Lysergic acid pyrrolidate

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MedKoo CAT#: 599266

CAS#: 2385-87-7

Description: Lysergic acid pyrrolidate is discontinued (DEA controlled substance). Lysergic acid pyrrolidate is an alkaloid.


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

Lysergic acid pyrrolidate is discontinued (DEA controlled substance).


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 599266
Name: Lysergic acid pyrrolidate
CAS#: 2385-87-7
Chemical Formula: C21H25N3O4
Exact Mass:
Molecular Weight: 383.44
Elemental Analysis: C, 65.78; H, 6.57; N, 10.96; O, 16.69


Synonym: Lysergic acid pyrrolidate; LPD-824; LPD 824; LPD824; LSD-25-pyrrolidate;

IUPAC/Chemical Name: (6aR,9R)-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxylic acid compound with pyrrolidine-1-carboxylic acid (1:1)

InChi Key: NIBGLCAHEXNKMV-BWTUWSSMSA-N

InChi Code: InChI=1S/C16H16N2O2.C5H9NO2/c1-18-8-10(16(19)20)5-12-11-3-2-4-13-15(11)9(7-17-13)6-14(12)18;7-5(8)6-3-1-2-4-6/h2-5,7,10,14,17H,6,8H2,1H3,(H,19,20);1-4H2,(H,7,8)/t10-,14-;/m1./s1

SMILES Code: [H][C@@]1(N(C)C[C@H](C(O)=O)C=C12)CC3=CNC4=C3C2=CC=C4.O=C(O)N5CCCC5


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: Liester MB. A review of lysergic acid diethylamide (LSD) in the treatment of addictions: historical perspectives and future prospects. Curr Drug Abuse Rev. 2014;7(3):146-56. Review. PubMed PMID: 25563445.

2: Gasser P, Holstein D, Michel Y, Doblin R, Yazar-Klosinski B, Passie T, Brenneisen R. Safety and efficacy of lysergic acid diethylamide-assisted psychotherapy for anxiety associated with life-threatening diseases. J Nerv Ment Dis. 2014 Jul;202(7):513-20. doi: 10.1097/NMD.0000000000000113. PubMed PMID: 24594678; PubMed Central PMCID: PMC4086777.

3: Himmelsbach M, Ferdig M, Rohrer T. Analysis of paspalic acid, lysergic acid, and iso-lysergic acid by capillary zone electrophoresis with UV- and quadrupole time-of-flight mass spectrometric detection. Electrophoresis. 2014 May;35(9):1329-33. doi: 10.1002/elps.201300224. Epub 2013 Oct 18. PubMed PMID: 24115177.

4: Dolder PC, Schmid Y, Haschke M, Rentsch KM, Liechti ME. Pharmacokinetics and Concentration-Effect Relationship of Oral LSD in Humans. Int J Neuropsychopharmacol. 2015 Jun 24;19(1). pii: pyv072. doi: 10.1093/ijnp/pyv072. PubMed PMID: 26108222; PubMed Central PMCID: PMC4772267.

5: Smith DE, Raswyck GE, Davidson LD. From Hofmann to the Haight Ashbury, and into the future: the past and potential of lysergic acid diethlyamide. J Psychoactive Drugs. 2014 Jan-Mar;46(1):3-10. Review. PubMed PMID: 24830180.

6: Havemann J, Vogel D, Loll B, Keller U. Cyclolization of D-lysergic acid alkaloid peptides. Chem Biol. 2014 Jan 16;21(1):146-55. doi: 10.1016/j.chembiol.2013.11.008. Epub 2013 Dec 19. PubMed PMID: 24361048.

7: Krebs TS, Johansen PØ. Lysergic acid diethylamide (LSD) for alcoholism: meta-analysis of randomized controlled trials. J Psychopharmacol. 2012 Jul;26(7):994-1002. doi: 10.1177/0269881112439253. Epub 2012 Mar 8. PubMed PMID: 22406913.

8: Merli D, Zamboni D, Protti S, Pesavento M, Profumo A. Electrochemistry and analytical determination of lysergic acid diethylamide (LSD) via adsorptive stripping voltammetry. Talanta. 2014 Dec;130:456-61. doi: 10.1016/j.talanta.2014.07.037. Epub 2014 Jul 22. PubMed PMID: 25159435.

9: Umezaki S, Yokoshima S, Fukuyama T. Total synthesis of lysergic acid. Org Lett. 2013 Aug 16;15(16):4230-3. doi: 10.1021/ol4019562. Epub 2013 Aug 6. Erratum in: Org Lett. 2014 Feb 21;16(4):1269. PubMed PMID: 23919892.

10: Liu Q, Zhang YA, Xu P, Jia Y. Total synthesis of (+)-lysergic acid. J Org Chem. 2013 Nov 1;78(21):10885-93. doi: 10.1021/jo4018777. Epub 2013 Oct 23. PubMed PMID: 24111583.

11: Paulke A, Kremer C, Wunder C, Toennes SW. Analysis of lysergic acid amide in human serum and urine after ingestion of Argyreia nervosa seeds. Anal Bioanal Chem. 2012 Aug;404(2):531-8. doi: 10.1007/s00216-012-6121-5. Epub 2012 Jun 14. PubMed PMID: 22695498.

12: Airado-Rodríguez D, Cruces-Blanco C, García-Campaña AM. Ultrasensitive analysis of lysergic acid diethylamide and its C-8 isomer in hair by capillary zone electrophoresis in combination with a stacking technique and laser induced fluorescence detection. Anal Chim Acta. 2015 Mar 25;866:90-8. doi: 10.1016/j.aca.2015.01.033. Epub 2015 Jan 23. PubMed PMID: 25732697.

13: Iwata A, Inuki S, Oishi S, Fujii N, Ohno H. Formal total synthesis of (+)-lysergic acid via zinc(II)-mediated regioselective ring-opening reduction of 2-alkynyl-3-indolyloxirane. J Org Chem. 2011 Jul 1;76(13):5506-12. doi: 10.1021/jo2008324. Epub 2011 Jun 8. PubMed PMID: 21598967.

14: Liu Q, Jia Y. Total synthesis of (+)-lysergic acid. Org Lett. 2011 Sep 16;13(18):4810-3. doi: 10.1021/ol2018467. Epub 2011 Aug 25. PubMed PMID: 21866948.

15: Passie T, Halpern JH, Stichtenoth DO, Emrich HM, Hintzen A. The pharmacology of lysergic acid diethylamide: a review. CNS Neurosci Ther. 2008 Winter;14(4):295-314. doi: 10.1111/j.1755-5949.2008.00059.x. Review. PubMed PMID: 19040555.

16: Blacha C, Schmid MM, Gahr M, Freudenmann RW, Plener PL, Finter F, Connemann BJ, Schönfeldt-Lecuona C. Self-inflicted testicular amputation in first lysergic acid diethylamide use. J Addict Med. 2013 Jan-Feb;7(1):83-4. doi: 10.1097/ADM.0b013e318279737b. PubMed PMID: 23222128.

17: Klotz JL, Bush LP, Smith DL, Shafer WD, Smith LL, Vevoda AC, Craig AM, Arrington BC, Strickland JR. Assessment of vasoconstrictive potential of D-lysergic acid using an isolated bovine lateral saphenous vein bioassay. J Anim Sci. 2006 Nov;84(11):3167-75. PubMed PMID: 17032812.

18: WRIGHT AM, MOCRHEAD M, WELSH JH. Actions of derivatives of lysergic acid on the heart of Venus mercenaria. Br J Pharmacol Chemother. 1962 Apr;18:440-50. PubMed PMID: 14008412; PubMed Central PMCID: PMC1482118.

19: NEUHOLD K, TAESCHLER M, CERLETTI A. [Central effects of lysergic acid diethylamide; studies on the localization of lysergic acid diethylamide effects]. Helv Physiol Pharmacol Acta. 1957;15(1):1-7. German. PubMed PMID: 13428196.

20: ISBELL H, MINER EJ, LOGAN CR. Cross tolerance between D-2-brom-lysergic acid diethylamide (BOL-148) and the D-diethylamide of lysergic acid (LSD-25). Psychopharmacologia. 1959 Nov 3;1:109-16. PubMed PMID: 14405871.