O-Acetylbufotenine

O-Acetylbufotenine (5-AcO-DMT, bufotenine acetate) is a tryptamine derivative which produces psychedelic-appropriate responding in animal studies. It is an acylated derivative of bufotenine with higher lipophilicity that allows it to cross the blood–brain barrier; once inside the brain, it is metabolised to bufotenine.^[1][2][3] It also acts directly as an agonist at 5-HT_1A and 5-HT_1D receptors.^[4]

O-Acetylbufotenine

Clinical data
Other names	O-Acetylbufotenin; Bufotenin acetate; 5-Acetoxy-N,N-dimethyltryptamine; 5-Acetoxy-DMT; 5-AcO-DMT
Identifiers
IUPAC name [3-[2-(dimethylamino)ethyl]-1H-indol-5-yl] acetate
CAS Number	16977-50-7 Y
PubChem CID	15480709
ChemSpider	23194786
ChEMBL	ChEMBL111000
CompTox Dashboard (EPA)	DTXSID701345666
Chemical and physical data
Formula	C14H18N2O2
Molar mass	246.310 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(=O)OC1=CC2=C(C=C1)NC=C2CCN(C)C
InChI InChI=1S/C14H18N2O2/c1-10(17)18-12-4-5-14-13(8-12)11(9-15-14)6-7-16(2)3/h4-5,8-9,15H,6-7H2,1-3H3 Key:BZFGYTBVFYYKOK-UHFFFAOYSA-N

See also

• 4-AcO-DMT
• 5-EtO-DMT
• 5-HO-AMT
• 5-HO-DiPT

References

1. Shulgin & Shulgin. TiHKAL #19. 5-HO-DMT
2. Gessner PK, Dankova JB (January 1975). "Brain Bufotenine from Administered Acetylbufotenine: Comparison of Its Tremorgenic Activity with That of N,N-Dimethyltryptamine and 5-Methoxy-N,N-Dimethyltryptamine". Pharmacologist. 17 (2): 259.
3. Winter JC, Amorosi DJ, Rice KC, Cheng K, Yu AM (September 2011). "Stimulus control by 5-methoxy-N,N-dimethyltryptamine in wild-type and CYP2D6-humanized mice". Pharmacology, Biochemistry, and Behavior. 99 (3): 311–5. doi:10.1016/j.pbb.2011.05.015. PMC 3129464. PMID 21624387.
4. Glennon RA, Hong SS, Bondarev M, Law H, Dukat M, Rakhi S, Power P, Fan E, Kinneau D, Kamboj R, Teitler M, Herrick-Davis K, Smith C (January 1996). "Binding of O-alkyl derivatives of serotonin at human 5-HT1D beta receptors". Journal of Medicinal Chemistry. 39 (1): 314–22. doi:10.1021/jm950498t. PMID 8568822.