N-Methylcyclopropanamine: Properties, Uses & FAQs

N-Methylcyclopropanamine is a secondary aliphatic amine featuring a strained cyclopropane ring, widely used as a versatile building block in organic and medicinal chemistry synthesis workflows.

Chemical Name

N-Methylcyclopropanamine

Compound Class

Secondary aliphatic amine

Core Structure

Cyclopropane ring with N-methyl secondary amine group

Primary Application

Building block for pharmaceutical and agrochemical synthesis

Product SKU

N725431

Reactivity

Nucleophilic amine; reacts with electrophiles including acyl chlorides, aldehydes, and isocyanates

What Is N-Methylcyclopropanamine?

N-Methylcyclopropanamine is a secondary amine in which a methyl group and a cyclopropyl group are both attached to the nitrogen atom. The cyclopropane ring imparts unique steric and electronic properties that distinguish it from simple linear or branched alkyl amines. The ring strain inherent to cyclopropane influences the basicity, reactivity, and three-dimensional shape of the molecule, making it a valuable scaffold in drug discovery and fine chemical synthesis.

The compound is a low-molecular-weight, volatile liquid at room temperature and should be handled with appropriate precautions for flammable, basic amines.

Key Chemical Properties

N-Methylcyclopropanamine behaves as a moderately strong nucleophile due to the nitrogen lone pair. The cyclopropyl group is known to exert a weak electron-donating effect through hyperconjugation with adjacent orbitals, subtly modulating the amine's basicity relative to N-methylcyclobutylamine or N-methylamine analogs.

Typical reactions of this secondary amine include:

• Acylation: reaction with acyl chlorides or anhydrides to form amides.
• Reductive amination: condensation with aldehydes or ketones followed by reduction to yield tertiary amines.
• Urea/carbamate formation: reaction with isocyanates or chloroformates.
• Sulfonamide formation: reaction with sulfonyl chlorides.

Storage under inert atmosphere at low temperature is recommended to prevent oxidation and moisture uptake.

Applications in Synthesis and Drug Discovery

The incorporation of cyclopropylamine motifs into drug candidates is a well-established medicinal chemistry strategy. The cyclopropyl group can improve metabolic stability, modulate lipophilicity (logP), and act as a bioisostere for other small ring systems or vinyl groups. N-Methylcyclopropanamine provides a ready-made N-methyl secondary amine handle for introduction of this motif via amide coupling, reductive amination, or nucleophilic substitution.

Representative areas of use include:

• Synthesis of protease inhibitors and kinase inhibitor intermediates.
• Preparation of agrochemical active ingredients.
• Construction of diverse compound libraries for high-throughput screening.
• Fragment-based drug discovery as a low-molecular-weight amine fragment.

Handling, Safety, and Storage

As a low-molecular-weight secondary amine, N-Methylcyclopropanamine is flammable and corrosive to mucous membranes. Standard precautions for handling volatile amines apply:

• Work in a well-ventilated fume hood.
• Wear chemical-resistant gloves, safety goggles, and appropriate lab coat.
• Avoid inhalation of vapors.
• Keep away from open flames and strong oxidizing agents.

Store tightly sealed in a cool, dry location under inert gas (nitrogen or argon). Consult the current Safety Data Sheet (SDS) provided with product N725431 for complete hazard, first-aid, and disposal information before use.

Ordering and Availability from Aladdin Scientific

N-Methylcyclopropanamine is available from Aladdin Scientific under SKU N725431. The product is intended for research and development use by qualified laboratory personnel. For current pricing, available pack sizes, purity specifications, and lead times, please visit the product page or contact our technical sales team. Bulk and custom quantities may be available upon request.

Frequently asked questions

What is N-Methylcyclopropanamine used for in organic synthesis?

N-Methylcyclopropanamine is primarily used as a secondary amine building block for constructing amide, urea, carbamate, and tertiary amine derivatives. Its cyclopropyl group adds conformational rigidity and is valued in medicinal chemistry for improving the pharmacokinetic profile of drug candidates.

How should N-Methylcyclopropanamine be stored to maintain stability?

The compound should be stored in a tightly sealed container under an inert atmosphere (nitrogen or argon) in a cool, dry place away from heat sources and oxidizing agents. Refrigerated storage is generally recommended for volatile amines to minimize evaporative loss and degradation.

Is N-Methylcyclopropanamine the same as cyclopropylmethylamine?

No. N-Methylcyclopropanamine (cyclopropyl-NH-CH₃) is a secondary amine where the nitrogen bears both a cyclopropyl group and a methyl group. Cyclopropylmethylamine (cyclopropylmethyl-NH₂) is a primary amine where the nitrogen bears a cyclopropylmethyl group and two hydrogens. They are structural isomers with different reactivity and properties.

What safety precautions are required when working with N-Methylcyclopropanamine?

Users should work in a well-ventilated fume hood, wear chemical-resistant gloves and safety goggles, and avoid inhaling vapors. The compound is flammable and should be kept away from ignition sources. Always consult the Safety Data Sheet (SDS) for product N725431 before use for complete hazard and emergency information.

What purity grades and pack sizes are available for N-Methylcyclopropanamine (N725431)?

Specific purity grades and available pack sizes for N725431 are listed on the Aladdin Scientific product page. For the most current specifications, pricing, and stock availability, please consult the product listing or contact Aladdin Scientific customer support directly.

References

1. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley-Interscience. General reference for amine reactivity and secondary amine chemistry.
2. Lovering, F.; Bikker, J.; Humblet, C. Escape from Flatland: Increasing Saturation as an Approach to Improving Clinical Success. J. Med. Chem. 2009, 52, 6752–6756. Relevant to cyclopropyl motif use in drug discovery. doi:10.1021/jm901241e
3. Aladdin Scientific Product Page: N-Methylcyclopropanamine, SKU N725431. Aladdin Scientific.

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