Tetrahydroisoquinoline

1,2,3,4- tetrahydroisoquinoline

Light yellow liquid

Liquid

1.05 g · cm -3 ( 20 ° C)

-30 ° C

232-233 ° C

20 g / l in water

1.5668 (20 ° C)

Attention

Template: Infobox chemical / molecular formula search available

As tetrahydroisoquinoline the secondary amine 1,2,3,4- tetrahydroisoquinoline is usually referred to. This consists of a benzene ring fused to the piperidine. Alternatively, the 5,6,7,8- tetrahydroisoquinoline is possible, which can be described as a pyridine -fused cyclohexane ring. The main body of tetrahydroisoquinoline derived from the amino acid tyrosine.

Properties

Tetrahydroisoquinoline has a flash point of 98 ° C.

Synthesis

Tetrahydroisoquinoline can be synthesized with elimination of water using the Pictet -Spengler reaction of phenylethylamine and formaldehyde in acidic medium. By using substituted phenethylamines or higher aldehydes, derivatives of tetrahydroisoquinoline are accessible.

Use

Some derivatives of tetrahydroisoquinoline have a pharmacological effect and are sometimes used as drugs:

  • Muscle relaxants such as tubocurarine
  • High blood pressure medicines such as ACE inhibitors, quinapril HCl or Quinapirilat and moexipril, and debrisoquine. These are all derivatives of 1,2,3,4- tetrahydroisoquinoline.
  • Incontinence such as solifenacin.

Tetrahydroisoquinoline alkaloids

CAS registry number PubChem Dangerous Substances Directive (67/548/EEC) Annulation Tubocurarine chloride CRC Handbook of Chemistry and Physics
766447
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