VR (nerve agent)

VR  Skeletal formula of VR

Ball-and-stick model of VR
Names
Preferred IUPAC name

S-[2-(Diethylamino)ethyl] O-(2-methylpropyl) methylphosphonothioate

Identifiers

CAS Number

* 159939-87-4 Y

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:140422

ChemSpider |

* 154981 N

PubChem CID

* 178033

UNII |

* LG34LSI9IU Y

CompTox Dashboard (EPA)

* DTXSID10897226

InChI

* InChI=1S/C11H26NO2PS/c1-6-12(7-2)8-9-16-15(5,13)14-10-11(3)4/h11H,6-10H2,1-5H3 N

Key: MNLAVFKVRUQAKW-UHFFFAOYSA-N N

* InChI=1/C11H26NO2PS/c1-6-12(7-2)8-9-16-15(5,13)14-10-11(3)4/h11H,6-10H2,1-5H3

Key: MNLAVFKVRUQAKW-UHFFFAOYAF

SMILES

* CCN(CC)CCSP(=O)(C)OCC(C)C

Properties

Chemical formula

| C11H26NO2PS
Molar mass | 267.368 g/mol

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

N verify (what is YN ?)

Infobox references

Chemical compound

Part of a series on

Chemical agents
Lethal agents

Blood

* Cyanogen chloride (CK)
* Hydrogen cyanide (AC)
* Arsine (SA)

Blister

* Ethyldichloroarsine (ED)
* Methyldichloroarsine (MD)
* Phenyldichloroarsine (PD)
* Lewisite (L)
* Mustard gas
(HD H HT HL HQ)

* Nitrogen mustard

* HN1
* HN2
* HN3

* Phosgene oxime (CX)
* C01-A035
* C01-A039

Nerve

|  G-agents

* Tabun (GA)
* Sarin (GB)
* Chlorosarin (GC)
* Soman (GD)
* Ethylsarin (GE)
* Cyclosarin (GF)
* GV

V-agents

* EA-3148
* V-sub x/GD-7
* VE
* VG
* VM
* VP
* VR
* VS
* VX

Novichok agents

* A-230
* A-232
* A-234
* A-242
* A-262
* C01-A035
* C01-A039
* C01-A042

Pulmonary/choking

* Chlorine
* Chloropicrin (PS)
* Phosgene (CG)

* Diphosgene (DP)
* Disulfur decafluoride

Vomiting

* Adamsite
* Chloropicrin
* Diphenylchlorarsine
* Diphenylcyanoarsine
* Diphenylamincyanoarsine

Incapacitating agents

* Agent 15 (BZ)
* Dimethylheptylpyran (DMHP)

* EA-3167
* Kolokol-1

* PAVA spray
* Sleeping gas

Riot-control (RCAs)

* Xylyl bromide
* Pepper spray (OC)
* CS
* CN (mace)
* CR

* List of chemical warfare agents

* v
* t
* e

VR (Russian VX, VXr, Soviet V-gas, GOSNIIOKhT substance No. 33, Agent "November") is a "V-series" unitary nerve agent closely related (it is an isomer) to the better-known VX nerve agent.[1] It became a prototype for the series of Novichok agents. According to chemical weapons expert Jonathan Tucker, the first binary formulation developed under the Soviet Foliant program was used to make Substance 33, differing from VX only in the alkyl substituents on its nitrogen and oxygen atoms. "This weapon was given the code name Novichok."[2]

## History

[edit]

The development of VR started in 1957, after the Soviet Union obtained information about detection of high level of toxicity in phosphorylthiocholines[3] (the same year Lars-Erik Tammelin published his first articles on fluorophosphorylcholines and phosphorylthiocholines in Acta Chemica Scandinavica) by a team from the Soviet Union's Scientific Research Institute No. 42 (NII-42). Sergei Zotovich Ivin, Leonid Soborovsky, and Iya Danilovna Shilakova jointly developed this analogue of VX. They completed their work in 1963 and were later awarded the Lenin Prize for their achievement.[4] A binary weapon comprising two less toxic precursors which mixed during flight to form Substance 33 was later developed by a team led by Nikolai Kuznetsov.[5]

In 1972 the Soviets opened Cheboksary Khimprom, a manufacturing plant for VR in Novocheboksarsk.[6] All facilities in USSR produced 15,557 tons of VR according to their declaration to the Organisation for the Prohibition of Chemical Weapons (OPCW),[7] although most if not all of this has now been destroyed under disarmament treaties.[8]

## Comparison to VX

[edit]

VR has similar lethal dose levels to VX (between 10–50 mg), as well as being similar in appearance.[9] However, due to usage of diethylamino radicals instead of diisopropylamino it is more prone to decomposition. The former are worse at sterically protecting the nitrogen atom from attacking either phosphorus or the α-carbon atom adjacent to sulfur than the latter. According to UK Defence Science and Technology Laboratory Detection Department scientists Robin M. Black and John M. Harrison, chemical stability was an important factor why of all the similarly toxic phosphorylthiocholines, ethyl N-2-diisopropylaminoethyl methylphosphonothiolate in particular (now known as VX), was weaponized in the West.[10]

According to Russian CW developer Vil Mirzayanov, in the late 1980s a group of GosNIIOKhT chemists led by Georgiy Drozd prepared a scientific report that Substance 33 had much lower shelf life than VX. The report, writes Mirzayanov, caused 'panic' in the institute top management and the military representative office, and later was met with administrative resistance. This finding was independently verified by another chemist Igor Revelskiy but his report wasn't approved either.[11]

Following the poisoning of Sergei and Yulia Skripal, former head of the GosNIIOKhT security department Nikolay Volodin said in an interview to Novaya Gazeta that Substance 33 was decomposing too quickly in combat conditions, and implied that this fact may have influenced the decision to continue research on the Novichok program.[12]

## Toxicity

[edit]

Both agents have similar symptoms and method of action to other nerve agents that act on cholinesterase, and treatment remains the same. However, the window for effectively treating second generation V series seizures is shorter, as they rapidly denature the acetylcholinesterase protein in a similar manner to soman, making treatment with the standard nerve gas antidote pralidoxime ineffective unless it is given very soon after exposure.[citation needed] Pre-treatment with pyridostigmine prior to exposure, and treatment with other drugs such as atropine and diazepam after exposure, will reduce symptoms of nerve agent toxicity but may not be sufficient to prevent death if a large dose of nerve agent has been absorbed. In addition to the standard seizures, some of the second generation V series agents are known to cause comas.

## See also

[edit]

* A-234 (nerve agent)
* Novichok agent

## References

[edit]

1. ^ Fedorov L. A. Undeclared Chemical War in Russia. Moscow, 1995 (Russian)
2. ^ Peplow, Mark (19 March 2018). "Nerve agent attack on spy used 'Novichok' poison". Chemical & Engineering News. 96 (12). American Chemical Society: 3. Retrieved 28 March 2018.
3. ^ Major General Antonov, Nikolai S. (1994). Khimicheskoe Oruzhiye na Rubezhe Dvukh Stoletii Химическое оружие на рубеже двух столетий [Chemical Weapons at the Turn of the Century] (PDF) (in Russian). Moscow: Progress. p. 22\. ISBN 5-01-004462-5. LCCN 96160418.
4. ^ Tucker, J. B.; War of Nerves; Anchor Books; New York; 2006; pp 181-182.
5. ^ Vil S. Mirzayanov. State Secrets. An Insider's Chronicle of the Russian Chemical Weapons Program. (2009) pp166-168. ISBN 978-1-4327-2566-2
6. ^ Tucker, J. B.; War of Nerves; Anchor Books; New York; 2006; pp 230–231.
7. ^ "Factsheets on Chemical and Biological Warfare Agents".
8. ^ "Chemical Weapons – Russian / Soviet Nuclear Forces".
9. ^ "VR". American Chemical Society.
10. ^ Black R.M., Harrison J.M. The chemistry of organophosphorus chemical warfare agents. Chapter 10 of The chemistry of organophosphorus compounds. Volume 4, Ter- and quinque-valent phosphorus acids and their derivatives. (1996) Black, R. M.; Harrison, J. M. (2009). "The Chemistry of Organophosphorus Chemical Warfare Agents". PATai's Chemistry of Functional Groups. doi:10.1002/9780470682531.pat0070. ISBN 978-0-471-95706-5.
11. ^ Mirzayanov, Vil S. (December 2008). State Secrets: An Insider's Chronicle of the Russian Chemical Weapons Program. Outskirts Press, Incorporated. ISBN 978-1-4327-1923-4.
12. ^ ""Новичок" — это слишком для одного Скрипаля"". Новая газета - Novayagazeta.ru. March 23, 2018.

* v
* t
* e

* Agents used in chemical warfare
* incapacitation
* riot control

Blood agents|

* Cyanogen
* Cyanogen bromide
* Cyanogen chloride (CK)
* Hydrogen cyanide (AC)
* Arsine
* Cacodyl cyanide
* Cacodyl oxide
* Hydrogen sulfide
* Phosphine
* Carbon monoxide
* Phosphorus trifluoride
* Methyl cyanoformate
* Iron pentacarbonyl
* Nickel tetracarbonyl
* 2,3,7,8-Tetrachlorodibenzodioxin
* Glycolonitrile
* Lactonitrile
* Acetone cyanohydrin
* Stibine
* Chloral cyanohydrin

Blister agents|

| Arsenicals|

* Ethyldichloroarsine (ED)
* Methyldichloroarsine (MD)
* Phenyldichloroarsine (PD)
* Lewisite (L)
* Lewisite 2 (L2)
* Lewisite 3 (L3)

|

Sulfur mustards|

* Levinstein mustard (EA-229)
* T
* Q
* CEES

Nitrogen mustards|

* HN1
* HN2
* HN3
* TL-301

Nettle agents|

* Phosgene oxime (CX)

Other|

* KB-16
* Dibutylchloromethyltin chloride
* Selenium oxychloride

Nerve agents|

| G-agents|

* Tabun (GA)
* Sarin (GB)
* Chlorosarin (ClGB)
* Thiosarin (SGB)
* Soman (GD)
* Chlorosoman (ClGD)
* Ethylsarin (GE)
* GH
* Cyclosarin (GF)
* GP
* Fluorotabun
* EA-1356
* EA-4352
* Crotylsarin

|

V-agents|

* EA-2192
* EA-3148
* VE
* VG
* VM
* VP
* VR
* VS
* VX
* EA-1763
* Chinese VX
* V-sub x (GD-7)

GV agents|

* GV (EA-5365)

Novichok agents|

* A-208
* A-232
* A-234
* A-242
* A-262
* C01-A035
* C01-A039
* C01-A042

Carbamates|

* Dimethylcarbamoyl fluoride
* EA-3887
* EA-3887A
* EA-3966
* EA-3990
* EA-4056
* T-1123
* T-1152
* T-1194
* Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide)
* TL-599
* TL-1238
* TL-1299
* TL-1317
* Miotine (AR-28/T-1843)
* 3152 CT
* 4-686-293-01 (Agent 1-10)

Other|

* Diisopropyl fluorophosphate
* Dicyclohexyl phosphorofluoridate
* EA-2012
* EA-2054
* EA-2098
* EA-2613
* 2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate
* Neopentylene fluorophosphate
* Selenophos
* Phospholine
* R-16661
* Ro 3-0422
* Methanesulfonyl fluoride
* Dimefox (TL-792)
* MSPI

Precursors|

* Acetonitrile
* AT
* ATO
* AlP
* A.P.C. complex
* Chlorosarin
* Chlorosoman
* Cyclohexanol
* 1,8-Dibromooctane
* N,N-Diisopropylaminoethanol (KB)
* EA-1250
* DIHP
* ZS
* DEHP
* EA-1224
* Dimethylamidophosphoric dichloride
* Dimethylamidophosphoric dicyanide
* DMHP
* Ethylphosphonoselenoic dichloride
* Formaldoxime
* Nital
* 4-Hydroxycoumarin
* Isopropyl alcohol (TB)
* Methyldichlorophosphine (SW)
* Methylphosphonyl difluoride (difluoro) (DF)
* Methylphosphonyl dichloride (dichloro)
* Nitromethane
* OPA mixture
* Phosphoryl chloride
* Phosphorus pentachloride
* Phosphorus trichloride (TH)
* Pinacolone
* Pinacolyl alcohol
* Phenacyl chloride
* QL
* 2,4,5-Trichlorophenol
* 3,3,5-Trimethylcyclohexanol
* Triethyl phosphite
* Trimethyl phosphite
* TC
* TG

Neurotoxins|

* Anatoxin-a
* Saxitoxin (TZ)
* Bungarotoxin
* Botulinum toxin (BTX)
* Tetanospasmin (TeNT)
* Ryanodine
* Ciguatoxin (CTX)
* Guanitoxin (GTX)
* Chlorophenylsilatrane
* Palytoxin (PTX)
* Maitotoxin (MTX)
* Tetrodotoxin
* Aconitine
* Brevetoxin (PbTX)
* Strychnine
* Antillatoxin (ATX)
* Tetraethyllead
* Dimethylmercury
* HN1 hydrochloride
* HN2 hydrochloride
* HN3 hydrochloride
* A-8564
* Picrotoxin
* Sulfuryl fluoride
* Tremorine
* Oxotremorine
* Batrachotoxin
* Tetramethylenedisulfotetramine (TETS)
* Bicyclic phosphates
* IPTBO
* TBPO
* TBPS
* Cloflubicyne
* Trimethylolpropane phosphite
* Domoic acid

Pulmonary/
choking agents|

* Chlorine
* Bromine
* Phosgene (CG)
* Fluorine
* Perfluoroisobutene
* Chloropicrin (PS)
* Dimethyl(trifluoromethylthio)arsine
* Diphosgene (DP)
* Disulfur decafluoride (Z)
* Acrolein
* Ethyl bromoacetate
* Perchloromethyl mercaptan
* Phenylcarbylamine chloride
* Tetranitromethane
* Tetrachlorodinitroethane
* Chlorine trifluoride
* Perchloryl fluoride
* Cadmium oxide
* Cadmium chloride
* Mercuric chloride
* Selenium dioxide
* Selenoyl fluoride
* Trifluoronitrosomethane
* Trichloronitrosomethane
* Nitric oxide
* Nitrogen dioxide
* Dinitrogen tetroxide
* Sulfur dioxide
* Phosphorus trichloride
* Methyl isocyanate
* Ethenone
* Methyl vinyl ketone
* Trifluoroacetyl chloride
* Salcomine
* Fluomine
* Uranium hexafluoride
* Diborane
* Green Cross

Vomiting agents|

* Adamsite (DM)
* Chloropicrin
* Litharge-glycerine
* Diphenylchlorarsine
* Diphenylcyanoarsine
* Cacodyl cyanide
* o-Dianisidine

Incapacitating
agents|

* BZ (CS-4030)
* Apomorphine
* Butyrophenone
* EA-4941 (CS-4640)
* Etorphine
* EA-2092
* CS-4297
* Etoxadrol
* Dimethylheptylpyran (DMHP)
* EA-2148
* EA-3167
* EA-3443
* Pethidine
* EA-3580
* Ibogaine
* EA-3834
* Kolokol-1
* LSD-25
* PAVA spray
* Psilocybin
* Sleeping gas
* Carfentanil
* JB-318
* JB-336
* CS-27349
* CAR-226,086
* CAR-301,060
* CAR-302,196
* CAR-302,282
* CAR-302,668
* Benperidol
* Desflurane
* Enflurane
* Bufotenin
* Isoflurane
* Halothane
* Sevoflurane
* Pentazocine
* Procarbazine
* Fluphenazine
* Chlorpromazine

Lachrymatory
agents|

* Xylyl bromide
* Pepper spray (OC)
* Mace (spray)
* CN
* CS
* CR
* CNS
* Benzyl chloride
* Benzyl bromide
* Benzyl iodide
* Bromobenzyl cyanide
* Thiophosgene
* Chloroacetone
* Bromoacetone
* Bromomethyl ethyl ketone
* Acrolein
* Phenacyl bromide
* Chloroacetophenone oxime
* Ethyl bromoacetate
* Ethyl iodoacetate
* Iodoacetone
* Allyl isothiocyanate
* Hexamethylene diisocyanate
* Crotonaldehyde
* DRC-5593

Malodorant agents|

* Thioacetone
* Allicin
* Skatole
* Cadaverine
* Putrescine

Cornea-clouding agents|

* Lewisite
* CX
* KB-16
* Methyl cyanoacrylate
* N-Methylmorpholine
* Allyl alcohol
* Osmium tetroxide
* Acrolein
* Cacodyl cyanide

Biological toxins|

* Abrin
* Aconitine
* Cyclopiazonic acid
* Histrionicotoxins
* Aflatoxins
* Anatoxin-a
* Batrachotoxin
* Botulinum toxin
* Brevetoxin
* Ciguatoxin
* Domoic acid
* Enterotoxin type B
* Grayanotoxin
* Guanitoxin
* Maitotoxin
* Modeccin
* Palytoxin
* Ricin
* Saxitoxin
* Shiga toxin
* T-2 mycotoxin
* Tetanospasmin
* Tetrodotoxin
* Volkensin
* Veratridine

Other|

* Methyl fluoroacetate
* Napalm (variants and mixtures)
* Fluoroethyl fluoroacetate
* Depleted uranium
* post-combustion uranium oxides
* Plutonium and its compounds
* Polonium
* White phosphorus

* List of chemical warfare agents
* CB military symbol

* v
* t
* e

Neurotoxins

Animal toxins|

* Batrachotoxin
* Bestoxin
* Birtoxin
* Bungarotoxin
* Charybdotoxin
* Conotoxin
* Fasciculin
* Huwentoxin
* Poneratoxin
* Saxitoxin
* Tetrodotoxin
* Vanillotoxin
* Spooky toxin (SsTx)
* Epibatidine
* Zetekitoxin AB
* Dendrotoxin

Bacterial|

* Botulinum toxin
* Tetanospasmin

Cyanotoxins|

* Anatoxin-a
* Guanitoxin
* BMAA
* Saxitoxin

Plant toxins|

* Aconitine
* Bicuculline
* Penitrem A
* Picrotoxin
* Strychnine
* Tutin
* Rotenone
* Ginkgotoxin
* Cicutoxin
* Oenanthotoxin
* Thujone
* Volkensin
* Veratridine

Mycotoxins|

* Ibotenic acid
* Muscarine
* Muscimol

Pesticides|

* Fenpropathrin
* Tetramethylenedisulfotetramine
* Bromethalin
* Crimidine
* Methamidophos
* Endosulfan
* Fipronil
* Phenylsilatrane
* Chlorophenylsilatrane
* Sulfuryl fluoride
* Mipafox
* Schradan
* Dimefox

Nerve agents|

* Cyclosarin
* EA-3148
* Novichok agent
* Sarin
* Soman
* Tabun
* VE
* VG
* VM
* VP
* VR
* VX
* GV
* EA-3990
* EA-4056
* T-1123
* Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide)
* Fluorotabun
* Chinese VX
* EA-2192

Bicyclic phosphates|

* TBPS
* TBPO
* IPTBO

Cholinergic neurotoxins|

* Acetylcholine mustard
* Catecholine
* Choline mustard
* Ethylcholine mustard
* Hemicholinium mustard

Psychoactive drugs|

* Alcohol
* Nitrous oxide

Other|

* Dimethylcadmium
* Dimethylmercury
* Toxopyrimidine
* IDPN
* Tetraethyllead

* v
* t
* e

Acetylcholine metabolism and transport modulators

Enzyme
(modulators)|

| ChATTooltip Choline acetyltransferase|

* 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

|

AChETooltip Acetylcholinesterase|

* 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
* Promecarb
* Propamocarb
* Propham
* Propoxur
* Thiodicarb
* Thiofanox; Stigmines: Distigmine
* Eptastigmine
* Ganstigmine
* Neostigmine +glycopyrronium bromide
* Phenserine
* Physostigmine
* Pyridostigmine
* Quilostigmine
* Rivastigmine
* Terestigmine; Others: Acotiamide
* Ambenonium
* Caffeine
* Donepezil
* EA-3990
* EA-4056
* Edrophonium
* Galantamine
* Huperzine A
* Huprine W
* Huprine X
* Huprine Y
* Ipidacrine
* Itopride
* Ladostigil
* Minaprine
* Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide)
* T-1123
* T-1152
* T-1194
* TL-599
* TL-1238
* Tacrine
* Zanapezil

* Irreversible: Organophosphates: 2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate
* Acephate
* 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
* Dicyclohexyl phosphorofluoridate
* Diisopropylphosphate
* Diisopropyl fluorophosphate
* 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
* EPN
* Ethion
* Ethoprop
* Fenamiphos
* Fenitrothion
* Fenthion
* Fluorotabun
* Fonofos
* Formothion
* Fosthiazate
* GD-42
* GH
* GT-45
* GV
* Guanitoxin
* Hexaethyl tetraphosphate (HETP)
* Isofluorophate
* Isoxathion
* Leptophos
* Malaoxon
* Malathion
* Mazidox
* Methamidophos
* Methidathion
* Methyl phenkapton
* Methylfluorophosphonylcholine (MFPCh)
* Metrifonate
* Mevinphos
* Mipafox
* Monocrotophos
* MSPI
* Naled
* Novichok agent
* Omethoate
* Oxydemeton-methyl
* Paraoxon
* Parathion
* Parathion-methyl
* Phorate
* Phosalone
* Phosfolan
* Phosmet
* Phosphamidon
* Phoxim
* Pirimiphos-methyl
* Profenofos
* Prothoate
* R-16661
* 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
* Ronnel
* Sarin (GB)
* Schradan
* Soman (GD)
* Sulfotep (TEDP)
* Tabun (GA)
* Tebupirimfos
* Temefos
* Terbufos
* Tetrachlorvinphos
* Tetraethyl pyrophosphate (TEPP)
* 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
* 3152 CT

* Reactivators: Asoxime chloride
* Methoxime
* Obidoxime
* Pralidoxime
* Trimedoxime bromide

BChETooltip Butyrylcholinesterase|

* Inhibitors: Affinine
* Affinisine
* Conodurine
* Cymserine
* Ladostigil
* Profenamine (ethopropazine)
* Rivastigmine
* Tacrine
* ZINC-12613047
* Many of the other AChE inhibitors listed above

Transporter
(modulators)|

| CHTTooltip Choline transporter|

* Inhibitors: Hemicholinium-3 (hemicholine)
* Triethylcholine

* Enhancers: Coluracetam

|

VAChTTooltip Vesicular acetylcholine transporter|

* Inhibitors: Vesamicol

Release
(modulators)|

| Inhibitors|

* SNAP-25Tooltip Synaptosomal-associated protein 25 inactivators: Botulinum toxin (A, C, E)

* VAMPTooltip Vesicle-associated membrane protein inactivators: Botulinum toxin (B, D, F, G)

* Others: Bungarotoxins (β-bungarotoxin, γ-bungarotoxin)

|

Enhancers|

* LPHNTooltip Latrophilin agonists: α-Latrotoxin

* Others: Atracotoxins (e.g., robustoxin, versutoxin)
* Crotoxin

See also
Receptor/signaling modulators
Muscarinic acetylcholine receptor modulators
Nicotinic acetylcholine receptor modulators
*[CID]: Compound ID
*[EPA]: U.S. Environmental Protection Agency
*[v]: View this template
*[t]: Discuss this template
*[e]: Edit this template
*[ChAT]: Choline acetyltransferase
*[AChE]: Acetylcholinesterase
*[BChE]: Butyrylcholinesterase
*[CHT]: Choline transporter
*[VAChT]: Vesicular acetylcholine transporter
*[SNAP-25]: Synaptosomal-associated protein 25
*[VAMP]: Vesicle-associated membrane protein
*[LPHN]: Latrophilin