RU-27849

RU-27849, also known as 4,α-methylenetryptamine (4,α-methylene-T), is a serotonin receptor modulator. It can be regarded as a conformationally restricted tricyclic derivative of tryptamine or a structurally simplified derivative of LSD. This molecule was developed during structure–activity relationship (SAR) studies of LSD.^[1][2][3][4]

Other namesRU27849; 4,α-Methylenetryptamine; 4,α-Methylene-T; 4-Amino-1,3,4,5-tetrahydrobenz[c,d]indole

Drug classSerotonin receptor modulator; Simplified/partial LSD analogue

ATC code

• None

CAS Number

• 77963-70-3

Quick facts Clinical data, Other names ...

RU-27849

Clinical data
Other names	RU27849; 4,α-Methylenetryptamine; 4,α-Methylene-T; 4-Amino-1,3,4,5-tetrahydrobenz[c,d]indole
Drug class	Serotonin receptor modulator; Simplified/partial LSD analogue
ATC code	None
Identifiers
IUPAC name 1,3,4,5-tetrahydrobenzo[c,d]indol-4-amine
CAS Number	77963-70-3
PubChem CID	132797
ChemSpider	117204
CompTox Dashboard (EPA)	DTXSID20999149
Chemical and physical data
Formula	C11H12N2
Molar mass	172.231 g·mol−1
3D model (JSmol)	Interactive image
SMILES C1C(CC2=CNC3=CC=CC1=C23)N
InChI InChI=1S/C11H12N2/c12-9-4-7-2-1-3-10-11(7)8(5-9)6-13-10/h1-3,6,9,13H,4-5,12H2 Key:JPTWSZJFCLJZJX-UHFFFAOYSA-N

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It shows affinity for serotonin receptors, including for the serotonin 5-HT₁, 5-HT_1A, and 5-HT₂ receptors (IC₅₀Tooltip half-maximal inhibitory concentration = 267–520 nM, 325–326 nM, and 1,964–2,900 nM, respectively).^[1][2][5] RU-27849's affinities for serotonin receptors are similar to but lower than those of tryptamine and dimethyltryptamine (DMT).^[1][2] It shows very weak affinity for dopamine receptors and weak associated activity.^[3]

The 6-methoxy derivative of RU-27849, which is to RU-27849 as 5-methoxytryptamine is to tryptamine, appears to have much higher affinity for serotonin receptors than RU-27849 itself (IC₅₀ ≈ 50 nM).^[2][6] A number of other derivatives also exist, including FHATHBIN (6-hydroxy), RU-28306 (N,N-dimethyl), RU-28251 (N,N-dipropyl), Bay R 1531 (LY-197206; 6-methoxy-N,N-dipropyl), LY-293284 ((4R)-6-acetyl-N,N-dipropyl), and LY-178210 (6-carboxamido-N,N-dipropyl), as well as NDTDI, among others.^[3][7][5][8]

RU-27849 was first described in the scientific literature by 1981.^[3][1][2][5]