Lysergamide

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MedKoo CAT#: 599276

CAS#: 478-94-4

Description: Lysergamide is discontinued (DEA controlled substance). Lysergamide is an alkaloid in abundance in tall fescue, resulted in vasoconstriction similar to that previously shown for the ergot alkaloids ergonovine and ergotamine.


Price and Availability

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Pricing updated 2020-10-28. Prices are subject to change without notice.

Lysergamide is discontinued (DEA controlled substance).


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 599276
Name: Lysergamide
CAS#: 478-94-4
Chemical Formula: C16H17N3O
Exact Mass: 267.1372
Molecular Weight: 267.33
Elemental Analysis: C, 71.89; H, 6.41; N, 15.72; O, 5.98


Synonym: Lysergamide; LSA; Ergine;

IUPAC/Chemical Name: (6aR,9R)-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide

InChi Key: GENAHGKEFJLNJB-QMTHXVAHSA-N

InChi Code: InChI=1S/C16H17N3O/c1-19-8-10(16(17)20)5-12-11-3-2-4-13-15(11)9(7-18-13)6-14(12)19/h2-5,7,10,14,18H,6,8H2,1H3,(H2,17,20)/t10-,14-/m1/s1

SMILES Code: [H][C@@]1(N(C)C[C@H](C(N)=O)C=C12)CC3=CNC4=C3C2=CC=C4


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>3 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code:
2934.99.03.00


References

1: Juszczak GR, Swiergiel AH. Recreational use of D-lysergamide from the seeds of Argyreia nervosa, Ipomoea tricolor, Ipomoea violacea, and Ipomoea purpurea in Poland. J Psychoactive Drugs. 2013 Jan-Mar;45(1):79-93. PubMed PMID: 23662334.

2: Oliver JW, Abney LK, Strickland JR, Linnabary RD. Vasoconstriction in bovine vasculature induced by the tall fescue alkaloid lysergamide. J Anim Sci. 1993 Oct;71(10):2708-13. PubMed PMID: 7901191.

3: Martínková L, Kren V, Cvak L, Ovesná M, Prepechalová I. Hydrolysis of lysergamide to lysergic acid by Rhodococcus equi A4. J Biotechnol. 2001 Nov 17;84(1):63-6. PubMed PMID: 11035188.

4: Klinke HB, Müller IB, Steffenrud S, Dahl-Sørensen R. Two cases of lysergamide intoxication by ingestion of seeds from Hawaiian Baby Woodrose. Forensic Sci Int. 2010 Apr 15;197(1-3):e1-5. doi: 10.1016/j.forsciint.2009.11.017. Epub 2009 Dec 16. PubMed PMID: 20018470.

5: JACOB J, JAVOY F, LAFILLE C. [ACTION OF VARIOUS ANESTHETICS ON HYPERTHERMIA INDUCED BY LYSERGAMIDE IN THE RABBIT]. J Physiol (Paris). 1964 May-Jun;56:375-6. French. PubMed PMID: 14219801.

6: Schindler EA, Gottschalk CH, Weil MJ, Shapiro RE, Wright DA, Sewell RA. Indoleamine Hallucinogens in Cluster Headache: Results of the Clusterbusters Medication Use Survey. J Psychoactive Drugs. 2015 Nov-Dec;47(5):372-81. doi: 10.1080/02791072.2015.1107664. Epub 2015 Nov 23. PubMed PMID: 26595349.

7: Jacob JJ, Girault JM. The influence of cyproheptadine and of D-lysergamide on the rise in temperature induced by intracerebroventricular 5-hydroxytryptamine, noradrenaline and dopamine in conscious rabbits. Eur J Pharmacol. 1974 Jun;27(1):59-67. PubMed PMID: 4854891.

8: THUILLIER J, NAKAJIMA H, GRANDJEAN JL, KURIHARA M. [Potentiation by certain analogous esters of centrophenoxine of hyperthermia induced in the rabbit by lysergamide]. C R Seances Soc Biol Fil. 1961;155:2139-42. French. PubMed PMID: 13921085.

9: Shymanovich T, Saari S, Lovin ME, Jarmusch AK, Jarmusch SA, Musso AM, Charlton ND, Young CA, Cech NB, Faeth SH. Alkaloid variation among epichloid endophytes of sleepygrass (Achnatherum robustum) and consequences for resistance to insect herbivores. J Chem Ecol. 2015 Jan;41(1):93-104. doi: 10.1007/s10886-014-0534-x. Epub 2014 Dec 11. PubMed PMID: 25501262.

10: Van Vunakis H, Farrow JT, Gjika HB, Levine L. Specificity of the antibody receptor site to D-lysergamide: model of a physiological receptor for lysergic acid diethylamide. Proc Natl Acad Sci U S A. 1971 Jul;68(7):1483-7. PubMed PMID: 5283939; PubMed Central PMCID: PMC389223.

11: Taus L. [Psychotherapy of exhibitionism with lysergamide (Spofa)]. Act Nerv Super (Praha). 1967 Nov;9(4):380-1. Czech. PubMed PMID: 5612950.

12: Mellan J, Hausner M. [Effects of lysergamide Spofa on spermiogenesis]. Act Nerv Super (Praha). 1968 Oct 3;10(3):274-5. Czech. PubMed PMID: 5702522.

13: Kotel'nikova VI, Nikolov NA. [Electrical activity of the smooth muscles of the digestive tract under the influence of lysergamide]. Fiziol Zh SSSR Im I M Sechenova. 1977 Aug;63(8):1203-6. Russian. PubMed PMID: 913673.

14: Borenstein P, Champion C, Cujo P. [Electroencephalographic action of 2 desynchronizing drugs (lysergamide and diapezam) on slow rhythms of organic origin or due to psychotropic drugs]. Ann Med Psychol (Paris). 1971 Feb;1(2):228-33. French. PubMed PMID: 5577428.

15: Guiti N, Djahanguiri B, Mehdizadeh H. [Quantitative analysis of repeated electroencephalograms in the dog under the effects of diethyl lysergamide (LSD25)]. Electroencephalogr Clin Neurophysiol. 1966 Jul;21(1):80-4. French. PubMed PMID: 4165370.

16: Borenstein P, Cujo P, Champion C. [Action of lysergamide on slow rhythms of organic origin or due to psychotropics]. Rev Electroencephalogr Neurophysiol Clin. 1971 Jan-Mar;1(1):111. French. PubMed PMID: 5173690.

17: Bastecký J, Podrouzek V, Vinar O. Alosteric changes in plasma proteins in healthy volunteers after administration of lysergamide. Act Nerv Super (Praha). 1978 Feb;20(1):82. PubMed PMID: 636793.

18: Matveev VF. [Pathomorphologic changes in the brains of experimental animals with chronic lysergamide poisoning]. Zh Nevropatol Psikhiatr Im S S Korsakova. 1970;70(12):1856-62. Russian. PubMed PMID: 5511525.

19: Huang X, Marona-Lewicka D, Pfaff RC, Nichols DE. Drug discrimination and receptor binding studies of N-isopropyl lysergamide derivatives. Pharmacol Biochem Behav. 1994 Mar;47(3):667-73. PubMed PMID: 8208787.

20: Sankar DV, Kumbar M. Quantum chemical studies on drug actions. IV. Correlation of substituent structures and anti-serotonin activity in lysergamide series. Res Commun Chem Pathol Pharmacol. 1974 Feb;7(2):259-74. PubMed PMID: 4818373.