4C-P

4C-P
Clinical data
Other names4C-Pr; 4C-PR; 4C-DOPR; 4C-DOPr; 4-Propyl-2,5-dimethoxy-α-ethylphenethylamine; 2,5-Dimethoxy-4-propyl-α-ethylphenethylamine
Drug classSerotonin 5-HT2 receptor agonist; Serotonin 5-HT2A receptor agonist
ATC code
  • None
Identifiers
  • 1-(2,5-dimethoxy-4-propylphenyl)butan-2-amine
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC15H25NO2
Molar mass251.370 g·mol−1
3D model (JSmol)
  • CCCC1=CC(=C(C=C1OC)CC(CC)N)OC
  • InChI=1S/C15H25NO2/c1-5-7-11-9-15(18-4)12(8-13(16)6-2)10-14(11)17-3/h9-10,13H,5-8,16H2,1-4H3
  • Key:JQUVOKBZTCXBPH-UHFFFAOYSA-N

4C-P, or 4C-Pr, also known as 4C-DOPR, as well as 4-propyl-2,5-dimethoxy-α-ethylphenethylamine, is a serotonin 5-HT2 receptor agonist of the phenethylamine, phenylisobutylamine, and 4C families related to Ariadne (4C-D).[1][2][3] It is a close analogue of the psychedelic drugs 2C-P and DOPR, with 2C-P having no substitution at the α carbon, DOPR having an α-methyl group, and 4C-P having an α-ethyl group.[2][4] The drug is a potent agonist of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors.[2] It shows similar efficacy as an agonist of these receptors as Ariadne, but has about 6.2-fold higher potency as a serotonin 5-HT2A receptor agonist in comparison.[2] Like Ariadne, 4C-P produces an attenuated head-twitch response relative to DOPR, with a similar maximal response as Ariadne.[2] The chemical synthesis of 4C-P has been described.[5][2] 4C-P was patented in 1977[6] and first described in the scientific literature by Alexander Shulgin and colleagues in 1980.[5] Subsequently, it was described in greater detail by Michael Cunningham and colleagues in 2023.[2]

See also

References

  1. ^ Duan W, Cao D, Wang S, Cheng J (January 2024). "Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants". Chemical Reviews. 124 (1): 124–163. doi:10.1021/acs.chemrev.3c00375. PMID 38033123. Ariadne (95) is a nonhallucinogenic 5-HT2AR agonist in the phenylalkylamine class of compounds,173 and its structure differs from that of DOM (91) by only an additional methyl group (Figure 11). A very recent SAR study by Cunningham et al. around ariadne showed that replacement of the 4-methyl group with a trifluoromethyl (96, 4C-TFM, EC50 = 28.6 nM, Emax = 79.9%) or an n-propyl (97, 4C-Pr, EC50 = 29.5 nM, Emax = 83.8%) led to good agonist potency at the 5-HT2AR in the Gq-dissociation BRET assay, while the cycolopropyl (98, 4CcycPr, EC50 = 153 nM, Emax = 75%) and MOM (99, 4C-MOM, EC50 = 441 nM, Emax = 77.8%) substitutions decreased compound potency.173 Ariadne showed lower signaling potency and efficacy compared to that of DOM in multiple signaling pathways examined, and it exhibited markedly more attenuated HTR effects than its hallucinogenic analogues.173
  2. ^ a b c d e f g Cunningham MJ, Bock HA, Serrano IC, Bechand B, Vidyadhara DJ, Bonniwell EM, et al. (January 2023). "Pharmacological Mechanism of the Non-hallucinogenic 5-HT2A Agonist Ariadne and Analogs". ACS Chemical Neuroscience. 14 (1): 119–135. doi:10.1021/acschemneuro.2c00597. PMC 10147382. PMID 36521179.
  3. ^ Shulgin A, Manning T, Daley PF (2011). The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley, CA: Transform Press. p. 343. ISBN 978-0-9630096-3-0. OCLC 709667010.
  4. ^ Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. ISBN 978-3-03788-700-4. OCLC 858805226. Archived from the original on 21 August 2025.
  5. ^ a b Standridge RT, Howell HG, Tilson HA, Chamberlain JH, Holava HM, Gylys JA, et al. (February 1980). "Phenylalkylamines with potential psychotherapeutic utility. 2. Nuclear substituted 2-amino-1-phenylbutanes". Journal of Medicinal Chemistry. 23 (2): 154–162. doi:10.1021/jm00176a010. PMID 7359529.
  6. ^ US 4034113A, Shulgin AT, "Treatment of senile geriatric patients to restore performance", issued 5 July 1977 
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