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Home Page > Alphabetical Index > BICARPHEN (QM-2)

BICARPHEN (QM-2) Prod. No L9032 - CAS # 57734-70-0
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Product Name BICARPHEN (QM-2)
(Syn.: Sequifenadine hydrochloride‚ QC-2MePh)
Product Code L9032
BICARPHEN (QM-2)

C22H27NO.HCl.2H2O
Molecular Formula C22H27NO.HCl.2H2O
Description

a semirigid molecular probe for different ion channels or receptors. Na+ channels blocker. Represents a new class of anti-histaminic (nonH1 or H2) and anti 5-HT anti-allergic drugs: potential antagonist of H-3 histamine and serotonine (non 5-HT2) receptors. Anti-pruritic. Diamine oxidase activator.

Quinuclidine derivative‚ C22H27NO.HCl.2H2O ‚ synthetic.
 
Biological Activity

For detailed information see the attached tables and abstracts.


Ion channels agent.

On Na+ channels (CA1-CA3 region of rat hippocampus neurons)‚ 2.5x10-4 M results in 100 % blocking effect‚ 2x10-6 M in 50%.

On isolated throat ganglia neurons of the snail Limnea stagnalis (patch-clamp whole-cell recording):

* On K+ channels: meagre reversible blockade at 10-5 M.

* No effect on Ca2+ or Cl- channels.


Anti-allergic.

Non-sedative low anti-cholinergic anti-histaminic of prolonged action combined with anti-serotonine activity: aerosol histamine bronchoconstriction prevention in guinea-pig : 80-90 % at 2 mg/kg‚ the same for 5-HT : > 2 mg/kg. (Phencarol: 0.2 and 1 mg/kg respectively). Prolonged action (3-4 hours) and enhanced anti-5-HT activity compared to Phencarol (1.5 hours); efficient against itches [1-3]. Non H-1‚ H-2 or 5-HT2 blocker: no binding to rat cortex H-1‚ H-2 receptors‚ 5-HT-2 receptors [4].



Low affinity to M-AChR.

pIC50 [3H]-quinuclidinyl-3-benzylate‚ rat brain (M-1)/heart (M-2) 5.63/5.33; guinea pig ileum 4.9 (Methylfurmethide)‚ 5.5 (ACh); Pridinol 7.3/6.8‚ Atropine 9.0/10.0.

Good penetration of biological membranes.

Diamine oxidase activator (75 mg/kg p.o.‚ rat lung‚ 60 min +52%‚ 180 min +44%) [5-6].

weak anti-AChE activity in vitro (human erythrocytes) Ki. 104 = 2.60‚ type of inhibition: mixed competitive/non competitive.
 
Chemical and Physical Properties
 
CAS No. 57734-70-0 Molecular Weight 393.96 Da.
RTECS Physical Form colorless crystal powder.
Merck Index No (13th Ed.) Melting point 277-279 °C (decomp.).
PubChem SID 210911 Solubility sparingly in water (25°C‚ 4 mM); better in 50% ethanol.
Purity min. 98 %.

(TLC [on "Silufol UV-254"‚ MeOH-NH3 (25 %) 10:1‚ Rf = 0.14. Visualization by UV-light followed by Dragendorff's reagent.]‚ NMR[CD3OD]).		 Optical Activity
Toxicity (LD50) mice (orally): 650 mg/kg.
mice (i.v.): 68 mg/kg.
Chemical Names (3-Quinuclidinyl)di(2-MethylPhenyl)Carbinol hydrochloride dihydrate‚ (3-quinuclidinyl)di(o-tolyl)methanol hydrochloride dihydrate.
Storage & Reconstitution Recommendations Stable in dry state and solution (up to 150 °C). Dissolves slowly‚ use heating or boiling. Solution for use: 10-3 M (2 mg in 5.01 ml).
Safety Recommendations Do not swallow‚ avoid extra-large quantity inhalation.
 
Bibliographic References
  1. Kaminka M.E. et al., Khim. Farm. Zh. (1976). 10(9):22-27
  2. Kaminka M.E. et al., Drugs of Today (1988). 24(10):701-703
  3. Kaminka M.E. et al., Farm. Toksikol (1988) (Russian). (2):21-26
  4. Gankina E.M. et al., Eksp. Klin. Farmacol. (1993) (Russian). (1):22-24
  5. Baumanis E.A. et al., Farm. Toksikol (1980) (Russian). (1):36-41
  6. Mashkovsky M.D. et al., "Further developments in research on the chemistry and pharmacology of synthetic quinuclidine derivatives." Progr. Drug. Res., (1983). 27:9-61
 
Prices
Code
Quantity
US $
€uro
L9032
1 x 1 mg
282.80
202.00
5 x 1 mg
1 131.20
808.00
 
External Links PubMed Biomedical Citations From PubMed Toxicology Citations From PubMed PubChem SID

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