A histamine H3 receptor agonist
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R-(−)-α-Methylhistamine (hydrochloride)

Item No. 25601

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(αR)-methyl-1H-imidazole-5-ethanamine, dihydrochloride
CAS Number
75614-89-0
Molecular Formula
C6H11N3 • 2HCl
Formula Weight
198.1
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: inbsolubleDMSO: 20 mg/mlEthanol: 1 mg/mlPBS (pH 7.2): 10 mg/ml
λmax
210, 315 nm
SMILES
C[C@@H](N)CC1=CN=CN1.Cl.Cl
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $36

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    5 mg

    $128

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    10 mg

    $236

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    25 mg

    $502

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    Product Description

    R-(−)-α-Methylhistamine is a histamine H3 receptor agonist with diverse biological activities.1 It inhibits the release of histamine induced by antidromic electrical stimulation of the sciatic nerve in rats when administered at doses ranging from 0.25 to 2 mg/kg, an effect that can be reversed by the selective histamine H3 receptor antagonist thioperamide (Item No. 10011127). R-(−)-α-Methylhistamine (0.5-50 nmol) inhibits gastric acid secretion in rats when administered intracerebroventricularly but not intravenously.2 It reduces isolation-induced vocalizations and aggressive behavior in a resident-intruder test in guinea pig pups and mice, respectively.3 R-(−)-α-Methylhistamine (30 mg/kg) decreases freezing time in a conditioned fear stress test in rats. It also acts synergistically with fentanyl to reduce nociception and plasma extravasation in a mouse model of chronic inflammation induced by complete Freund's adjuvant.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ohkubo, T., Shibata, M., Inoue, M., et al. Autoregulation of histamine release via the histamine H3 receptor on mast cells in the rat skin. Arch. Int. Pharmacodyn. Ther. 328(3), 307-314 (1994).

    2. Barocelli, E., Ballabeni, V., Chiavarini, M., et al. R-α-methylhistamine-induced inhibition of gastric acid secretion in pylorus-ligated rats via central histamine H3 receptors. Br. J. Pharmacol. 115(7), 1326-1330 (1995).

    3. Yokoyama, F., Yamauchi, M., Oyama, M., et al. Anxiolytic-like profiles of histamine H3 receptor agonists in animal models of anxiety: A comparative study with antidepressants and benzodiazepine anxiolytic. Psychopharmacol. (Berl) 205(2), 177-187 (2009).

    4. Poveda, R., Fernández-Dueñas, V., Fernández, A., et al. Synergistic interaction between fentanyl and the histamine H3 receptor agonist R-(α)-methylhistamine, on the inhibition of nociception and plasma extravasation in mice. Eur. J. Pharmacol. 53-56 (2006).