Lysergic acid hydroxyethylamide

Structural formula
General
Surname	D -lysergic acid hydroxyethylamide
other names	9,10-didehydro- N - (1-hydroxyethyl) -6-methylergoline-8-carboxamide; Lysergic acid methyl carbinolamide; Organic LSD;
Molecular formula	C 18 H 21 N 3 O 2
External identifiers / databases
EC number	222-086-0
ECHA InfoCard	100.020.079
PubChem	134553
ChemSpider	27470958
Wikidata	Q1501665
properties
Molar mass	311.38 g mol −1
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Lysergic acid hydroxyethylamide , LSH for short , is an ergot alkaloid , the chemical structure of which is similar to that of LSD and especially that of lysergic acid ethylamide.

Occurrence and history

The D -lysergic acid derivative LSH occurs in various mushrooms and bindweed plants. It was first discovered in 1960 in the fungus Claviceps paspali . In 1963 it was found that this also occurs in well-known psychoactive bindweed plants (in the seeds, as well as partly in the plant itself).

According to Albert Hofmann, it is one of the main active ingredients in these psychoactive bindweed plants. It is synthesized by symbiotic fungi on the plants (with ergometrine as a precursor / intermediate stage). In aqueous and, above all, alkaline ambient conditions, it breaks down into ergine (LSA) and acetaldehyde , which is why, according to Hofmann, it is easily decomposed into LSA in the course of an extraction process, and which is probably one of the reasons why Hofmann did not originally discover it.

Fresh seeds of the bindweed (as well as partly the plant itself) have a large proportion of LSH, which breaks down into LSA over time until only LSA is present in older seeds. Some analysis methods (e.g. mass spectrometers ) also partially decompose it.

effect

There are no known attempts on humans. Tests on animals showed that LSH could have effects similar to LSD.

literature

Albert Hofmann : LSD - my problem child. The discovery of a “miracle drug” . Klett-Cotta, Stuttgart 1979; 2nd edition Stuttgart 2001, ISBN 3-608-94300-5 .
Richard E. Schultes , Albert Hofmann: plants of the gods . AT Verlag, 1998, ISBN 3-85502-645-9 .

Individual evidence

↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ Gerhard G. Habermehl, Peter E. Hammann, Hans C. Krebs and W. Ternes: Naturstoffchemie - An Introduction , p. 203, Springer, 2008, ISBN 3-540-73732-4 .
↑ Arcamone et al .: Production of lysergic acid derivatives by a strain of Claviceps paspali Stevens and Hall in submerged culture. In: Nature . Volume 187, July 1960, pp. 238-239, PMID 13794048 .
↑ Gröger D .: About the occurrence of ergoline derivatives in Ipomoea species . In: Flora . Volume 153, 1963, pp. 373-382.
↑ Albert Hofmann: LSD - my problem child. The discovery of a “miracle drug” , p. 130, Deutscher Taschenbuch Verlag GmbH & Co. KG, 9th edition, 2001.
↑ Schardl et al .: Plant-symbiotic fungi as chemical engineers: multi-genome analysis of the clavicipitaceae reveals dynamics of alkaloid loci. In: PLoS genetics. Volume 9, number 2, 2013, p. E1003323, doi : 10.1371 / journal.pgen.1003323 , PMID 23468653 , PMC 3585121 (free full text).
^ Albert Hofmann: Die Mutterkornalkaloide , p. 34, 1964.
↑ Heim et al .: The psychological effects of the Mexican drug "Ololiuqui" on humans , p. 47, Psychopharmacologia (Berl.) 13, 1968.
↑ Albert Hofmann: Teonanacatl and Ololiuqui, two ancient magic drugs of Mexico , Bulletin on Narcotics, 23, 1971, p 3-14.
↑ Albert Hofmann et al .: The active ingredients of the third Aztec magic drug or The solution to the 'Ololiuqui' riddle , German Medical Weekly, Number 18, 1961, pp. 885-888.
↑ Sabine Hellwig: Ergoline alkaloid occurrences in Convolvulaceae: Biochemical and ecological interaction of a plant-fungus symbiosis , dissertation, Bonn, 2007.
↑ J. Nowak, M. Woźniakiewicz, P. Klepacki, A. Sowa, P. Kościelniak: Identification and determination of ergot alkaloids in Morning Glory cultivars. In: Analytical and bioanalytical chemistry. Volume 408, number 12, May 2016, pp. 3093-3102, doi : 10.1007 / s00216-016-9322-5 , PMID 26873205 , PMC 4830885 (free full text).
^ A. Glasser: Some pharmacological actions of D-lysergic acid methyl carbinolamide. In: Nature . Volume 189, January 1961, pp. 313-314, PMID 13705953 .

[NV-1] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[2] Gerhard G. Habermehl, Peter E. Hammann, Hans C. Krebs and W. Ternes: Naturstoffchemie - An Introduction , p. 203, Springer, 2008, ISBN 3-540-73732-4 .

[3] Arcamone et al .: Production of lysergic acid derivatives by a strain of Claviceps paspali Stevens and Hall in submerged culture. In: Nature . Volume 187, July 1960, pp. 238-239, PMID 13794048 .

[4] Gröger D .: About the occurrence of ergoline derivatives in Ipomoea species . In: Flora . Volume 153, 1963, pp. 373-382.

[5] Albert Hofmann: LSD - my problem child. The discovery of a “miracle drug” , p. 130, Deutscher Taschenbuch Verlag GmbH & Co. KG, 9th edition, 2001.

[6] Schardl et al .: Plant-symbiotic fungi as chemical engineers: multi-genome analysis of the clavicipitaceae reveals dynamics of alkaloid loci. In: PLoS genetics. Volume 9, number 2, 2013, p. E1003323, doi : 10.1371 / journal.pgen.1003323 , PMID 23468653 , PMC 3585121 (free full text).

[7] Albert Hofmann: Die Mutterkornalkaloide , p. 34, 1964.

[8] Heim et al .: The psychological effects of the Mexican drug "Ololiuqui" on humans , p. 47, Psychopharmacologia (Berl.) 13, 1968.

[9] Albert Hofmann: Teonanacatl and Ololiuqui, two ancient magic drugs of Mexico , Bulletin on Narcotics, 23, 1971, p 3-14.

[10] Albert Hofmann et al .: The active ingredients of the third Aztec magic drug or The solution to the 'Ololiuqui' riddle , German Medical Weekly, Number 18, 1961, pp. 885-888.

[11] Sabine Hellwig: Ergoline alkaloid occurrences in Convolvulaceae: Biochemical and ecological interaction of a plant-fungus symbiosis , dissertation, Bonn, 2007.

[12] J. Nowak, M. Woźniakiewicz, P. Klepacki, A. Sowa, P. Kościelniak: Identification and determination of ergot alkaloids in Morning Glory cultivars. In: Analytical and bioanalytical chemistry. Volume 408, number 12, May 2016, pp. 3093-3102, doi : 10.1007 / s00216-016-9322-5 , PMID 26873205 , PMC 4830885 (free full text).

[13] A. Glasser: Some pharmacological actions of D-lysergic acid methyl carbinolamide. In: Nature . Volume 189, January 1961, pp. 313-314, PMID 13705953 .