Chemistry:Nantenine

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 ;
PubChem CID	197001;
ChemSpider	170619 ;
UNII	XE0AU8C122;
ChEMBL	ChEMBL467094 ;
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 ; Key:WSVWKHTVFGTTKJ-AWEZNQCLSA-N ;
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Short description: Chemical compound

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

↑ "Serotonergic receptor antagonist from Nandina domestica Thunberg". Journal of Pharmaceutical Sciences 73 (4): 568–70. April 1984. doi:10.1002/jps.2600730435. PMID 6726648.
↑ "Alkaloids of Corydalis slivenensis". Planta Medica 44 (3): 168–70. March 1982. doi:10.1055/s-2007-971432. PMID 17402105.
↑ "Structure-activity relationship studies with (+/-)-nantenine derivatives for alpha1-adrenoceptor antagonist activity". European Journal of Pharmacology 437 (3): 173–8. February 2002. doi:10.1016/S0014-2999(02)01303-1. PMID 11890906.
↑ "(+/-)-Nantenine analogs as antagonists at human 5-HT(2A) receptors: C1 and flexible congeners". Bioorganic & Medicinal Chemistry Letters 19 (9): 2530–2. May 2009. doi:10.1016/j.bmcl.2009.03.048. PMID 19328689.
↑ "Nantenine: an antagonist of the behavioral and physiological effects of MDMA in mice". Psychopharmacology 173 (3–4): 270–7. May 2004. doi:10.1007/s00213-003-1741-2. PMID 14740148.

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[pmid6726648-1] "Serotonergic receptor antagonist from Nandina domestica Thunberg". Journal of Pharmaceutical Sciences 73 (4): 568–70. April 1984. doi:10.1002/jps.2600730435. PMID 6726648.

[pmid17402105-2] "Alkaloids of Corydalis slivenensis". Planta Medica 44 (3): 168–70. March 1982. doi:10.1055/s-2007-971432. PMID 17402105.

[pmid11890906-3] "Structure-activity relationship studies with (+/-)-nantenine derivatives for alpha1-adrenoceptor antagonist activity". European Journal of Pharmacology 437 (3): 173–8. February 2002. doi:10.1016/S0014-2999(02)01303-1. PMID 11890906.

[pmid19328689-4] "(+/-)-Nantenine analogs as antagonists at human 5-HT(2A) receptors: C1 and flexible congeners". Bioorganic & Medicinal Chemistry Letters 19 (9): 2530–2. May 2009. doi:10.1016/j.bmcl.2009.03.048. PMID 19328689.

[pmid14740148-5] "Nantenine: an antagonist of the behavioral and physiological effects of MDMA in mice". Psychopharmacology 173 (3–4): 270–7. May 2004. doi:10.1007/s00213-003-1741-2. PMID 14740148.

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v t e Adrenergic receptor modulators
α₁	Agonists: 6-FNE Amidephrine Anisodine Buspirone Cirazoline Corbadrine Desglymidodrine Dexisometheptene Dipivefrine Dopamine Droxidopa (L-DOPS) Ephedrine Epinephrine Etilefrine Etilevodopa Ethylnorepinephrine Indanidine Isometheptene L-DOPA (levodopa) L-Phenylalanine L-Tyrosine Melevodopa Metaraminol Methoxamine Methyldopa Midodrine Naphazoline Norepinephrine Octopamine (drug) Oxymetazoline Phenylephrine Phenylpropanolamine Pseudoephedrine Synephrine Tetryzoline Tiamenidine XP21279 Xylometazoline Antagonists: Abanoquil Adimolol Ajmalicine Alfuzosin Amosulalol Anisodamine Arotinolol Atiprosin Atypical antipsychotics (e.g., brexpiprazole, clozapine,Chemistry:Olanzapine
α₂	Agonists: (R)-3-Nitrobiphenyline 4-NEMD 6-FNE Amitraz Apraclonidine Brimonidine Cannabivarin Clonidine Corbadrine Detomidine Dexmedetomidine Dihydroergotamine Dipivefrine Dopamine Droxidopa (L-DOPS) Etilevodopa Ephedrine Ergotamine Epinephrine Etilefrine Ethylnorepinephrine Guanabenz Guanfacine Guanoxabenz L-DOPA (levodopa) L-Phenylalanine L-Tyrosine Lofexidine Medetomidine Melevodopa Methyldopa Mivazerol Naphazoline Norepinephrine Oxymetazoline Phenylpropanolamine Piperoxan Pseudoephedrine Rezatomidine Rilmenidine Romifidine Talipexole Tasipimidine Tetrahydrozoline Tiamenidine Tizanidine Tolonidine Urapidil Vatinoxan XP21279 Xylazine Xylometazoline Antagonists: 1-PP Adimolol Amesergide Aptazapine Atipamezole Atypical antipsychotics (e.g., asenapine, Chemistry:Brexpiprazole
β	Agonists: Abediterol Alifedrine Amibegron Arbutamine Arformoterol Arotinolol BAAM Bambuterol Befunolol Bitolterol Broxaterol Buphenine Carbuterol Carmoterol Cimaterol Clenbuterol Colterol Corbadrine Denopamine Dipivefrine Dobutamine Dopamine Dopexamine Droxidopa (L-DOPS) Ephedrine Epinephrine Etafedrine Etilefrine Etilevodopa Ethylnorepinephrine Fenoterol Formoterol Hexoprenaline Higenamine Indacaterol Isoetarine Isoprenaline Isoxsuprine L-DOPA (levodopa) L-Phenylalanine L-Tyrosine Levosalbutamol Mabuterol Melevodopa Methoxyphenamine Methyldopa Mirabegron Norepinephrine Orciprenaline Oxyfedrine PF-610355 Phenylpropanolamine Pirbuterol Prenalterol Ractopamine Procaterol Pseudoephedrine Reproterol Rimiterol Ritodrine Salbutamol Salmeterol Solabegron Terbutaline Tretoquinol Tulobuterol Vilanterol Xamoterol XP21279 Zilpaterol Zinterol Antagonists: Acebutolol Adaprolol Adimolol Afurolol Alprenolol Alprenoxime Amosulalol Ancarolol Arnolol Arotinolol Atenolol Befunolol Betaxolol Bevantolol Bisoprolol Bopindolol Bornaprolol Brefonalol Bucindolol Bucumolol Bufetolol Bufuralol Bunitrolol Bunolol Bupranolol Butaxamine Butidrine Butofilolol Capsinolol Carazolol Carpindolol Carteolol Carvedilol Celiprolol Cetamolol Cicloprolol Cinamolol Cloranolol Cyanopindolol Dalbraminol Dexpropranolol Diacetolol Dichloroisoprenaline Dihydroalprenolol Dilevalol Diprafenone Draquinolol Ecastolol Epanolol Ericolol Ersentilide Esatenolol Esprolol Eugenodilol Exaprolol Falintolol Flestolol Flusoxolol Hydroxycarteolol Hydroxytertatolol ICI-118,551 Idropranolol Indenolol Indopanolol Iodocyanopindolol Iprocrolol Isoxaprolol Isamoltane Labetalol Landiolol Levobetaxolol Levobunolol Levomoprolol Medroxalol Mepindolol Metipranolol Metoprolol Moprolol Nadolol Nadoxolol Nebivolol Nifenalol Nipradilol Oxprenolol Pacrinolol Pafenolol Pamatolol Pargolol Penbutolol Pindolol Practolol Primidolol Procinolol Pronethalol Propafenone Propranolol Ridazolol Ronactolol Soquinolol Sotalol Spirendolol SR 59230A Sulfinalol Talinolol Tazolol Tertatolol Tienoxolol Tilisolol Timolol Tiprenolol Tolamolol Toliprolol Xibenolol Xipranolol

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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
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
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