25TFM-NBOMe

25TFM-NBOMe (also known as NBOMe-2C-TFM, 2C-TFM-NBOMe, and Cimbi-138) is a derivative of the phenethylamine hallucinogen 2C-TFM, discovered by Ralf Heim at the Free University of Berlin by 2000.^[1][2] It can be taken to produce psychedelic effects similar to 25I-NBOMe and 25D-NBOMe.^{[citation needed]}

25TFM-NBOMe

Clinical data
Other names	NBOMe-2C-TFM; 2C-TFM-NBOMe; Cimbi-138
Drug class	Serotonin 5-HT2 receptor agonist; Serotonergic psychedelic; Hallucinogen
Identifiers
IUPAC name 2-(4-trifluoromethyl-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine
CAS Number	1027161-33-6 Y
PubChem CID	10067667
ChemSpider	8243207 Y
UNII	X3V8LI2TUV
CompTox Dashboard (EPA)	DTXSID40435135
Chemical and physical data
Formula	C19H22F3NO3
Molar mass	369.384 g·mol−1
3D model (JSmol)	Interactive image
SMILES FC(F)(F)c1c(OC)cc(c(OC)c1)CCNCc2ccccc2OC
InChI InChI=1S/C19H22F3NO3/c1-24-16-7-5-4-6-14(16)12-23-9-8-13-10-18(26-3)15(19(20,21)22)11-17(13)25-2/h4-7,10-11,23H,8-9,12H2,1-3H3 Y Key:FBHVTQIAHOTPAM-UHFFFAOYSA-N Y
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Interactions

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

Pharmacodynamics

25TFM-NBOMe activities

Target	Affinity (Ki, nM)
5-HT1A	ND
5-HT1B	ND
5-HT1D	1,817
5-HT1E	ND
5-HT1F	ND
5-HT2A	0.35–0.49 (Ki) 0.96–2.0 (EC50Tooltip half-maximal effective concentration) 80–92% (EmaxTooltip maximal efficacy)
5-HT2B	1.1 (Ki) ND (EC50) ND (Emax)
5-HT2C	2.7 (Ki) (rat) 11.5 (EC50) 110% (Emax)
5-HT3	ND
5-HT4	ND
5-HT5A	8,128
5-HT6	23.4
5-HT7	5,974
α1A–α1D	ND
α2A–α2C	ND
β1–β3	ND
D1–D5	ND
H1–H4	ND
M1–M5	ND
I1	ND
σ1, σ2	ND
ORs	ND
TAAR1Tooltip Trace amine-associated receptor 1	ND
SERTTooltip Serotonin transporter	ND (Ki) ND (IC50Tooltip half-maximal inhibitory concentration) ND (EC50)
NETTooltip Norepinephrine transporter	ND (Ki) ND (IC50) ND (EC50)
DATTooltip Dopamine transporter	ND (Ki) ND (IC50) ND (EC50)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [3][4][5][6]

25TFM-NBOMe acts as a potent partial agonist for the serotonin 5-HT_2A receptor, though its relative potency is disputed, with some studies finding it to be of lower potency than 25I-NBOMe,^[7][8] while others show it to be of similar or higher potency,^[9] possibly because of differences in the assay used.^[10]

History

25TFM-NBOMe was first described in the scientific literature by Ralf Heim and colleagues at the Free University of Berlin by 2000.^[1][2]

Society and culture

Legal status

United Kingdom

This substance is a Class A drug in the United Kingdom as a result of the N-benzylphenethylamine catch-all clause in the Misuse of Drugs Act 1971.^[11]

See also

• 25-NB
• DOTFM
• TFMFly