Clausenamide

Clausenamide

Clinical data
Drug class	Serotonin 5-HT2A receptor agonist; Psychoplastogen
ATC code	None
Identifiers
IUPAC name 3-hydroxy-5-[hydroxy(phenyl)methyl]-1-methyl-4-phenylpyrrolidin-2-one
CAS Number	103541-15-7
PubChem CID	5315946
ChemSpider	4475124
Chemical and physical data
Formula	C18H19NO3
Molar mass	297.354 g·mol^−1
3D model (JSmol)	Interactive image
SMILES CN1C(C(C(C1=O)O)C2=CC=CC=C2)C(C3=CC=CC=C3)O
InChI InChI=1S/C18H19NO3/c1-19-15(16(20)13-10-6-3-7-11-13)14(17(21)18(19)22)12-8-4-2-5-9-12/h2-11,14-17,20-21H,1H3 Key:WGYGSZOQGYRGIP-UHFFFAOYSA-N

Clausenamide is an alkaloid found in Clausena lansium (wampee), an evergreen tree native to Southeast Asia and southern China.^[1][2] The compound has multiple chiral centers and many possible enantiomers or stereoisomers.^[1][2] Some of its isomers, especially (–)-cis-clausenamide, show psychoplastogenic effects that may be due to serotonin 5-HT_2A receptor partial agonism.^[2] In a BRET assay, (–)-cis-clausenamide showed modest potency and efficacy as a serotonin 5-HT_2A receptor partial agonist (EC₅₀Tooltip half-maximal effective concentration = 490 nM; E_maxTooltip maximal efficacy = 28.4%).^[2] A number of other biological activities of clausenamide have also been described, and the compound has potential medical applications.^[1][3] Clausenamide was first isolated and described in the scientific literature by 1987.^[4] The psychoplastogenic activity of clausenamide was described by David E. Olson and colleagues in 2026.^[2]

See also

• Cyclized phenethylamine
• Non-hallucinogenic 5-HT_2A receptor agonist
• List of miscellaneous 5-HT_2A receptor agonists
• 2C-B-PYR

References

1. Chu SF, Zhang JT (December 2014). "Recent advances in the study of (-)clausenamide: chemistry, biological activities and mechanism of action". Acta Pharmaceutica Sinica. B. 4 (6): 417–423. doi:10.1016/j.apsb.2014.10.004. PMC 4629111. PMID 26579412.
2. Ou Y, Khatib YA, Mosswood A, Roy TK, Gutierrez DA, Olson DE, et al. (May 2026). "Synthesis of Clausenamide Isomers and Evaluation of Their Potential as Cortical Neuroplastogens". ACS Chemical Neuroscience acschemneuro.5c00767. doi:10.1021/acschemneuro.5c00767. PMID 42089448.
3. Chu S, Liu S, Duan W, Cheng Y, Jiang X, Zhu C, et al. (June 2016). "The anti-dementia drug candidate, (-)-clausenamide, improves memory impairment through its multi-target effect". Pharmacology & Therapeutics. 162: 179–187. doi:10.1016/j.pharmthera.2016.01.002. PMID 26812265.
4. Yang MH, Cao YH, Li WX, Yang YQ, Chen YY, Huang L (January 1987). "[Isolation and structural elucidation of clausenamide from the leaves of Clausena lansium (Lour.) Skeels]". Yao Xue Xue Bao = Acta Pharmaceutica Sinica (in Chinese). 22 (1): 33–40. PMID 3604690.