Salvinorine

Aztec sage

Salvinorine crystals

The salvinorins are a group of structurally closely related diterpenoid secondary metabolites of the Aztec sage ( Salvia divinorum ).

Overview

Salvinorin A was isolated in 1982 as the first substance out of nine individual representatives of salvinorins (A – H, J) . Salvinorin A is a hallucinogen with dissociative effects. Salvinorine B – E are considered to be psychotropically inactive, Salvinorin F has no known psychotropic effects. Salvinorin A was identified as a selective agonist of κ opioid - receptor . Binding to this receptor has also been demonstrated for salvinorin G in low concentrations.

Salvinorin A is the most potent known naturally occurring psychoactive substance, with an effective dose from 200 µg . It is noticeable that in contrast to other natural hallucinogens such as DMT , psilocybin or mescaline , or comparable synthetic drugs such as LSD or 2C-B , the substance does not have a basic nitrogen atom.

Salvinorine
Surname	R ¹	R ²	Molecular formula	molar mass	CAS number	PubChem
Salvinorin A	-OCOCH ₃	-	C ₂₃ H ₂₈ O ₈	432.46 g mol ⁻¹	83729-01-5	128563
Salvinorin B	-OH	-	C ₂₁ H ₂₆ O ₇	390.43 g mol ⁻¹	92545-30-7	11440685
Salvinorin C	-OCOCH ₃	-OCOCH ₃	C ₂₅ H ₃₀ O ₉	475.29 g mol ⁻¹	385785-99-9	-
Salvinorin D	-OCOCH ₃	-OH	C ₂₃ H ₂₈ O ₈	432.47 g mol ⁻¹	540770-13-6	-
Salvinorin E	-OH	-OCOCH ₃	C ₂₃ H ₂₈ O ₈	432.47 g mol ⁻¹	540770-14-7	-
Salvinorin F	-OH	-H	C ₂₁ H ₂₆ O ₆	374.43 g mol ⁻¹	540770-15-8	-
Salvinorin G	= O	-OCOCH ₃	C ₂₃ H ₂₆ O ₈	430.45 g mol ⁻¹	866622-54-0	-
Salvinorin H	-OH	-OH	C ₂₁ H ₂₆ O ₇	390.43 g mol ⁻¹	872004-62-1	-
Salvinorin I	-	-	C ₂₁ H ₂₈ O ₇	392.45 g mol ⁻¹	917951-71-4	-
17 α- salvinorin J.	-	-	C ₂₃ H ₃₀ O ₈	434.49 g mol ⁻¹	1157894-83-1	-
17 β- salvinorin J.	-	-	C ₂₃ H ₃₀ O ₈	434.49 g mol ⁻¹	1157894-85-3	-

The isolation of another compound that can be assigned to the salvinorines was recently published. The structure of salvinorin J is similar to that of salvinorin E, however, C-17 is not formed as a lactone , but as a hemiacetal .

Synthetically produced salvinorin analogs

Due to their high pharmacological effectiveness, further derivatives have now been produced synthetically, some of which are even more effective than salvinorin A on the κ-opioid receptor. Structurally related substances are also Herkinorin , Divinatorin and Salvinicin .

Legal status

In Germany, with the 21st BtMÄndV, Salvia divinorum (plants and plant parts) was included in Appendix I of the BtMG and is therefore one of the “non-marketable narcotics”.

literature

DM Turner: Salvinorin: The Psychedelic Essence of Salvia Divinorum . Panther Press, 1996, ISBN 0-9642636-2-9 (English).
Jochen Gartz: Salvia divinorum - The fortune telling sage . Nachtschatten Verlag, 2001, ISBN 3-907080-28-9 , 80 pages.
Bastian Borschke: Salvia Divinorum and other psychoactive species of sage . Grüne Kraft, 2002, ISBN 3-930442-55-8 , 32 pages.
Salvia divinorum . In: Entheogene Blätter , Issue # 16, 09/2003, ISSN 1610-0107 .
Thomas E. Prisinzano, Richard B. Rothman: Salvinorin A Analogs as Probes in Opioid Pharmacology . In: Chemical Reviews , 2008, 108, pp. 1732-1743. doi: 10.1021 / cr0782269

Web links

Commons : Salvinorine - collection of images, videos and audio files

Daniel Siebert: Salvinorin (English)

Individual evidence

^ A Ortega, JF Blount, PS Manchand: Salvinorin, a new trans-neoclerodane diterpene from Salvia divinorum (Labiatae) . In: J. Chem. Soc., Perkin Trans. 1 . 1982, pp. 2505-2508. doi : 10.1039 / P19820002505 .
↑ KA MacLean, MW Johnson, CJ Reissig, TE Prisinzano, RR Griffiths: Dose-related effects of salvinorin A in humans: dissociative, hallucinogenic, and memory effects. In: Psychopharmacology. Volume 226, number 2, March 2013, pp. 381-392, doi : 10.1007 / s00213-012-2912-9 , PMID 23135605 , PMC 3581702 (free full text).
↑ BL Roth et al .: Salvinorin A: A potent naturally occurring nonnitrogenous opioid selective agonist . In: PNAS . Volume 99, 2002, pp. 11934-11939. PMID 12192085 doi: 10.1073 / pnas.182234399 .
↑ Timothy A. Vortherms, Bryan L. Roth: Salvinorin A - From Natural Product to Human Therapeutics. In: Molecular Interventions , 2006, Vol. 6, No. 5, pp. 257-265. doi: 10.1124 / mi.6.5.7 .
^ DJ Siebert: Salvia divinorum and salvinorin A: new pharmacologic findings. (PDF; 284 kB) In: J. Ethnopharmacol , Volume 43, 1994, pp. 53-56. PMID 16426651 .
↑ R. Marushia: Salvia divinorum: The Botany, Ethnobotany, Biochemistry and Future of a Mexican Mint. ( Memento of the original from October 7, 2007 in the Internet Archive ) Info: The archive link was inserted automatically and has not yet been checked. Please check the original and archive link according to the instructions and then remove this notice. (PDF; 54 kB) In: Ethnobotany , 2002 @1@ 2

↑ Lukasz Kutrzeba, Ferreira, Zjawiony: Salvinorins J from Salvia divinorum: Mutarotation in the Neoclerodane System . In: J. Nat. Prod . 72, No. 7, 2009, pp. 1361-1363. doi : 10.1021 / np900181q .

↑ TA Munro, KK Duncan, W Xu, Y Wang, LY Liu-Chen, WA Carlezon, BM Cohen, C Béguin: Standard protecting groups create potent and selective kappa opioids: salvinorin B alkoxymethyl ethers . In: Bioorganic & Medicinal Chemistry . 16, No. 3, February 2008, pp. 1279-86. doi : 10.1016 / j.bmc.2007.10.067 . PMID 17981041 . PMC 2568987 (free full text).

[Ortega-1] A Ortega, JF Blount, PS Manchand: Salvinorin, a new trans-neoclerodane diterpene from Salvia divinorum (Labiatae) . In: J. Chem. Soc., Perkin Trans. 1 . 1982, pp. 2505-2508. doi : 10.1039 / P19820002505 .

[PMID23135605-2] KA MacLean, MW Johnson, CJ Reissig, TE Prisinzano, RR Griffiths: Dose-related effects of salvinorin A in humans: dissociative, hallucinogenic, and memory effects. In: Psychopharmacology. Volume 226, number 2, March 2013, pp. 381-392, doi : 10.1007 / s00213-012-2912-9 , PMID 23135605 , PMC 3581702 (free full text).

[3] BL Roth et al .: Salvinorin A: A potent naturally occurring nonnitrogenous opioid selective agonist . In: PNAS . Volume 99, 2002, pp. 11934-11939. PMID 12192085 doi: 10.1073 / pnas.182234399 .

[Vortherms-4] Timothy A. Vortherms, Bryan L. Roth: Salvinorin A - From Natural Product to Human Therapeutics. In: Molecular Interventions , 2006, Vol. 6, No. 5, pp. 257-265. doi: 10.1124 / mi.6.5.7 .

[5] DJ Siebert: Salvia divinorum and salvinorin A: new pharmacologic findings. (PDF; 284 kB) In: J. Ethnopharmacol , Volume 43, 1994, pp. 53-56. PMID 16426651 .

[6] R. Marushia: Salvia divinorum: The Botany, Ethnobotany, Biochemistry and Future of a Mexican Mint. ( Memento of the original from October 7, 2007 in the Internet Archive ) Info: The archive link was inserted automatically and has not yet been checked. Please check the original and archive link according to the instructions and then remove this notice. (PDF; 54 kB) In: Ethnobotany , 2002 @1@ 2

[Kutrzeba-7] Lukasz Kutrzeba, Ferreira, Zjawiony: Salvinorins J from Salvia divinorum: Mutarotation in the Neoclerodane System . In: J. Nat. Prod . 72, No. 7, 2009, pp. 1361-1363. doi : 10.1021 / np900181q .

[MunroDuncan-8] TA Munro, KK Duncan, W Xu, Y Wang, LY Liu-Chen, WA Carlezon, BM Cohen, C Béguin: Standard protecting groups create potent and selective kappa opioids: salvinorin B alkoxymethyl ethers . In: Bioorganic & Medicinal Chemistry . 16, No. 3, February 2008, pp. 1279-86. doi : 10.1016 / j.bmc.2007.10.067 . PMID 17981041 . PMC 2568987 (free full text).