Lysergol

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

MedKoo CAT#: 530230

CAS#: 602-85-7

Description: Lysergol is discontinued (DEA controlled substance).


Price and Availability

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Pricing updated 2020-12-05. Prices are subject to change without notice.

Lysergol is discontinued (DEA controlled substance).


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 530230
Name: Lysergol
CAS#: 602-85-7
Chemical Formula: C16H18N2O
Exact Mass: 254.1419
Molecular Weight: 254.333
Elemental Analysis: C, 75.56; H, 7.13; N, 11.01; O, 6.29


Synonym: Lysergol

IUPAC/Chemical Name: Ergoline, 9,10-didehydro-8-hydroxymethyl-6-methyl-

InChi Key: BIXJFIJYBLJTMK-GENIYJEYSA-N

InChi Code: InChI=1S/C16H18N2O/c1-18-8-10(9-19)5-13-12-3-2-4-14-16(12)11(7-17-14)6-15(13)18/h2-5,7,10,15,17,19H,6,8-9H2,1H3/t10?,15-/m1/s1

SMILES Code: [H][C@@]1(N(C)CC(CO)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: Bhunia S, Chaudhuri S, Bisai A. Total Syntheses of Pyroclavine, Festuclavine, Lysergol, and Isolysergol via a Catalytic Asymmetric Nitro-Michael Reaction. Chemistry. 2017 Aug 22;23(47):11234-11238. doi: 10.1002/chem.201702459. Epub 2017 Aug 2. PubMed PMID: 28686308.

2: Milde B, Pawliczek M, Jones PG, Werz DB. Enantioselective Total Synthesis of (+)-Lysergol: A Formal anti-Carbopalladation/Heck Cascade as the Key Step. Org Lett. 2017 Apr 7;19(7):1914-1917. doi: 10.1021/acs.orglett.7b00675. Epub 2017 Mar 30. PubMed PMID: 28357872.

3: Yuan H, Guo Z, Luo T. Synthesis of (+)-Lysergol and Its Analogues To Assess Serotonin Receptor Activity. Org Lett. 2017 Feb 3;19(3):624-627. doi: 10.1021/acs.orglett.6b03779. Epub 2017 Jan 20. PubMed PMID: 28106398.

4: 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.

5: Smirnov VM, Sveshnikov DS, Myasnikov IL, Kuznetsova TE, Samko YN. [Evidences of Existence of Serotoninergic Nerves, Enhancing Duodenal Motility]. Vestn Ross Akad Med Nauk. 2015;(6):718-26. Review. Russian. PubMed PMID: 27093800.

6: Mace WJ, Lunn KL, Kaur N, Lloyd-West CM. Variation in the expression of ergot alkaloids between individual tillers of perennial ryegrass. Front Chem. 2014 Nov 24;2:107. doi: 10.3389/fchem.2014.00107. eCollection 2014. PubMed PMID: 25505785; PubMed Central PMCID: PMC4241844.

7: Paulke A, Kremer C, Wunder C, Wurglics M, Schubert-Zsilavecz M, Toennes SW. Identification of legal highs--ergot alkaloid patterns in two Argyreia nervosa products. Forensic Sci Int. 2014 Sep;242:62-71. doi: 10.1016/j.forsciint.2014.06.025. Epub 2014 Jun 30. PubMed PMID: 25036782.

8: Ajazuddin, Alexander A, Qureshi A, Kumari L, Vaishnav P, Sharma M, Saraf S, Saraf S. Role of herbal bioactives as a potential bioavailability enhancer for Active Pharmaceutical Ingredients. Fitoterapia. 2014 Sep;97:1-14. doi: 10.1016/j.fitote.2014.05.005. Epub 2014 May 23. Review. PubMed PMID: 24862064.

9: Pesqueira A, Harmon DL, Branco AF, Klotz JL. Bovine lateral saphenous veins exposed to ergopeptine alkaloids do not relax. J Anim Sci. 2014 Mar;92(3):1213-8. doi: 10.2527/jas.2013-7142. Epub 2014 Feb 3. PubMed PMID: 24492541.

10: Luo M, Wang XS, Roth BL, Golbraikh A, Tropsha A. Application of quantitative structure-activity relationship models of 5-HT1A receptor binding to virtual screening identifies novel and potent 5-HT1A ligands. J Chem Inf Model. 2014 Feb 24;54(2):634-47. doi: 10.1021/ci400460q. Epub 2014 Feb 12. PubMed PMID: 24410373; PubMed Central PMCID: PMC3985444.

11: Maurya A, Dwivedi GR, Darokar MP, Srivastava SK. Antibacterial and synergy of clavine alkaloid lysergol and its derivatives against nalidixic acid-resistant Escherichia coli. Chem Biol Drug Des. 2013 Apr;81(4):484-90. doi: 10.1111/cbdd.12103. Epub 2013 Mar 21. PubMed PMID: 23290001.

12: Fallarero A, Pohjanoksa K, Wissel G, Parkkisenniemi-Kinnunen UM, Xhaard H, Scheinin M, Vuorela P. High-throughput screening with a miniaturized radioligand competition assay identifies new modulators of human α2-adrenoceptors. Eur J Pharm Sci. 2012 Dec 18;47(5):941-51. doi: 10.1016/j.ejps.2012.08.021. Epub 2012 Sep 12. PubMed PMID: 22982401.

13: Sveshnikov DS, Smirnov VM, Myasnikov IL, Kuchuk AV. Study of the nature of sympathetic trunk nerve fibers enhancing gastric motility. Bull Exp Biol Med. 2012 Jan;152(3):283-5. PubMed PMID: 22803066.

14: Merkel S, Köppen R, Koch M, Emmerling F, Nehls I. Lysergol monohydrate. Acta Crystallogr Sect E Struct Rep Online. 2012 Feb 1;68(Pt 2):o523. doi: 10.1107/S1600536812002632. Epub 2012 Jan 25. PubMed PMID: 22347120; PubMed Central PMCID: PMC3275264.

15: Patil S, Dash RP, Anandjiwala S, Nivsarkar M. Simultaneous quantification of berberine and lysergol by HPLC-UV: evidence that lysergol enhances the oral bioavailability of berberine in rats. Biomed Chromatogr. 2012 Oct;26(10):1170-5. doi: 10.1002/bmc.2674. Epub 2011 Dec 30. PubMed PMID: 22213237.

16: Maurya A, Verma RK, Srivastava SK. Quantitative determination of bioactive alkaloids lysergol and chanoclavine in Ipomoea muricata by reversed-phase high-performance liquid chromatography. Biomed Chromatogr. 2012 Sep;26(9):1096-100. doi: 10.1002/bmc.1753. Epub 2011 Nov 25. PubMed PMID: 22120837.

17: Gooneratne SR, Scannell M, Wellby M, Fletcher L. Changes in concentrations of lysergol in urine and prolactin in plasma, rectal temperature and respiration rate in sheep selected for resistance or susceptibility to ryegrass staggers and fed ergovaline. N Z Vet J. 2011 Sep;59(5):233-8. doi: 10.1080/00480169.2011.601538. PubMed PMID: 21851300.

18: Inuki S, Iwata A, Oishi S, Fujii N, Ohno H. Enantioselective total synthesis of (+)-lysergic acid, (+)-lysergol, and (+)-isolysergol by palladium-catalyzed domino cyclization of allenes bearing amino and bromoindolyl groups. J Org Chem. 2011 Apr 1;76(7):2072-83. doi: 10.1021/jo102388e. Epub 2011 Mar 1. PubMed PMID: 21361331.

19: Deck JA, Martin SF. Enantioselective synthesis of (+)-isolysergol via ring-closing metathesis. Org Lett. 2010 Jun 4;12(11):2610-3. doi: 10.1021/ol100819f. PubMed PMID: 20462232; PubMed Central PMCID: PMC2879020.

20: Maurya A, Srivastava SK. Large-scale separation of clavine alkaloids from Ipomoea muricata by pH-zone-refining centrifugal partition chromatography. J Chromatogr B Analyt Technol Biomed Life Sci. 2009 Jun 15;877(18-19):1732-6. doi: 10.1016/j.jchromb.2009.04.036. Epub 2009 May 3. PubMed PMID: 19467935.