Schradan

Names
Preferred IUPAC name

Octamethyldiphosphoric tetraamide

Other names

OMPA, Octamethyl pyrophosphoramide

Identifiers

CAS Number

* 152-16-9

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:82148

ChemSpider |

* 8685

EC Number |

* 205-801-0

KEGG |

* C19015

PubChem CID

* 9037

RTECS number |

* UX5950000

UNII |

* D77OYM46S1

UN number | 3018

InChI

* InChI=1S/C8H24N4O3P2/c1-9(2)16(13,10(3)4)15-17(14,11(5)6)12(7)8/h1-8H3

Key: SZKKRCSOSQAJDE-UHFFFAOYSA-N

SMILES

* CN(C)P(=O)(N(C)C)OP(=O)(N(C)C)N(C)C

Properties

Chemical formula

| C8H24N4O3P2
Molar mass | 286.253 g·mol−1
Density | 1.09
Hazards
Main hazards | Toxic
GHS pictograms |
GHS Signal word | Danger

GHS hazard statements

| H300, H310, H330, H371, H373, H412

GHS precautionary statements

| P260, P262, P264, P270, P271, P273, P280, P284, P301+310, P302+350, P304+340, P309+311, P310, P314, P320, P321, P322, P330, P361, P363, P403+233, P405, P501

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

Infobox references

Schradan, named after Gerhard Schrader, is an obsolete organophosphate insecticide.[1] Schradan itself is a weak cholinesterase inhibitor and requires metabolic activation to become active.[2]

## See also

* Dimefox
* Mipafox

## References

1. ↑ GARDINER, JE; KILBY, BA (April 1952). "Biochemistry of organic phosphorus insecticides. I. The mammalian metabolism of bis(dimethylamino) phosphonous anhydride (Schradan).". The Biochemical Journal 51 (1): 78–85. doi:10.1042/bj0510078. PMID 14944535.
2. ↑ DAVISON, AN (October 1955). "The conversion of schra dan (OMPA) and parathion into inhibitors of cholinesterase by mammalian liver.". The Biochemical Journal 61 (2): 203–9. doi:10.1042/bj0610203. PMID 13260199.

* v
* t
* e

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

* 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: [[Chemistry:BungaroBungarotoxins (Beta-Bungarotoxin|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

* v
* t
* e

Pest control: Insecticides

Carbamates|

* Aldicarb
* Bendiocarb
* Carbaryl
* Carbofuran
* Ethienocarb
* Fenobucarb
* Oxamyl
* Methomyl
* Propoxur

Inorganic compounds|

* Aluminium phosphide
* Boric acid
* Chromated copper arsenate
* Copper(II) arsenate
* Copper(I) cyanide
* Cryolite
* Diatomaceous earth
* Lead hydrogen arsenate
* Paris Green
* Scheele's Green

Insect growth regulators|

* Benzoylureas
* Diflubenzuron
* Flufenoxuron
* Hydroprene
* Lufenuron
* Methoprene
* Pyriproxyfen

Neonicotinoids|

* Acetamiprid
* Clothianidin
* Dinotefuran
* Imidacloprid
* Nitenpyram
* Nithiazine
* Thiacloprid
* Thiamethoxam

Organochlorides|

* Aldrin
* Beta-HCH
* Carbon tetrachloride
* Chlordane
* Cyclodiene
* 1,2-DCB
* 1,4-DCB
* 1,1-DCE
* 1,2-DCE
* DDD
* DDE
* DDT
* Dicofol
* Dieldrin
* Endosulfan
* Endrin
* Heptachlor
* Kepone
* Lindane
* Methoxychlor
* Mirex
* Tetradifon
* Toxaphene

Organophosphorus|

* Acephate
* Azamethiphos
* Azinphos-methyl
* Bensulide
* Chlorethoxyfos
* Chlorfenvinphos
* Chlorpyrifos
* Chlorpyrifos-methyl
* Coumaphos
* Demeton-S-methyl
* Diazinon
* Dichlorvos
* Dicrotophos
* Diisopropyl fluorophosphate
* Dimefox
* Dimethoate
* Dioxathion
* Disulfoton
* Ethion
* Ethoprop
* Fenamiphos
* Fenitrothion
* Fenthion
* Fosthiazate
* Isoxathion
* Malathion
* Methamidophos
* Methidathion
* Mevinphos
* Mipafox
* Monocrotophos
* Naled
* Omethoate
* Oxydemeton-methyl
* Parathion
* Parathion-methyl
* Phenthoate
* Phorate
* Phosalone
* Phosmet
* Phoxim
* Pirimiphos-methyl
* Quinalphos
* Schradan
* Temefos
* Tebupirimfos
* Terbufos
* Tetrachlorvinphos
* Tribufos
* Trichlorfon

Pyrethroids|

* Acrinathrin
* Allethrins
* Bifenthrin
* Bioallethrin
* Cyfluthrin
* Cyhalothrin
* Cypermethrin
* Cyphenothrin
* Deltamethrin
* Empenthrin
* Esfenvalerate
* Etofenprox
* Fenpropathrin
* Fenvalerate
* Flumethrin
* Imiprothrin
* Metofluthrin
* Permethrin
* Phenothrin
* Prallethrin
* Pyrethrin (I, II; chrysanthemic acid)
* Pyrethrum
* Resmethrin
* Silafluofen
* Tefluthrin
* Tetramethrin
* Tralomethrin
* Transfluthrin

Ryanoids|

* Chlorantraniliprole
* Cyantraniliprole
* Flubendiamide
* Ryanodine
* Ryanodol

Other chemicals|

* Afoxolaner
* Amitraz
* Azadirachtin
* Buprofezin
* Chlordimeform
* Chlorfenapyr
* Cyromazine
* Fenazaquin
* Fenoxycarb
* Fipronil
* Fluralaner
* Hydramethylnon
* Indoxacarb
* Limonene
* Lotilaner
* Pyridaben
* Pyriprole
* Ryanodine
* Sarolaner
* Sesamex
* Spinosad
* Sulfluramid
* Tebufenozide
* Tebufenpyrad
* Veracevine
* Xanthone
* Metaflumizone

Metabolites|

* Oxon
* Malaoxon
* Paraoxon
* TCPy

Biopesticides|

* Bacillus thuringiensis
* Baculovirus
* Beauveria bassiana
* Beauveria brongniartii
* Metarhizium acridum
* Metarhizium anisopliae
* Nomuraea rileyi
* Lecanicillium lecanii
* Paecilomyces fumosoroseus
* Paenibacillus popilliae
* Purpureocillium lilacinum

* v
* t
* e

Neurotoxins

Animal|

* 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
* Anatoxin-a(S)
* BMAA
* Saxitoxin

Plant|

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

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

Other|

* Dimethylmercury
* Toxopyrimidine
* IDPN

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Original source: https://en.wikipedia.org/wiki/Schradan. Read more

|

Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Schradan&oldid=823519"
*[CID]: Compound ID
*[H300]: Fatal if swallowed
*[H310]: Fatal in contact with skin
*[H330]: Fatal if inhaled
*[H371]: May cause damage to organs
*[H373]: May cause damage to organs through prolonged or repeated exposure
*[H412]: Harmful to aquatic life with long lasting effects
*[P260]: Do not breathe dust/fume/gas/mist/vapours/spray
*[P262]: Do not get in eyes, on skin, or on clothing
*[P264]: Wash … thoroughly after handling
*[P270]: Do not eat, drink or smoke when using this product
*[P271]: Use only outdoors or in a well-ventilated area
*[P273]: Avoid release to the environment
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P284]: Wear respiratory protection
*[P301+310]: IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician
*[P302+350]: IF ON SKIN: Gently wash with soap and water
*[P304+340]: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
*[P309+311]: IF exposed or you feel unwell: Call a POISON CENTER or doctor/physician
*[P310]: Immediately call a POISON CENTER or doctor/physician
*[P314]: Get Medical advice/attention if you feel unwell
*[P320]: Specific treatment is urgent (see … on this label)
*[P321]: Specific treatment (see … on this label)
*[P322]: Specific measures (see … on this label)
*[P330]: Rinse mouth
*[P361]: Remove/Take off immediately all contaminated clothing
*[P363]: Wash contaminated clothing before reuse
*[P403+233]: Store in a well ventilated place. Keep container tightly closed
*[P405]: Store locked up
*[P501]: Dispose of contents/container to …
*[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