Tiamenidine

Tiamenidine

Systematic (IUPAC) name
N-(2-chloro-4-methylthiophen-3-yl)-4,5-dihydro-1H-imidazol-2-amine
Clinical data
Trade names	Sundralen, Symcorad, Symcor
Pharmacokinetic data
Biological half-life	2.3–5 hours
Identifiers
CAS Number	31428-61-2 Y
ATC code	C02AC (WHO)
PubChem	CID: 39974
ChemSpider	36548 Y
UNII	195V08O55G Y
KEGG	D06127 Y
ChEMBL	CHEMBL295409 Y
Chemical data
Formula	C8H10ClN3S
Molecular mass	215.70 g/mol
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
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Tiamenidine (BAN, USAN, INN, also known as thiamenidine, Hoe 440) is a imidazoline compound that shares many of the pharmacological properties of clonidine. It acts as a cetrally-acting α1 and α1 adrenergic receptor antagonist (with IC50 4.85μM and 0.0091μM, respectively). In hypertensive volunteers, like clonidine, it significantly increased sinus node recovery time and lowered cardiac output. It was marketed (as tiamenidine hydrochloride) by Sanofi-Aventis under the brand name Sundralen for the management of essential hypertension.

Synthesis

Tiamenidine synthesis:

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