Benzylisoquinoline

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Benzylisoquinoline
Benzylisoquinoline structure.svg
Names
Preferred IUPAC name
1-Benzylisoquinoline
Systematic IUPAC name
1-(Phenylmethyl)isoquinoline
Identifiers
3D model (JSmol)
ChemSpider
Properties
C16H13N
Molar mass 219.28112 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

1-Benzylisoquinoline is a chemical compound, and the structural backbone of many alkaloids with a wide variety of structures, including papaverine, noscapine, codeine, morphine, apomorphine, berberine, protopine, tubocurarine, and sanguinarine.

Biosynthesis[edit]

Plants producing benzylisoquinoline alkaloids have a common biosynthetic pathway, making use of two units of L-tyrosine. One tyrosine molecule is metabolised to dopamine which constitutes the isoquinoline part, while the benzylic part is mostly formed from tyramine, itself the decarboxylation product of tyrosine.

Many benzylisoquinolines have a methylated nitrogen atom as well as functional groups containing oxygen (−OH, −OCH3, −OCH2O−) in positions 6, 7, 3′ and 4′. The latter come from the precursors mentioned above, namely tyrosine, dopamine and their derivatives.

Examples of benzylisoquinoline alkaloids[edit]

See also[edit]

References[edit]