Salvinorin A

Structural formula
General
Surname	Salvinorin A
other names	(2 S , 4a R , 6a R , 7 R , 9 S , 10a S , 10b R ) -Methyl-9-acetoxy-2- (furan-3-yl) -6a, 10b-dimethyl-4,10-dioxo -dodecahydro-1 H -benzo [ f ] -isochromene-7-carboxylate; Divinor A;
Molecular formula	C 23 H 28 O 8
Brief description	colorless solid
External identifiers / databases
EC number	689-027-2
ECHA InfoCard	100.215.796
PubChem	128563
Wikidata	Q413512
Drug information
Mechanism of action	selective agonist at κ opioid - receptors
properties
Molar mass	432.46 g mol −1
Physical state	firmly
density	1.29 g cm −3
Melting point	242-244 ° C
solubility	poor in DMSO (10 g l −1 ) and ethanol (3 g l −1 ); good in chloroform ;
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Salvinorin A is the only psychoactive representative of the salvinorine group .

Occurrence

Aztec sage ( Salvia divinorum )

The diterpenoid occurs naturally as a secondary metabolite in Aztec sage ( Salvia divinorum ) in amounts of a maximum of 3.7 mg / g dry weight.

Pharmacology and effects of salvinorin A

Salvinorin A is a selective agonist of κ opioid - receptor identified. The κ agonism is the reason for the hallucinogenic effect; this occurs at doses between 150 and 500 μg. Salvinorin A differs significantly in its pharmacodynamics from the “classic hallucinogens ” such as LSD . In contrast to these, salvinorin A does not act on the 5-HT _2A receptor . A number of compounds with κ-opioid agonistic effects are known to have psychoactive / hallucinogenic effects, including pentazocine .

literature

CW Cunningham, RB Rothman, TE Prisinzano: Neuropharmacology of the naturally occurring kappa-opioid hallucinogen salvinorin A. In: Pharmacological reviews. Volume 63, number 2, June 2011, pp. 316-347, doi : 10.1124 / pr.110.003244 , PMID 21444610 , PMC 3082450 (free full text) (review).

Individual evidence

↑ ^a ^b ^c ^d Data sheet Salvinorin A from Sigma-Aldrich , accessed on June 15, 2011 ( PDF ).
^ Valdes, LJ III et al (1984): Divinorin A, a Psychotropic Terpenoid, and Divinorin B from the Hallucinogenic Mexican Mint, Salvia divinorum
↑ ^a ^b D. C. Ayres (Ed.): Dictionary of natural products. Volume 4, M - Q. CRC Press, 1994, ISBN 0-412-46620-1 , p. 2143.
^ ^A ^b Dietrich Frohne, Hans Jürgen Pfänder: Poisonous plants: a handbook for doctors, pharmacists, toxicologists, biologists and veterinarians. 2nd edition, Wiley-Blackwell, 2005, ISBN 1-874545-94-4 , p. 240.
↑ BL Roth, K. Baner u. a .: Salvinorin A: a potent naturally occurring nonnitrogenous kappa opioid selective agonist. In: Proceedings of the National Academy of Sciences . Volume 99, Number 18, September 2002, pp. 11934-11939, doi : 10.1073 / pnas.182234399 . PMID 12192085 . PMC 129372 (free full text).

[sigma-1] Data sheet Salvinorin A from Sigma-Aldrich , accessed on June 15, 2011 ( PDF ).

[Erowid-2] Valdes, LJ III et al (1984): Divinorin A, a Psychotropic Terpenoid, and Divinorin B from the Hallucinogenic Mexican Mint, Salvia divinorum

[ayres-3] D. C. Ayres (Ed.): Dictionary of natural products. Volume 4, M - Q. CRC Press, 1994, ISBN 0-412-46620-1 , p. 2143.

[poispl-4] A ^b Dietrich Frohne, Hans Jürgen Pfänder: Poisonous plants: a handbook for doctors, pharmacists, toxicologists, biologists and veterinarians. 2nd edition, Wiley-Blackwell, 2005, ISBN 1-874545-94-4 , p. 240.

[PMID12192085-5] BL Roth, K. Baner u. a .: Salvinorin A: a potent naturally occurring nonnitrogenous kappa opioid selective agonist. In: Proceedings of the National Academy of Sciences . Volume 99, Number 18, September 2002, pp. 11934-11939, doi : 10.1073 / pnas.182234399 . PMID 12192085 . PMC 129372 (free full text).