Tetrahydroisoquinoline is a secondary amine with the chemical formula C₉H₁₁N.

Reactions

Like other secondary amines, tetrahydroisoquinoline can be oxidized to the corresponding nitrone

Nitrone

A nitrone is the N-oxide of an imine and a functional group in organic chemistry. The general structure is R1R2C=NR3+O- where R3 is different from H.A nitrone is 1,3-dipole in 1,3-dipolar cycloadditions...

 using hydrogen peroxide

Hydrogen peroxide

Hydrogen peroxide is the simplest peroxide and an oxidizer. Hydrogen peroxide is a clear liquid, slightly more viscous than water. In dilute solution, it appears colorless. With its oxidizing properties, hydrogen peroxide is often used as a bleach or cleaning agent...

, catalyzed by selenium dioxide

Selenium dioxide

Selenium dioxide is the chemical compound with the formula SeO2. This colorless solid is one of the most frequently encountered compounds of selenium.-Properties:...

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Tetrahydroisoquinolines

The tetrahydroisoquinoline skeleton is commonly encountered in pharmaceutical drugs, notably quaternary ammonium muscle relaxants such as tubocurarine

Tubocurarine

Tubocurarine is a neuromuscular-blocking drug or skeletal muscle relaxant in the category of non-depolarizing neuromuscular-blocking drugs, used adjunctively in anesthesia to provide skeletal muscle relaxation during surgery or mechanical ventilation...

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Toxicology

Tetrahydroisoquinoline derivatives may be formed in the body as metabolites of some drugs, and this was once thought to be involved in the development of alcoholism

Alcoholism

Alcoholism is a broad term for problems with alcohol, and is generally used to mean compulsive and uncontrolled consumption of alcoholic beverages, usually to the detriment of the drinker's health, personal relationships, and social standing...

. This theory has now been discredited and is no longer generally accepted by the scientific community, but endogenous production of neurotoxic tetrahydroisoquinoline derivatives such as norsalsolinol

Norsalsolinol

Norsalsolinol is a chemical compound that is produced naturally in the body through metabolism of dopamine. It has been shown to be a selective dopaminergic neurotoxin, and has been suggested as a possible cause of neurodegenerative conditions such as Parkinson's disease and the brain damage...

 continue to be investigated as possible causes for some conditions such as Parkinson's disease

Parkinson's disease

Parkinson's disease is a degenerative disorder of the central nervous system...

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4'-Ar-tetrahydroisoquinolines

These useful drugs like nomifensine

Nomifensine

Nomifensine is a norepinephrine-dopamine reuptake inhibitor developed by a team at Hoechst AG in the 1960s.. The drug was test-marketed in the United States by Hoechst AG , i.e. a drug that increases the amount of synaptic norepinephrine and dopamine available to receptors by blocking the dopamine...

 and diclofensine

Diclofensine

Diclofensine is a stimulant drug which acts as a triple monoamine reuptake inhibitor, primarily inhibiting the reuptake of dopamine and noradrenaline...

are made as follows:
Natural sources of these alkaloids: cherylline and latifine.