Lumi-LSD

Last updated

Lumi-LSD
Lumi-LSD structure.png
Clinical data
Other namesLumiLSD; 10-Hydroxy-9,10-dihydro-LSD; 9,10-Dihydro-10-hydroxy-LSD; 10-OH-9,10-DH-LSD; Lumilysergic acid diethylamide; N,N-Diethyl-9,10-dihydro-10-hydroxylysergamide; N,N-Diethyl-10-hydroxy-6-methylergoline-8β-carboxamide
ATC code
  • None
Identifiers
  • (6aR,9R)-N,N-Diethyl-10a-hydroxy-7-methyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide
Chemical and physical data
Formula C20H27N3O2
Molar mass 341.455 g·mol−1
3D model (JSmol)
  • CCN(C(=O)[C@H]1CN(C)[C@H]2C(C1)(O)c1cccc3c1c(C2)c[nH]3)CC
  • InChI=1S/C20H27N3O2/c1-4-23(5-2)19(24)14-10-20(25)15-7-6-8-16-18(15)13(11-21-16)9-17(20)22(3)12-14/h6-8,11,14,17,21,25H,4-5,9-10,12H2,1-3H3/t14-,17-,20?/m1/s1
  • Key:CNOVTUIIXCTFII-TUYPYBPCSA-N

Lumi-LSD, also known as 10-hydroxy-9,10-dihydro-LSD or as N,N-diethyl-9,10-dihydro-10-hydroxylysergamide, is a lysergamide and chemical degradation product of the psychedelic drug lysergic acid diethylamide (LSD). [1] [2] LSD is converted into lumi-LSD by exposure to light, specifically ultraviolet light. [1] [3] [4] [5] [2] Lumi-LSD might also be a metabolite of LSD, but this remains unconfirmed. [3]

Contents

Pharmacology

Pharmacodynamics

Lumi-LSD showed 0.01% (i.e., 10,000-fold lower) of the antiserotonergic activity of LSD in the isolated rat uterus in vitro . [6] [7] As such, lumi-LSD was regarded as essentially inactive in this assay. [6] [7] Similarly, lumi-LSD shows abolished physiological and behavioral effects in animals [8] [9] and is said to be inactive in terms of hallucinogenic effects in humans. [8] [9] [10] [4] [5] Likewise, in contrast to LSD, lumi-LSD was found to be inactive in terms of electroencephalogram (EEG) changes in rabbits. [11]

Chemistry

Unlike LSD, lumi-LSD is not fluorescent. [3] [12]

Other lumi-lysergamides are also known. [13] [14]

History

Lumi-LSD was first described in the scientific literature by at least 1955. [13] [15]

See also

References

  1. 1 2 Herian M (2022). "Pharmacological Action of LSD: LSD Effect on the Neurotransmission and Animal Behavior". Handbook of Substance Misuse and Addictions. Cham: Springer International Publishing. pp. 1–19. doi:10.1007/978-3-030-67928-6_131-2. ISBN   978-3-030-67928-6. The stability of LSD is conditioned by its storage in the form of aqueous salt solution at a low temperature, without access to oxygen and light. Too high pH value of the solution results in the transformation to an inactive form of iso-LSD, light can also convert LSD to inactive lumi-LSD. Moreover, a chlorine-free environment is needed. Thus, the storage condition must be strictly controlled (Nichols 2016).
  2. 1 2 Niwaguchi T, Inoue T (1971). "Photodecomposition of Lysergic Acid Diethylamide (LSD)". Proceedings of the Japan Academy. 47 (10): 747–750. doi: 10.2183/pjab1945.47.747 . ISSN   0021-4280 . Retrieved 30 June 2025.
  3. 1 2 3 Dolder P (2017). The Pharmacology of d-Lysergic Acid Diethylamide (LSD) (PDF) (Thesis). University of Basel. doi:10.5451/UNIBAS-006786123. Both human studies used fluorimetric assays for the measurements of their plasma samples. They made use of LSD's fluorescence and its UV-light catalyzed hydration to the non-fluorescent lumi-LSD (10-Hydroxy-9,10-dihydro-LSD) (48, 49). [...] Figure 2 shows possible and already identified metabolites of LSD. [...] 10-Hydroxy-9,10-dihydro-LSD (lumi-LSD) Proposed but unconfirmed metabolite (43) Formed under UV light (48,49)
  4. 1 2 Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN   978-0-12-433951-4.
  5. 1 2 Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN   0-9630096-9-9. OCLC   38503252. "A second and separate point of instability is the double bond that lies between this 8-position and the aromatic ring. Water or alcohol can add to this site, especially in the presence of light (sunlight with its ultraviolet energy is notoriously bad) to form a product that has been called lumi-LSD, which is totally inactive in man."
  6. 1 2 Cerletti A, Doepfner W (January 1958). "Comparative study on the serotonin antagonism of amide derivatives of lysergic acid and of ergot alkaloids". The Journal of Pharmacology and Experimental Therapeutics. 122 (1): 124–136. doi:10.1016/S0022-3565(25)11933-2. PMID   13502837.
  7. 1 2 Rothlin E (March 1957). "Lysergic acid diethylamide and related substances". Annals of the New York Academy of Sciences. 66 (3): 668–676. Bibcode:1957NYASA..66..668R. doi:10.1111/j.1749-6632.1957.tb40756.x. PMID   13425249.
  8. 1 2 Cerletti A (1959). "Comparison of Abnormal Behavioral States Induced by Psychotropic Drugs in Animals and Man". In Bradley PB, Deniker P, Radouco-Thomas C (eds.). Proceedings of the 1st International Congress of Neuro-Psychopharmacology, Rome, September 1958. Amsterdam: Elsevier. pp. 117–123. Archived from the original on 30 March 2025.
  9. 1 2 Hofmann A (1968). "Psychotomimetic Agents". In Burger A (ed.). Drugs Affecting the Nervous System. Vol. 2. New York: Marcel Dekker. pp. 169–235 (210–212). 3. CHEMICAL MODIFICATIONS OF LSD-25 In order to investigate the SAR, the molecular structure of LSD was modified in the following ways: [...] (3) saturation of the double bond in position 9, 10, [...] The double bond at the 9,10 position was saturated with hydrogen (195) or by addition of the elements of water (205). [...] 6. PHARMACOLOGICAL EFFECTS AND PSYCHIC ACTIVITY OF LSD-25 DERIVATIVES [...] A more or less comprehensive pharmacological analysis of the many derivatives mentioned in Sections and 3 was carried out (229). Some of them were also studied in human beings. In order to compare the pharmacological effects and psychic activity, Cerletti (230) selected 18 typical modifications of LSD, as depicted in Figure 5.2. [...] Fig. 5.2. Correlation between psychotropic and pharmacological activity of lysergic acid derivatives. [...] TABLE 5.3 [...] On the left-hand side the psychotomimetic activity is indicated in relative logarithmic value, LSD being taken as 100 (standard). The values are derived mainly from investigations by Isbell et al. (246), but some were also obtained from personal studies (261). The stereoisomers of LSD (see Section 5.3,D.2) and the derivatives in which the double bond in ring D has been saturated are practically devoid of psychic activity. [...] Of all the many modifications of LSD none has been found so far which exceeds LSD in psychic activity. The right-hand side of Figure 5.2 shows the pharmacological effects of these derivatives expressed in relative logarithmic values. The strong line represents the syndrome of excitation, which, as already mentioned in the case of LSD, is caused by stimulation of sympathetic centers and consists of mydriasis, piloerection, hyperthermia, etc. Thc hyperthermic effect in rabbits is a good index of the central autonomic stimulation. With some compounds, e.g.. the pyrogenic effect (P) parallels the general syndrome of excitation (E-syndrome. continuous line). In the case of compounds with substitution in position 1 the hyperthermic effect is weaker than the other symptoms of sympathetic stimulation, and therefore an average value is marked with a dotted line (total E-syndrome). The thinner line of this diagram is an expression of the antagonism of these agents to serotonin. The antagonism to serotonin is a characteristic feature of LSD, as has already been mentioned.
  10. ↑ Shulgin AT (1980). "Profiles of psychedelic drugs". Journal of Psychedelic Drugs. 12 (2): 173–174. doi:10.1080/02791072.1980.10471571. PMID   7420434.
  11. ↑ Siddik ZH, Barnes RD, Dring LG, Smith RL, Williams RT (October 1979). "The fate of lysergic acid DI[14C]ethylamide ([14C]LSD) in the rat, guinea pig and rhesus monkey and of [14C]iso-LSD in rat". Biochemical Pharmacology. 28 (20): 3093–3101. doi:10.1016/0006-2952(79)90618-x. PMID   117811. EEG studies. Synthetic and biosynthetic metabolites of LSD were injected intravenously into conscious restrained male chinchilla rabbits. With LSD itself, de-ethyl-LSD, 12-hydroxy-LSD, 12-methoxy-LSD, 13-hydroxy-LSD, 13-methoxy-LSD and 13-hydroxy-LSD glucuronide, a persistent alerting EEG trace was seen as indicated by an increase in frequency and decrease in amplitude of the waveform. No changes were observed after administration of lysergic acid, di-LSD-disulphide [10], nor-LSD, 14-hydroxy-LSD-glucuronide, 14-methoxy-LSD, lumi-LSD or the metabolic 2-oxo-LSD. [...] Preliminary studies have indicated that some of the metabolites of LSD, as well as the drug itself. produce an activation of the EEG of the conscious rabbit suggesting they may have central activity. These findings will be published elsewhere.
  12. ↑ Moffat AC (1978). "Drug metabolism and analysis. Analytical chemistry and drug metabolism" . Proceedings of the Analytical Division of the Chemical Society. 15 (8): 237. doi:10.1039/ad9781500237. ISSN   0306-1396 . Retrieved 30 June 2025.
  13. 1 2 Stoll A, Schlientz W (1955). "Über Belichtungsprodukte von Mutterkornalkaloiden. 39. Mitteilung über Mutterkornalkaloide" . Helvetica Chimica Acta. 38 (3): 585–594. doi:10.1002/hlca.19550380305. ISSN   0018-019X . Retrieved 30 June 2025.
  14. ↑ Sankar DV (1975). LSD - A Total Study (PDF). Westbury, N.Y.: PJD Publications. pp. 69, 102. ISBN   978-0-9600290-3-7. LCCN   72-95447.
  15. ↑ Cerletti A, Konzett H (1956). "Spezifische Hemmung von 5-Oxytryptamin-Effekten durch Lysergsäurediäthylamid und ähnliche Körper" . Naunyn-Schmiedebergs Archiv für Experimentelle Pathologie und Pharmakologie (in German). 228 (1–2). doi:10.1007/BF00259761. ISSN   0028-1298 . Retrieved 30 June 2025.


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