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Chemical compound
Sinomenine Other names Cocculine ATC code
(9α,13α,14α)-4-Hydroxy-3,7-dimethoxy-17-methyl-7,8-didehydromorphinan-6-one
CAS Number PubChem CID ChemSpider UNII ChEMBL CompTox Dashboard (EPA ) ECHA InfoCard 100.003.722 Formula C 19 H 23 N O 4 Molar mass −1 3D model (JSmol )
CN1CC[C@@]23CC(=O)C(=C[C@@H]2[C@@H]1CC4=C3C(=C(C=C4)OC)O)OC
InChI=1S/C19H23NO4/c1-20-7-6-19-10-14(21)16(24-3)9-12(19)13(20)8-11-4-5-15(23-2)18(22)17(11)19/h4-5,9,12-13,22H,6-8,10H2,1-3H3/t12-,13+,19-/m1/s1
N Key:INYYVPJSBIVGPH-QHRIQVFBSA-N
N N Y (what is this?) (verify)
Sinomenine or cocculine is an alkaloid found in the root of the climbing plant Sinomenium acutum herbal medicine in these countries for rheumatism and arthritis .[ 1] morphinan derivative, related to opioids such as levorphanol and the non-opioid cough suppressant dextromethorphan . Its anti-rheumatic effects are thought to be primarily mediated via release of histamine ,[ 2] prostaglandin , leukotriene and nitric oxide synthesis may also be involved.[ 3]
^ Zhao ZZ, Liang ZT, Zhou H, Jiang ZH, Liu ZQ, Wong YF, et al. (January 2005). "Quantification of sinomenine in caulis sinomenii collected from different growing regions and wholesale herbal markets by a modified HPLC method" . Biological & Pharmaceutical Bulletin . 28 (1): 105–9. doi :10.1248/bpb.28.105 PMID 15635172 . ^ Yamasaki H (February 1976). "Pharmacology of sinomenine, an anti-rheumatic alkaloid from Sinomenium acutum". Acta Medica Okayama . 30 (1): 1–20. PMID 61710 . ^ Liu L, Riese J, Resch K, Kaever V (November 1994). "Impairment of macrophage eicosanoid and nitric oxide production by an alkaloid from Sinomenium acutum". Arzneimittel-Forschung . 44 (11): 1223–6. PMID 7848335 .
Ionotropic
GABAA Tooltip γ-Aminobutyric acid A receptor
Positive modulators (abridged; see here for a full list): α-EMTBL Alcohols (e.g., drinking alcohol , 2M2B )Anabolic steroids Avermectins (e.g., ivermectin )Barbiturates (e.g., phenobarbital )Benzodiazepines (e.g., diazepam )Bromide compounds (e.g., potassium bromide )Carbamates (e.g., meprobamate )Carbamazepine Chloralose Chlormezanone Clomethiazole Dihydroergolines (e.g., ergoloid (dihydroergotoxine) )Etazepine Etifoxine Fenamates (e.g., mefenamic acid )Flavonoids (e.g., apigenin , hispidulin )Fluoxetine Flupirtine Imidazoles (e.g., etomidate )Kava constituents (e.g., kavain )Lanthanum Loreclezole Monastrol Neuroactive steroids (e.g., allopregnanolone , cholesterol , THDOC )Niacin Niacinamide Nonbenzodiazepines (e.g., β-carbolines (e.g., abecarnil ), cyclopyrrolones (e.g., zopiclone ), imidazopyridines (e.g., zolpidem ), pyrazolopyrimidines (e.g., zaleplon ))Norfluoxetine Petrichloral Phenols (e.g., propofol )Phenytoin Piperidinediones (e.g., glutethimide )Propanidid Pyrazolopyridines (e.g., etazolate )Quinazolinones (e.g., methaqualone )Retigabine (ezogabine) ROD-188 Skullcap constituents (e.g., baicalin )Stiripentol Sulfonylalkanes (e.g., sulfonmethane (sulfonal) )Topiramate Valerian constituents (e.g., valerenic acid )Volatiles /gases (e.g., chloral hydrate , chloroform , diethyl ether , paraldehyde , sevoflurane )Negative modulators: 1,3M1B 3M2B 11-Ketoprogesterone 17-Phenylandrostenol α3IA α5IA (LS-193,268) β-CCB β-CCE β-CCM β-CCP β-EMGBL Anabolic steroids Amiloride Anisatin β-Lactams (e.g., penicillins , cephalosporins , carbapenems )Basmisanil Bemegride Bicyclic phosphates (TBPS , TBPO , IPTBO )BIDN Bilobalide Bupropion CHEB Chlorophenylsilatrane Cicutoxin Cloflubicyne Cyclothiazide DHEA DHEA-S Dieldrin (+)-DMBB DMCM DMPC EBOB Etbicyphat FG-7142 (ZK-31906) Fiproles (e.g., fipronil )Flavonoids (e.g., amentoflavone , oroxylin A )Flumazenil Fluoroquinolones (e.g., ciprofloxacin )Flurothyl Furosemide Golexanolone Iomazenil (123 I) IPTBO Isopregnanolone (sepranolone) L-655,708 Laudanosine Lindane MaxiPost Morphine Morphine-3-glucuronide MRK-016 Naloxone Naltrexone Nicardipine Nonsteroidal antiandrogens (e.g., apalutamide , bicalutamide , enzalutamide , flutamide , nilutamide )Oenanthotoxin Pentylenetetrazol (pentetrazol) Phenylsilatrane Picrotoxin (i.e., picrotin , picrotoxinin and dihydropicrotoxinin )Pregnenolone sulfate Propybicyphat PWZ-029 Radequinil Ro 15-4513 Ro 19-4603 RO4882224 RO4938581 Sarmazenil SCS Suritozole TB-21007 TBOB TBPS TCS-1105 Terbequinil TETS Thujone U-93631 Zinc ZK-93426 GABAA -ρ Tooltip γ-Aminobutyric acid A-rho receptor
Metabotropic
GABAB Tooltip γ-Aminobutyric acid B receptor
Receptor (ligands )
GlyR Tooltip Glycine receptor
Positive modulators: Alcohols (e.g., brometone , chlorobutanol (chloretone) , ethanol (alcohol) , tert -butanol (2M2P)tribromoethanol , trichloroethanol , trifluoroethanol )Alkylbenzene sulfonate Anandamide Barbiturates (e.g., pentobarbital , sodium thiopental )Chlormethiazole D12-116 Dihydropyridines (e.g., nicardipine )Etomidate Ginseng constituents (e.g., ginsenosides (e.g., ginsenoside-Rf ))Glutamic acid (glutamate) Ivermectin Ketamine Neuroactive steroids (e.g., alfaxolone , pregnenolone (eltanolone) , pregnenolone acetate , minaxolone , ORG-20599 )Nitrous oxide Penicillin G Propofol Tamoxifen Tetrahydrocannabinol Triclofos Tropeines (e.g., atropine , bemesetron , cocaine , LY-278584 , tropisetron , zatosetron )Volatiles /gases (e.g., chloral hydrate , chloroform , desflurane , diethyl ether (ether) , enflurane , halothane , isoflurane , methoxyflurane , sevoflurane , toluene , trichloroethane (methyl chloroform) , trichloroethylene )Xenon Zinc Antagonists: 2-Aminostrychnine 2-Nitrostrychnine 4-Phenyl-4-formyl-N-methylpiperidine αEMBTL Bicuculline Brucine Cacotheline Caffeine Colchicine Colubrine Cyanotriphenylborate Dendrobine Diaboline Endocannabinoids (e.g., 2-AG , anandamide (AEA) )Gaboxadol (THIP) Gelsemine iso-THAZ Isobutyric acid Isonipecotic acid Isostrychnine Laudanosine N-Methylbicuculline N-Methylstrychnine N,N-Dimethylmuscimol Nipecotic acid Pitrazepin Pseudostrychnine Quinolines (e.g., 4-hydroxyquinoline , 4-hydroxyquinoline-3-carboxylic acid , 5,7-CIQA , 7-CIQ , 7-TFQ , 7-TFQA )RU-5135 Sinomenine Strychnine Thiocolchicoside Tutin Negative modulators: Amiloride Benzodiazepines (e.g., bromazepam , clonazepam , diazepam , flunitrazepam , flurazepam )Corymine Cyanotriphenylborate Daidzein Dihydropyridines (e.g., nicardipine , nifedipine , nitrendipine )Furosemide Genistein Ginkgo constituents (e.g., bilobalide , ginkgolides (e.g., ginkgolide A , ginkgolide B , ginkgolide C , ginkgolide J , ginkgolide M ))Imipramine NBQX Neuroactive steroids (e.g., 3α-androsterone sulfate , 3β-androsterone sulfate , deoxycorticosterone , DHEA sulfate , pregnenolone sulfate , progesterone )Opioids (e.g., codeine , dextromethorphan , dextrorphan , levomethadone , levorphanol , morphine , oripavine , pethidine , thebaine )Picrotoxin (i.e., picrotin and picrotoxinin )PMBA Riluzole Tropeines (e.g., bemesetron , LY-278584 , tropisetron , zatosetron )Verapamil Zinc NMDAR Tooltip N-Methyl-D-aspartate receptor
Transporter (blockers )
GlyT1 Tooltip Glycine transporter 1 GlyT2 Tooltip Glycine transporter 2
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