Rescinnamine

Structural formula
General
Surname	Rescinnamine
other names	"Reserpine" (revised); 11.17 α- Dimethoxy-18 β - (3,4,5-trimethoxyphenyl-2-propenyloxy) -3 β , 20 α -yohimbane-16 β -carboxylic acid methyl ester;
Molecular formula	C 35 H 42 N 2 O 9
Brief description	fine needles
External identifiers / databases
EC number	246-471-8
ECHA InfoCard	100.042.232
PubChem	5280954
ChemSpider	4444446
DrugBank	DB01180
Wikidata	Q409978
Drug information
ATC code	C02 AA01
properties
Molar mass	634.71 g · mol -1
Physical state	firmly
Melting point	238-239 ° C
solubility	easily in chloroform , glacial acetic acid and benzene , little in ethanol , not in water
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Caution
H and P phrases	H: 302-312-332
	P: ?
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Rescinnamine is an indole alkaloid that occurs in various Rauvolfia species, especially in the Indian snake root , for whose antihypertensive and calming effect it is primarily responsible, along with reserpine . It differs from this in terms of its chemical structure only in the esterification of the C-18 hydroxyl group of the base body with 3,4,5-trimethoxycinnamic acid (TMZA) instead of 3,4,5-trimethoxybenzoic acid (TMBS).

Rescinnamine is not reserpine

Because of these similarities, Erich Haack and his colleagues gave the new alkaloid they isolated in 1954 the trivial name "reserpine". But since the research group around Emil Schlittler used this name almost simultaneously for the Haack et al. "Raubasinin" called reserpine and this name was then adopted by others, they changed the name to "Rescinnamine" for the sake of clarity. Regardless of this, the names of both alkaloids are still mixed up today.

application

Rescinnamine is found in total extracts of Rauvolfia serpentina and contributes to their calming and antihypertensive effect by moderately lowering dopamine , norepinephrine and serotonin levels. In terms of quality, its pharmacological profile corresponds to that of reserpine, the differences are more of a quantitative nature: while its sedative and bradycardic effects are significantly lighter than that of reserpine, its hypotensive effect is only slightly weaker than that of reserpine. Also, the effects of rescinnamine do not last that long. In Germany, along with other Rauvolfia alkaloids, it was contained in Modenol ^® (from Hoffmann-La Roche ) and Diuraupur ^® (then Giulini Pharma ); in the USA there are numerous monopreparations.

In addition to being used for therapeutic purposes, rescinnamine is also used in research as a comparative substance to reserpine.

Analytics

The specific angle of rotation is −87 ° to −97 ° (c = 1, chloroform). The additional double bond of the TMZS compared to the TMBS ester enables a differentiation between rescinnamine and reserpine by bromination , since an electrophilic addition of bromine is possible on them. The resulting change in the absorption spectrum is characteristic of rescinnamine.

Individual evidence

↑ ^a ^b ^c Entry on rescinnamine. In: Römpp Online . Georg Thieme Verlag, accessed on June 13, 2014.
↑ ^a ^b ^c Roth, Daunderer, Kormann: Toxic Plants - Plant Poisons . Hüthig Jehle Rehm, 1994. ISBN 3-609-64810-4 . P. 906.
↑ Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A labeling of rescinnamine in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), which was accessed on July 11, 2020, is reproduced from a self-classification by the distributor .
↑ Haack, Popelak, Spingler, Kaiser: Reserpinin, a new alkaloid from Rauwolfia serpentina Benth . In: Naturwissenschaften (1954), Vol. 41, pp. 214–215.
↑ Haack, Popelak, Spingler: Rauwolfia alkaloids Reserpinin and rescinnamine . In: Naturwissenschaften (1955), Vol. 42, p. 47.
↑ Furukawa, Sano, Kohno, Koga, Nagasaki: Selective Depleting Effect of Syrosingopine on Brain Catecholamine Levels with Relation to Morphine Analgesia in the Rat . In: Pharmacology, Biochemistry and Behavior (1976), Vol. 4, pp. 419-425.
↑ Wink, van Wyk, Wink: Handbook of poisonous and psychoactive plants . Wissenschaftliche Verlagsgesellschaft, Stuttgart, 2008. ISBN 3-8047-2425-6 . Pp. 200, 268 and 402.
^ Kähler: Rauwolfia alkaloids . Boehringer Mannheim, Mannheim, 1970. pp. 80-81.
↑ cf. Almeida, Guzmán: Rescinnamine and reserpine - a comparative study of their ¹³ C NMR spectra . In: Journal of Pharmaceutical and Biomedical Analysis (1988), Vol. 6, pp. 185-189.
Or: Carmona-Guzmán, Balón, Sánchez: Kinetics of the Oxidation of Rescinnamine by Peroxodisulfate. In: Reaction Kinetics and Catalysis Letters (1986), Vol. 31, pp. 121-126.
Or: Furukawa, Sano, Kohno, Koga, Nagasaki: Selective Depleting Effect of Syrosingopine on Brain Catecholamine Levels with Relation to Morphine Analgesia in the Rat . In: Pharmacology, Biochemistry and Behavior (1976), Vol. 4, pp. 419-425.
↑ Missan, Ciacco, McMullen, Pazdera, Grenfell: Analytical Methods for Rescinnamine . In: Journal of the American Pharmaceutical Association (1960), Vol. 49, pp. 7-13.

[römpp-1] Entry on rescinnamine. In: Römpp Online . Georg Thieme Verlag, accessed on June 13, 2014.

[roth-2] Roth, Daunderer, Kormann: Toxic Plants - Plant Poisons . Hüthig Jehle Rehm, 1994. ISBN 3-609-64810-4 . P. 906.

[3] Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A labeling of rescinnamine in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), which was accessed on July 11, 2020, is reproduced from a self-classification by the distributor .

[4] Haack, Popelak, Spingler, Kaiser: Reserpinin, a new alkaloid from Rauwolfia serpentina Benth . In: Naturwissenschaften (1954), Vol. 41, pp. 214–215.

[5] Haack, Popelak, Spingler: Rauwolfia alkaloids Reserpinin and rescinnamine . In: Naturwissenschaften (1955), Vol. 42, p. 47.

[6] Furukawa, Sano, Kohno, Koga, Nagasaki: Selective Depleting Effect of Syrosingopine on Brain Catecholamine Levels with Relation to Morphine Analgesia in the Rat . In: Pharmacology, Biochemistry and Behavior (1976), Vol. 4, pp. 419-425.

[7] Wink, van Wyk, Wink: Handbook of poisonous and psychoactive plants . Wissenschaftliche Verlagsgesellschaft, Stuttgart, 2008. ISBN 3-8047-2425-6 . Pp. 200, 268 and 402.

[8] Kähler: Rauwolfia alkaloids . Boehringer Mannheim, Mannheim, 1970. pp. 80-81.

[9] . Almeida, Guzmán: Rescinnamine and reserpine - a comparative study of their ¹³ C NMR spectra . In: Journal of Pharmaceutical and Biomedical Analysis (1988), Vol. 6, pp. 185-189.
Or: Carmona-Guzmán, Balón, Sánchez: Kinetics of the Oxidation of Rescinnamine by Peroxodisulfate. In: Reaction Kinetics and Catalysis Letters (1986), Vol. 31, pp. 121-126.
Or: Furukawa, Sano, Kohno, Koga, Nagasaki: Selective Depleting Effect of Syrosingopine on Brain Catecholamine Levels with Relation to Morphine Analgesia in the Rat . In: Pharmacology, Biochemistry and Behavior (1976), Vol. 4, pp. 419-425.

[10] Missan, Ciacco, McMullen, Pazdera, Grenfell: Analytical Methods for Rescinnamine . In: Journal of the American Pharmaceutical Association (1960), Vol. 49, pp. 7-13.