25I-NBOMe

Structural formula
General
Surname	25I-NBOMe
other names	2- (4-iodo-2,5-dimethoxyphenyl) -N - [(2-methoxyphenyl) methyl] ethanamine; 2C-I-NBOMe; ([ 11 C] Cimbi-5);
Molecular formula	C 18 H 22 INO 3
Brief description	white solid (hydrochloride)
External identifiers / databases
PubChem	10251906
ChemSpider	8427392
Wikidata	Q4632141
properties
Molar mass	427.27 g mol −1
Physical state	firmly
Melting point	157.3 ° C (hydrochloride)
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

25I-NBOMe (or 2C-I-NBOMe ) is a research chemical with hallucinogenic and psychedelic effects, which, due to its structure, belongs to the groups of phenol ethers and phenethylamines . The effect is attributed, among other things, to the properties of the 25I-NBOMes as a potent agonist on the serotonin receptor 5-HT _2A . 25I-NBOMe is a derivative of 2C-I .

history

25I-NBOMe was developed in 2003 by Ralf Heim at the Free University of Berlin as part of his doctoral thesis "Synthesis and pharmacology of potent 5-HT _2A receptor agonists with N-2-methoxybenzyl partial structure" . The ¹¹ C -labeled compound ([ ¹¹ C] Cimbi-5) of 25I-NBOMe was synthesized at the University of Copenhagen and validated as a radiotracer for positron emission tomography (PET).

Pharmacodynamics

25I-NBOMe binds to the individual receptors with the following K _i values:

receptor	K _i (nM)	±
5-HT _2A	0.044
5-HT _2C	2
5-HT ₆	73	12
µ-opioid	82	14th
H ₁	189	35
5-HT _2B	231	73
k-opioid	288	50

Legal status

Germany

25I-NBOMe was recommended on May 6, 2013 at the 40th meeting of the Narcotics Expert Committee of the Federal Institute for Drugs and Medical Devices for inclusion in Annex I to Section 1 (1) BtMG. An actual admission took place with the 28th ordinance amending the narcotics regulations on December 6, 2014. Like the related 25B-NBoMe, it has been subject to the Narcotics Act (Germany) since then and its possession and trade are therefore illegal.

European Union

On September 25th, 2014 the EU banned 25I-NBOMe, MDPV , AH-7921 and methoxetamine . The manufacture and sale of the substance is therefore prohibited. The EU states had a year to implement the ban.

literature

Ralf Heim: Synthesis and pharmacology of potent 5-HT _2A receptor agonists with N-2-methoxybenzyl partial structure. Development of a new structure-effect concept. Free University of Berlin, 2003.
John F. Casale, Patrick A. Hays, US Department of Justice Drug Enforcement Administration: Characterization of Eleven 2,5-Dimethoxy-N- (2-methoxybenzyl) phenethylamine (NBOMe) Derivatives and Differentiation from their 3- and 4-Methoxybenzyl Analogues - Part I (PDF; 4.39 MB), Microgram Journal, Volume 9, Number 2

Web links

25I-NBOMe . In: Erowid . (English)
isomerdesign.com: 25I-NBOMe (English)
EMCDDA: Report on the risk assessment of 2- (4-iodo-2,5-dimethoxyphenyl) -N- (2-methoxybenzyl) ethanamine (25I-NBOME) in the framework of the Council Decision on new psychoactive substances (English)

Individual evidence

↑ ^a ^b SWGDRUG Monographs: 25I-NBOMe Monograph (PDF; 457 kB), accessed on April 12, 2013.

↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

↑ Ralf Heim: Synthesis and pharmacology of potent 5-HT2A receptor agonists with N-2-methoxybenzyl partial structure. Development of a new structure-effect concept. . diss.fu-berlin.de. Retrieved April 12, 2013.

↑ ^a ^b A. Ettrup, M. Palner, et al .: Radiosynthesis and Evaluation of 11C-CIMBI-5 as a 5-HT2A Receptor Agonist Radioligand for PET. In: Journal of Nuclear Medicine. 51, 2010, pp. 1763-1770, doi : 10.2967 / jnumed.109.074021 .

↑ Hansen, M. Design and Synthesis of Selective Serotonin Receptor Agonists for Positron Emission Tomography Imaging of the Brain. PhD Thesis, University of Copenhagen, 2011. ( Memento of the original from October 22, 2013 in the Internet Archive ) Info: The archive link was inserted automatically and has not yet been checked. Please check the original and archive link according to the instructions and then remove this notice. @1@ 2Template: Webachiv / IABot / bitnest.ca
↑ Nichols DE, Frescas SP, Chemel BR, Rehder KS, Zhong D, Lewin AH: High Specific Activity Tritium-Labeled N- (2-methoxybenzyl) -2,5-dimethoxy-4-iodophenethylamine (INBMeO): A High Affinity 5 -HT2A Receptor-Selective Agonist Radioligand . In: Bioorganic & Medicinal Chemistry . 16, No. 11, June 2008, pp. 6116-23. doi : 10.1016 / j.bmc.2008.04.050 . PMID 18468904 . PMC 2719953 (free full text).
↑ Implementing decision of the Council of September 25, 2014 (2014/688 / EU) (PDF) accessed on October 17, 2014.
↑ Aerzteblatt.de: EU bans four dangerous designer drugs, September 26, 2014, accessed on October 17, 2014.
↑ Rp-online.de: MDPV, 25I-NBOMe, AH-7921 and Methoxetamine EU bans four novel drugs, September 25, 2014 accessed on October 17, 2014.

[SWGDRUG-1] SWGDRUG Monographs: 25I-NBOMe Monograph (PDF; 457 kB), accessed on April 12, 2013.

[NV-2] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[ralfheim-3] Ralf Heim: Synthesis and pharmacology of potent 5-HT2A receptor agonists with N-2-methoxybenzyl partial structure. Development of a new structure-effect concept. . diss.fu-berlin.de. Retrieved April 12, 2013.

[DOI10.2967/jnumed.109.074021-4] A. Ettrup, M. Palner, et al .: Radiosynthesis and Evaluation of 11C-CIMBI-5 as a 5-HT2A Receptor Agonist Radioligand for PET. In: Journal of Nuclear Medicine. 51, 2010, pp. 1763-1770, doi : 10.2967 / jnumed.109.074021 .