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SML0329

Sigma-Aldrich

Carcinine dihydrochloride

≥98% (HPLC)

Synonym(s):

β-Alanylhistamine dihydrochloride, 3-Amino-N-[2-(1H-imidazol-4-yl)ethyl]propanamide dihydrochloride, Alistin, Beta-Alanylhistamine dihydrochloride

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About This Item

Empirical Formula (Hill Notation):
C8H14N4O · 2HCl
CAS Number:
57022-38-5
Molecular Weight:
255.14
MDL number:
MFCD22200567
UNSPSC Code:
12352200
PubChem Substance ID:
329825334
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

H2O: >15 mg/mL

storage temp.

−20°C

SMILES string

Cl.Cl.NCCC(=O)NCCc1cnc[nH]1

InChI

1S/C8H14N4O.2ClH/c9-3-1-8(13)11-4-2-7-5-10-6-12-7;;/h5-6H,1-4,9H2,(H,10,12)(H,11,13);2*1H

InChI key

ZQTUNIWBUQUKAM-UHFFFAOYSA-N

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General description

Carcinine, a natural peptide derivative, with a β-alanyl residue and a histamine, carries an imidazole ring. In mammals, carcinine is present in the brain, muscle, intestine and liver tissues.

Application

Carcinine dihydrochloride has been used to study its effects on dopaminergic neuron degeneration.

Biochem/physiol Actions

Carcinine (β-alanyl histamine) is a selective histamine H3 antagonist, 100-1000-fold selective for H3 over H2 and H1, that also functions as an antioxidant and as a chemical chaperone to reduce non-enzymatic glycation of proteins and maintain native folding of proteins.
Carcinine can scavenge a toxic product, called 4-hydroxynonenal (4-HNE), obtained during lipid oxidation. It has a protective role from oxidative damage on photoreceptor cells. Carcinine also exhibits lipid-peroxidase activity.

Features and Benefits

This compound is featured on the Histamine Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H315,H318,H335

Hazard Classifications

Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Lea D Marchette et al.
Investigative ophthalmology & visual science, 53(7), 3572-3583 (2012-05-12)
Oxidative stress induces retinal damage and contributes to vision loss in progressive retinopathies. Carcinine (β-alanyl-histamine) is a natural imidazole-containing peptide derivative with antioxidant activity. It is predicted to scavenge 4-hydroxynonenal (4-HNE), a toxic product of lipid oxidation. The aim of
Pei Zhou et al.
Brain, behavior, and immunity, 76, 61-73 (2018-11-09)
The activation of microglial cells is presumed to play a key role in the pathogenesis of Parkinson's disease (PD). The activity of microglia is regulated by the histamine-4 receptor (H4R), thus providing a novel target that may prevent the progression

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