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H128

Sigma-Aldrich

(R)(−)-α-Methylhistamine dihydrochloride

solid, ≥98% (HPLC)

Synonym(s):

(R)(−)-α-Methyl-1H-imidazole-4-ethanamine dihydrochloride

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About This Item

Empirical Formula (Hill Notation):
C6H11N3 · 2HCl
CAS Number:
75614-89-0
Molecular Weight:
198.09
MDL number:
MFCD00083176
UNSPSC Code:
12352116
PubChem Substance ID:
24277778
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

solid

optical activity

[α]22/D −4°, c = 0.8 in H2O(lit.)

storage condition

desiccated

color

white to off-white

solubility

H2O: soluble

SMILES string

Cl.Cl.C[C@@H](N)Cc1c[nH]cn1

InChI

1S/C6H11N3.2ClH/c1-5(7)2-6-3-8-4-9-6;;/h3-5H,2,7H2,1H3,(H,8,9);2*1H/t5-;;/m1../s1

InChI key

IZHCNQFUWDFPCW-ZJIMSODOSA-N

Gene Information

human ... HRH3(11255)

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Application

(R)(−)-α-Methylhistamine dihydrochloride has been used as an agonist for the histamine H3 cell lines. It has also been used in the antagonist assay for the histamine H3 cell lines.

Biochem/physiol Actions

(R)(−)-α-Methylhistamine dihydrochloride is a potent, selective H3 histamine receptor agonist which crosses the blood-brain barrier. It can inhibit histamine synthesis and release.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - 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

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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Magdalena Kotańska et al.
Biochemical pharmacology, 168, 193-203 (2019-07-12)
Histamine H3 receptors ligands act anorectic by blocking the H3 autoreceptors in the CNS, that results in increased synthesis and disinhibition of histamine release. Histamine further influencing H1 receptors participates in the leptin-dependent inhibition of food intake. It also affects
Structure-activity relations of histamine analogs. XX. Absolute configuration and histamine-like activity of enantiomeric α-methyl histamines.
Gerhard, et al.
Archives of Pharmacal Research, 313, 709-709 (1980)
J M Arrang et al.
Nature, 327(6118), 117-123 (1987-05-14)
New drugs selective for histamine H3-receptors can be used to establish that these receptors are involved in the feedback control of histamine synthesis and release, and to demonstrate their distribution in the brain and peripheral tissues. These drugs provide new
R Oishi et al.
Journal of neurochemistry, 52(5), 1388-1392 (1989-05-01)
To study the feedback control by histamine (HA) H3-receptors on the synthesis and release of HA at nerve endings in the brain, the effects of a potent and selective H3-agonist, (R)-alpha-methylhistamine, and an H3-antagonist, thioperamide, on the pargyline-induced accumulation of
Xu-Dong Wang et al.
Nature communications, 10(1), 3201-3201 (2019-07-22)
Pulmonary neuroendocrine (NE) cancer, including small cell lung cancer (SCLC), is a particularly aggressive malignancy. The lineage-specific transcription factors Achaete-scute homolog 1 (ASCL1), NEUROD1 and POU2F3 have been reported to identify the different subtypes of pulmonary NE cancers. Using a

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