N-(3-(Dimethylamino)propyl)octanamide: Properties & Applications

N-(3-(Dimethylamino)propyl)octanamide is a synthetic fatty acid amide featuring a C8 acyl chain linked to a dimethylaminopropyl head group, conferring amphiphilic character relevant to surfactant, lipid-biology, and drug-delivery research.

IUPAC Name

N-[3-(dimethylamino)propyl]octanamide

Molecular Formula

C13H28N2O

Molecular Weight

228.38 g/mol

Compound Class

Fatty acid amide / tertiary amine

Key Structural Feature

Octanoyl (C8) acyl chain with dimethylaminopropyl terminus

Aladdin SKU

C1043312

Chemical Structure and Physicochemical Properties

N-(3-(Dimethylamino)propyl)octanamide (SKU: C1043312) belongs to the class of N-acyl fatty acid amides. Its structure comprises a straight-chain octanoyl (capryloyl, C8) group covalently bonded via an amide linkage to a 3-(dimethylamino)propylamine moiety. The resulting molecule carries both a hydrophobic alkyl tail and a hydrophilic, pH-titratable tertiary amine head group, yielding pronounced amphiphilic behaviour.

The molecular formula is C₁₃H₂₈N₂O with a molecular weight of approximately 228.38 g/mol. The tertiary amine (pK_a typically 9–10 for analogous dimethylaminopropyl amides) can be protonated under physiological or mildly acidic conditions, imparting cationic character that is exploited in formulation science. The amide bond itself confers metabolic stability relative to ester analogues.

Note for procurement: Researchers should confirm purity specification, counterion form (free base vs. salt), and storage conditions with Aladdin Scientific prior to ordering.

Synthesis and Preparation Context

The compound is most straightforwardly prepared by reacting octanoic acid (caprylic acid) or its activated derivative (e.g., octanoyl chloride or the N-hydroxysuccinimide ester) with 3-(dimethylamino)propylamine (DMAPA) under mild conditions. This condensation proceeds efficiently without racemisation concerns, as no stereocentres are involved. Aqueous workup or column chromatography can be used to isolate the product in high purity.

Alternative routes include direct amide coupling using carbodiimide reagents (e.g., EDC or DCC) in the presence of a catalytic base. Solvent choice (dichloromethane, DMF, or ethyl acetate) and temperature control are critical parameters for yield optimisation. Researchers should refer to primary literature and validated protocols for scale-specific guidance.

Review flag: Specific yield and reaction-time data have not been sourced from primary literature and are not quoted here; users should consult peer-reviewed synthetic procedures before replication.

Research Applications

The combination of a medium-chain fatty acyl group and a titratable tertiary amine makes N-(3-(Dimethylamino)propyl)octanamide valuable in several research domains:

• Surfactant and formulation science: Analogous dimethylaminopropyl fatty acid amides are widely used as foam boosters, viscosity modifiers, and conditioning agents. This compound can serve as a model or building-block reagent for investigating structure–activity relationships in amphiphile design.
• Lipid nanoparticle (LNP) research: Ionisable lipid-like amides are of significant interest as components of nucleic-acid delivery systems. The ionisable amine head group facilitates endosomal escape under acidic conditions, a key mechanism exploited in LNP-based RNA therapeutics. This compound may serve as a reference or probe molecule in mechanistic studies.
• Membrane biophysics: Amphiphilic amides can be incorporated into model lipid membranes to study phase behaviour, membrane fluidity, and protein–lipid interactions.
• Antimicrobial research: Medium-chain fatty acid amides with cationic head groups have been explored for antimicrobial activity against gram-positive and gram-negative bacteria; this compound may be screened in such contexts.

Review flag: Specific biological activity data for this exact compound were not available in the source material; all application statements reflect class-level knowledge and require primary literature validation.

Handling, Storage, and Safety Considerations

As with most amine-containing organic reagents, N-(3-(Dimethylamino)propyl)octanamide should be handled in a well-ventilated fume hood using appropriate personal protective equipment, including nitrile gloves, safety glasses, and a lab coat. The tertiary amine moiety may cause skin and mucous membrane irritation on prolonged contact.

Storage conditions should follow the supplier's certificate of analysis. In general, fatty acid amides of this class are stored at room temperature or at 2–8 °C in a tightly sealed container away from strong acids, oxidising agents, and moisture. Researchers should consult the Safety Data Sheet (SDS) provided by Aladdin Scientific for hazard classifications, first-aid measures, and disposal guidance before use.

Review flag: Specific GHS hazard classification, flash point, and stability data for this compound should be verified against the Aladdin SDS; no SDS data were provided in the source material.

Frequently asked questions

What is the CAS number or PubChem CID for N-(3-(Dimethylamino)propyl)octanamide?

The source material references PubChem identifier TJY-250415. Researchers should verify the definitive CAS number and PubChem CID directly on the Aladdin Scientific product page (SKU: C1043312) or via PubChem prior to use in regulatory or publication contexts.

Is N-(3-(Dimethylamino)propyl)octanamide the same as cocamidopropyl dimethylamine?

No. Cocamidopropyl dimethylamine (CAPDMA) is a commercial mixture derived from coconut oil fatty acids and therefore contains a distribution of chain lengths (C8–C18). N-(3-(Dimethylamino)propyl)octanamide is the pure, single-chain C8 (octanoyl) homologue, making it a well-defined reference compound suitable for mechanistic and structure–activity studies.

Can this compound be used as an ionisable lipid component in nanoparticle formulations?

Its ionisable tertiary amine and hydrophobic acyl tail make it structurally analogous to ionisable lipids used in lipid nanoparticle (LNP) research. However, its relatively short C8 chain and lack of additional structural complexity (e.g., unsaturation or branching) may limit its efficacy compared to optimised LNP lipids. It is best positioned as a model compound or mechanistic probe rather than a clinical-grade delivery lipid.

What purity and grade is available from Aladdin Scientific?

Purity and grade specifications for SKU C1043312 should be confirmed directly on the Aladdin Scientific website or by contacting customer support, as these details were not specified in the available source material.

References

1. PubChem Compound Summary for N-(3-(Dimethylamino)propyl)octanamide, PubChem identifier TJY-250415. National Library of Medicine.
2. Aladdin Scientific product page: N-(3-(Dimethylamino)propyl)octanamide, SKU C1043312.

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.