2-Oxo-3-hydroxy-lysergide

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 530744

CAS#: 111295-09-1

Description: 2-Oxo-3-hydroxy-lysergide is discontinued (DEA controlled substance).


Chemical Structure

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2-Oxo-3-hydroxy-lysergide
CAS# 111295-09-1

Theoretical Analysis

MedKoo Cat#: 530744
Name: 2-Oxo-3-hydroxy-lysergide
CAS#: 111295-09-1
Chemical Formula: C20H25N3O3
Exact Mass: 355.1896
Molecular Weight: 355.438
Elemental Analysis: C, 67.58; H, 7.09; N, 11.82; O, 13.50

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: 2-Oxo-3-hydroxy-lysergide

IUPAC/Chemical Name: 2-Oxo-3-hydroxy lysergic acid diethylamide

InChi Key: YSZSHHCNLVHCNV-VRORWYBRSA-N

InChi Code: InChI=1S/C20H25N3O3/c1-4-23(5-2)18(24)12-9-14-13-7-6-8-15-17(13)20(26,19(25)21-15)10-16(14)22(3)11-12/h6-9,12,16,26H,4-5,10-11H2,1-3H3,(H,21,25)/t12-,16-,20?/m1/s1

SMILES Code: [H][C@@]1(N(C[C@@H](C=C12)C(N(CC)CC)=O)C)CC3(O)C(NC4=C3C2=CC=C4)=O

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

Preparing Stock Solutions

The following data is based on the product molecular weight 355.438 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Mardal M, Johansen SS, Thomsen R, Linnet K. Advantages of analyzing postmortem brain samples in routine forensic drug screening-Case series of three non-natural deaths tested positive for lysergic acid diethylamide (LSD). Forensic Sci Int. 2017 Sep;278:e14-e18. doi: 10.1016/j.forsciint.2017.07.025. Epub 2017 Jul 30. PubMed PMID: 28803722.

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5: Dolder PC, Liechti ME, Rentsch KM. Development and validation of a rapid turboflow LC-MS/MS method for the quantification of LSD and 2-oxo-3-hydroxy LSD in serum and urine samples of emergency toxicological cases. Anal Bioanal Chem. 2015 Feb;407(6):1577-84. doi: 10.1007/s00216-014-8388-1. Epub 2014 Dec 27. PubMed PMID: 25542574.

6: Mendoza A, Rodríguez-Gil JL, González-Alonso S, Mastroianni N, López de Alda M, Barceló D, Valcárcel Y. Drugs of abuse and benzodiazepines in the Madrid Region (Central Spain): seasonal variation in river waters, occurrence in tap water and potential environmental and human risk. Environ Int. 2014 Sep;70:76-87. doi: 10.1016/j.envint.2014.05.009. Epub 2014 Jun 6. PubMed PMID: 24908641.

7: Mendoza A, López de Alda M, González-Alonso S, Mastroianni N, Barceló D, Valcárcel Y. Occurrence of drugs of abuse and benzodiazepines in river waters from the Madrid Region (Central Spain). Chemosphere. 2014 Jan;95:247-55. doi: 10.1016/j.chemosphere.2013.08.085. Epub 2013 Sep 29. PubMed PMID: 24083902.

8: Favretto D, Frison G, Maietti S, Ferrara SD. LC-ESI-MS/MS on an ion trap for the determination of LSD, iso-LSD, nor-LSD and 2-oxo-3-hydroxy-LSD in blood, urine and vitreous humor. Int J Legal Med. 2007 Jul;121(4):259-65. Epub 2006 Feb 23. PubMed PMID: 16496170.

9: Johansen SS, Jensen JL. Liquid chromatography-tandem mass spectrometry determination of LSD, ISO-LSD, and the main metabolite 2-oxo-3-hydroxy-LSD in forensic samples and application in a forensic case. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Oct 15;825(1):21-8. Epub 2005 Jan 26. PubMed PMID: 16154519.

10: Horn CK, Klette KL, Stout PR. LC-MS analysis of 2-oxo-3-hydroxy LSD from urine using a Speedisk positive-pressure processor with Cerex PolyChrom CLIN II columns. J Anal Toxicol. 2003 Oct;27(7):459-63. PubMed PMID: 14607000.

11: Burnley BT, George S. The development and application of a gas chromatography-mass spectrometric (GC-MS) assay to determine the presence of 2-oxo-3-hydroxy-LSD in urine. J Anal Toxicol. 2003 May-Jun;27(4):249-52. PubMed PMID: 12820748.

12: Skopp G, Pötsch L, Mattern R, Aderjan R. Short-term stability of lysergic acid diethylamide (LSD), N-desmethyl-LSD, and 2-oxo-3-hydroxy-LSD in urine, assessed by liquid chromatography-tandem mass spectrometry. Clin Chem. 2002 Sep;48(9):1615-8. PubMed PMID: 12194952.

13: Klette KL, Horn CK, Stout PR, Anderson CJ. LC-mS analysis of human urine specimens for 2-oxo-3-hydroxy LSD: method validation for potential interferants and stability study of 2-oxo-3-hydroxy LSD under various storage conditions. J Anal Toxicol. 2002 May-Jun;26(4):193-200. PubMed PMID: 12054358.

14: Klette KL, Anderson CJ, Poch GK, Nimrod AC, ElSohly MA. Metabolism of lysergic acid diethylamide (LSD) to 2-oxo-3-hydroxy LSD (O-H-LSD) in human liver microsomes and cryopreserved human hepatocytes. J Anal Toxicol. 2000 Oct;24(7):550-6. PubMed PMID: 11043658.

15: Sklerov JH, Magluilo J Jr, Shannon KK, Smith ML. Liquid chromatography-electrospray ionization mass spectrometry for the detection of lysergide and a major metabolite, 2-oxo-3-hydroxy-LSD, in urine and blood. J Anal Toxicol. 2000 Oct;24(7):543-9. PubMed PMID: 11043657.

16: Poch GK, Klette KL, Anderson C. The quantitation of 2-oxo-3-hydroxy lysergic acid diethylamide (O-H-LSD) in human urine specimens, a metabolite of LSD: comparative analysis using liquid chromatography-selected ion monitoring mass spectrometry and liquid chromatography-ion trap mass spectrometry. J Anal Toxicol. 2000 Apr;24(3):170-9. PubMed PMID: 10774536.

17: Reuschel SA, Percey SE, Liu S, Eades DM, Foltz RL. Quantitative determination of LSD and a major metabolite, 2-oxo-3-hydroxy-LSD, in human urine by solid-phase extraction and gas chromatography-tandem mass spectrometry. J Anal Toxicol. 1999 Sep;23(5):306-12. PubMed PMID: 10488916.

18: Verstraete AG, Van de Velde EJ. 2-oxo-3-hydroxy-LSD: an important LSD metabolite? Acta Clin Belg. 1999;53 Suppl 1:94-6. PubMed PMID: 10216992.

19: Poch GK, Klette KL, Hallare DA, Manglicmot MG, Czarny RJ, McWhorter LK, Anderson CJ. Detection of metabolites of lysergic acid diethylamide (LSD) in human urine specimens: 2-oxo-3-hydroxy-LSD, a prevalent metabolite of LSD. J Chromatogr B Biomed Sci Appl. 1999 Mar 5;724(1):23-33. PubMed PMID: 10202954.