7-Hydroxy-DMT

7-Hydroxy-DMT
Clinical data
Other names7-HO-DMT; 7-OH-DMT; 7-Hydroxy-N,N-dimethyltryptamine
Drug classSerotonin receptor modulator
ATC code
  • None
Identifiers
  • 3-[2-(dimethylamino)ethyl]-1H-indol-7-ol
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC12H16N2O
Molar mass204.273 g·mol−1
3D model (JSmol)
  • CN(C)CCC1=CNC2=C1C=CC=C2O
  • InChI=1S/C12H16N2O/c1-14(2)7-6-9-8-13-12-10(9)4-3-5-11(12)15/h3-5,8,13,15H,6-7H2,1-2H3
  • Key:FZFHBMMTKKWEQH-UHFFFAOYSA-N

7-Hydroxy-DMT (7-HO-DMT), also known as 7-hydroxy-N,N-dimethyltryptamine, is a serotonin receptor modulator of the tryptamine family related to dimethyltryptamine (DMT).[1][2] It is the 7-hydroxy derivative of DMT and is a positional isomer of psilocin (4-HO-DMT), bufotenin (5-HO-DMT), and 6-HO-DMT.[1][2] The drug shows affinity for serotonin receptors in the rat fundus strip.[1][2] However, it had the lowest serotonin receptor affinity of any other assessed compounds in a series of assessed tryptamines.[1][2] In a later study, its affinity (Ki) for the serotonin 5-HT2A receptor was >10,000 nM.[3][4] 7-Hydroxy-DMT is said to be biologically active in animals but to show low potency.[1] The drug was first described in the scientific literature by at least 1962.[5][6] It is a Schedule I controlled substance in the United States as a positional isomer of psilocin.[7][8]

See also

References

  1. ^ a b c d e Glennon RA, Rosecrans JA (1982). "Indolealkylamine and phenalkylamine hallucinogens: a brief overview". Neuroscience and Biobehavioral Reviews. 6 (4): 489–497. doi:10.1016/0149-7634(82)90030-6. PMID 6757811.
  2. ^ a b c d Glennon RA, Gessner PK (April 1979). "Serotonin receptor binding affinities of tryptamine analogues". Journal of Medicinal Chemistry. 22 (4): 428–432. doi:10.1021/jm00190a014. PMID 430481.
  3. ^ Lyon RA, Titeler M, Seggel MR, Glennon RA (January 1988). "Indolealkylamine analogs share 5-HT2 binding characteristics with phenylalkylamine hallucinogens". European Journal of Pharmacology. 145 (3): 291–297. doi:10.1016/0014-2999(88)90432-3. PMID 3350047.
  4. ^ Glennon RA, Seggel MR (14 November 1989). "Interaction of Phenylisopropylamines with Central 5-HT2 Receptors: Analysis by Quantitative Structure—Activity Relationships". Probing Bioactive Mechanisms. Vol. 413. Washington, DC: American Chemical Society. pp. 264–280. doi:10.1021/bk-1989-0413.ch018. ISBN 978-0-8412-1702-7.
  5. ^ Curtis DR, Davis R (April 1962). "Pharmacological studies upon neurones of the lateral geniculate nucleus of the cat". British Journal of Pharmacology and Chemotherapy. 18 (2): 217–246. doi:10.1111/j.1476-5381.1962.tb01404.x. PMC 1482133. PMID 13882768.
  6. ^ Clarke EG (January 1967). "The identification of some proscribed psychedelic drugs". Journal - Forensic Science Society. 7 (1): 46–50. doi:10.1016/s0015-7368(67)70370-9. PMID 6074429.
  7. ^ Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026) (PDF), United States: U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division, January 2026
  8. ^ Drug Enforcement Administration (3 December 2007). "Definition of "Positional Isomer" as It Pertains to the Control of Schedule I Controlled Substances". Federal Register.
This article is issued from Wikipedia. The text is available under Creative Commons Attribution-Share Alike 4.0 unless otherwise noted. Additional terms may apply for the media files.