[4-(Methylamino)cyclohexyl]methanol
[CAS# 400898-77-3]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Amine
• Name: [4-(Methylamino)cyclohexyl]methanol
• Synonyms: [trans-4-(Aminomethyl)cyclohexyl]methanol
• Molecular Formula: C₈H₁₇NO
• Molecular Weight: 143.23
• CAS Registry Number: 400898-77-3
• EC Number: 846-270-0
• SMILES: CNC1CCC(CC1)CO

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H315-H318-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P354+P338-P317-P319-P321-P332+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	-
Serious eye damage	Eye Dam.	1	-
Specific target organ toxicity - single exposure	STOT SE	3	-

• Transport Information: UN 3077

Discovery and Applications

[4-(Methylamino)cyclohexyl]methanol, also known as MXE or methoxythamine precursor, is a versatile compound with the molecular formula C8H17NO and a molecular weight of 143.23 g/mol. It features a cyclohexyl ring substituted with a methylamino group at the para position and a methanol group at the 1 position, making it a valuable intermediate for the synthesis of a wide range of compounds, especially in the pharmaceutical industry.

The discovery of [4-(methylamino)cyclohexyl]methanol can be linked to the development of arylcyclohexylamine derivatives, which have attracted attention for their potential psychoactive and anesthetic properties. MXE itself is closely related to ketamine and phencyclidine (PCP), two compounds that were originally studied for their isolated anesthetic effects in the mid-20th century. The synthesis of MXE and its precursors, including [4-(methylamino)cyclohexyl]methanol, was driven by the quest to develop novel compounds with improved pharmacological properties and safety margins.

The typical synthesis of [4-(methylamino)cyclohexyl]methanol involves the methylation of cyclohexanone followed by reduction and methylation of the resulting product. The process can be summarized as the reaction of cyclohexanone with methylamine to form [4-(methylamino)cyclohexanone]. The intermediate is then reduced to [4-(methylamino)cyclohexanone]methanol using a reducing agent such as sodium borohydride.

[4-(methylamino)cyclohexyl]methanol is a precursor for the synthesis of MXE, which, although a recreational drug, has also been studied for potential medical applications as an anesthetic and antidepressant. It facilitates the synthesis of compounds with dissociative properties that can be used in clinical and research settings.

In chemical research, this compound is used to explore the structure-activity relationships of aromatic cyclohexylamines. Its unique structural features allow for the study of various pharmacological effects and the development of safer analogs for potential therapeutic uses.

It is a key intermediate in the development of synthetic pathways to produce other cyclohexylamines. Its reactivity and functional groups make it a versatile building block in organic synthesis, facilitating the creation of complex molecules.

References

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