Benzylisoquinoline

Benzylisoquinoline

Names
IUPAC name 1-(Phenylmethyl)isoquinoline
Identifiers
CAS Number	6907-59-1
ChemSpider	21830
Jmol interactive 3D	Image
PubChem	23345
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 Key: IZTUINVRJSCOIR-UHFFFAOYSA-N
SMILES c13ccccc3ccnc1Cc2ccccc2
Properties
Chemical formula	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).
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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