Cyclanoline

Cyclanoline is an acetylcholinesterase inhibitor isolated from Stephania venosa tuber.

Cyclanoline
Identifiers

3D model (JSmol)	Interactive image
ChEBI	CHEBI:76923
ChemSpider	2339606
PubChem CID	3082134
CompTox Dashboard (EPA)	DTXSID00171789
InChI InChI=1S/C20H23NO4/c1-21-7-6-13-9-19(25-3)17(22)10-14(13)16(21)8-12-4-5-18(24-2)20(23)15(12)11-21/h4-5,9-10,16H,6-8,11H2,1-3H3,(H-,22,23)/p+1/t16-,21-/m0/s1 Key: LKLWVKCEYSPQHL-KKSFZXQISA-O
SMILES COc1ccc2C[C@H]3c4cc(O)c(OC)cc4CC[N@@+]3(C)Cc2c1O
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

External links

Acetylcholinesterase inhibitors from Stephania venosa tuber

Acetylcholine metabolism and transport modulators

Enzyme
(modulators)

ChAT	Inhibitors: 1-(-Benzoylethyl)pyridinium 2-(α-Naphthoyl)ethyltrimethylammonium 3-Chloro-4-stillbazole 4-(1-Naphthylvinyl)pyridine Acetylseco hemicholinium-3 Acryloylcholine AF64A B115 BETA CM-54,903 N,N-Dimethylaminoethylacrylate N,N-Dimethylaminoethylchloroacetate
AChE	Inhibitors: Reversible: Carbamates: Aldicarb Aminocarb Bendiocarb Bufencarb Carbaryl Carbendazim Carbetamide Carbofuran Carbosulfan Chlorbufam Chloropropham Dimetilan Ethienocarb Ethiofencarb Fenobucarb Formetanate Formparanate Methiocarb Methomyl Metolcarb Miotine Oxamyl Phenmedipham Pinmicarb Pirimicarb Propamocarb Propham Propoxur Thiofanox; Stigmines: Distigmine Eptastigmine Ganstigmine Neostigmine Phenserine Physostigmine Pyridostigmine Quilostigmine Rivastigmine Terestigmine; Others: Acotiamide Ambenonium Caffeine Donepezil EA-3990 EA-4056 Edrophonium Galantamine Huperzine A Ipidacrine Itopride Ladostigil Minaprine Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide) T-1123 TL-599 TL-1238 Tacrine Zanapezil Irreversible: Organophosphates: 2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate Acephate Anatoxin-a(S) Armine Azinphos-ethyl Azinphos-methyl BAY-29952 Bensulide Cadusafos Carbophenothion Chlorethoxyfos Chlorfenvinphos Chlorpyrifos Chlorpyrifos-methyl Coumaphos Crotylsarin Cyanophos Cyclosarin (GF) Demephion Demeton Demeton-S-methyl Dialifor Diazinon Dichlorvos Dicrotophos Diisopropyl fluorophosphate Diisopropylphosphate Dimefox Dimethoate Dimethyl 4-(methylthio)phenyl phosphate Dioxathion Disulfoton EA-2012 EA-2054 EA-2098 EA-2192 EA-2613 EA-3148 EA-4352 Echothiophate Ethylsarin (GE) Endothion Ethion Ethoprop Fenamiphos Fenitrothion Fenthion Fluorotabun Fonofos Formothion Fosthiazate GD-42 GH GT-45 GV Hexaethyl tetraphosphate Isofluorophate Isoxathion Leptophos Malaoxon Malathion Methamidophos Methidathion Methyl phenkapton Methylfluorophosphonylcholine (MFPCh) Metrifonate Mevinphos Mipafox Monocrotophos Naled Novichok agent Omethoate Oxydemeton-methyl Paraoxon Parathion Parathion-methyl Phorate Phosalone Phosfolan Phosmet Phosphamidon Phoxim Pirimiphos-methyl Profenofos Prothoate Ro 3-0340 Ro 3-0346 Ro 3-0347 Ro 3-0351 Ro 3-0352 Ro 3-0397 Ro 3-0411 Ro 3-0412 Ro 3-0417 Ro 3-0419 Ro 3-0422 Ro 3-0433 Sarin (GB) Schradan Soman (GD) Tabun (GA) Tebupirimfos Temefos Terbufos Tetrachlorvinphos Tetraethyl pyrophosphate Triazofos Tribufos Trichlorfon Trichloronate Tricresyl phosphate VE VG VM VP VS VR VX; Others: Demecarium Fasciculins (green mamba toxins) (1, 2, 3, 4) Onchidal (Onchidella binneyi) Methanesulfonyl fluoride Unsorted: α-Pinene α-Viniferin Affinine Affinisine Arisugacin A Bulbocapnine Conodurine Coronaridine Corydaline Corynoline Crimidine Cyclanoline Cymserine Harmaline Kobophenol A Lactucopicrin Lycorine Phosacetim Rosmarinic acid Stercuronium iodide Taspine Tetrahydrocannabinol Ungeremine Ungiminorine Dimethylcarbamoyl fluoride BW284C51 TMTFA Reactivators: Asoxime chloride Methoxime Obidoxime Pralidoxime Trimedoxime bromide
BChE	Inhibitors: Affinine Affinisine Conodurine Cymserine Ladostigil Profenamine (ethopropazine) Rivastigmine Tacrine ZINC-12613047 Many of the other AChE inhibitors listed above

Transporter
(modulators)

CHT	Inhibitors: Hemicholinium-3 (hemicholine) Triethylcholine Enhancers: Coluracetam
VAChT	Inhibitors: Vesamicol

Release
(modulators)

Inhibitors	SNAP-25 inactivators: Botulinum toxin (A, C, E) VAMP inactivators: Botulinum toxin (B, D, F, G) Others: Bungarotoxins (β-bungarotoxin, γ-bungarotoxin)
Enhancers	LPHN agonists: α-Latrotoxin Others: Atracotoxins (e.g., robustoxin, versutoxin) Crotoxin

See also: Receptor/signaling modulators • Muscarinic acetylcholine receptor modulators • Nicotinic acetylcholine receptor modulators

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