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7-MeO-DMT

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7-MeO-DMT
Clinical data
Other names7-OMe-DMT; 7-Methoxy-DMT; 7-Methoxy-N,N-dimethyltryptamine
Drug classSerotonin receptor modulator
ATC code
  • None
Identifiers
  • 2-(7-methoxy-1H-indol-3-yl)-N,N-dimethylethanamine
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC13H18N2O
Molar mass218.300 g·mol−1
3D model (JSmol)
  • CN(C)CCC1=CNC2=C1C=CC=C2OC
  • InChI=1S/C13H18N2O/c1-15(2)8-7-10-9-14-13-11(10)5-4-6-12(13)16-3/h4-6,9,14H,7-8H2,1-3H3
  • Key:GCEZYLSUTMYNRN-UHFFFAOYSA-N

7-MeO-DMT, or 7-OMe-DMT, also known as 7-methoxy-N,N-dimethyltryptamine, is a serotonin receptor modulator of the tryptamine family.[1] It is the 7-methoxy derivative of the serotonergic psychedelic dimethyltryptamine (DMT) and is a positional isomer of 5-MeO-DMT, 4-MeO-DMT, and 6-MeO-DMT.[1]

Pharmacology

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In an early study using the isolated rat stomach fundus strip, the drug showed very low serotonin receptor affinity (A2 = 4,677 nM) that was about 56-fold lower than that of 5-MeO-DMT.[2][3][4] However, this assay was subsequently found to be an unreliable predictor of hallucinogenic activity.[5] In subsequent studies, 7-MeO-DMT bound to the serotonin 5-HT2A receptor (Ki = 5,400–5,440 nM) and had 9- to 59-fold lower affinity than 5-MeO-DMT and 5- to 17-fold lower affinity than DMT.[1][6][7] It showed no detectable affinity for the serotonin 5-HT2C receptor (Ki = >10,000 nM), but did show affinity for the serotonin 5-HT1A receptor (Ki = 1,760 nM).[7] Its affinity for the serotonin 5-HT1A receptor was 160-fold lower than that of 5-MeO-DMT and was 9-fold lower than that of DMT.[7] 7-MeO-DMT has also been assessed at the serotonin 5-HT1E and 5-HT1F receptors (Ki = >10,000 nM and 2,620 nM, respectively).[8]

7-MeO-DMT substitutes for the atypical psychedelic 5-MeO-DMT in rodent drug discrimination tests.[4] The drug was only briefly mentioned in Alexander Shulgin's 1997 book TiHKAL and is not known to have been tested in humans.[2][9] Hence, it is unknown whether 7-MeO-DMT produces psychedelic effects in humans.[2][9]

History

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7-MeO-DMT was first described in the scientific literature by at least 1968.[10]

See also

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References

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  1. ^ a b c Duan W, Cao D, Wang S, Cheng J (January 2024). "Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants". Chemical Reviews. 124 (1): 124–163. doi:10.1021/acs.chemrev.3c00375. PMID 38033123. Nevertheless, substitutions at positions 6 or 7 were reported to reduce or even abolish the binding ability to 5-HT2 receptors. For example, 6-OMe-DMT (35, Ki = 7300 nM) and 7-OMe-DMT (36, Ki = 5400 nM) exhibited reduced affinity compared to that of DMT (Ki = 1200 nM) at [3H]-ketanserin-labeled 5-HT2Rs.124
  2. ^ a b c 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.
  3. ^ 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.
  4. ^ a b Glennon RA, Young R, Rosecrans JA, Kallman MJ (1980). "Hallucinogenic agents as discriminative stimuli: a correlation with serotonin receptor affinities". Psychopharmacology. 68 (2): 155–158. doi:10.1007/BF00432133. PMID 6776558.
  5. ^ Nichols DE, Schooler D, Yeung MC, Oberlender RA, Zabik JE (September 1984). "Unreliability of the rat stomach fundus as a predictor of hallucinogenic activity in substituted phenethylamines". Life Sciences. 35 (13): 1343–1348. doi:10.1016/0024-3205(84)90390-4. PMID 6482656.
  6. ^ 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.
  7. ^ a b c Glennon RA, Dukat M, Grella B, Hong S, Costantino L, Teitler M, et al. (August 2000). "Binding of beta-carbolines and related agents at serotonin (5-HT(2) and 5-HT(1A)), dopamine (D(2)) and benzodiazepine receptors". Drug and Alcohol Dependence. 60 (2): 121–132. doi:10.1016/s0376-8716(99)00148-9. PMID 10940539.
  8. ^ Klein MT, Dukat M, Glennon RA, Teitler M (June 2011). "Toward selective drug development for the human 5-hydroxytryptamine 1E receptor: a comparison of 5-hydroxytryptamine 1E and 1F receptor structure-affinity relationships". The Journal of Pharmacology and Experimental Therapeutics. 337 (3): 860–867. doi:10.1124/jpet.111.179606. PMC 3101003. PMID 21422162.
  9. ^ a b Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252.
  10. ^ Gessner PK, Godse DD, Krull AH, McMullan JM (March 1968). "Structure-activity relationships among 5-methoxy-n:n-dimethyltryptamine, 4-hydroxy-n:n-dimethyltryptamine (psilocin) and other substituted tryptamines". Life Sciences. 7 (5): 267–277. doi:10.1016/0024-3205(68)90200-2. PMID 5641719.
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