Pralidoxime Iodide

Names

[ CAS No. ]:
94-63-3

[ Name ]:
Pralidoxime Iodide

[Synonym ]:
2-Pyridinealdoxime methiodide
2-hydroxyiminomethyl-1-methylpyridinium iodide
protopamiodide
EINECS 202-349-6
1-methyl-2-hydroxyiminomethylpyridinium iodide
Pyridinium, 2-[(E)-(hydroxyimino)methyl]-1-methyl-, iodide (1:1)
pralidoximemethiodide
PRALIDOXIMELODIDE
PYRIDINE-2-CARBOXALDOXIME METHIODIDE
PRALIDOXIME IODIDE
MFCD00011982
pyridin-2-aldoxin
p-2-am
2-PAM
2-pamiodide
2-[(E)-(Hydroxyimino)methyl]-1-methylpyridinium iodide
2-[(hydroxyimino)methyl]-1-methylpyridinium iodide

Biological Activity

[Description]:

Pralidoxime iodide is a reactivator of acetylcholinesterase (AChE). Pralidoxime iodide reactivates nerve agent, which inhibits AChE via direct nucleophilic attack by the oxime moiety on the phosphorus center of the bound nerve agent. Pralidoxime iodide is an antidote for organophosphate poisoning[1][2].

[Related Catalog]:

Research Areas >> Neurological Disease

Signaling Pathways >> Neuronal Signaling >> AChE

[In Vivo]

Pralidoxime iodide (10-150 mg/kg; i.m.) reverses paraoxon-induced respiratory toxicity in mice[3]. Animal Model: Male F1B6D2 mice (toxic but non-lethal model of diethylparaoxon in awake, unrestrained mice)[3] Dosage: 10, 50, 100 and 150 mg/kg Administration: Intramuscularly Result: Reversal of diethylparaoxon-induced respiratory toxicity at 150 mg/kg.

[References]

[1]. Cadieux CL, et al. Probing the activity of a non-oxime reactivator for acetylcholinesterase inhibited by organophosphorus nerve agents. Chem Biol Interact. 2016;259(Pt B):133‐141.

[2]. Eyer P, Buckley N. Pralidoxime for organophosphate poisoning. Lancet. 2006;368(9553):2110‐2111.

[3]. Houzé P, et al. High Dose of Pralidoxime Reverses Paraoxon-Induced Respiratory Toxicity in Mice. Turk J Anaesthesiol Reanim. 2018;46(2):131‐138.

Chemical & Physical Properties

[ Density]:
1.7439 g/ml

[ Melting Point ]:
220 °C (dec.)(lit.)

[ Molecular Formula ]:
C₇H₉IN₂O

[ Molecular Weight ]:
264.064

[ Exact Mass ]:
263.975952

[ PSA ]:
36.47000

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UU4375000

CHEMICAL NAME :: Pyridinium, 2-formyl-1-methyl-, iodide, oxime

CAS REGISTRY NUMBER :: 94-63-3

LAST UPDATED :: 199710

DATA ITEMS CITED :: 12

MOLECULAR FORMULA :: C7-H9-N2-O.I

MOLECULAR WEIGHT :: 264.08

WISWESSER LINE NOTATION :: T6KJ A1 B1UNQ &Q &I

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 305 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: BJPCAL British Journal of Pharmacology and Chemotherapy. (London, UK) V.1-33, 1946-68. For publisher information, see BJPCBM. Volume(issue)/page/year: 13,202,1958

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 178 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 129,31,1960

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 249 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 129,31,1960

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JPMSAE Journal of Pharmaceutical Sciences. (American Pharmaceutical Assoc., 2215 Constitution Ave., NW, Washington, DC 20037) V.50- 1961- Volume(issue)/page/year: 53,1143,1964

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 136 mg/kg

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - other changes

REFERENCE :: ABBIA4 Archives of Biochemistry and Biophysics. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.31- 1951- Volume(issue)/page/year: 60,261,1956

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 140 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: AEHLAU Archives of Environmental Health. (Heldref Pub., 4000 Albemarle St., NW, Washington, DC 20016) V.1- 1960- Volume(issue)/page/year: 5,21,1962

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 145 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 132,50,1961

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 240 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 14,5,1964 *** REVIEWS *** TOXICOLOGY REVIEW JPMSAE Journal of Pharmaceutical Sciences. (American Pharmaceutical Assoc., 2215 Constitution Ave., NW, Washington, DC 20037) V.50- 1961- Volume(issue)/page/year: 53,1143,1964 TOXICOLOGY REVIEW JAMAAP JAMA, Journal of the American Medical Association. (AMA, 535 N. Dearborn St., Chicago, IL 60610) V.1- 1883- Volume(issue)/page/year: 166,1834,1958 TOXICOLOGY REVIEW AJMEAZ American Journal of Medicine. (Technical Pub., 875 Third Ave., New York, NY 10022) V.1- 1946- Volume(issue)/page/year: 50,475,1971

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn:Harmful;

[ Risk Phrases ]:
R22

[ Safety Phrases ]:
S36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
UU4375000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

A trivalent approach for determining in vitro toxicology: Examination of oxime K027.

J. Appl. Toxicol. 35(2) , 219-27, (2014)

Unforeseen toxic effects contribute to compound attrition during preclinical evaluation and clinical trials. Consequently, there is a need to correlate in vitro toxicity to in vivo and clinical outcom...

Reactions of methylphosphonic difluoride with human acetylcholinesterase and oximes--Possible therapeutic implications.

Toxicol. Lett. 231(1) , 92-8, (2014)

Highly toxic organophosphorus (OP) nerve agents are well characterized regarding chemical, biological and toxicological properties and the effectiveness of standard atropine and oxime therapy. Open li...

An in vivo zebrafish screen identifies organophosphate antidotes with diverse mechanisms of action.

J. Biomol. Screen. 18(1) , 108-15, (2013)

Organophosphates are a class of highly toxic chemicals that includes many pesticides and chemical weapons. Exposure to organophosphates, either through accidents or acts of terrorism, poses a signific...

Related Compounds

The content on this webpage is sourced from various professional data sources. If you have any questions or concerns regarding the content, please feel free to contact service1@chemsrc.com.