1-Hydroxymethyl-LSD

Last updated

1-Hydroxymethyl-LSD
1-Hydroxymethyl-LSD.svg
Clinical data
Other namesOML-632; OML632; 1-Hydroxymethyllysergic acid diethylamide; 1-Hydroxymethyl-d-lysergic acid diethylamide; 1-Oxy-methyl-LSD; 1-Oxymethyl-LSD; Oxymethyl-LSD
Routes of
administration 		Oral
Drug class Serotonin receptor modulator; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Identifiers
  • (6aR,9R)-N,N-Diethyl-4-(hydroxymethyl)-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide
CAS Number
Chemical and physical data
Formula C21H27N3O2
Molar mass 353.466 g·mol−1
3D model (JSmol)
  • CCN(C(=O)[C@H]1CN(C)[C@H]2C(=C1)c1cccc3c1c(C2)cn3CO)CC
  • InChI=1S/C21H27N3O2/c1-4-23(5-2)21(26)15-9-17-16-7-6-8-18-20(16)14(12-24(18)13-25)10-19(17)22(3)11-15/h6-9,12,15,19,25H,4-5,10-11,13H2,1-3H3/t15-,19-/m1/s1
  • Key:MCNBQMJSTKRHKK-DNVCBOLYSA-N

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]

Contents

It 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] However, OML-632 may simply act as a prodrug of LSD. [6]

OML-632 was first described in the scientific literature by 1957. [11] [12] [4] [13] The compound has been mistakenly referred to as "1-methoxy-LSD" or "1-MeO-LSD" in some publications. [14] [15] [16]

See also

References

  1. ↑ Shulgin AT (1982). "Chemistry of Psychotomimetics". In Hoffmeister F, Stille G (eds.). Psychotropic Agents, Part III: Alcohol and Psychotomimetics, Psychotropic Effects of Central Acting Drugs. Handbook of Experimental Pharmacology. Vol. 55 / 3. Berlin: Springer Berlin Heidelberg. pp. 3–29. doi:10.1007/978-3-642-67770-0_1. ISBN   978-3-642-67772-4. OCLC   8130916.
  2. ↑ Shulgin AT (1976). "Psychotomimetic Agents". In Gordon M (ed.). Psychopharmacological Agents: Use, Misuse and Abuse. Medicinal Chemistry: A Series of Monographs. Vol. 4. Academic Press. pp. 59–146. doi:10.1016/b978-0-12-290559-9.50011-9. ISBN   978-0-12-290559-9.
  3. ↑ Shulgin AT (1980). "Hallucinogens". In Burger A, Wolf ME (eds.). Burger's Medicinal Chemistry. Vol. 3 (4 ed.). New York: Wiley. pp. 1109–1137. ISBN   978-0-471-01572-7. OCLC   219960627.
  4. 1 2 Abramson HA (1959). "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. doi:10.1080/00223980.1959.9916341. ISSN   0022-3980.
  5. 1 2 Fanchamps A (1978). "Some Compounds With Hallucinogenic Activity". In Berde B, Schild HO (eds.). Ergot Alkaloids and Related Compounds. Handbook of Experimental Pharmacology (HEP). Vol. 49. Berlin, Heidelberg: Springer Berlin Heidelberg. pp. 567–614. doi:10.1007/978-3-642-66775-6_8. ISBN   978-3-642-66777-0. Archived from the original on 30 March 2025. Table 2. Psychotomimetic activity and some pharmacodynamic effects of structural analogues of LSD [...]
  6. 1 2 3 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. ↑ Rutschmann J, Stadler PA (1978). "Chemical Background". Ergot Alkaloids and Related Compounds. Berlin, Heidelberg: Springer Berlin Heidelberg. pp. 29–85. doi:10.1007/978-3-642-66775-6_2. ISBN   978-3-642-66777-0.
  8. ↑ Abramson HA (1968). "Derivatives of d-Lysergic Acid and Model Psychoses". In Rupp C (ed.). Mind as a Tissue: Proceedings of the Fifth International Research Conference Held at the Lankenau Hospital, Philadelphia, Pennsylvania. New York: Harper and Row. pp. 134–169. OCLC   442122. Archived from the original on 30 March 2025.
  9. ↑ Abramson HA (March 1965). "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. doi:10.3109/02770906509107712. PMID   14285481.
  10. ↑ Konzett H, Cerletti A (1956). "Spezifische Hemmung von 5-Oxytryptamin-Effekten durch Lysergsäurediäthylamid und ähnliche Körper" [Specific inhibition of serotonin effects by lysergic acid diethylamide and similar compounds]. Naunyn-Schmiedebergs Archiv für Experimentelle Pathologie und Pharmakologie (in German). 228 (1–2). doi:10.1007/BF00259761. ISSN   0028-1298 . Retrieved 5 June 2025.
  11. ↑ 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.
  12. ↑ Rothlin E (September 1957). "Pharmacology of lysergic acid diethylamide and some of its related compounds". The Journal of Pharmacy and Pharmacology. 9 (9): 569–587. doi:10.1111/j.2042-7158.1957.tb12312.x. PMID   13463749.
  13. ↑ Cerletti A (September 1958). "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.
  14. ↑ Kumbar M, Sankar DV (July 1973). "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. PMID   4734018. Archived from the original on 29 March 2025. Table I: Structure and Several Biological Activities of Lysergates [...]
  15. ↑ Sankar DV, Kumbar M (February 1974). "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. PMID   4818373. Archived from the original on 29 March 2025. Table I: Quantum Chemical Data on Lysergamide Derivatives [...]
  16. ↑ Gupta SP, Singh P, Bindal MC (1 December 1983). "QSAR studies on hallucinogens" . Chemical Reviews. 83 (6): 633–649. doi:10.1021/cr00058a003. ISSN   0009-2665. TABLE XII. Antiserotonin and Hallucinogenic Activities and Hückel's Total MO Energy of LSD and its Analogues [...]



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