NBoc-DMT

Chemical compound

Chemical structure of N-Boc-DMT

N-Boc-DMT (N-tert-butoxycarbonyl-N,N-dimethyltryptamine) is a synthetic compound that belongs to the class of tryptamines. It is a derivative of dimethyltryptamine (DMT), a well-known psychedelic compound, and is used primarily in chemical research.

Chemical Structure and Properties

N-Boc-DMT is characterized by the presence of a tert-butoxycarbonyl (Boc) protecting group attached to the nitrogen atom of the indole ring. This modification makes N-Boc-DMT more stable than DMT, which is beneficial for certain types of chemical synthesis and research applications.

The chemical formula of N-Boc-DMT is C₁₇H₂₄N₂O₂, and it has a molar mass of 288.39 g/mol. The presence of the Boc group increases the molecular weight compared to DMT.

Synthesis

The synthesis of N-Boc-DMT typically involves the protection of the amine group of DMT with a Boc group. This is achieved through a reaction with di-tert-butyl dicarbonate (Boc₂O) in the presence of a base such as triethylamine. The reaction proceeds under mild conditions and results in the formation of N-Boc-DMT as a stable intermediate.

Applications in Research

N-Boc-DMT is primarily used in the field of organic chemistry as a protected form of DMT. The Boc group serves as a protecting group that can be removed under acidic conditions, allowing for further chemical modifications of the tryptamine core. This makes N-Boc-DMT a valuable intermediate in the synthesis of more complex tryptamine derivatives.

Pharmacology

While N-Boc-DMT itself is not known to have significant pharmacological activity, it is related to DMT, which is a potent psychedelic compound. DMT acts as an agonist at the 5-HT_2A receptor, which is believed to be responsible for its psychedelic effects. However, the Boc group in N-Boc-DMT likely prevents it from interacting with these receptors in the same way.

Safety and Handling

As with many chemical compounds used in research, N-Boc-DMT should be handled with care. Appropriate laboratory safety procedures should be followed, including the use of personal protective equipment such as gloves and goggles. It should be stored in a cool, dry place, away from incompatible substances.

Related Pages

• Dimethyltryptamine
• Tryptamine
• Protecting group
• Organic synthesis