25I-NBOMe
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25I-NBOMe
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| Systematic (IUPAC) name | |
| 2-(4-iodo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine | |
| Clinical data | |
| Pregnancy cat. | ? |
| Legal status | ? |
| Identifiers | |
| CAS number | 919797-19-6  1043868-97-8 (hydrochloride) |
| ATC code | None |
| PubChem | CID 10251906 |
| ChemSpider | 8427392 |
| Chemical data | |
| Formula | C18H22INO3 |
| Mol. mass | 427.277 g/mol |
| SMILES | eMolecules & PubChem |
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25I-NBOMe (NBOMe-2C-I, BOM-CI, Cimbi-5, Solaris) is a derivative of the phenethylamine hallucinogen 2C-I, discovered in 2003 by Ralf Heim at the Free University of Berlin,[1] and subsequently investigated in more detail by a team at Purdue University led by David Nichols.[2]
25I-NBOMe acts as a highly potent agonist for the human 5-HT2A receptor,[3][4] with a Ki of 0.044 nM, making it some sixteen times the potency of 2C-I itself, and a radiolabelled form of 25I-NBOMe can be used for mapping the distribution of 5-HT2A receptors in the brain.[5][6] In vitro tests showed this compound acted as an agonist but animal studies have not been reported. While the N-benzyl derivatives of 2C-I were significantly increased in potency compared to 2C-I, the N-benzyl derivatives of DOI were inactive.[7]
Anecdotal reports from human users suggest 25I-NBOMe to be an active hallucinogen at a dose of as little as 500 mcg, making it a similar potency to other phenethylamine derived hallucinogens such as bromo-dragonfly.[citation needed] It came to media attention in early 2012 after a cluster of seven non-fatal overdoses with the drug, in or around Richmond, Virginia.[8][9][10] The drug is not active orally and must be taken buccally, sublingualy or smoked, snorted (not recommended) as it is active at as low as 300 mcg that way.
Effects
- Mild visuals occur (small patterns begin moving and some objects may appear as 2D)
- Feelings of love, as well as sexual thoughts
- Unpleasant chemical taste in your mouth (not eased by drinking any liquids)
- Mild anxiety
- Nausea, abdominal pain
- Time perception is affected
- Confusion (extreme confusion and panic in higher doses)
See also
- 2CBCB-NBOMe (NBOMe-TCB-2)
- 2CBFly-NBOMe (NBOMe-2CB-Fly)
- 25C-NBOMe (NBOMe-2CC)
- 25B-NBOMe (NBOMe-2CB)
- 25I-NBMD (NBMD-2CI)
- 25I-NBOH (NBOH-2CI)
- 25I-NBF (NBF-2CI)
- 5-MeO-NBpBrT
References
- ^ Ralf Heim PhD. Synthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur. Entwicklung eines neuen Struktur-Wirkungskonzepts. (German)
- ^ Michael Robert Braden PhD. Towards a biophysical understanding of hallucinogen action. Purdue University 2007.
- ^ Ettrup, A.; Hansen, M.; Santini, M. A.; Paine, J.; Gillings, N.; Palner, M.; Lehel, S.; Herth, M. M. et al (2010). "Radiosynthesis and in vivo evaluation of a series of substituted 11C-phenethylamines as 5-HT2A agonist PET tracers". European Journal of Nuclear Medicine and Molecular Imaging 38 (4): 681–693. doi:10.1007/s00259-010-1686-8. ISBN 0025901016868. PMID 21174090.
- ^ Silva ME, Heim R, Strasser A, Elz S, Dove S (January 2011). "Theoretical studies on the interaction of partial agonists with the 5-HT(2A) receptor". Journal of Computer-aided Molecular Design 25 (1): 51–66. doi:10.1007/s10822-010-9400-2. PMID 21088982.
- ^ Nichols DE, Frescas SP, Chemel BR, Rehder KS, Zhong D, Lewin AH (June 2008). "High Specific Activity Tritium-Labeled N-(2-methoxybenzyl)-2,5-dimethoxy-4-iodophenethylamine (INBMeO): A High Affinity 5-HT2A Receptor-Selective Agonist Radioligand". Bioorganic & Medicinal Chemistry 16 (11): 6116–23. doi:10.1016/j.bmc.2008.04.050. PMC 2719953. PMID 18468904. //www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2719953.
- ^ Ettrup, A.; Palner, M.; Gillings, N.; Santini, M. A.; Hansen, M.; Kornum, B. R.; Rasmussen, L. K.; Nagren, K. et al (2010). "Radiosynthesis and Evaluation of 11C-CIMBI-5 as a 5-HT2A Receptor Agonist Radioligand for PET". Journal of Nuclear Medicine 51 (11): 1763. doi:10.2967/jnumed.109.074021. PMID 20956470.
- ^ Braden, MR; Parrish, JC; Naylor, JC; Nichols, DE (2006). "Molecular interaction of serotonin 5-HT2A receptor residues Phe339(6.51) and Phe340(6.52) with superpotent N-benzyl phenethylamine agonists". Molecular Pharmacology 70 (6): 1956–64. doi:10.1124/mol.106.028720. PMID 17000863.
- ^ Kids overdosing on new drug. Laura Geller, WWBT NBC12, Feb 18, 2012
- ^ Chesterfield mom warns of designer drug overdoses. Laura Geller, WWBT NBC12, March 8, 2012
- ^ New street drug causing concern among medics. Vanessa Araiza, WBRC, Feb 28, 2012
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