Benzylisoquinoline

Benzylisoquinoline

Names
Preferred IUPAC name 1-Benzylisoquinoline
Systematic IUPAC name 1-(Phenylmethyl)isoquinoline
Identifiers
CAS Number	6907-59-1 N
3D model (Jmol)	Interactive image
ChemSpider	21830 Y
PubChem CID	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 Y Key: IZTUINVRJSCOIR-UHFFFAOYSA-N Y
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).
N  (what is YN ?)
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.

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.

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)