Diisopropyl fluorophosphate

Structural formula
General
Surname	Diisopropyl fluorophosphate
other names	Diisopropyl phosphofluoridate; Diproxy (2) phosphoryl fluoride; Diisopropyl fluorophosphate; Fluostigmine; Isofluorophate;
Molecular formula	C 6 H 14 FO 3 P
Brief description	colorless liquid
External identifiers / databases
EC number	200-247-6
ECHA InfoCard	100,000,225
PubChem	5936
ChemSpider	5723
DrugBank	DB00677
Wikidata	Q384993
properties
Molar mass	184.15 g mol −1
Physical state	liquid
density	1.06 g cm −3
Melting point	−82 ° C
Vapor pressure	0.77 h Pa (20 ° C); 12 h Pa (62 ° C);
safety instructions
GHS labeling of hazardous substances danger
H and P phrases	H: 300 + 310 + 330
	P: 260-262-280-301 + 310 + 330-302 + 352 + 310-304 + 340 + 310-403-233
Toxicological data	36.8 mg kg −1 ( LD 50 , mouse , oral ) ; > 117 mg kg −1 ( LD 50 , rabbit , transdermal ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Diisopropyl fluorophosphate ( DFP or DIFP ) is a chemical compound from the group of organic phosphoric acid esters . The colorless liquid acts like many other members of the group of substances as a neurotoxin .

history

DFP was first developed and produced by the British during World War II . It was intended to use DFP as a tactical mixture with mustard gas ( mustard ). This would have made it a contact poison .

Extraction and presentation

DFP can be obtained by reacting 2-propanol with phosphorus trichloride , which is then chlorinated and then substituted to fluorine.

use

In the ophthalmology DFP as miotic for treatment of glaucoma used (glaucoma). In biochemical tests it is used as an inhibitor of acetylcholinesterase and serine proteases . No actual use of DFP in war operations is known.

Biological importance

toxicity

Diisopropyl fluorophosphate prevents the breakdown of the neurotransmitter acetylcholine through an irreversible (non-reversible) reaction in the active center of the enzyme acetylcholinesterase . A connection is created between the inhibitor diisopropyl fluorophosphate and the enzyme acetylcholinesterase. The subsequent permanent excitation (permanent depolarization) of the synapses by acetylcholine in the affected nerve cells leads to severe cramps and death . Acetylcholine acts as a transmitter substance during arousal in the parasympathetic (vegetative) nervous system and at the neuromuscular synapses. The effect of diisopropyl fluorophosphate is given by the fact that it is with serine side chains in the active site of many enzymes covalently connects.

Symptoms

With little contact , there is difficulty in breathing , headache and a feeling of pressure in the chest. Significant sweats , visual disturbances , associated with eye pain and increased excretion of nasal secretions , saliva and tear fluid occur . A narrowing of the pupil ( miosis ) can also be observed.
With stronger contact, these signs can also be observed and diarrhea and vomiting occur , combined with impaired consciousness and cramps .
In the case of severe poisoning , the symptoms mentioned above increase . Uncontrolled stool and urine leakage occur. Death occurs due to respiratory paralysis .

safety instructions

First aid

If breathing has stopped : see respiration and ventilation .
Ventilation is not possible with a contact poison .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on diisopropyl fluorophosphate in the GESTIS substance database of the IFA , accessed on January 21, 2020(JavaScript required) .
↑ Entry on isofluorophate. In: Römpp Online . Georg Thieme Verlag, accessed on April 9, 2014.
↑ Patent US2409039 : Halogenated compounds and process for making same. Registered January 28, 1944 , published October 8, 1946 , Applicant: Monsanto , Inventor: Edgar E Hardy, Gennady M Kosolapoff. ‌
↑ Rufus O. Okotore: Essentials of Enzymology. Xlibris Corporation, 2015, ISBN 978-1-503-52722-5 , p. 164 ( limited preview in Google Book Search).

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on diisopropyl fluorophosphate in the GESTIS substance database of the IFA , accessed on January 21, 2020(JavaScript required) .

[2] Entry on isofluorophate. In: Römpp Online . Georg Thieme Verlag, accessed on April 9, 2014.

[3] Patent US2409039 : Halogenated compounds and process for making same. Registered January 28, 1944 , published October 8, 1946 , Applicant: Monsanto , Inventor: Edgar E Hardy, Gennady M Kosolapoff. ‌

[books-k4eEBwAAQBAJ-166-4] Rufus O. Okotore: Essentials of Enzymology. Xlibris Corporation, 2015, ISBN 978-1-503-52722-5 , p. 164 ( limited preview in Google Book Search).