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Merck
CN

SML0329

Carcinine dihydrochloride

≥98% (HPLC)

Synonym(s):

Alistin, β-Alanylhistamine dihydrochloride, 3-Amino-N-[2-(1H-imidazol-4-yl)ethyl]propanamide dihydrochloride, 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
NACRES:
NA.77
PubChem Substance ID:
329825334
UNSPSC Code:
12352200
MDL number:
MFCD22200567

Key Documents

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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

SMILES string

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

InChI key

ZQTUNIWBUQUKAM-UHFFFAOYSA-N

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

H2O: >15 mg/mL

storage temp.

−20°C

Quality Level

100

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.
Carcinine is a selective histamine H3 antagonist; antioxidant.

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

signalword

Danger

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000489783
0000375719
0000375719
0000130118
0000130119

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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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