Acetiamine

Acetiamine
Clinical data
Other names	NSC-290686, diacetylthiamine
Identifiers
	IUPAC name [(Z)-3-acetylsulfanyl-4-[(4-amino-2-methylpyrimidin-5-yl)methyl-formylamino]pent-3-enyl] acetate;
CAS Number	299-89-8;
PubChem CID	3033984;
DrugBank	DB21187;
ChemSpider	2298543;
UNII	SIJ2OU269U;
ChEBI	CHEBI:748398;
ChEMBL	ChEMBL421556;
CompTox Dashboard (EPA)	DTXSID801043380 ;
Chemical and physical data
Formula	C16H22N4O4S
Molar mass	366.44 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1=NC=C(C(=N1)N)CN(C=O)/C(=C(/CCOC(=O)C)\SC(=O)C)/C;
	InChI InChI=1S/C16H22N4O4S/c1-10(15(25-13(4)23)5-6-24-12(3)22)20(9-21)8-14-7-18-11(2)19-16(14)17/h7,9H,5-6,8H2,1-4H3,(H2,17,18,19)/b15-10-; Key:ISIPQAHMLLFSFR-GDNBJRDFSA-N;

Acetiamine, also known as O,S-diacetylthiamine, is a small molecule drug.^[1]^[2]^[3]^[4]

It is a fat-soluble open ring derivative of thiamine (vitamin B₁). It is prepared by first treating thiamine with base to produce the ring-opened thiol-type vitamin B₁ followed by acetylation using acetic anhydride to form the thioester.^[5]^[6]^[7]^[8]

Acetiamine is enzymatically leaved in liver to generate thiamine and acetate.^[9] Hence acetiamine is a prodrug of thiamine.

References

↑ PubChem. "Acetiamine". PubChem. Retrieved 2026-08-31.
↑ "Acetiamine (CAS 299-89-8) | Lipid-Soluble Thiamine Prodrug | BenchChem". www.benchchem.com. Retrieved 2026-08-31.
↑ "Compound: ACETIAMINE (CHEMBL421556)". www.ebi.ac.uk. Retrieved 2026-08-31.
↑ "acetiamine (CHEBI:748398)". www.ebi.ac.uk. Retrieved 2026-08-31.
↑ Matsukawa T, Kawasaki H (1953). "Studies on Vitamin B₁ and Related Compounds. XLV". Yakugaku Zasshi. 73 (7): 705–708. doi:10.1248/yakushi1947.73.7_705.
↑ Matsukawa T, Kawasaki H (1953). "Studies on Vitamin B₁ and Related Compounds. XLVI". Yakugaku Zasshi. 73 (7): 709–712. doi:10.1248/yakushi1947.73.7_709.
↑ Takamizawa A, Hirai K, Matsui K (1963). "Studies of the Pyrimidine Derivatives. XXV. The Reaction of Alkoxycarbonylthiocyanates and Related Compounds with the Sodium Salt of Thiamine". Bulletin of the Chemical Society of Japan. 36 (9): 1214–1220. doi:10.1246/bcsj.36.1214.
↑ Gauthier B, Tixier R, Uzan A (1963). "[On the Thiamines with an Open Thiazole Ring. Study of O,S-Diacetylthiamine]". Annales Pharmaceutiques Francaises (in French). 21: 655–666. PMID 14091313.
↑ Suzuoki-Zirô, Suzuoki-Tuneko (1954). "Enzymatic Hydrolysis of the —S—CO— Linkage". Nature. 173 (4393): 83–84. doi:10.1038/173083b0.

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