Toxiferine

Toxiferine
Identifiers

CAS Number	302-30-7
PubChem	CID 5281411
ChemSpider	4444760
UNII	9M7D9K3OJI
ChEMBL	CHEMBL231047
Chemical data
Formula	C₄₀H₄₆N₄O₂
Molar mass	614.82 g/mol
SMILES [H][C@@]12[C@@]3(CC[N+]2(C)C/C4=C/CO)[C@@]5([H])N(C6=C3C=CC=C6)/C=C7[C@]([C@@]8(CC[N+]9(C)C/%10)[C@]9([H])C[C@]\7([H])C%10=C/CO)([H])N(C%11=C8C=CC=C%11)/C=C5/[C@]4([H])C1

Toxiferine (C-toxiferine I) is a curare toxin. It is a bisindole alkaloid derived from Strychnos toxifera and a nicotinic acetylcholine receptor antagonist.

It is a muscle relaxant that causes paralysis of skeletal muscle, which takes approximately 2 hours to recovery for a moderate dose, and 8 hours of total paralysis with a 20-fold paralytic dose.^[1]

References

↑ Page 330 in: The Alkaloids: v. 1: A Review of Chemical Literature (Specialist Periodical Reports). Cambridge, Eng: Royal Society of Chemistry. 1971. ISBN 0-85186-257-8.

Toxins

Clostridium:	tetani Tetanospasmin Tetanolysin perfringens Alpha toxin Enterotoxin difficile A B botulinum Botox

other:	Anthrax toxin Listeriolysin O

Cocci

Streptolysin Leukocidin Panton-Valentine leukocidin

Staphylococcus	Staphylococcus aureus alpha/beta/delta Exfoliatin Toxic shock syndrome toxin Staphylococcal Enterotoxin B (SEB)

Plant toxins

Invertebrate toxins

scorpion:	Androctonus australis hector insect toxin Charybdotoxin Maurotoxin Agitoxin Margatoxin Slotoxin Scyllatoxin Hefutoxin Lq2 Birtoxin Bestoxin BmKAEP Phaiodotoxin Imperatoxin Pi3

spider:	Latrotoxin Alpha-latrotoxin CSTX Cupiennins PhTx3 Stromatoxin Vanillotoxin Huwentoxin

mollusca:	Conotoxin Eledoisin Onchidal Saxitoxin Tetrodotoxin

Vertebrate toxins

fish:	Ciguatera Tetrodotoxin

amphibian:	(+)-Allopumiliotoxin 267A Batrachotoxin Bufotoxins Arenobufagin Bufotalin Bufotenin Cinobufagin Marinobufagin Epibatidine Histrionicotoxin Pumiliotoxin 251D Samandarin Samandaridine Tarichatoxin

reptile/snake venom:	Bungarotoxin Alpha-Bungarotoxin Beta-Bungarotoxin Calciseptine Taicatoxin Calcicludine Cardiotoxin III

note: some toxins are produced by lower species and pass through intermediate species

Category
Commons
WikiProject

Cholinergics

Receptor ligands

mACh	Agonists: 77-LH-28-1 AC-42 AC-260,584 Aceclidine Acetylcholine AF30 AF150(S) AF267B AFDX-384 Alvameline AQRA-741 Arecoline Bethanechol Butyrylcholine Carbachol CDD-0034 CDD-0078 CDD-0097 CDD-0098 CDD-0102 Cevimeline Choline cis-Dioxolane Ethoxysebacylcholine Itameline LY-593,039 L-689,660 LY-2,033,298 McNA343 Methacholine Milameline Muscarine NGX-267 Ocvimeline Oxotremorine PD-151,832 Pilocarpine RS86 Sabcomeline SDZ 210-086 Sebacylcholine Suberyldicholine Talsaclidine Tazomeline Thiopilocarpine Vedaclidine VU-0029767 VU-0090157 VU-0152099 VU-0152100 VU-0238429 WAY-132,983 Xanomeline YM-796 Antagonists: 3-Quinuclidinyl benzilate 4-DAMP Aclidinium bromide Anisodamine Anisodine Antihistamines (first-generation) (e.g., brompheniramine, chlorphenamine, cyproheptadine, dimenhydrinate, diphenhydramine, doxylamine, mepyramine (pyrilamine), phenindamine, pheniramine, promethazine, tripelennamine, triprolidine) Atropine Atropine methonitrate Atypical antipsychotics (e.g., clozapine, olanzapine, quetiapine, zotepine) Benactyzine Benzatropine (benztropine) Benzilylcholine mustard Benzydamine BIBN 99 Biperiden Bornaprine CAR-226,086 CAR-301,060 CAR-302,196 CAR-302,282 CAR-302,368 CAR-302,537 CAR-302,668 CS-27349 Cyclobenzaprine Cyclopentolate Darifenacin DAU-5884 Dimethindene Dexetimide DIBD Dicyclomine (dicycloverine) Ditran EA-3167 EA-3443 EA-3580 EA-3834 Etanautine Etybenzatropine (ethybenztropine) Flavoxate Himbacine HL-031,120 Ipratropium bromide J-104,129 Hyoscyamine Mamba toxin 3 Mamba toxin 7 Mazaticol Mebeverine Methoctramine Metixene N-Ethyl-3-piperidyl benzilate N-Methyl-3-piperidyl benzilate Orphenadrine Otenzepad Oxybutynin PBID PD-102,807 PD-0298029 Phenglutarimide Phenyltoloxamine Pirenzepine Piroheptine Procyclidine Profenamine RU-47,213 SCH-57,790 SCH-72,788 SCH-217,443 Scopolamine (hyoscine) Solifenacin Telenzepine Tetracyclic antidepressants (e.g., amoxapine, maprotiline, mianserin, mirtazapine) Tiotropium bromide Tolterodine Tricyclic antidepressants (e.g., amitriptyline, butriptyline, clomipramine, desipramine, dosulepin (dothiepin), doxepin, imipramine, lofepramine, nortriptyline, protriptyline, trimipramine) Trihexyphenidyl Tripitamine Tropatepine Tropicamide Typical antipsychotics (e.g., chlorpromazine, loxapine, thioridazine) WIN-2299 Xanomeline Zamifenacin

nACh	Agonists: 5-HIAA A-84,543 A-366,833 A-582,941 A-867,744 ABT-202 ABT-418 ABT-560 ABT-894 Acetylcholine Altinicline Anabasine Anatoxin-a AR-R17779 Butinoline Butyrylcholine Carbachol Choline Cotinine Cytisine Decamethonium Desformylflustrabromine Dianicline Dimethylphenylpiperazinium Epibatidine Epiboxidine Ethanol Ethoxysebacylcholine EVP-4473 EVP-6124 Galantamine GTS-21 Ispronicline Ivermectin Levamisole Lobeline MEM-63,908 (RG-3487) Morantel Nicotine (tobacco) NS-1738 PHA-543,613 PHA-709,829 PNU-120,596 PNU-282,987 Pozanicline Rivanicline RJR-2429 Sazetidine A SB-206553 Sebacylcholine SIB-1508Y SIB-1553A SSR-180,711 Suberyldicholine Suxamethonium (succinylcholine) TC-1698 TC-1734 TC-1827 TC-2216 TC-5214 TC-5619 TC-6683 Tebanicline Tropisetron UB-165 Varenicline WAY-317,538 XY-4083 Antagonists: 18-MAC 18-MC α-Neurotoxins (e.g., α-bungarotoxin, α-cobratoxin, α-conotoxin, many others) ABT-126 Alcuronium Allopregnanolone Amantadine Anatruxonium AQW051 Atracurium Barbiturates (e.g., pentobarbital, sodium thiopental) Bungarotoxins (e.g., α-bungarotoxin, κ-bungarotoxin) Bupropion Chandonium Chlorisondamine Cisatracurium Coclaurine Coronaridine Cyclopropane Dacuronium Decamethonium Dehydronorketamine Desflurane Dextromethorphan Dextropropoxyphene Dextrorphan Diadonium DHβE Dihydrochandonium Dimethyltubocurarine (metocurine) Dipyrandium Dizocilpine (MK-801) Doxacurium Encenicline Enflurane Esketamine Fazadinium Gallamine Halothane Hexafluronium Hexamethonium (benzohexonium) Hydroxybupropion Hydroxynorketamine Ibogaine Isoflurane Ketamine Kynurenic acid Laudexium (laudolissin) Levacetylmethadol Levomethadone Malouetine ME-18-MC Mecamylamine Memantine Methadone Methorphan (racemethorphan) Methyllycaconitine Metocurine Mivacurium Morphanol (racemorphan) Neramexane Nitrous oxide Norketamine Pancuronium bromide Pempidine Pentamine Pentolinium Phencyclidine Pipecuronium Progesterone Promegestone Radafaxine Rapacuronium Reboxetine Rocuronium Sevoflurane Surugatoxin Thiocolchicoside Toxiferine Tramadol Trimetaphan camsilate (trimethaphan camsylate) Tropeinium Tubocurarine Vanoxerine Vecuronium Xenon

Transporter ligands

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

VAChT	Inhibitors: Vesamicol

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 Bendiocarb Bufencarb Caffeine Carbaryl Carbendazim Carbetamide Carbofuran Chlorbufam Chloropropham Ethienocarb Ethiofencarb Fenobucarb Fenoxycarb Formetanate Furadan Ladostigil Methiocarb Methomyl Miotine Oxamyl Phenmedipham Pinmicarb Pirimicarb Propamocarb Propham Propoxur; Stigmines: Distigmine bromide Eptastigmine Ganstigmine Neostigmine Phenserine Physostigmine Pyridostigmine bromide Quilostigmine Rivastigmine Terestigmine; Others: Acotiamide Ambenonium Donepezil Caffeine Edrophonium Galantamine Huperzine A Ipidacrine Minaprine Tacrine Zanapezil Irreversible: Organophosphates: Acephate Azinphos-methyl Bensulide Cadusafos Chlorethoxyfos Chlorfenvinphos Chlorpyrifos Chlorpyrifos-methyl Coumaphos Cyclosarin Demeton Demeton-S-methyl Diazinon Dichlorvos Dicrotophos Diisopropyl fluorophosphate Diisopropylphosphate Dimethoate Dioxathion Disulfoton EA-3148 Echothiophate Ethion Ethoprop Fenamiphos Fenitrothion Fenthion Fosthiazate GV Isofluorophate Isoxathion Malaoxon Malathion Methamidophos Methidathion Metrifonate Mevinphos Monocrotophos Naled Novichok agent Omethoate Oxydemeton-methyl Paraoxon Parathion Parathion-methyl Phorate Phosalone Phosmet Phoxim Pirimiphos-methyl Sarin Soman Tabun Tebupirimfos Temefos Terbufos Tetrachlorvinphos Tribufos Trichlorfon VE VG VM VR VX; Others: Demecarium Fasciculins (green mamba toxins) (1, 2, 3, 4) Onchidal (Onchidella binneyi) Reactivators: Asoxime Obidoxime Pralidoxime

BChE	Inhibitors: Cymserine Many of the AChE inhibitors listed above

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: Atracotoxin (e.g., robustoxin, versutoxin) Crotoxin

Others

Precursors	Choline (lecithin) Citicoline Cyprodenate Dimethylethanolamine Glycerophosphocholine Meclofenoxate (centrophenoxine) Phosphatidylcholine Phosphatidylethanolamine Phosphorylcholine Pirisudanol

Cofactors	Acetic acid Acetylcarnitine Acetyl-coA Vitamin B₅

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