(3R-cis)-1-(6-methoxy-4-quinolyl)-3-(3-vinyl-4-piperidyl)propan-1-one monohydrochloride

(3R-cis)-1-(6-methoxy-4-quinolyl)-3-(3-vinyl-4-piperidyl)propan-1-one monohydrochloride Property

Melting point:

184 ±4°

storage temp. 

Hygroscopic, -20°C Freezer, Under inert atmosphere

solubility 

DMSO (Slightly), Water (Slightly, Sonicated)

form 

Solid

color 

Pale Yellow to Yellow

Water Solubility 

Water: 15 mg/mL (41.57 mM)

Stability:

Very Hygroscopic

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H312Harmful in contact with skin

H332Harmful if inhaled

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P322Specific measures (see …on this label).

P330Rinse mouth.

P363Wash contaminated clothing before reuse.

P501Dispose of contents/container to..…

(3R-cis)-1-(6-methoxy-4-quinolyl)-3-(3-vinyl-4-piperidyl)propan-1-one monohydrochloride Chemical Properties,Usage,Production

Description

Although this alkaloid from the bark of Cinchona species was first isolated by Howard in 1871, it had earlier been prepared by Pasteur by heating the acid sulphate of quinine and Hesse subsequently prepared it in a similar manner from quinidine. The identity of the alkaloid with quinotoxine, formed by heating quinine in H20 or dilute AcOH was proved by von Miller and his co-workers. The base forms a bitter, yellow varnish having [α]_D + 38.6° (CHCI 3 ) and is normally purified through the oxalate nonahydrate which has m.p. 166-7°C;[α]²⁰_D + 24°. The alkaloid yields crystalline salts, the hydrochloride forming colourless leaflets, m.p. l80-2°C; [α]]^13.7_D + 16 26° (H20); the oxime, m.p. l12-6°C; dipicrolonate, m.p. 210°C; the (+)-tropate monohydrate, m.p. l12-3°C or l16-8°C (dry). The p-bromophenylhydrazone forms yellow crystals, m.p. 141°C. Both the N-methyl and N-ethyl derivatives are yellow oils, the former yielding a hydrochloride monohydrate, m.p. l53-5°C; [α]²³_D + 16.6° (H20) and the latter the corresponding hydrochloride, m.p. 202-4°C; [α]²³_D + 68.1 ° (H20). The N-benzoyl derivative crystallizes from C6H6 or MeOH with m.p. l13-4°C; [α]²²_D + 36° (c 2.0, EtOH).
According to de Caro, the minimum lethal dose for white rats is 0.32 gm/kilo compared with 1.25 gm/kilo for quinine and, although it has no anti-malarial action, the alkaloid appears to be less toxic than formerly supposed.

Uses

An isomer of quinine; occurs naturally as the d-form. Present in small quantities in cinchona barks. Vasodilator (cerebral).

in vivo

References

Pasteur.,Jahresb., 473 (1853)
Howard.,f. Chem. Soc., 24, 6! (! 871)
Howard., ibid, 25, 101 (1872)
Hesse., Annalen, 178, 244 (1875)
von Miller, Rohde, Fussenegger., Ber., 33,3228 (1900)
Heidelberger, Jacobs.,J. Amer. Chem. Soc., 41,832 (1919)
Heidelberger, Jacobs., ibid, 44, 1093 (1922)
Frankel, Diamant., Ber., 58,554 (1925)
Prostenik, Prelog., Helv. Chim. Acta, 26, 1965 (1943)
Toxicology :
de Caro., Arch. expo Path. Pharm., 164,314 (1932)