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T1505

Sigma-Aldrich

Tetraisopropyl pyrophosphoramide

butyrylcholinesterase inhibitor

Synonym(s):

Tetra(monoisopropyl)pyrophosphortetramide, iso-OMPA

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About This Item

Empirical Formula (Hill Notation):
C12H32N4O3P2
CAS Number:
513-00-8
Molecular Weight:
342.36
EC Number:
208-149-5
MDL number:
MFCD00048272
UNSPSC Code:
12352202
PubChem Substance ID:
24278724
NACRES:
NA.77

biological source

synthetic

mp

149-151 °C

storage temp.

−20°C

SMILES string

CC(C)NP(=O)(NC(C)C)OP(=O)(NC(C)C)NC(C)C

InChI

1S/C12H32N4O3P2/c1-9(2)13-20(17,14-10(3)4)19-21(18,15-11(5)6)16-12(7)8/h9-12H,1-8H3,(H2,13,14,17)(H2,15,16,18)

InChI key

IOIMDJXKIMCMIG-UHFFFAOYSA-N

Gene Information

human ... ACHE(43) , BCHE(590)

Application

Tetraisopropyl pyrophosphoramide has been used:
  • as a butyrylcholinesterase inhibitor to determine the proportions of butyrylcholinesterase (BChE) in cat and tiger plasma
  • to inhibit wild-type BChE in acetylcholinesterase assay
  • to selectively block the enzymatic activity of AChE

Biochem/physiol Actions

Selective inhibitor of butyrylcholinesterase

Warning

WARNING: Extremely hazardous! Be aware of the risk and familiar with safety procedures before you use this product.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300 + H310 + H330

Hazard Classifications

Acute Tox. 1 Inhalation - Acute Tox. 2 Dermal - Acute Tox. 2 Oral

Storage Class Code

6.1B - Non-combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Ilaria Corsi et al.
Comparative biochemistry and physiology. Toxicology & pharmacology : CBP, 145(3), 413-419 (2007-02-28)
To address the potential role of cholinesterase enzymes in the invasive capacity of species, the present study investigated ChE activity in the invasive freshwater bivalve Anodonta woodiana (Lea, 1834) comparing it with that of the indigenous species, Anodonta sp. (Linnaeus
Resistance to organophosphorus agent toxicity in transgenic mice expressing the G117H mutant of human butyrylcholinesterase
Wang YW, et al.
Toxicology and Applied Pharmacology, 196(3), 356-366 (2004)
Ming-Kuem Lin et al.
Molecules (Basel, Switzerland), 23(12) (2018-11-24)
The seeds of Cuscuta chinensis Lam. and C. campestris Yuncker have been commonly used as Chinese medical material for preventing aging. Our previous studies have found that C. chinensis and C. campestris possess anti-inflammatory activities in rodents. However, their other
Liyi Geng et al.
PloS one, 8(6), e67446-e67446 (2013-07-11)
Gene transfer of a human cocaine hydrolase (hCocH) derived from butyrylcholinesterase (BChE) by 5 mutations (A199S/F227A/S287G/A328W/Y332G) has shown promise in animal studies for treatment of cocaine addiction. To predict the physiological fate and immunogenicity of this enzyme in humans, a
A A Kousba et al.
Toxicology, 188(2-3), 219-232 (2003-05-28)
The primary mechanism of action for organophosphorus (OP) insecticides such as chlorpyrifos (CPF) involves the inhibition of acetylcholinesterase (AChE) by their active oxon metabolites resulting in a wide range of neurotoxic effects. These oxons also inhibit other cholinesterases (ChE) such
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