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词条 Benzylisoquinoline
释义

  1. Biosynthesis

  2. Examples of benzylisoquinoline alkaloids

  3. See also

  4. References

{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 458441421
| ImageFile = Benzylisoquinoline structure.svg
| ImageSize = 200px
| PIN = 1-Benzylisoquinoline
| SystematicName = 1-(Phenylmethyl)isoquinoline
| Section1 = {{Chembox Identifiers
| CASNo_Ref = {{cascite|changed|??}}
| CASNo = 6907-59-1
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = IZTUINVRJSCOIR-UHFFFAOYSA-N
| PubChem = 23345
| SMILES = c13ccccc3ccnc1Cc2ccccc2
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 21830
| Section2 = {{Chembox Properties
| Formula = C16H13N
| MolarMass = 219.28112 g/mol
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility =
}}

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

See also

  • Morphinan

References

  • Benzylisoquinoline biosynthesis by cultivated plant cells and isolated enzymes

2 : Alkaloids|Isoquinolines

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