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P5780

Sigma-Aldrich

Putrescine dihydrochloride

powder, BioReagent, suitable for cell culture

Synonym(s):

1,4-Butanediamine dihydrochloride, 1,4-Diaminobutane dihydrochloride, Tetramethylenediamine dihydrochloride

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About This Item

Linear Formula:
NH2(CH2)4NH2 · 2HCl
CAS Number:
333-93-7
Molecular Weight:
161.07
Beilstein/REAXYS Number:
3906680
EC Number:
206-375-9
MDL number:
MFCD00012526
UNSPSC Code:
12352207
PubChem Substance ID:
24898707
NACRES:
NA.75

biological source

microbial
synthetic

Quality Level

200

product line

BioReagent

assay

≥97% (TLC)

form

powder

technique(s)

cell culture | mammalian: suitable

mp

280 °C (dec.) (lit.)

solubility

H2O: 100 mg/mL

SMILES string

Cl[H].Cl[H].NCCCCN

InChI

1S/C4H12N2.2ClH/c5-3-1-2-4-6;;/h1-6H2;2*1H

InChI key

XXWCODXIQWIHQN-UHFFFAOYSA-N

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General description

Putrescine is an end product of fatty acid metabolism in dead tissues. It is a volatile diamine with pungent odour. It is synthesized by the decarboxylation of ornithine in the presence of enzyme, ornithine decarboxylase. Molecular docking studies reveal the binding of putrescine to human receptors called the trace amine-associated receptors (TAAR6 and TAAR8), present in olfactory epithelium.

Application

Putrescine dihydrochloride has been used as medium component in F-12 + GlutaMax medium for mice ganglia culture, retinal ganglion cell culture and in HCT116 colon carcinoma cells for ornithine decarboxylase (ODC) assay.

Biochem/physiol Actions

Binds to the polyamine modulatory site of the NMDA receptor and potentiates NMDA-induced currents; precursor of spermidine.
Putrescine is regarded as a marker of stress in plants. External supplementation of putrescine helps wheat plants to overcome drought stress. It is crucial for cell proliferation in animals and modulates abscisic acid (ABA) levels during cold stress in Arabidopsis plants. It serves as an attractant for predators.

pictograms

CorrosionSkull and crossbones
GHS05,GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 3 Dermal - Acute Tox. 4 Oral - Eye Dam. 1 - Skin Corr. 1B

Storage Class

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 1

ppe

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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Polyamines and abiotic stress in plants: a complex relationship1
Minocha R, et al.
Frontiers in Plant Science, 5, 175-175 (2014)
Putrescine is involved in Arabidopsis freezing tolerance and cold acclimation by regulating abscisic acid levels in response to low temperature
Cuevas JC, et al.
Plant Physiology, 148(2), 1094-1105 (2008)
Identifying human diamine sensors for death related putrescine and cadaverine molecules
Izquierdo C, et al.
PLoS Computational Biology, 14(1), e1005945-e1005945 (2018)
Ornithine decarboxylase activity in tumor cell lines correlates with sensitivity to cell death induced by histone deacetylase inhibitors
Saunders LR and Verdin E
Molecular Cancer Therapeutics, 5(11), 2777-2785 (2006)
A new assay for nerve fiber repulsion
Fassold A and Strau RH
Annals of the New York Academy of Sciences, 1193(1), 43-47 (2010)
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