1-Benzylisoquinoline
From DrugPedia: A Wikipedia for Drug discovery
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| 1-Benzylisoquinoline
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| Systematic (IUPAC) name | |
| 1-(phenylmethyl)isoquinoline | |
| Identifiers | |
| CAS number | |
| ATC code | ? |
| PubChem | |
| ChemSpider | |
| Chemical data | |
| Formula | C16H13N |
| Mol. mass | 219.28112 |
| SMILES | & |
| Synonyms | 1-(phenylmethyl)isoquinoline |
| Pharmacokinetic data | |
| Bioavailability | ? |
| Metabolism | ? |
| Half life | ? |
| Excretion | ? |
| Therapeutic considerations | |
| Pregnancy cat. |
? |
| Legal status | |
| Routes | ? |
Contents |
[edit] Description
1-Benzylisoquinoline is the structural backbone of many alkaloids with a wide variety of structures, including papaverine, noscapine, codeine, morphine, apomorphine, berberine, protopine and tubocurarine.
[edit] 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.
[edit] General Properties
*Molecular Weight
219.28112
*Molecular Formula
C16H13N
*IUPAC NAME
1-(phenylmethyl)isoquinoline
*Canonical Smiles
C1=CC=C(C=C1)CC2=NC=CC3=CC=CC=C32
*Isomeric Smiles
N/A
*XLogP
3.9
*Topological Polar Surface Area
12.9
[edit] External Links
[edit] References
- Benzylisoquinoline biosynthesis by cultivated plant cells and isolated enzymes
- Organic Syntheses, Coll. Vol. 6, p. 115, 1988
