4C-B

4C-B
Names
	IUPAC name 1-(2,5-Dimethoxy-4-bromophenyl)butan-2-amine
	Other names 4C-DOB, DOB-B
Identifiers
CAS Number	69294-23-1;
3D model (JSmol)	Interactive image;
ChemSpider	23256805;
PubChem CID	12140147;
CompTox Dashboard (EPA)	DTXSID101336665 ;
	InChI InChI=1S/C12H18BrNO2/c1-4-9(14)5-8-6-12(16-3)10(13)7-11(8)15-2/h6-7,9H,4-5,14H2,1-3H3 Key: QQPRORAZQWLMTQ-UHFFFAOYSA-N;
	SMILES CCC(CC1=CC(=C(C=C1OC)Br)OC)N;
Properties
Chemical formula	C12H18BrNO2
Molar mass	288.185 g·mol−1
Melting point	204-206
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

4C-B (also known as 4C-DOB or DOB-B) is a lesser-known psychedelic drug which is related to 2C-B and DOB.^[1] It is a reasonably potent 5-HT_2A receptor partial agonist with a K_i of 7.6nM, but has relatively low efficacy (15% relative to 5-HT).^[2] It is briefly mentioned in Alexander Shulgin's book PiHKAL (Phenethylamines i Have Known And Loved) but was never tested by him,^[3] however it has subsequently been tested by other researchers and was found to be active in a dose range of 50-80mg with a duration of around 8 hours, though with generally milder effects than 2C-B or DOB.^[4]

References

^ Standridge RT, et al. Phenylalkylamines with potential psychotherapeutic utility. 2. Nuclear substituted 2-amino-1-phenylbutanes. J. Med. Chem. 1980, 23, 2, 154–162. doi:10.1021/jm00176a010
^ Glennon RA, Bondarev ML, Khorana N, Young R, May JA, Hellberg MR, McLaughlin MA, Sharif NA. Beta-oxygenated analogues of the 5-HT2A serotonin receptor agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane. J Med Chem. 2004 Nov 18;47(24):6034-41. doi:10.1021/jm040082s PMID 15537358
^ Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.
^ Daniel Trachsel; David Lehmann & Christoph Enzensperger (2013). Phenethylamine: Von der Struktur zur Funktion. Nachtschatten Verlag AG. p. 832. ISBN 978-3-03788-700-4.

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[1] Standridge RT, et al. Phenylalkylamines with potential psychotherapeutic utility. 2. Nuclear substituted 2-amino-1-phenylbutanes. J. Med. Chem. 1980, 23, 2, 154–162. doi:10.1021/jm00176a010

[2] Glennon RA, Bondarev ML, Khorana N, Young R, May JA, Hellberg MR, McLaughlin MA, Sharif NA. Beta-oxygenated analogues of the 5-HT2A serotonin receptor agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane. J Med Chem. 2004 Nov 18;47(24):6034-41. doi:10.1021/jm040082s PMID 15537358

[3] Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.

[Trachsel-4] Daniel Trachsel; David Lehmann & Christoph Enzensperger (2013). Phenethylamine: Von der Struktur zur Funktion. Nachtschatten Verlag AG. p. 832. ISBN 978-3-03788-700-4.

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See also

References