Reticuline

This article is about an alkaloid chemical. For the connective-tissue fiber, see reticular fiber.

Reticuline is a tetrahydroisoquinoline alkaloid. It is also classified as a benzylisoquinoline alkaloid.^[1]

Reticuline

Names
IUPAC name 3,10-Dimethoxy-8,8a-secoberbine-2,9-diol
Systematic IUPAC name (1S)-1-[(3-Hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol
Identifiers
CAS Number	485-19-8 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL401501 N
ChemSpider	388724 N
ECHA InfoCard	100.006.920
KEGG	C02105 Y
PubChem CID	439653
UNII	X35Z551WT4 Y
CompTox Dashboard (EPA)	DTXSID001317199
InChI InChI=1S/C19H23NO4/c1-20-7-6-13-10-19(24-3)17(22)11-14(13)15(20)8-12-4-5-18(23-2)16(21)9-12/h4-5,9-11,15,21-22H,6-8H2,1-3H3/t15-/m0/s1 N Key: BHLYRWXGMIUIHG-HNNXBMFYSA-N N InChI=1/C19H23NO4/c1-20-7-6-13-10-19(24-3)17(22)11-14(13)15(20)8-12-4-5-18(23-2)16(21)9-12/h4-5,9-11,15,21-22H,6-8H2,1-3H3/t15-/m0/s1 Key: BHLYRWXGMIUIHG-HNNXBMFYBI
SMILES CN1CCC2=CC(=C(C=C2[C@@H]1CC3=CC(=C(C=C3)OC)O)O)OC
Properties
Chemical formula	C19H23NO4
Molar mass	329.396 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Occurrence

Reticuline is found in opium and a variety of plants including Lindera aggregata,^[2] Annona squamosa,^[3] and Ocotea fasciculata (also known as Ocotea duckei).^[4]

Physiological effects

In rodents reticuline possesses potent central nervous system depressing effects.^[4] It is the precursor of morphine and many other alkaloids. It is also toxic to dopaminergic neurons causing a form of atypical parkinsonism known as Guadeloupean Parkinsonism.^[5]

Metabolism

3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase uses S-adenosyl methionine and 3'-hydroxy-N-methyl-(S)-coclaurine to produce S-adenosylhomocysteine and (S)-reticuline.

Reticuline oxidase uses (S)-reticuline and O₂ to produce (S)-scoulerine and H₂O₂.

Salutaridine synthase uses (R)-reticuline, NADPH, H⁺, and O₂ to produce salutaridine, NADP⁺, and H₂O. Salutaridine can then be transformed progressively to thebaine, oripavine, and morphine.

1,2-dehydroreticulinium reductase (NADPH) uses (R)-reticuline and NADP⁺ to produce 1,2-dehydroreticulinium, NADPH, and H⁺.