Reticuline

{{This|an alkaloid chemical|the connective-tissue fiber|reticular fiber}}

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 398757401

| Name = Reticuline

| ImageFile = File:Reticuline.png

| ImageFile2 = File:Reticuline 3D.png

| IUPACName = 3,10-Dimethoxy-8,8a-secoberbine-2,9-diol

| SystematicName = (1S)-1-[(3-Hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol

| OtherNames =

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 485-19-8

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = X35Z551WT4

| SMILES = CN1CCC2=CC(=C(C=C2[C@@H]1CC3=CC(=C(C=C3)OC)O)O)OC

| PubChem = 439653

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 388724

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = C02105

| 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

| InChIKey = BHLYRWXGMIUIHG-HNNXBMFYBI

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = BHLYRWXGMIUIHG-HNNXBMFYSA-N

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 401501

}}

|Section2={{Chembox Properties

| C=19 | H=23 | N=1 | O=4

}}

}}

Reticuline is an alkaloid found in opium and a variety of plants including Lindera aggregata,{{cite journal |doi=10.1016/j.chroma.2008.10.017 |title=Simultaneous determination of four alkaloids in Lindera aggregata by ultra-high-pressure liquid chromatography–tandem mass spectrometry |year=2008 |last1=Han |first1=Zheng |last2=Zheng |first2=Yunliang |last3=Chen |first3=Na |last4=Luan |first4=Lianjun |last5=Zhou |first5=Changxin |last6=Gan |first6=Lishe |last7=Wu |first7=Yongjiang |journal=Journal of Chromatography A |volume=1212 |pages=76–81 |pmid=18951552 |issue=1–2}} Annona squamosa,{{cite journal|author1=Dholvitayakhun, Achara |author2=Trachoo, Nathanon |author3=Sakee, Uthai | title=Potential applications for Annona squamosa leaf extract in the treatment and prevention of foodborne bacterial disease | journal=Natural Product Communications | year= 2013 | volume= 8 | issue= 3 | pages= 385–388 | pmid=23678817 |display-authors=etal|doi=10.1177/1934578X1300800327 | doi-access=free }} and Ocotea fasciculata (also known as Ocotea duckei).{{cite journal |doi=10.1016/S0378-8741(98)00044-0 |title=Central depressant effects of reticuline extracted from Ocotea duckei in rats and mice |year=1998 |last1=de Morais |first1=Liana Clébia Soares Lima |last2=Barbosa-Filho |first2=José Maria |last3=de Almeida |first3=Reinaldo Nóbrega |journal=Journal of Ethnopharmacology |volume=62 |pages=57–61 |pmid=9720612 |issue=1}}

Experiments in rodents suggest reticuline possesses potent central nervous system depressing effects. 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.{{Cite book|title=Bradley's neurology in clinical practice|others=Daroff, Robert B.,, Jankovic, Joseph,, Mazziotta, John C.,, Pomeroy, Scott Loren,, Bradley, W. G. (Walter George)|isbn=9780323339162|edition=Seventh|location=London|oclc=932031625|date = 2015-10-25}}