C-DMT

{{For|the anabolic steroid abbreviated as CDMT|Chlorodehydromethyltestosterone}}

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| class = Serotonin receptor agonist

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| PubChem = 547452

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| ChemSpiderID = 476501

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| ChEMBL = 161241

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| synonyms = N,N-Dimethyl-3-indenylethylamine; 3-(2-Dimethylaminoethyl)indene; N,N-Dimethyl-2-(3H-inden-1-yl)ethylamine

| IUPAC_name = 2-(3H-inden-1-yl)-N,N-dimethylethanamine

| C=13 | H=17 | N=1

| SMILES = CN(C)CCC1=CCC2=CC=CC=C21

| StdInChI = 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

| StdInChIKey = FOBWFOXXVASKOU-UHFFFAOYSA-N

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C-DMT, also known as N,N-dimethyl-2-(3H-inden-1-yl)ethylamine, is a serotonin receptor agonist and a 3-indenylethylamine derivative.{{cite journal | vauthors = Nichols DE | title=Structure–activity relationships of serotonin 5-HT2A agonists | journal=Wiley Interdisciplinary Reviews: Membrane Transport and Signaling | volume=1 | issue=5 | date=2012 | issn=2190-460X | doi=10.1002/wmts.42 | doi-access=free | pages=559–579 | quote=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.}}{{cite journal | vauthors = Glennon RA, Gessner PK | title = Serotonin receptor binding affinities of tryptamine analogues | journal = Journal of Medicinal Chemistry | volume = 22 | issue = 4 | pages = 428–432 | date = April 1979 | pmid = 430481 | doi = 10.1021/jm00190a014 }}{{cite journal | vauthors = Winter JC, Gessner PK, Godse DD | title = Synthesis of some 3-indenealkylamines. Comparison of the biological activity of 3-indenealkylamines and 3-benzo[b]thiophenealkylamines with their tryptamine isosteres | journal = Journal of Medicinal Chemistry | volume = 10 | issue = 5 | pages = 856–858 | date = September 1967 | pmid = 6048491 | doi = 10.1021/jm00317a022 }} It is an analogue and bioisostere of the tryptamine psychedelic N,N-dimethyltryptamine (DMT) in which the indole ring has been replaced with an indene ring. Put another way, the nitrogen atom in the indole ring of DMT has been replaced with a carbon atom to make an indene ring.

The drug shows similar affinity for and potency in activating the serotonin receptors in the rat fundus strip compared to DMT. These findings suggest that the indole-ring nitrogen atom of tryptamines is not essential for serotonergic activity. On the other hand however, C-DMT showed dramatically lower affinities for the serotonin 5-HT_1E and 5-HT_1F receptors compared to DMT (8- and 65-fold, respectively).{{cite journal | vauthors = Klein MT, Dukat M, Glennon RA, Teitler M | title = Toward selective drug development for the human 5-hydroxytryptamine 1E receptor: a comparison of 5-hydroxytryptamine 1E and 1F receptor structure-affinity relationships | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 337 | issue = 3 | pages = 860–867 | date = June 2011 | pmid = 21422162 | pmc = 3101003 | doi = 10.1124/jpet.111.179606 }}

The effects of C-DMT in animals and humans, and whether it produces hallucinogenic effects, do not appear to be known.