6249-56-5

Basic information

• Product Name: (3-CARBOXYPROPYL)TRIMETHYLAMMONIUM CHLORIDE
• Synonyms: (3-carboxypropyl)trimethyl-ammoniuchloride;3-carboxy-n,n,n-trimethyl-1-propanaminiuchloride;3-carboxy-n,n,n-trimethyl-1-propanaminiumchloride;gamma-butyrobetain-chlorid;(3-CARBOXYPROPYL)TRIMETHYLAMMONIUM CHLORIDE;GAMMA-BUTYROBETAINE HYDROCHLORIDE;DEOXYCARNITINE HYDROCHLORIDE;(3-CARBOXYPROPYL)TRIMETHYLAMMONIUMCHLORI DE PRACTIC
• CAS NO: 6249-56-5
• Molecular Formula: C₇H₁₆NO₂*Cl
• Molecular Weight: 181.66
• Product Categories: Aliphatics;Intermediates
• Mol File: 6249-56-5.mol
• Article Data: 8

Chemical Properties

• Melting Point: 220 °C (dec.)(lit.)
• Appearance: /
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Water (Slightly), Methanol (Slightly)
• CAS DataBase Reference: (3-CARBOXYPROPYL)TRIMETHYLAMMONIUM CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (3-CARBOXYPROPYL)TRIMETHYLAMMONIUM CHLORIDE(6249-56-5)
• EPA Substance Registry System: (3-CARBOXYPROPYL)TRIMETHYLAMMONIUM CHLORIDE(6249-56-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: BP3850000
• Hazardous Substances Data: 6249-56-5(Hazardous Substances Data)

Usage

Description

(3-Carboxypropyl)trimethylammonium chloride, also known as CPTMA, is a synthetic compound that is structurally related to carnitine. It possesses a quaternary ammonium group and a carboxylic acid functional group, which contribute to its unique properties and applications. CPTMA is widely utilized in various fields due to its ability to act as a transporter substrate and its potential in enhancing the efficiency of certain processes.

Uses

Used in Pharmaceutical Research:
(3-Carboxypropyl)trimethylammonium chloride is used as a transporter substrate for the cloning and sequencing of human carnitine transporter 2 (CT2). Its role in this process is crucial for understanding the function and regulation of CT2, which is involved in the transport of carnitine and its derivatives across cell membranes. This knowledge can be applied to develop novel therapeutic strategies for various diseases and conditions related to carnitine metabolism.
Used in Drug Delivery Systems:
In the field of drug delivery, (3-Carboxypropyl)trimethylammonium chloride can be employed as a carrier molecule to enhance the transport and bioavailability of various drugs. Its structural similarity to carnitine allows it to interact with carnitine transporters, potentially improving the delivery of therapeutic agents to target cells and tissues.
Used in Chemical Synthesis:
CPTMA can also be utilized as a building block or intermediate in the synthesis of various complex organic compounds, particularly those involving quaternary ammonium and carboxylic acid functional groups. Its unique structure makes it a valuable component in the development of new pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Analytical Chemistry:
(3-Carboxypropyl)trimethylammonium chloride can be used as a reagent or reference compound in analytical chemistry, particularly in the development of new methods for the detection and quantification of carnitine and its related compounds. Its distinct chemical properties can be exploited to improve the sensitivity and selectivity of analytical techniques, such as chromatography and mass spectrometry.
Used in Biotechnology:
In the biotechnology industry, CPTMA can be employed as a tool to study the function and regulation of carnitine transporters, as well as to develop novel expression systems for the production of recombinant proteins involved in carnitine metabolism. This can lead to a better understanding of the biological roles of carnitine and its derivatives, and the development of new biotechnological applications.

InChI:InChI=1/C7H15NO2.ClH/c1-8(2,3)6-4-5-7(9)10;/h4-6H2,1-3H3;1H

Upstream product

• 693-11-8 4-dimethylamino-butyric acid 
• 6257-10-9 N,N'-dicyclohexyl-O-methyl isourea 
• 3153-37-5 methyl 4-chlorobutyrate 
• 75-50-3 trimethylamine 
• 51963-62-3 ethyl γ-(trimethylammonio)butyrate chloride 
• 69954-66-1 4-(dimethylamino)butyric acid hydrochloride 
• 872-50-4 1-methyl-pyrrolidin-2-one 
• 56-12-2 4-amino-n-butyric acid 
• 74-88-4 methyl iodide 
• 627-00-9 γ-chlorobutyric acid 
• 3153-36-4 4-chloro-butyric acid ethyl ester 

Downstream Products

• 1017319-41-3 C₁₅H₂₆N₃O₂⁽¹⁺⁾*Cl^(1-) 
• 1228192-20-8 C₃₀H₄₂N₂O₃PSi⁽¹⁺⁾*Cl^(1-) 
• 44985-79-7 L-carnitine 
• 124563-42-4 p-nitrophenyl γ-(trimethylammonio)butyrate chloride 
• 125063-92-5 <4-(trimethylammonio)butyryl>-Phe-β-Ala-ACHPA-Ile N-<(4-amino-2-methyl-5-pyrimidinyl)methyl>amide chloride 
• 51963-62-3 ethyl γ-(trimethylammonio)butyrate chloride 

Relevant articles and documents

Enhancing electrospray ionization efficiency of peptides by derivatization

With the advent of electrospray ionization mass spectrometry, the world was given a new way to look at complex peptide mixtures. Identification of proteins via their signature peptides requires ionization of a representative portion of the peptides derived from proteins by proteolysis. Unfortunately, matrix effects prohibited electrospray ionization of many peptides. This paper describes the development of a new labeling reagent that simultaneously adds a permanent positive charge to peptides and increases their hydrophobicity to enhance their ionization efficiency. The labeling agent is preactivated with N-hydroxysuccinimide to react with primary amines to form a peptide bond. In the most dramatic case, ionization efficiency of the peptide ADRDQYELLCLDNTRKPVDEYK increased 500-fold after derivatization as opposed to other peptides where ionization efficiency was impacted little. Ionization efficiency of peptides was enhanced roughly 10-fold in general by derivatization. Peptides of less than 500 Da experienced the greatest increase in ionization efficiency by derivatization. Poor ionization efficiency of native peptides was found to be due more to their inherent structural properties than the matrix in which ionization occurs.

Nanoscale Biodegradable Organic–Inorganic Hybrids for Efficient Cell Penetration and Drug Delivery

We report a comprehensive study on novel, highly efficient, and biodegradable hybrid molecular transporters. To this end, we designed a series of cell-penetrating, cube-octameric silsesquioxanes (COSS), and investigated cellular uptake by confocal microscopy and flow cytometry. A COSS with dense spatial arrangement of guanidinium groups displayed fast uptake kinetics and cell permeation at nanomolar concentrations in living HeLa cells. Efficient uptake was also observed in bacteria, yeasts, and archaea. The COSS-based carrier was significantly more potent than cell-penetrating peptides (CPPs) and displayed low toxicity. It efficiently delivered a covalently attached cytotoxic drug, doxorubicin, to living tumor cells. As the uptake of fluorescently labeled carrier remained in the presence of serum, the system could be considered particularly attractive for the in vivo delivery of therapeutics.

Exploiting neighboring-group interactions for the self-selection of a catalytic unit

(Figure Presented) A good neighbor is better than a far-away friend: A tethering strategy is used to self-select groups that assist in the cleavage of a neighboring carboxylic ester moiety (see picture, TSA=transition-state analogue). A correlation is observed between the amplification at thermodynamic equilibrium and the catalytic efficiency.