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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[1]
  • to inhibit wild-type BChE in acetylcholinesterase assay[2]
  • to selectively block the enzymatic activity of AChE[3]

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCC2020
BCCB0397
BCBW4257
BCBQ3831V
BCBQ3831

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Souren Mkrtchian et al.
Experimental physiology, 105(9), 1634-1647 (2020-07-12)
What is the central question of this study? Are carotid bodies (CBs) modulated by the damage-associated molecular patterns (DAMPs) and humoral factors of aseptic tissue injury? What are the main findings and their importance? DAMPs (HMGB1, S100 A8/A9) and blood
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)
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
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
Determination of the DNA sequences of acetylcholinesterase and butyrylcholinesterase from cat and demonstration of the existence of both in cat plasma.
Bartels CF, et al.
Biochemical Pharmacology, 60(4), 479-487 (2018)
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