Reticuline

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Reticuline

IUPAC name (1S)-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-ol
Identifiers
CAS number	485-19-8^Y
PubChem	439653
ChEMBL	CHEMBL401501^N
Jmol-3D images	Image 1
SMILES CN1CCC2=CC(=C(C=C2[C@@H]1CC3=CC(=C(C=C3)OC)O)O)OC
Properties
Molecular formula	C₁₉H₂₃NO₄
Molar mass	329.39 g/mol
Exact mass	329.162708
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Reticuline is a chemical compound that can be found in Lindera aggregata.^[1] It is also one of the alkaloids found in opium.

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.

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

References

^ Simultaneous determination of four alkaloids in Lindera aggregata by ultra-high-pressure liquid chromatography–tandem mass spectrometry. Zheng Han, Yunliang Zheng, Na Chen, Lianjun Luan, Changxin Zhou, Lishe Gan and Yongjiang Wu, Journal of Chromatography A, Volume 1212, Issues 1-2, 28 November 2008, Pages 76-81

v t e Opium components

Alkaloids	16-Hydroxythebaine Berberine Canadine Codamine Coptisine Coreximine Cycloartenol Cycloartenone Cyclolaudenol Dehydroreticuline Dihydrosanguinarine Glaucine Isoboldine Isocorypalmine Laudanidine Magnoflorine Narceine Narceinone Norlaudanosoline Norsanguinarine Oripavine Oxysanguinarine Palaudine Papaverrubine B (O-methyl-porphyroxine) Papaverrubine C (epiporphyroxine) Reticuline Salutaridine (sinoacutine) Sanguinarine Scoulerine Somniferine Stepholidine

Morphine group (Phenanthrenes. Includes opioids)	Codeine Morphine Narcotoline Neopine Perparin Papaverrubine D (porphyroxine) Pseudocodeine Pseudomorphine Thebaine

Isoquinolines	Cotarnine Eupaverine Hydrocotarnine Laudanosine Laudanine Noscapine (narcotine) Papaverine Papaveraldine Xanthaline

Protopine group	α-Allocryptopine α-Fagarine Corycavamine Corycavine Cryptopine Protopine

Tetrahydroprotoberberine group	Corydaline Corybulbine Isocorybulbine Capaurine

Aporphine group	Dicentrine Glaucine Corytuberine Cularine Corydine Isocorydine Bulbocapnine

Phtalide-isoquinolines	Adulmine Bicuculline Bicucine Corlumine

α-Naphthaphenanthridines	Chelidonine β-Homochelidonoine Chelerythrine Sanguinarine

Other components	Meconic acid

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