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C-DMT

From Wikipedia, the free encyclopedia
For the anabolic steroid abbreviated as CDMT, seeChlorodehydromethyltestosterone.

Pharmaceutical compound
C-DMT
Clinical data
Other namesN,N-Dimethyl-3-indenylethylamine; 3-(2-Dimethylaminoethyl)indene;N,N-Dimethyl-2-(3H-inden-1-yl)ethylamine
Drug classSerotonin receptor agonist
ATC code
  • None
Identifiers
  • 2-(3H-inden-1-yl)-N,N-dimethylethanamine
PubChemCID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC13H17N
Molar mass187.286 g·mol−1
3D model (JSmol)
  • CN(C)CCC1=CCC2=CC=CC=C21
  • InChI=1S/C13H17N/c1-14(2)10-9-12-8-7-11-5-3-4-6-13(11)12/h3-6,8H,7,9-10H2,1-2H3
  • Key:FOBWFOXXVASKOU-UHFFFAOYSA-N

C-DMT, also known asN,N-dimethyl-2-(3H-inden-1-yl)ethylamine, is aserotonin receptor agonist and a 3-indenylethylaminederivative.[1][2][3] It is ananalogue andbioisostere of thetryptaminepsychedelicN,N-dimethyltryptamine (DMT) in which theindolering has been replaced with anindene ring.[1][2][3] Put another way, thenitrogenatom in the indole ring of DMT has been replaced with acarbon atom to make an indene ring.[1][2]

The drug shows similaraffinity for andpotency in activating theserotonin receptors in the rat fundus strip compared to DMT.[1][2][3] These findings suggest that the indole-ring nitrogen atom of tryptamines is not essential forserotonergic activity.[1][2][3] On the other hand however, C-DMT showed dramatically lower affinities for theserotonin5-HT1E and5-HT1F receptors compared to DMT (8- and 65-fold, respectively).[4]

The effects of C-DMT in animals and humans, and whether it produceshallucinogenic effects, do not appear to be known.[1]

See also

[edit]

References

[edit]
  1. ^abcdefNichols DE (2012)."Structure–activity relationships of serotonin 5-HT2A agonists".Wiley Interdisciplinary Reviews: Membrane Transport and Signaling.1 (5):559–579.doi:10.1002/wmts.42.ISSN 2190-460X.Early work with benzo[b]thiophenes 6 and 3-indenalkylamines 7 (Figure 5) demonstrated that for compounds lacking ring substituents, the ability to act as agonists in the rat fundus was about the same as for the tryptamines themselves.8 That is, the indole NH was not essential to activate the 5-HT2 receptor in the rat fundus. No modern studies have been carried out to assess affinity at 5-HT2A receptors. [...] FIGURE 5 | Potential bioisosteres of tryptamines by replacing N(1) with sulfur or CH2.
  2. ^abcdeGlennon 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. ^abcdWinter JC, Gessner PK, Godse DD (September 1967). "Synthesis of some 3-indenealkylamines. Comparison of the biological activity of 3-indenealkylamines and 3-benzo[b]thiophenealkylamines with their tryptamine isosteres".Journal of Medicinal Chemistry.10 (5):856–858.doi:10.1021/jm00317a022.PMID 6048491.
  4. ^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.

External links

[edit]
5-HT1
5-HT1A
5-HT1B
5-HT1D
5-HT1E
5-HT1F
5-HT2
5-HT2A
5-HT2B
5-HT2C
5-HT3–7
5-HT3
5-HT4
5-HT5A
5-HT6
5-HT7
Tryptamines
4-Hydroxytryptamines
andesters/ethers
5-Hydroxy- and
5-methoxytryptamines
N-Acetyltryptamines
α-Alkyltryptamines
Cyclized tryptamines
Isotryptamines
Related compounds
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