Name: Deucravacitinib / Methan-d3-amine hydrochloride
CAS Number: 7436-22-8
EINECS Number: 231-089-6
Chemical Formula: CD₃NH₂·HCl or CH₂D₃N·ClH or CH₃D₃ClN
Molecular weight: 70.54 g/mol
InChI: InChI=1S/CH₅N.ClH/c1-2;/h2H2,1H3;1H/i1D3;
InChIKey: NQMRYBIKMRVZLB-NIIDSAIPSA-N
Density: Undetermined / No data
Boiling point: 225-230 °C (15 mmHg) / 86 °C (7 mmHg)
Flash point: No data
Water solubility: Very soluble in water; soluble in ethanol, methanol, and DMSO; slightly soluble in water (some literature indicates); insoluble in ether, ethyl acetate, chloroform, and acetone
Vapor pressure: 3970 mmHg at 25°C (some data sources indicate) / No data
Refractive index: Undetermined / No data
Storage conditions Store in a tightly closed, cool, dry place; purged with inert gas; at room temperature or 2-8°C; protected from light and moisture.
Sensitivity: Hygroscopically sensitive, extremely deliquescent.
Appearance: White to off-white crystalline powder or solid.
Specific Gravity: Undetermined / No data available.
Color: White to off-white.
BRN (Reaxys Registry Number): 4140467
MDL Number: MFCD00064559
Hazard Symbols: Xi (Irritant) / H302 (Harmful if swallowed)
Risk Phrases (R phrases): R36/37/38 (Irritation to eyes, respiratory system, and skin)
Safety Phrases (S phrases): S26 (In case of accidental contact with eyes, rinse immediately with plenty of water and consult a doctor); S36 (Wear appropriate protective clothing); S24/25 (Avoid contact with skin and eyes)
HS Code 29211190 (Methylamine and its salts)
I. Properties
Deuterated methylamine hydrochloride is a stable deuterated organic compound, belonging to the deuterated derivative hydrochloride family of methylamine. It is physically a white to off-white crystalline powder or solid, with a melting point typically in the range of 232-234°C (literature values). This compound exhibits significant hygroscopicity and deliquescence, therefore requiring strict moisture protection during storage and handling. Its chemical properties are similar to methylamine hydrochloride, but due to the substitution of three hydrogen atoms on the methyl group with deuterium (D), it exhibits unique isotopic labeling characteristics in nuclear magnetic resonance (NMR) and mass spectrometry (MS) analyses. Deuterated purity is typically above 98% to 99 atom % D. This substance is stable at room temperature, but contact with strong oxidizing agents and strong bases should be avoided to prevent decomposition or reaction. Its aqueous solution is acidic (pH approximately 5-7), soluble in polar solvents such as DMSO and methanol, but has low solubility in nonpolar solvents such as diethyl ether and chloroform.
II. Applications
Deuterated methylamine hydrochloride is an important chemical synthesis intermediate widely used in pharmaceutical research and development, organic synthesis, and analytical chemistry. Its main applications include:
Deuterated Drug Synthesis:** As a key intermediate in the synthesis of deuterated drug molecules, such as deuterated drugs like deuterated clindamycinib, it improves the metabolic stability and pharmacokinetic properties of drugs by introducing deuterium atoms.
Nuclear Magnetic Resonance (NMR) Studies:** Used as an NMR solvent or standard to aid in the analysis of molecular structure and reaction mechanisms, particularly in hydrogen-deuterium exchange studies.
Mass Spectrometry (MS):** Used as an internal standard or reference standard in analytical techniques such as liquid chromatography-mass spectrometry (LC-MS) to improve the accuracy of quantitative analysis.
Organic synthesis building blocks: Used to prepare other deuterated amines, heterocyclic compounds, and functional molecules; a fundamental reagent in deuteration chemistry research.
Isotope labeling studies: Introducing deuterium labeling in reaction mechanism studies, metabolic pathway tracing, and hydrogen-deuterium exchange processes.
III. Preparation Methods The main methods for preparing deuterated methylamine hydrochloride are as follows, combining common synthetic routes from patent literature and chemical databases:
Method 1: Deuterated nitromethane reduction method (common industrial method)
Preparation of deuterated nitromethane: In the presence of a base (such as sodium hydride, deuterated sodium hydroxide, potassium carbonate, etc.) and a phase transfer catalyst, nitromethane is reacted with heavy water (D₂O), and deuterated nitromethane (CD₃NO₂) is obtained through hydrogen-deuterium exchange. The process can be repeated if necessary to improve deuteration purity.
Reduction Reaction: Deuterated nitromethane is dissolved in an inert solvent (such as THF or methanol), and hydrogen gas (H₂) is introduced in the presence of a catalyst (such as 10% palladium on carbon, Pd-C) to carry out a reduction reaction, producing deuterated methylamine (CD₃NH₂).
Salt Formation: Hydrochloric acid (HCl) is added dropwise to the reaction solution for acidification, converting deuterated methylamine to its hydrochloride salt. The catalyst is removed by filtration, and the filtrate is concentrated under reduced pressure to obtain crude deuterated methylamine hydrochloride.
Purification: High-purity product is obtained by recrystallization or other purification methods.
Method Two: Deuterated Methanol Derivatization Method
Preparation of Deuterated p-Toluenesulfonate Methyl Ester: Deuterated methanol (CD₃OD) is reacted with p-toluenesulfonyl chloride (TsCl) under alkaline conditions to produce deuterated p-toluenesulfonate methyl ester (CD₃OTs).
Amination: CD₃OTs are reacted with an amino protecting agent (such as triphenylmethane or phthalimide) to introduce a deuterated methyl group.
Deprotection and Salt Formation: The protecting group is removed by acidolysis, and finally reacted with hydrochloric acid to obtain deuterated methylamine hydrochloride.
Method 3: N-(1,1,1-trideuterated methyl)benzosuccinimide Method
Deuterated methylamine hydrochloride is directly generated by reacting N-(1,1,1-trideuterated methyl)benzosuccinimide with acid. This method is suitable for specific laboratory synthesis.
IV. Safety Information
Hazard Overview
GHS Hazard Categories: Acute toxicity (oral, Category 4); Skin corrosion/irritation (Category 2); Serious eye damage/eye irritation (Category 2A); Specific target organ toxicity (single exposure, respiratory irritation, Category 3).
Warning Words: WARNING
Hazard Statement: H302 (Harmful if swallowed); H315 (Causes skin irritation); H319 (Causes serious eye irritation); H335 (May cause respiratory irritation).
Safe Handling and Protection
Personal Protection: Wear appropriate protective gloves, safety glasses or face shield, respirator (half-face or full-face), and protective clothing when handling.
Ventilation Requirements: Operate in a well-ventilated environment. Avoid inhaling dust or vapors.
Avoid Contact: Avoid direct contact with skin and eyes; avoid inhaling dust; avoid contact with strong oxidizers and strong alkalis.
Storage Conditions: Store in a tightly closed container in a cool, dry, and well-ventilated place; it is recommended to use an inert gas (such as nitrogen or argon) for protection; keep away from sources of fire and heat; store separately from oxidizers and alkalis.
Emergency Measures:
Skin Contact: Immediately wash with plenty of soap and water.
Eye Contact: Immediately flush with plenty of water for at least 15 minutes and seek medical attention.
Inhalation: Immediately move to fresh air, keep the airway open, and provide artificial respiration or oxygen if necessary.
Ingestion: Rinse mouth, drink plenty of warm water, induce vomiting (only for conscious individuals), and seek immediate medical attention.
Disposal: Dispose of in accordance with local regulations; avoid discharge into sewers or the environment.
Transportation Information:
UN Number: No specific UN number (usually transported as general chemicals).
Packaging Category: Packed according to regulations for flammable solids or irritants.
Customs Supervision: Import and export must comply with relevant regulations for hazardous chemicals; provide an MSDS and compliant declaration.
V. Our Production Advantages and Capacity
Regular production capacity: From kilograms (kg) to tens of kilograms, flexibly adjustable according to orders.
Single batch output: Multiple specifications available, including 0.5 kg / 1 kg / 5 kg.
Customization Capacity: Supports gradient scale-up from milligram (mg) samples to kilogram (kg) commercial batches.
Delivery Time: Samples: 1–2 weeks; Regular batches: 3–4 weeks; Bulk orders: Negotiable.
Packaging Specifications: 1 g / 5 g / 10 g / 100 g / 1 kg / 5 kg, custom packaging supported.
Storage and Transportation: Inert atmosphere (nitrogen/argon) sealed packaging, cold chain or ambient temperature transportation, worldwide delivery.
Post time: May-15-2026
