Benzylisoquinoline

Benzylisoquinoline

Names
IUPAC name 1-(Phenylmethyl)isoquinoline
Identifiers
CAS Registry Number	6907-59-1 N
ChemSpider	21830 Y
InChI InChI=1S/C16H13N/c1-2-6-13(7-3-1)12-16-15-9-5-4-8-14(15)10-11-17-16/h1-11H,12H2 Y Key: IZTUINVRJSCOIR-UHFFFAOYSA-N Y
Jmol-3D images	Image
PubChem	23345
SMILES c13ccccc3ccnc1Cc2ccccc2
Properties
Chemical formula	C16H13N
Molar mass	219.28112 g/mol
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
N verify (what is: Y/N?)
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

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

• 

  Papaverine

• 

  Noscapine

• 

  Apomorphine (one additional ring closure)

• 

  Morphine (two additional ring closures)

• 

  Berberine (one additional ring closure with incorporated N-methyl)

• 

  Protopine (with opened pyridine ring)

• 

  Tubocurarine (composed of two benzylisoquinoline units)

See also

• Morphinan

References

• Benzylisoquinoline biosynthesis by cultivated plant cells and isolated enzymes