptor agonist (IC50 = 9.1 nM).[2] It also acts as an α1-adrenergic receptor agonist to a far lesser extent (IC50 = 4.85 μM).[2] In hypertensive volunteers, like clonidine, it significantly increased sinus node recovery time and lowered cardiac output.[3] It was marketed (as tiamenidine hydrochloride) by Sanofi-Aventis[4] under the brand name Sundralen[5] for the management of essential hypertension.[6]

Trade namesSundralen, Symcorad, Symcor
ATC code
Quick facts Clinical data, Trade names ...
Tiamenidine
Clinical data
Trade namesSundralen, Symcorad, Symcor
ATC code
Pharmacokinetic data
Elimination half-life2.3–5 hours[1]
Identifiers
  • N-(2-chloro-4-methylthiophen-3-yl)-4,5-dihydro-1H-imidazol-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC8H10ClN3S
Molar mass215.70 g·mol−1
3D model (JSmol)
  • Clc2scc(c2N/C1=N/CCN1)C
  • InChI=1S/C8H10ClN3S/c1-5-4-13-7(9)6(5)12-8-10-2-3-11-8/h4H,2-3H2,1H3,(H2,10,11,12) checkY
  • Key:CVWILQHZFWRYPB-UHFFFAOYSA-N checkY
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Synthesis

ChemDrug Synthesis:[7] Patent:[8]

Reaction of thiourea 1 with methyl iodide gives the corresponding S-methyl analogue (2), followed by heating with ethylenediamine, completes the synthesis of tiamenidine (3).

See also

References

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