Chemistry:OML-632

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OML-632, also known as 1-hydroxymethyllysergic acid diethylamide (1-hydroxymethyl-LSD), is a psychedelic drug of the lysergamide family related to lysergic acid diethylamide (LSD).[1][2][3][4][5][6][7]

Interactions

Pharmacology

Pharmacodynamics

OML-632 has about 66% of the hallucinogenic potency of LSD in humans (which is stated as active at 50–100 μg) and about 59% of the antiserotonergic activity of LSD in the isolated rat uterus in vitro.[8][9][5][6][10][11] However, OML-632 may simply act as a prodrug of LSD.[6][11] It has also been said to serve as a metabolic intermediate in the demethylation of 1-methyl-LSD (MLD-41) into LSD.[11]

History

OML-632 was first described in the scientific literature by 1957.[12][13][4][14] The compound has been mistakenly referred to as "1-methoxy-LSD" or "1-MeO-LSD" in some publications.[15][16][17]

See also

  • Substituted lysergamide
  • MLD-41 (1-methyl-LSD)
  • ALD-52 (1-acetyl-LSD)
  • 1P-LSD (1-propionyl-LSD)

References

  1. ↑ "Chemistry of Psychotomimetics". Psychotropic Agents, Part III: Alcohol and Psychotomimetics, Psychotropic Effects of Central Acting Drugs. Handbook of Experimental Pharmacology. 55 / 3. Berlin: Springer Berlin Heidelberg. 1982. pp. 3–29. doi:10.1007/978-3-642-67770-0_1. ISBN 978-3-642-67772-4. OCLC 8130916. https://bitnest.netfirms.com/external/10.1007/978-3-642-67770-0_1. 
  2. ↑ "Psychotomimetic Agents". Psychopharmacological Agents: Use, Misuse and Abuse. Medicinal Chemistry: A Series of Monographs. 4. Academic Press. 1976. pp. 59–146. doi:10.1016/b978-0-12-290559-9.50011-9. ISBN 978-0-12-290559-9. https://bitnest.netfirms.com/external/10.1016/B978-0-12-290559-9.50011-9. 
  3. ↑ "Hallucinogens". Burger's Medicinal Chemistry. 3 (4 ed.). New York: Wiley. 1980. pp. 1109–1137. ISBN 978-0-471-01572-7. OCLC 219960627. https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=6ac0c892ee380436f614d3aae0686ef617b2e0c5. 
  4. ↑ 4.0 4.1 "Lysergic Acid Diethylamide (LSD-25): XXIX. The Response Index as a Measure of Threshold Activity of Psychotropic Drugs in Man". The Journal of Psychology 48 (1): 65–78. 1959. doi:10.1080/00223980.1959.9916341. ISSN 0022-3980. 
  5. ↑ 5.0 5.1 "Some Compounds With Hallucinogenic Activity". Ergot Alkaloids and Related Compounds. Handbook of Experimental Pharmacology (HEP). 49. Berlin, Heidelberg: Springer Berlin Heidelberg. 1978. pp. 567–614. doi:10.1007/978-3-642-66775-6_8. ISBN 978-3-642-66777-0. https://bibliography.maps.org/resources/download/8769#page=30. "Table 2. Psychotomimetic activity and some pharmacodynamic effects of structural analogues of LSD [...]" 
  6. ↑ 6.0 6.1 6.2 Mangner TJ (1978). Potential Psychotomimetic Antagonists. N,N-diethyl-1-methyl-3-aryl-1,2,5,6-tetrahydropyridine-5-carboxamides (Ph.D. thesis). University of Michigan. doi:10.7302/11268. Archived from the original on 30 March 2025. 1-Hydroxymethyl LSD (25) was found to have about two-thirds the activity of LSD by Cerletti52 and Abramson,5,53 but since both 1-hydroxymethyl-LSD and 1-acetyl-LSD "are very easily hydrolyzed under alkaline conditions,"62 the high potency of these compounds might be a result of their in vivo hydrolysis to the active LSD. [...] Table 1. Human psychotomimetic potencies of LSD analogs. [...]
  7. ↑ "Chemical Background". Ergot Alkaloids and Related Compounds. Berlin, Heidelberg: Springer Berlin Heidelberg. 1978. pp. 29–85. doi:10.1007/978-3-642-66775-6_2. ISBN 978-3-642-66777-0. 
  8. ↑ "Derivatives of d-Lysergic Acid and Model Psychoses". Mind as a Tissue: Proceedings of the Fifth International Research Conference Held at the Lankenau Hospital, Philadelphia, Pennsylvania. New York: Harper and Row. 1968. pp. 134–169. OCLC 442122. https://bibliography.maps.org/resources/download/20311. 
  9. ↑ "Lysergic acid diethyl amide (LSD-25): XXXVII. Antiserotonin action of lysergic acid derivatives in allergy and neuropsychiatry". The Journal of Asthma Research 2 (3): 257–262. March 1965. doi:10.3109/02770906509107712. PMID 14285481. 
  10. ↑ "Spezifische Hemmung von 5-Oxytryptamin-Effekten durch Lysergsäurediäthylamid und ähnliche Körper" (in de). Naunyn-Schmiedebergs Archiv für Experimentelle Pathologie und Pharmakologie 228 (1–2). 1956. doi:10.1007/BF00259761. ISSN 0028-1298. http://link.springer.com/10.1007/BF00259761. Retrieved 5 June 2025. 
  11. ↑ 11.0 11.1 11.2 "Stereochemical Aspects of Hallucinogenesis". Biochemistry and Physiology of Substance Abuse. 3. Boca Raton, Fla.: CRC Press. 1991. pp. 1–39. ISBN 978-0-8493-4463-3. OCLC 26748320. https://bitnest.netfirms.com/external/Books/BiochemistryPhysiologySubstanceAbuse3.1. "The 1-hydroxymethyl derivative was estimated to be 66% as potent as LSD, and it also serves as a metabolic intermediate in the demethylation of 1-methyl LSD, which itself is about 1/3 as active as LSD.160,193" 
  12. ↑ "Lysergic acid diethylamide and related substances". Annals of the New York Academy of Sciences 66 (3): 668–676. March 1957. doi:10.1111/j.1749-6632.1957.tb40756.x. PMID 13425249. Bibcode: 1957NYASA..66..668R. 
  13. ↑ "Pharmacology of lysergic acid diethylamide and some of its related compounds". The Journal of Pharmacy and Pharmacology 9 (9): 569–587. September 1957. doi:10.1111/j.2042-7158.1957.tb12312.x. PMID 13463749. 
  14. ↑ "Comparison of Abnormal Behavioral States Induced by Psychotropic Drugs in Animals and Man". Proceedings of the 1st International Congress of Neuro-Psychopharmacology, Rome, September 1958. Amsterdam: Elsevier. 1959. pp. 117–123. https://bibliography.maps.org/resources/download/19108. 
  15. ↑ "Quantum chemical studies on drug actions. 3. Correlation of hallucinogenic and anti-serotonin activity of lysergic acid derivatives with quantum chemical data". Research Communications in Chemical Pathology and Pharmacology 6 (1): 65–100. July 1973. PMID 4734018. https://bibliography.maps.org/resources/download/14168#page=10. "Table I: Structure and Several Biological Activities of Lysergates [...]". 
  16. ↑ "Quantum chemical studies on drug actions. IV. Correlation of substituent structures and anti-serotonin activity in lysergamide series". Research Communications in Chemical Pathology and Pharmacology 7 (2): 259–274. February 1974. PMID 4818373. https://bibliography.maps.org/resources/download/20652#page=7. "Table I: Quantum Chemical Data on Lysergamide Derivatives [...]". 
  17. ↑ "QSAR studies on hallucinogens". Chemical Reviews 83 (6): 633–649. 1 December 1983. doi:10.1021/cr00058a003. ISSN 0009-2665. https://bitnest.netfirms.com/external/10.1021/cr00058a003#page=11. "TABLE XII. Antiserotonin and Hallucinogenic Activities and Hückel's Total MO Energy of LSD and its Analogues [...]". 



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