4C-B

4C-B, also known as 4C-DOB or DOB-B, as well as 4-bromo-2,5-dimethoxy-α-ethylphenethylamine, is a lesser-known psychedelic drug of the phenethylamine, phenylisobutylamine, and 4C families related to 2C-B and DOB.^[1] It is a reasonably potent 5-HT_2A receptor partial agonist with a K_i of 7.6 nM, 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 Daniel Trachsel and colleagues and was found to be active in a dose range of 50 to 80 mg with a duration of around 8 hours, producing pronounced psychedelic effects, though with generally milder effects than 2C-B or DOB.^[4]

4C-B

Clinical data
Other names	4C-DOB; DOB-B; 4-Bromo-2,5-dimethoxy-α-ethylphenethylamine
Routes of administration	Oral
Drug class	Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code	None
Identifiers
IUPAC name 1-(4-bromo-2,5-dimethoxyphenyl)butan-2-amine
CAS Number	69294-23-1
PubChem CID	12140147
ChemSpider	23256805
ChEMBL	ChEMBL365711
CompTox Dashboard (EPA)	DTXSID101336665
Chemical and physical data
Formula	C12H18BrNO2
Molar mass	288.185 g·mol−1
3D model (JSmol)	Interactive image
Melting point	204 to 206 °C (399 to 403 °F)
SMILES CCC(CC1=CC(=C(C=C1OC)Br)OC)N
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

See also

• 4C (psychedelics)
• 4C-T-2
• Ariadne (psychedelic) (4C-D)
• ZC-B

References

1. Standridge RT, Howell HG, Tilson HA, Chamberlain JH, Holava HM, Gylys JA, Partyka RA, Shulgin AT (February 1980). "Phenylalkylamines with potential psychotherapeutic utility. 2. Nuclear substituted 2-amino-1-phenylbutanes". Journal of Medicinal Chemistry. 23 (2): 154–62. doi:10.1021/jm00176a010. PMID 7359529.
2. Glennon RA, Bondarev ML, Khorana N, Young R, May JA, Hellberg MR, McLaughlin MA, Sharif NA (November 2004). "Beta-oxygenated analogues of the 5-HT2A serotonin receptor agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane". Journal of Medicinal Chemistry. 47 (24): 6034–41. doi:10.1021/jm040082s. PMID 15537358.
3. Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.
4. Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: Von der Struktur zur Funktion. Nachtschatten Verlag AG. p. 832. ISBN 978-3-03788-700-4. Das α-Ethylhomologon von 2C-B (6) trägt den Namen (303; auch 4C-B) und wurde von Rausch eingehender untersucht [140, 145]. Es vermochte eine ausgeprägte psychedelische Wirkung mit Bewusstseinsvertiefung, Euphorie und Sensationen besonders im Bereich des Tastsinns hervorzurufen (50—80mg, rund acht Stunden Wirkdauer). Visuelle Pseudohalluzinationen traten kaum auf. Das Iodoanalogon DOI-B (304) wurde nur bis zu einer Dosierung von 4mg geprüft und zeigte dabei keinerlei Wirkungen [8].

External links

• 4C-B - Isomer Design