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Nantenine

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Nantenine
Clinical data

ATC code	none
Identifiers
IUPAC name (S)-1,2-Dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-benzo[de][1,3]benzodioxolo[5,6-g]quinoline
CAS Number	2565-01-7^Y
PubChem CID	197001
ChemSpider	170619^N
UNII	XE0AU8C122
ChEMBL	ChEMBL467094^N
CompTox Dashboard (EPA)	DTXSID70180343
Chemical and physical data
Formula	C₂₀H₂₁NO₄
Molar mass	339.391 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CN1CCC2=CC(=C(C3=C2[C@@H]1CC4=CC5=C(C=C43)OCO5)OC)OC
InChI InChI=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^N Key:WSVWKHTVFGTTKJ-AWEZNQCLSA-N^N
^NY (what is this?) (verify)

Nantenine is an alkaloid found in the plant Nandina domestica^[1] as well as some Corydalis species.^[2] It is an antagonist of both the α₁-adrenergic receptor^[3] and the serotonin 5-HT_2A receptor,^[4] and blocks both the behavioral and physiological effects of MDMA in animals.^[5]

References

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^ Shoji N, Umeyama A, Takemoto T, Ohizumi Y (April 1984). "Serotonergic receptor antagonist from Nandina domestica Thunberg". Journal of Pharmaceutical Sciences. 73 (4): 568–70. doi:10.1002/jps.2600730435. PMID 6726648.

^ Kiryakov HG, Iskrenova E, Daskalova E, Kuzmanov B, Evstatieva L (March 1982). "Alkaloids of Corydalis slivenensis". Planta Medica. 44 (3): 168–70. doi:10.1055/s-2007-971432. PMID 17402105.

^ Indra B, Matsunaga K, Hoshino O, Suzuki M, Ogasawara H, Ohizumi Y (February 2002). "Structure-activity relationship studies with (+/-)-nantenine derivatives for alpha1-adrenoceptor antagonist activity". European Journal of Pharmacology. 437 (3): 173–8. doi:10.1016/S0014-2999(02)01303-1. PMID 11890906.

^ Chaudhary S, Pecic S, Legendre O, Navarro HA, Harding WW (May 2009). "(+/-)-Nantenine analogs as antagonists at human 5-HT(2A) receptors: C1 and flexible congeners". Bioorganic & Medicinal Chemistry Letters. 19 (9): 2530–2. doi:10.1016/j.bmcl.2009.03.048. PMC 2677726. PMID 19328689.

^ Fantegrossi WE, Kiessel CL, Leach PT, Van Martin C, Karabenick RL, Chen X, Ohizumi Y, Ullrich T, Rice KC, Woods JH (May 2004). "Nantenine: an antagonist of the behavioral and physiological effects of MDMA in mice". Psychopharmacology. 173 (3–4): 270–7. doi:10.1007/s00213-003-1741-2. hdl:2027.42/46360. PMID 14740148. S2CID 8425621.