250694-07-6

Basic information

• Product Name: 3-(tetradecylcarbamoylamino)-4-trimethylammonio-butanoate
• Synonyms: 3-(tetradecylcarbamoylamino)-4-trimethylammonio-butanoate;TEGLICAR
• CAS NO: 250694-07-6
• Molecular Formula: C₂₂H₄₅N₃O₃
• Molecular Weight: 399.61100
• Mol File: 250694-07-6.mol
• Article Data: 2

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: white crystalline powder
• Density: g/cm³
• Storage Temp.: -20°C
• CAS DataBase Reference: 3-(tetradecylcarbamoylamino)-4-trimethylammonio-butanoate(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(tetradecylcarbamoylamino)-4-trimethylammonio-butanoate(250694-07-6)
• EPA Substance Registry System: 3-(tetradecylcarbamoylamino)-4-trimethylammonio-butanoate(250694-07-6)

Safety Data

• Hazardous Substances Data: 250694-07-6(Hazardous Substances Data)

Usage

General Description

ST1326 contains an aliphatic carbon chain and is structurally similar to palmitoylcarnitine.

Biochem/physiol Actions

ST1326 is a reversible inhibitor of carnitine palmitoyltransferases. It shows anti tumor action in leukemia cell lines.

InChI:InChI=1/C22H45N3O3/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-23-22(28)24-20(18-21(26)27)19-25(2,3)4/h20H,5-19H2,1-4H3,(H2-,23,24,26,27,28)

Synthetic route

tetradecyl isocyanate (4877-14-9) + (R)-3-(amino)-4-(trimethylammonio)butanoate (98063-21-9) → teglicar (250694-07-6)

Conditions	Yield
tetrabutyl-ammonium chloride In methanol at 5 - 20℃;	90%
In dimethyl sulfoxide at 40℃; for 60h;	57%

Methyl 4-bromobutyrate (4897-84-1) + teglicar (250694-07-6) → (R)-4-trimethylammonium-3-(tetradecylcarbamoylamino)-butyrate of 3-(methoxycarbonyl)-propyl bromide

Conditions	Yield
In N,N-dimethyl-formamide at 50℃;	87%

methanol (67-56-1) + teglicar (250694-07-6) → methyl (R)-4-trimethylammonium-3-(tetradecylcarbamoyl)-amino-butyrate chloride

Conditions	Yield
With thionyl chloride at 0 - 40℃; for 72h;	12%

teglicar (250694-07-6) → (R)-4-trimethylammonium-3-(tetradecylcarbamoyl)amino-butyrate hydrochloride

Conditions	Yield
With hydrogenchloride In water

Upstream product

• 4877-14-9 tetradecyl isocyanate 
• 98063-21-9 Emeriamine 

Relevant articles and documents

Discovery of a long-chain carbamoyl aminocarnitine derivative, a reversible carnitine palmitoyltransferase inhibitor with antiketotic and antidiabetic activity

The synthesis and pharmacological activity of reversible CPT I inhibitors as potential antiketotic and antidiabetic drugs are reported. Such inhibitors constitute a series of enantiomerically pure aminocarnitine derivatives having the general formula (CH3)3N+CH2CH(ZR) CH2COO- (with Z = ureido, carbamate, sulfonamide, and sulfamide moieties; R = C7-C14 linear alkyl chains). A primary pharmacological screening based on the evaluation of CPT I activity in intact rat liver (L-CPT I) mitochondria revealed the best activity for the (R) forms of ureidic derivative 17 (ZR = NHCONHR, R = C14), sulfonamidic derivative 7 (ZR = NHSO2R, R = C12), and sulfamidic derivative 9 (ZR = NHSO2NHR, R = C11). The IC50 values are 1.1, 0.7, and 0.8 μM, respectively. For the carbamic derivative 11 (ZR = NHCOOR, R = C8), an IC50 of 9.5 μM was observed. In addition, an extraordinarily high selectivity toward the liver isoform with respect to the heart isoform (muscle-CPT I M-CPT I) was found for the ureidic compound 17 (IC50(M-CPT I) vs IC50(L-CPTI) = 39.4), as well as for other ureidic or carbamic compounds. Diabetic db/db mice treated orally with 17 and 7 for 45 days at a dose of 50 mg/kg twice a day showed a good reduction of serum glucose levels with respect to the untreated db/db mice (p a potential antiketotic and antidiabetic drug.