2C-Bu

Last updated

2C-Bu
2C-Bu.svg
Clinical data
Other names4-Butyl-2,5-dimethoxyphenethylamine; 2,5-Dimethoxy-4-butylphenethylamine; 2C-BU
Drug class Serotonin receptor modulator; Serotonin 5-HT2A receptor agonist
ATC code
  • None
Identifiers
  • 2-(4-butyl-2,5-dimethoxyphenyl)ethan-1-amine
CAS Number
PubChem CID
Chemical and physical data
Formula C14H23NO2
Molar mass 237.343 g·mol−1
3D model (JSmol)
  • CCCCC1=CC(=C(C=C1OC)CCN)OC
  • InChI=1S/C14H23NO2/c1-4-5-6-11-9-14(17-3)12(7-8-15)10-13(11)16-2/h9-10H,4-8,15H2,1-3H3
  • Key:WVGDKSDIKCPRKV-UHFFFAOYSA-N

2C-Bu, also known as 4-butyl-2,5-dimethoxyphenethylamine, is a serotonin receptor modulator of the phenethylamine and 2C families. [1] [2] It is the 2C analogue of the DOx derivative DOBU. [1] [3] [4]

Contents

Use and effects

2C-Bu was not included in Alexander Shulgin's book PiHKAL (Phenethylamines I Have Known and Loved) and its properties and effects in humans are unknown. [3] [1]

Pharmacology

Pharmacodynamics

2C-Bu is a potent and high-efficacy serotonin 5-HT2A receptor partial agonist, with an EC50 Tooltip half-maximal effective concentration of 3.9 to 29 nM and an Emax Tooltip maximal efficacy of 71 to 93%. [2]

Chemistry

Analogues

2C-Bu follows 2C-D, 2C-E, and 2C-P in the homologous series of 4-alkylated 2C derivatives. [1] Higher homologues of 2C-Bu including 2C-Am and 2C-Hx are also known and have been characterized. [2]

2C-Bu has several notable skeletal isomers, including 2C-iBu, 2C-tBu, and 2C-sBu. [1] [5] 2C-iBu and 2C-tBu are both active and produce hallucinogen-type effects in animals and/or humans. [6] [7] [8] [5] This is in spite of 2C-tBu being predicted to be inactive [5] and DOTB (the DOx analogue of 2C-tBu) being inactive as a hallucinogen in animals and humans. [3] [9] 2C-iBu may have reduced hallucinogenic potency than other 2C drugs and is being developed as a potential anti-inflammatory medication. [7] [8]

History

2C-Bu was said by Daniel Trachsel and colleagues in 2013 to be completely unknown. [1] However, the drug was subsequently characterized in 2025. [2]

See also

References

  1. 1 2 3 4 5 6 Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German). Solothurn: Nachtschatten-Verlag. pp. 763–764, 766–767, 771, 901. ISBN   978-3-03788-700-4. OCLC   858805226 . Retrieved 29 January 2025.
  2. 1 2 3 4 Simon IA, Pottie E, Harpsøe K, Jensen AA, Kristensen JL, Stove CP, et al. (9 April 2025), Exploring a Druggable Hydrophobic Tunnel in the 5-HT2A Receptor with Potent Phenethylamines, doi:10.26434/chemrxiv-2025-s9rhl , retrieved 12 November 2025
  3. 1 2 3 Shulgin AT, Shulgin A (1991). "#63 DOBU 2,5-DIMETHOXY-4-(n)-BUTYLAMPHETAMINE". PiHKAL: A Chemical Love Story (1st ed.). Berkeley, CA: Transform Press. ISBN   978-0-9630096-0-9. OCLC   25627628.
  4. ↑ Seggel MR, Yousif MY, Lyon RA, Titeler M, Roth BL, Suba EA, et al. (March 1990). "A structure-affinity study of the binding of 4-substituted analogues of 1-(2,5-dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors". Journal of Medicinal Chemistry. 33 (3): 1032–1036. doi:10.1021/jm00165a023. PMID   2308135.
  5. 1 2 3 Varty GB, Canal CE, Mueller TA, Hartsel JA, Tyagi R, Avery K, et al. (April 2024). "Synthesis and Structure-Activity Relationships of 2,5-Dimethoxy-4-Substituted Phenethylamines and the Discovery of CYB210010: A Potent, Orally Bioavailable and Long-Acting Serotonin 5-HT2 Receptor Agonist". J Med Chem. 67 (8): 6144–6188. doi:10.1021/acs.jmedchem.3c01961. PMID   38593423. The 4-tert-butyl group was considered as a spot for potential hydroxylation by cytochrome P450s to discover analogs with short-lasting effects. However, 2C-t-Bu was a potent agonist at the 5-HT2A receptor (Ki = 9.9 nM, EC50 = 4.2 nM) and elicited a robust HTR (Supporting Information, Table S1), providing in vivo evidence that the tert-butyl group is not rapidly metabolized to an inactive compound in mice, despite predictions.
  6. ↑ Shulgin A, Manning T, Daley PF (2011). "#60. DOM". The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds . Vol. 1. Berkeley, CA: Transform Press. pp. 118–129. ISBN   978-0-9630096-3-0. OCLC   709667010. 2c-IB: [...] (15) Synthesis (from 2,5-dimethoxyisobutylbenzene) (Mueller, 2006); although this compound was reported here, a structure-search in Chemical Abstracts does not produce a CAS registry number (16) Threshold activity in humans at 5 mg orally; long duration (about 20 hours; Mueller, 2006). [...] Mueller, M. (2006) Personal communication with A.T. Shulgin.
  7. 1 2 WOpublished, Nichols CD, Billac G, Nichols DE,"Compounds and methods for treating inflammatory disorders",published 15 October 2020
  8. 1 2 Raz S (February 2020). Eleusis Drug Development Overview. LSX World Congress 2020.
  9. ↑ Oberlender RA (May 1989). "Stereoselective aspects of hallucinogenic drug action and drug discrimination studies of entactogens". Purdue e-Pubs. Purdue University. Retrieved 17 February 2025. Table 7. Hallucinogenic potency of 4-alkyl-2,5-dimethoxyamphetamines.a [...] DOTB: [...] Hallucinogenic Potencyb: -c. [...] c this compound has not been established as hallucinogenic. [...] Within this homologous series, optimum activity is straight chain alkyl group, two and three carbons in length 1975). The potency increases by an order of magnitude as associated with a (Shulgin and Dyer, the 4-hydrogen of 2,5-DMA is replaced by a short alkyl chain, then decreases if the chain length exceeds four carbons. In addition, the lack of hallucinogenic activity for the tertiary butyl derivative, DOTB, suggested that branching of the 4-alkyl substituent was not tolerated. [...] In a study employing 5-MeO-DMT as the training drug in rats, DOTB and DOAM were distinguishable from this hallucinogen, while 2,5-DMA and DOM were not (Glennon et al., 1981). This was consistent with the studies described above. Surprisingly, however, stimulus generalization was not observed for DOET, DOPR, and DOBU (Glennon et al., 1981a). [...] Aldous et al. (1974) noted steric restrictions on the 4-substituent in the rabbit hyperthermia model since the 4-isopropyl derivative was more potent than the 4-tert-butyl analogue, DOTB. Additional studies with DOTB, which contains a more highly hindered benzylic carbon, indicate that hallucinogen-like activity may actually be abolished in man (Shulgin and Dyer, 1975) and drastically attenuated in animals (Glennon et al., 1982).
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