Nantenine

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 376961098

| IUPAC_name = (S)-1,2-Dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-benzo[de][1,3]benzodioxolo[5,6-g]quinoline

| image = Nantenine.png

| image_class = skin-invert-image

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| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 2565-01-7

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = XE0AU8C122

| ATC_prefix = none

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| PubChem = 197001

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

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

| ChEMBL = 467094

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

| ChemSpiderID = 170619

| synonyms =

| C=20 | H=21 | N=1 | O=4

| SMILES = CN1CCC2=CC(=C(C3=C2[C@@H]1CC4=CC5=C(C=C43)OCO5)OC)OC

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

| StdInChI = 1S/C20H21NO4/c1-21-5-4-11-7-17(22-2)20(23-3)19-13-9-16-15(24-10-25-16)8-12(13)6-14(21)18(11)19/h7-9,14H,4-6,10H2,1-3H3/t14-/m0/s1

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

| StdInChIKey = WSVWKHTVFGTTKJ-AWEZNQCLSA-N

}}

Nantenine is an alkaloid found in the plant Nandina domestica{{cite journal |vauthors=Shoji N, Umeyama A, Takemoto T, Ohizumi Y |title=Serotonergic receptor antagonist from Nandina domestica Thunberg |journal=Journal of Pharmaceutical Sciences |volume=73 |issue=4 |pages=568–70 |date=April 1984 |pmid=6726648 |doi= 10.1002/jps.2600730435}} as well as some Corydalis species.{{cite journal |vauthors=Kiryakov HG, Iskrenova E, Daskalova E, Kuzmanov B, Evstatieva L |title=Alkaloids of Corydalis slivenensis |journal=Planta Medica |volume=44 |issue=3 |pages=168–70 |date=March 1982 |pmid=17402105 |doi=10.1055/s-2007-971432 }} It is an antagonist of both the α₁-adrenergic receptor{{cite journal |vauthors=Indra B, Matsunaga K, Hoshino O, Suzuki M, Ogasawara H, Ohizumi Y |title=Structure-activity relationship studies with (+/-)-nantenine derivatives for alpha1-adrenoceptor antagonist activity |journal=European Journal of Pharmacology |volume=437 |issue=3 |pages=173–8 |date=February 2002 |pmid=11890906 |doi= 10.1016/S0014-2999(02)01303-1 }} and the serotonin 5-HT_2A receptor,{{cite journal |vauthors=Chaudhary S, Pecic S, Legendre O, Navarro HA, Harding WW |title=(+/-)-Nantenine analogs as antagonists at human 5-HT(2A) receptors: C1 and flexible congeners |journal=Bioorganic & Medicinal Chemistry Letters |volume=19 |issue=9 |pages=2530–2 |date=May 2009 |pmid=19328689 |doi=10.1016/j.bmcl.2009.03.048 |pmc=2677726}} and blocks both the behavioral and physiological effects of MDMA in animals.{{cite journal |vauthors=Fantegrossi WE, Kiessel CL, Leach PT, Van Martin C, Karabenick RL, Chen X, Ohizumi Y, Ullrich T, Rice KC, Woods JH |title=Nantenine: an antagonist of the behavioral and physiological effects of MDMA in mice |journal=Psychopharmacology |volume=173 |issue=3–4 |pages=270–7 |date=May 2004 |pmid=14740148 |doi=10.1007/s00213-003-1741-2 |hdl=2027.42/46360 |s2cid=8425621 |hdl-access=free }}