Tiamenidine

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]

Tiamenidine

Clinical data
Trade names	Sundralen, Symcorad, Symcor
ATC code	C02AC (WHO)
Pharmacokinetic data
Elimination half-life	2.3–5 hours[1]
Identifiers
IUPAC name N-(2-chloro-4-methylthiophen-3-yl)-4,5-dihydro-1H-imidazol-2-amine
CAS Number	31428-61-2 N
PubChem CID	39974
ChemSpider	36548 Y
UNII	195V08O55G
KEGG	D06127 Y
ChEMBL	ChEMBL295409 Y
CompTox Dashboard (EPA)	DTXSID80185349
Chemical and physical data
Formula	C8H10ClN3S
Molar mass	215.70 g·mol−1
3D model (JSmol)	Interactive image
SMILES Clc2scc(c2N/C1=N/CCN1)C
InChI 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) Y Key:CVWILQHZFWRYPB-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

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

• Clonidine
• Tizanidine