Lysergic acid alpha-hydroxyethylamide

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MedKoo CAT#: 530733

CAS#: 3343-15-5

Description: Lysergic acid alpha-hydroxyethylamide id discontinued (DEA controlled substance). Lysergic acid alpha-hydroxyethylamide has reproductive effect.


Price and Availability

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Pricing updated 2020-10-29. Prices are subject to change without notice.

Lysergic acid alpha-hydroxyethylamide id discontinued (DEA controlled substance).


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 530733
Name: Lysergic acid alpha-hydroxyethylamide
CAS#: 3343-15-5
Chemical Formula: C18H21N3O2
Exact Mass: 311.1634
Molecular Weight: 311.385
Elemental Analysis: C, 69.43; H, 6.80; N, 13.49; O, 10.28


Synonym: Lysergic acid alpha-hydroxyethylamide

IUPAC/Chemical Name: (S)-9,10-Didehydro-N-(1-hydroxyethyl)-6-methylergoline-8beta-carboxamide

InChi Key: WYTJZJPVCDWOOI-KANYHAFZSA-N

InChi Code: InChI=1S/C18H21N3O2/c1-10(22)20-18(23)12-6-14-13-4-3-5-15-17(13)11(8-19-15)7-16(14)21(2)9-12/h3-6,8,10,12,16,19,22H,7,9H2,1-2H3,(H,20,23)/t10-,12+,16+/m0/s1

SMILES Code: [H][C@@]1(N(C)C[C@H](C(N[C@@H](O)C)=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:
2934.99.9001


References

1: Paulke A, Kremer C, Wunder C, Wurglics M, Schubert-Zsilavecz M, Toennes SW. Studies on the alkaloid composition of the Hawaiian Baby Woodrose Argyreia nervosa, a common legal high. Forensic Sci Int. 2015 Apr;249:281-93. doi: 10.1016/j.forsciint.2015.02.011. Epub 2015 Feb 19. PubMed PMID: 25747328.

2: 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.

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: Yue DC, Yang YP, Huo ZM, Yang YC, He LY. [Biosynthesis of lysergic acid alpha-hydroxyethylamide. I. Natural selection of Claviceps paspali Stev and Hall]. Zhongguo Yi Xue Ke Xue Yuan Xue Bao. 1983 Aug;5(4):259-61. Chinese. PubMed PMID: 6228324.

5: Mantle PG, Mortimer PH, White EP. Mycotoxic tremorgens of Claviceps paspali and Penicillium cyclopium: a comparative study of effects on sheep and cattle in relation to natural staggers syndromes. Res Vet Sci. 1978 Jan;24(1):49-56. PubMed PMID: 625600.

6: ARCAMONE F, CHAIN EB, FERRETTI A, PENNELLA P. Formation of 2,3-dihydroxybenzoic acid in fermentation liquors during the submerged culture production of lysergic acid alpha-hydroxyethylamide by Claviceps paspali Stevens and Hall. Nature. 1961 Nov 11;192:552-3. PubMed PMID: 13862060.